Merge branch 'soru/modularize-e2ee' into 'master'

split encryption stuff to other library

See merge request famedly/famedlysdk!333

lib/encryption.dart

@@ -0,0 +1,23 @@
+/*
+ *   Famedly Matrix SDK
+ *   Copyright (C) 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+library encryption;
+
+export './encryption/encryption.dart';
+export './encryption/key_manager.dart';
+export './encryption/utils/key_verification.dart';

lib/encryption/encryption.dart

@@ -0,0 +1,283 @@
+/*
+ *   Famedly Matrix SDK
+ *   Copyright (C) 2019, 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+import 'dart:convert';
+
+import 'package:famedlysdk/famedlysdk.dart';
+import 'package:famedlysdk/matrix_api.dart';
+import 'package:pedantic/pedantic.dart';
+import 'key_manager.dart';
+import 'olm_manager.dart';
+import 'key_verification_manager.dart';
+
+class Encryption {
+  final Client client;
+  final bool debug;
+  final bool enableE2eeRecovery;
+
+  bool get enabled => olmManager.enabled;
+
+  /// Returns the base64 encoded keys to store them in a store.
+  /// This String should **never** leave the device!
+  String get pickledOlmAccount => olmManager.pickledOlmAccount;
+
+  String get fingerprintKey => olmManager.fingerprintKey;
+  String get identityKey => olmManager.identityKey;
+
+  KeyManager keyManager;
+  OlmManager olmManager;
+  KeyVerificationManager keyVerificationManager;
+
+  Encryption({
+    this.client,
+    this.debug,
+    this.enableE2eeRecovery,
+  }) {
+    keyManager = KeyManager(this);
+    olmManager = OlmManager(this);
+    keyVerificationManager = KeyVerificationManager(this);
+  }
+
+  Future<void> init(String olmAccount) async {
+    await olmManager.init(olmAccount);
+  }
+
+  void handleDeviceOneTimeKeysCount(Map<String, int> countJson) {
+    olmManager.handleDeviceOneTimeKeysCount(countJson);
+  }
+
+  void onSync() {
+    keyVerificationManager.cleanup();
+  }
+
+  Future<void> handleToDeviceEvent(ToDeviceEvent event) async {
+    if (['m.room_key', 'm.room_key_request', 'm.forwarded_room_key']
+        .contains(event.type)) {
+      // a new room key or thelike. We need to handle this asap, before other
+      // events in /sync are handled
+      await keyManager.handleToDeviceEvent(event);
+    }
+    if (event.type.startsWith('m.key.verification.')) {
+      // some key verification event. No need to handle it now, we can easily
+      // do this in the background
+      unawaited(keyVerificationManager.handleToDeviceEvent(event));
+    }
+  }
+
+  Future<ToDeviceEvent> decryptToDeviceEvent(ToDeviceEvent event) async {
+    return await olmManager.decryptToDeviceEvent(event);
+  }
+
+  Event decryptRoomEventSync(String roomId, Event event) {
+    if (event.type != EventTypes.Encrypted ||
+        event.content['ciphertext'] == null) return event;
+    Map<String, dynamic> decryptedPayload;
+    try {
+      if (event.content['algorithm'] != 'm.megolm.v1.aes-sha2') {
+        throw (DecryptError.UNKNOWN_ALGORITHM);
+      }
+      final String sessionId = event.content['session_id'];
+      final String senderKey = event.content['sender_key'];
+      final inboundGroupSession =
+          keyManager.getInboundGroupSession(roomId, sessionId, senderKey);
+      if (inboundGroupSession == null) {
+        throw (DecryptError.UNKNOWN_SESSION);
+      }
+      final decryptResult = inboundGroupSession.inboundGroupSession
+          .decrypt(event.content['ciphertext']);
+      final messageIndexKey = event.eventId +
+          event.originServerTs.millisecondsSinceEpoch.toString();
+      var haveIndex = inboundGroupSession.indexes.containsKey(messageIndexKey);
+      if (haveIndex &&
+          inboundGroupSession.indexes[messageIndexKey] !=
+              decryptResult.message_index) {
+        // TODO: maybe clear outbound session, if it is ours
+        throw (DecryptError.CHANNEL_CORRUPTED);
+      }
+      inboundGroupSession.indexes[messageIndexKey] =
+          decryptResult.message_index;
+      if (!haveIndex) {
+        // now we persist the udpated indexes into the database.
+        // the entry should always exist. In the case it doesn't, the following
+        // line *could* throw an error. As that is a future, though, and we call
+        // it un-awaited here, nothing happens, which is exactly the result we want
+        client.database?.updateInboundGroupSessionIndexes(
+            json.encode(inboundGroupSession.indexes),
+            client.id,
+            roomId,
+            sessionId);
+      }
+      decryptedPayload = json.decode(decryptResult.plaintext);
+    } catch (exception) {
+      // alright, if this was actually by our own outbound group session, we might as well clear it
+      if (client.enableE2eeRecovery &&
+          (keyManager
+                      .getOutboundGroupSession(roomId)
+                      ?.outboundGroupSession
+                      ?.session_id() ??
+                  '') ==
+              event.content['session_id']) {
+        keyManager.clearOutboundGroupSession(roomId, wipe: true);
+      }
+      if (exception.toString() == DecryptError.UNKNOWN_SESSION) {
+        decryptedPayload = {
+          'content': event.content,
+          'type': EventTypes.Encrypted,
+        };
+        decryptedPayload['content']['body'] = exception.toString();
+        decryptedPayload['content']['msgtype'] = 'm.bad.encrypted';
+      } else {
+        decryptedPayload = {
+          'content': <String, dynamic>{
+            'msgtype': 'm.bad.encrypted',
+            'body': exception.toString(),
+          },
+          'type': EventTypes.Encrypted,
+        };
+      }
+    }
+    if (event.content['m.relates_to'] != null) {
+      decryptedPayload['content']['m.relates_to'] =
+          event.content['m.relates_to'];
+    }
+    return Event(
+      content: decryptedPayload['content'],
+      type: decryptedPayload['type'],
+      senderId: event.senderId,
+      eventId: event.eventId,
+      roomId: event.roomId,
+      room: event.room,
+      originServerTs: event.originServerTs,
+      unsigned: event.unsigned,
+      stateKey: event.stateKey,
+      prevContent: event.prevContent,
+      status: event.status,
+      sortOrder: event.sortOrder,
+    );
+  }
+
+  Future<Event> decryptRoomEvent(String roomId, Event event,
+      {bool store = false, String updateType = 'timeline'}) async {
+    final doStore = () async {
+      await client.database?.storeEventUpdate(
+        client.id,
+        EventUpdate(
+          eventType: event.type,
+          content: event.toJson(),
+          roomID: event.roomId,
+          type: updateType,
+          sortOrder: event.sortOrder,
+        ),
+      );
+      if (updateType != 'history') {
+        event.room?.setState(event);
+      }
+    };
+    if (event.type != EventTypes.Encrypted) {
+      return event;
+    }
+    event = decryptRoomEventSync(roomId, event);
+    if (event.type != EventTypes.Encrypted) {
+      if (store) {
+        await doStore();
+      }
+      return event;
+    }
+    if (client.database == null) {
+      return event;
+    }
+    await keyManager.loadInboundGroupSession(
+        roomId, event.content['session_id'], event.content['sender_key']);
+    event = decryptRoomEventSync(roomId, event);
+    if (event.type != EventTypes.Encrypted && store) {
+      await doStore();
+    }
+    return event;
+  }
+
+  /// Encrypts the given json payload and creates a send-ready m.room.encrypted
+  /// payload. This will create a new outgoingGroupSession if necessary.
+  Future<Map<String, dynamic>> encryptGroupMessagePayload(
+      String roomId, Map<String, dynamic> payload,
+      {String type = EventTypes.Message}) async {
+    final room = client.getRoomById(roomId);
+    if (room == null || !room.encrypted || !enabled) {
+      return payload;
+    }
+    if (room.encryptionAlgorithm != 'm.megolm.v1.aes-sha2') {
+      throw ('Unknown encryption algorithm');
+    }
+    if (keyManager.getOutboundGroupSession(roomId) == null) {
+      await keyManager.loadOutboundGroupSession(roomId);
+    }
+    await keyManager.clearOutboundGroupSession(roomId);
+    if (keyManager.getOutboundGroupSession(roomId) == null) {
+      await keyManager.createOutboundGroupSession(roomId);
+    }
+    final sess = keyManager.getOutboundGroupSession(roomId);
+    if (sess == null) {
+      throw ('Unable to create new outbound group session');
+    }
+    final Map<String, dynamic> mRelatesTo = payload.remove('m.relates_to');
+    final payloadContent = {
+      'content': payload,
+      'type': type,
+      'room_id': roomId,
+    };
+    var encryptedPayload = <String, dynamic>{
+      'algorithm': 'm.megolm.v1.aes-sha2',
+      'ciphertext':
+          sess.outboundGroupSession.encrypt(json.encode(payloadContent)),
+      'device_id': client.deviceID,
+      'sender_key': identityKey,
+      'session_id': sess.outboundGroupSession.session_id(),
+      if (mRelatesTo != null) 'm.relates_to': mRelatesTo,
+    };
+    sess.sentMessages++;
+    await keyManager.storeOutboundGroupSession(roomId, sess);
+    return encryptedPayload;
+  }
+
+  Future<Map<String, dynamic>> encryptToDeviceMessagePayload(
+      DeviceKeys device, String type, Map<String, dynamic> payload) async {
+    return await olmManager.encryptToDeviceMessagePayload(
+        device, type, payload);
+  }
+
+  Future<Map<String, dynamic>> encryptToDeviceMessage(
+      List<DeviceKeys> deviceKeys,
+      String type,
+      Map<String, dynamic> payload) async {
+    return await olmManager.encryptToDeviceMessage(deviceKeys, type, payload);
+  }
+
+  void dispose() {
+    keyManager.dispose();
+    olmManager.dispose();
+    keyVerificationManager.dispose();
+  }
+}
+
+abstract class DecryptError {
+  static const String NOT_ENABLED = 'Encryption is not enabled in your client.';
+  static const String UNKNOWN_ALGORITHM = 'Unknown encryption algorithm.';
+  static const String UNKNOWN_SESSION =
+      'The sender has not sent us the session key.';
+  static const String CHANNEL_CORRUPTED =
+      'The secure channel with the sender was corrupted.';
+}

lib/encryption/key_manager.dart

@@ -0,0 +1,517 @@
+/*
+ *   Famedly Matrix SDK
+ *   Copyright (C) 2019, 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+import 'dart:convert';
+
+import 'package:pedantic/pedantic.dart';
+import 'package:famedlysdk/famedlysdk.dart';
+import 'package:famedlysdk/matrix_api.dart';
+import 'package:olm/olm.dart' as olm;
+
+import './encryption.dart';
+import './utils/session_key.dart';
+import './utils/outbound_group_session.dart';
+
+class KeyManager {
+  final Encryption encryption;
+  Client get client => encryption.client;
+  final outgoingShareRequests = <String, KeyManagerKeyShareRequest>{};
+  final incomingShareRequests = <String, KeyManagerKeyShareRequest>{};
+  final _inboundGroupSessions = <String, Map<String, SessionKey>>{};
+  final _outboundGroupSessions = <String, OutboundGroupSession>{};
+  final Set<String> _loadedOutboundGroupSessions = <String>{};
+  final Set<String> _requestedSessionIds = <String>{};
+
+  KeyManager(this.encryption);
+
+  /// clear all cached inbound group sessions. useful for testing
+  void clearInboundGroupSessions() {
+    _inboundGroupSessions.clear();
+  }
+
+  void setInboundGroupSession(String roomId, String sessionId, String senderKey,
+      Map<String, dynamic> content,
+      {bool forwarded = false}) {
+    final oldSession =
+        getInboundGroupSession(roomId, sessionId, senderKey, otherRooms: false);
+    if (oldSession != null) {
+      return;
+    }
+    if (content['algorithm'] != 'm.megolm.v1.aes-sha2') {
+      return;
+    }
+    olm.InboundGroupSession inboundGroupSession;
+    try {
+      inboundGroupSession = olm.InboundGroupSession();
+      if (forwarded) {
+        inboundGroupSession.import_session(content['session_key']);
+      } else {
+        inboundGroupSession.create(content['session_key']);
+      }
+    } catch (e) {
+      inboundGroupSession.free();
+      print(
+          '[LibOlm] Could not create new InboundGroupSession: ' + e.toString());
+      return;
+    }
+    if (!_inboundGroupSessions.containsKey(roomId)) {
+      _inboundGroupSessions[roomId] = <String, SessionKey>{};
+    }
+    _inboundGroupSessions[roomId][sessionId] = SessionKey(
+      content: content,
+      inboundGroupSession: inboundGroupSession,
+      indexes: {},
+      key: client.userID,
+    );
+    client.database?.storeInboundGroupSession(
+      client.id,
+      roomId,
+      sessionId,
+      inboundGroupSession.pickle(client.userID),
+      json.encode(content),
+      json.encode({}),
+    );
+    // TODO: somehow try to decrypt last message again
+    final room = client.getRoomById(roomId);
+    if (room != null) {
+      room.onSessionKeyReceived.add(sessionId);
+    }
+  }
+
+  SessionKey getInboundGroupSession(
+      String roomId, String sessionId, String senderKey,
+      {bool otherRooms = true}) {
+    if (_inboundGroupSessions.containsKey(roomId) &&
+        _inboundGroupSessions[roomId].containsKey(sessionId)) {
+      return _inboundGroupSessions[roomId][sessionId];
+    }
+    if (!otherRooms) {
+      return null;
+    }
+    // search if this session id is *somehow* found in another room
+    for (final val in _inboundGroupSessions.values) {
+      if (val.containsKey(sessionId)) {
+        return val[sessionId];
+      }
+    }
+    return null;
+  }
+
+  /// Loads an inbound group session
+  Future<SessionKey> loadInboundGroupSession(
+      String roomId, String sessionId, String senderKey) async {
+    if (roomId == null || sessionId == null || senderKey == null) {
+      return null;
+    }
+    if (_inboundGroupSessions.containsKey(roomId) &&
+        _inboundGroupSessions[roomId].containsKey(sessionId)) {
+      return _inboundGroupSessions[roomId][sessionId]; // nothing to do
+    }
+    final session = await client.database
+        ?.getDbInboundGroupSession(client.id, roomId, sessionId);
+    if (session == null) {
+      final room = client.getRoomById(roomId);
+      final requestIdent = '$roomId|$sessionId|$senderKey';
+      if (client.enableE2eeRecovery &&
+          room != null &&
+          !_requestedSessionIds.contains(requestIdent)) {
+        // do e2ee recovery
+        _requestedSessionIds.add(requestIdent);
+        unawaited(request(room, sessionId, senderKey));
+      }
+      return null;
+    }
+    if (!_inboundGroupSessions.containsKey(roomId)) {
+      _inboundGroupSessions[roomId] = <String, SessionKey>{};
+    }
+    final sess = SessionKey.fromDb(session, client.userID);
+    if (!sess.isValid) {
+      return null;
+    }
+    _inboundGroupSessions[roomId][sessionId] = sess;
+    return sess;
+  }
+
+  /// clear all cached inbound group sessions. useful for testing
+  void clearOutboundGroupSessions() {
+    _outboundGroupSessions.clear();
+  }
+
+  /// Clears the existing outboundGroupSession but first checks if the participating
+  /// devices have been changed. Returns false if the session has not been cleared because
+  /// it wasn't necessary.
+  Future<bool> clearOutboundGroupSession(String roomId,
+      {bool wipe = false}) async {
+    final room = client.getRoomById(roomId);
+    final sess = getOutboundGroupSession(roomId);
+    if (room == null || sess == null) {
+      return true;
+    }
+    if (!wipe) {
+      // first check if the devices in the room changed
+      final deviceKeys = await room.getUserDeviceKeys();
+      deviceKeys.removeWhere((k) => k.blocked);
+      final deviceKeyIds = deviceKeys.map((k) => k.deviceId).toList();
+      deviceKeyIds.sort();
+      if (deviceKeyIds.toString() != sess.devices.toString()) {
+        wipe = true;
+      }
+      // next check if it needs to be rotated
+      final encryptionContent = room.getState(EventTypes.Encryption)?.content;
+      final maxMessages = encryptionContent != null &&
+              encryptionContent['rotation_period_msgs'] is int
+          ? encryptionContent['rotation_period_msgs']
+          : 100;
+      final maxAge = encryptionContent != null &&
+              encryptionContent['rotation_period_ms'] is int
+          ? encryptionContent['rotation_period_ms']
+          : 604800000; // default of one week
+      if (sess.sentMessages >= maxMessages ||
+          sess.creationTime
+              .add(Duration(milliseconds: maxAge))
+              .isBefore(DateTime.now())) {
+        wipe = true;
+      }
+      if (!wipe) {
+        return false;
+      }
+    }
+    sess.dispose();
+    _outboundGroupSessions.remove(roomId);
+    await client.database?.removeOutboundGroupSession(client.id, roomId);
+    return true;
+  }
+
+  Future<void> storeOutboundGroupSession(
+      String roomId, OutboundGroupSession sess) async {
+    if (sess == null) {
+      return;
+    }
+    await client.database?.storeOutboundGroupSession(
+        client.id,
+        roomId,
+        sess.outboundGroupSession.pickle(client.userID),
+        json.encode(sess.devices),
+        sess.creationTime,
+        sess.sentMessages);
+  }
+
+  Future<OutboundGroupSession> createOutboundGroupSession(String roomId) async {
+    await clearOutboundGroupSession(roomId, wipe: true);
+    final room = client.getRoomById(roomId);
+    if (room == null) {
+      return null;
+    }
+    final deviceKeys = await room.getUserDeviceKeys();
+    deviceKeys.removeWhere((k) => k.blocked);
+    final deviceKeyIds = deviceKeys.map((k) => k.deviceId).toList();
+    deviceKeyIds.sort();
+    final outboundGroupSession = olm.OutboundGroupSession();
+    try {
+      outboundGroupSession.create();
+    } catch (e) {
+      outboundGroupSession.free();
+      print('[LibOlm] Unable to create new outboundGroupSession: ' +
+          e.toString());
+      return null;
+    }
+    final rawSession = <String, dynamic>{
+      'algorithm': 'm.megolm.v1.aes-sha2',
+      'room_id': room.id,
+      'session_id': outboundGroupSession.session_id(),
+      'session_key': outboundGroupSession.session_key(),
+    };
+    setInboundGroupSession(
+        roomId, rawSession['session_id'], encryption.identityKey, rawSession);
+    final sess = OutboundGroupSession(
+      devices: deviceKeyIds,
+      creationTime: DateTime.now(),
+      outboundGroupSession: outboundGroupSession,
+      sentMessages: 0,
+      key: client.userID,
+    );
+    try {
+      await client.sendToDevice(deviceKeys, 'm.room_key', rawSession);
+      await storeOutboundGroupSession(roomId, sess);
+      _outboundGroupSessions[roomId] = sess;
+    } catch (e, s) {
+      print(
+          '[LibOlm] Unable to send the session key to the participating devices: ' +
+              e.toString());
+      print(s);
+      sess.dispose();
+      return null;
+    }
+    return sess;
+  }
+
+  OutboundGroupSession getOutboundGroupSession(String roomId) {
+    return _outboundGroupSessions[roomId];
+  }
+
+  Future<void> loadOutboundGroupSession(String roomId) async {
+    if (_loadedOutboundGroupSessions.contains(roomId) ||
+        _outboundGroupSessions.containsKey(roomId) ||
+        client.database == null) {
+      return; // nothing to do
+    }
+    _loadedOutboundGroupSessions.add(roomId);
+    final session =
+        await client.database.getDbOutboundGroupSession(client.id, roomId);
+    if (session == null) {
+      return;
+    }
+    final sess = OutboundGroupSession.fromDb(session, client.userID);
+    if (!sess.isValid) {
+      return;
+    }
+    _outboundGroupSessions[roomId] = sess;
+  }
+
+  /// Request a certain key from another device
+  Future<void> request(Room room, String sessionId, String senderKey) async {
+    // while we just send the to-device event to '*', we still need to save the
+    // devices themself to know where to send the cancel to after receiving a reply
+    final devices = await room.getUserDeviceKeys();
+    final requestId = client.generateUniqueTransactionId();
+    final request = KeyManagerKeyShareRequest(
+      requestId: requestId,
+      devices: devices,
+      room: room,
+      sessionId: sessionId,
+      senderKey: senderKey,
+    );
+    await client.sendToDevice(
+        [],
+        'm.room_key_request',
+        {
+          'action': 'request',
+          'body': {
+            'algorithm': 'm.megolm.v1.aes-sha2',
+            'room_id': room.id,
+            'sender_key': senderKey,
+            'session_id': sessionId,
+          },
+          'request_id': requestId,
+          'requesting_device_id': client.deviceID,
+        },
+        encrypted: false,
+        toUsers: await room.requestParticipants());
+    outgoingShareRequests[request.requestId] = request;
+  }
+
+  /// Handle an incoming to_device event that is related to key sharing
+  Future<void> handleToDeviceEvent(ToDeviceEvent event) async {
+    if (event.type == 'm.room_key_request') {
+      if (!event.content.containsKey('request_id')) {
+        return; // invalid event
+      }
+      if (event.content['action'] == 'request') {
+        // we are *receiving* a request
+        if (!event.content.containsKey('body')) {
+          return; // no body
+        }
+        if (!client.userDeviceKeys.containsKey(event.sender) ||
+            !client.userDeviceKeys[event.sender].deviceKeys
+                .containsKey(event.content['requesting_device_id'])) {
+          return; // device not found
+        }
+        final device = client.userDeviceKeys[event.sender]
+            .deviceKeys[event.content['requesting_device_id']];
+        if (device.userId == client.userID &&
+            device.deviceId == client.deviceID) {
+          return; // ignore requests by ourself
+        }
+        final room = client.getRoomById(event.content['body']['room_id']);
+        if (room == null) {
+          return; // unknown room
+        }
+        final sessionId = event.content['body']['session_id'];
+        final senderKey = event.content['body']['sender_key'];
+        // okay, let's see if we have this session at all
+        if ((await loadInboundGroupSession(room.id, sessionId, senderKey)) ==
+            null) {
+          return; // we don't have this session anyways
+        }
+        final request = KeyManagerKeyShareRequest(
+          requestId: event.content['request_id'],
+          devices: [device],
+          room: room,
+          sessionId: sessionId,
+          senderKey: senderKey,
+        );
+        if (incomingShareRequests.containsKey(request.requestId)) {
+          return; // we don't want to process one and the same request multiple times
+        }
+        incomingShareRequests[request.requestId] = request;
+        final roomKeyRequest =
+            RoomKeyRequest.fromToDeviceEvent(event, this, request);
+        if (device.userId == client.userID &&
+            device.verified &&
+            !device.blocked) {
+          // alright, we can forward the key
+          await roomKeyRequest.forwardKey();
+        } else {
+          client.onRoomKeyRequest
+              .add(roomKeyRequest); // let the client handle this
+        }
+      } else if (event.content['action'] == 'request_cancellation') {
+        // we got told to cancel an incoming request
+        if (!incomingShareRequests.containsKey(event.content['request_id'])) {
+          return; // we don't know this request anyways
+        }
+        // alright, let's just cancel this request
+        final request = incomingShareRequests[event.content['request_id']];
+        request.canceled = true;
+        incomingShareRequests.remove(request.requestId);
+      }
+    } else if (event.type == 'm.forwarded_room_key') {
+      // we *received* an incoming key request
+      if (event.encryptedContent == null) {
+        return; // event wasn't encrypted, this is a security risk
+      }
+      final request = outgoingShareRequests.values.firstWhere(
+          (r) =>
+              r.room.id == event.content['room_id'] &&
+              r.sessionId == event.content['session_id'] &&
+              r.senderKey == event.content['sender_key'],
+          orElse: () => null);
+      if (request == null || request.canceled) {
+        return; // no associated request found or it got canceled
+      }
+      final device = request.devices.firstWhere(
+          (d) =>
+              d.userId == event.sender &&
+              d.curve25519Key == event.encryptedContent['sender_key'],
+          orElse: () => null);
+      if (device == null) {
+        return; // someone we didn't send our request to replied....better ignore this
+      }
+      // TODO: verify that the keys work to decrypt a message
+      // alright, all checks out, let's go ahead and store this session
+      setInboundGroupSession(
+          request.room.id, request.sessionId, request.senderKey, event.content,
+          forwarded: true);
+      request.devices.removeWhere(
+          (k) => k.userId == device.userId && k.deviceId == device.deviceId);
+      outgoingShareRequests.remove(request.requestId);
+      // send cancel to all other devices
+      if (request.devices.isEmpty) {
+        return; // no need to send any cancellation
+      }
+      await client.sendToDevice(
+          request.devices,
+          'm.room_key_request',
+          {
+            'action': 'request_cancellation',
+            'request_id': request.requestId,
+            'requesting_device_id': client.deviceID,
+          },
+          encrypted: false);
+    } else if (event.type == 'm.room_key') {
+      if (event.encryptedContent == null) {
+        return; // the event wasn't encrypted, this is a security risk;
+      }
+      final String roomId = event.content['room_id'];
+      final String sessionId = event.content['session_id'];
+      if (client.userDeviceKeys.containsKey(event.sender) &&
+          client.userDeviceKeys[event.sender].deviceKeys
+              .containsKey(event.content['requesting_device_id'])) {
+        event.content['sender_claimed_ed25519_key'] = client
+            .userDeviceKeys[event.sender]
+            .deviceKeys[event.content['requesting_device_id']]
+            .ed25519Key;
+      }
+      setInboundGroupSession(roomId, sessionId,
+          event.encryptedContent['sender_key'], event.content,
+          forwarded: false);
+    }
+  }
+
+  void dispose() {
+    for (final sess in _outboundGroupSessions.values) {
+      sess.dispose();
+    }
+    for (final entries in _inboundGroupSessions.values) {
+      for (final sess in entries.values) {
+        sess.dispose();
+      }
+    }
+  }
+}
+
+class KeyManagerKeyShareRequest {
+  final String requestId;
+  final List<DeviceKeys> devices;
+  final Room room;
+  final String sessionId;
+  final String senderKey;
+  bool canceled;
+
+  KeyManagerKeyShareRequest(
+      {this.requestId,
+      this.devices,
+      this.room,
+      this.sessionId,
+      this.senderKey,
+      this.canceled = false});
+}
+
+class RoomKeyRequest extends ToDeviceEvent {
+  KeyManager keyManager;
+  KeyManagerKeyShareRequest request;
+  RoomKeyRequest.fromToDeviceEvent(ToDeviceEvent toDeviceEvent,
+      KeyManager keyManager, KeyManagerKeyShareRequest request) {
+    this.keyManager = keyManager;
+    this.request = request;
+    sender = toDeviceEvent.sender;
+    content = toDeviceEvent.content;
+    type = toDeviceEvent.type;
+  }
+
+  Room get room => request.room;
+
+  DeviceKeys get requestingDevice => request.devices.first;
+
+  Future<void> forwardKey() async {
+    if (request.canceled) {
+      keyManager.incomingShareRequests.remove(request.requestId);
+      return; // request is canceled, don't send anything
+    }
+    var room = this.room;
+    final session = await keyManager.loadInboundGroupSession(
+        room.id, request.sessionId, request.senderKey);
+    var forwardedKeys = <dynamic>[keyManager.encryption.identityKey];
+    for (final key in session.forwardingCurve25519KeyChain) {
+      forwardedKeys.add(key);
+    }
+    await requestingDevice.setVerified(true, keyManager.client);
+    var message = session.content;
+    message['forwarding_curve25519_key_chain'] = forwardedKeys;
+
+    message['session_key'] = session.inboundGroupSession
+        .export_session(session.inboundGroupSession.first_known_index());
+    // send the actual reply of the key back to the requester
+    await keyManager.client.sendToDevice(
+      [requestingDevice],
+      'm.forwarded_room_key',
+      message,
+    );
+    keyManager.incomingShareRequests.remove(request.requestId);
+  }
+}

lib/encryption/key_verification_manager.dart

@@ -0,0 +1,83 @@
+/*
+ *   Famedly Matrix SDK
+ *   Copyright (C) 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+import 'package:famedlysdk/famedlysdk.dart';
+import './encryption.dart';
+import './utils/key_verification.dart';
+
+class KeyVerificationManager {
+  final Encryption encryption;
+  Client get client => encryption.client;
+
+  KeyVerificationManager(this.encryption);
+
+  final Map<String, KeyVerification> _requests = {};
+
+  Future<void> cleanup() async {
+    for (final entry in _requests.entries) {
+      var dispose = entry.value.canceled ||
+          entry.value.state == KeyVerificationState.done ||
+          entry.value.state == KeyVerificationState.error;
+      if (!dispose) {
+        dispose = !(await entry.value.verifyActivity());
+      }
+      if (dispose) {
+        entry.value.dispose();
+        _requests.remove(entry.key);
+      }
+    }
+  }
+
+  void addRequest(KeyVerification request) {
+    if (request.transactionId == null) {
+      return;
+    }
+    _requests[request.transactionId] = request;
+  }
+
+  Future<void> handleToDeviceEvent(ToDeviceEvent event) async {
+    if (!event.type.startsWith('m.key.verification')) {
+      return;
+    }
+    // we have key verification going on!
+    final transactionId = KeyVerification.getTransactionId(event.content);
+    if (transactionId == null) {
+      return; // TODO: send cancel with unknown transaction id
+    }
+    if (_requests.containsKey(transactionId)) {
+      await _requests[transactionId].handlePayload(event.type, event.content);
+    } else {
+      final newKeyRequest =
+          KeyVerification(encryption: encryption, userId: event.sender);
+      await newKeyRequest.handlePayload(event.type, event.content);
+      if (newKeyRequest.state != KeyVerificationState.askAccept) {
+        // okay, something went wrong (unknown transaction id?), just dispose it
+        newKeyRequest.dispose();
+      } else {
+        _requests[transactionId] = newKeyRequest;
+        client.onKeyVerificationRequest.add(newKeyRequest);
+      }
+    }
+  }
+
+  void dispose() {
+    for (final req in _requests.values) {
+      req.dispose();
+    }
+  }
+}

lib/encryption/olm_manager.dart

@@ -0,0 +1,433 @@
+/*
+ *   Famedly Matrix SDK
+ *   Copyright (C) 2019, 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+import 'dart:convert';
+
+import 'package:canonical_json/canonical_json.dart';
+import 'package:famedlysdk/famedlysdk.dart';
+import 'package:famedlysdk/matrix_api.dart';
+import 'package:olm/olm.dart' as olm;
+import './encryption.dart';
+
+class OlmManager {
+  final Encryption encryption;
+  Client get client => encryption.client;
+  olm.Account _olmAccount;
+
+  /// Returns the base64 encoded keys to store them in a store.
+  /// This String should **never** leave the device!
+  String get pickledOlmAccount =>
+      enabled ? _olmAccount.pickle(client.userID) : null;
+  String get fingerprintKey =>
+      enabled ? json.decode(_olmAccount.identity_keys())['ed25519'] : null;
+  String get identityKey =>
+      enabled ? json.decode(_olmAccount.identity_keys())['curve25519'] : null;
+
+  bool get enabled => _olmAccount != null;
+
+  OlmManager(this.encryption);
+
+  /// A map from Curve25519 identity keys to existing olm sessions.
+  Map<String, List<olm.Session>> get olmSessions => _olmSessions;
+  final Map<String, List<olm.Session>> _olmSessions = {};
+
+  Future<void> init(String olmAccount) async {
+    if (olmAccount == null) {
+      try {
+        await olm.init();
+        _olmAccount = olm.Account();
+        _olmAccount.create();
+        if (await uploadKeys(uploadDeviceKeys: true) == false) {
+          throw ('Upload key failed');
+        }
+      } catch (_) {
+        _olmAccount?.free();
+        _olmAccount = null;
+      }
+    } else {
+      try {
+        await olm.init();
+        _olmAccount = olm.Account();
+        _olmAccount.unpickle(client.userID, olmAccount);
+      } catch (_) {
+        _olmAccount?.free();
+        _olmAccount = null;
+      }
+    }
+  }
+
+  /// Adds a signature to this json from this olm account.
+  Map<String, dynamic> signJson(Map<String, dynamic> payload) {
+    if (!enabled) throw ('Encryption is disabled');
+    final Map<String, dynamic> unsigned = payload['unsigned'];
+    final Map<String, dynamic> signatures = payload['signatures'];
+    payload.remove('unsigned');
+    payload.remove('signatures');
+    final canonical = canonicalJson.encode(payload);
+    final signature = _olmAccount.sign(String.fromCharCodes(canonical));
+    if (signatures != null) {
+      payload['signatures'] = signatures;
+    } else {
+      payload['signatures'] = <String, dynamic>{};
+    }
+    if (!payload['signatures'].containsKey(client.userID)) {
+      payload['signatures'][client.userID] = <String, dynamic>{};
+    }
+    payload['signatures'][client.userID]['ed25519:${client.deviceID}'] =
+        signature;
+    if (unsigned != null) {
+      payload['unsigned'] = unsigned;
+    }
+    return payload;
+  }
+
+  /// Checks the signature of a signed json object.
+  bool checkJsonSignature(String key, Map<String, dynamic> signedJson,
+      String userId, String deviceId) {
+    if (!enabled) throw ('Encryption is disabled');
+    final Map<String, dynamic> signatures = signedJson['signatures'];
+    if (signatures == null || !signatures.containsKey(userId)) return false;
+    signedJson.remove('unsigned');
+    signedJson.remove('signatures');
+    if (!signatures[userId].containsKey('ed25519:$deviceId')) return false;
+    final String signature = signatures[userId]['ed25519:$deviceId'];
+    final canonical = canonicalJson.encode(signedJson);
+    final message = String.fromCharCodes(canonical);
+    var isValid = false;
+    final olmutil = olm.Utility();
+    try {
+      olmutil.ed25519_verify(key, message, signature);
+      isValid = true;
+    } catch (e) {
+      isValid = false;
+      print('[LibOlm] Signature check failed: ' + e.toString());
+    } finally {
+      olmutil.free();
+    }
+    return isValid;
+  }
+
+  /// Generates new one time keys, signs everything and upload it to the server.
+  Future<bool> uploadKeys(
+      {bool uploadDeviceKeys = false, int oldKeyCount = 0}) async {
+    if (!enabled) {
+      return true;
+    }
+
+    // generate one-time keys
+    // we generate 2/3rds of max, so that other keys people may still have can
+    // still be used
+    final oneTimeKeysCount =
+        (_olmAccount.max_number_of_one_time_keys() * 2 / 3).floor() -
+            oldKeyCount;
+    _olmAccount.generate_one_time_keys(oneTimeKeysCount);
+    final Map<String, dynamic> oneTimeKeys =
+        json.decode(_olmAccount.one_time_keys());
+
+    // now sign all the one-time keys
+    final signedOneTimeKeys = <String, dynamic>{};
+    for (final entry in oneTimeKeys['curve25519'].entries) {
+      final key = entry.key;
+      final value = entry.value;
+      signedOneTimeKeys['signed_curve25519:$key'] = <String, dynamic>{};
+      signedOneTimeKeys['signed_curve25519:$key'] = signJson({
+        'key': value,
+      });
+    }
+
+    // and now generate the payload to upload
+    final keysContent = <String, dynamic>{
+      if (uploadDeviceKeys)
+        'device_keys': {
+          'user_id': client.userID,
+          'device_id': client.deviceID,
+          'algorithms': [
+            'm.olm.v1.curve25519-aes-sha2',
+            'm.megolm.v1.aes-sha2'
+          ],
+          'keys': <String, dynamic>{},
+        },
+    };
+    if (uploadDeviceKeys) {
+      final Map<String, dynamic> keys =
+          json.decode(_olmAccount.identity_keys());
+      for (final entry in keys.entries) {
+        final algorithm = entry.key;
+        final value = entry.value;
+        keysContent['device_keys']['keys']['$algorithm:${client.deviceID}'] =
+            value;
+      }
+      keysContent['device_keys'] =
+          signJson(keysContent['device_keys'] as Map<String, dynamic>);
+    }
+
+    final response = await client.api.uploadDeviceKeys(
+      deviceKeys: uploadDeviceKeys
+          ? MatrixDeviceKeys.fromJson(keysContent['device_keys'])
+          : null,
+      oneTimeKeys: signedOneTimeKeys,
+    );
+    _olmAccount.mark_keys_as_published();
+    await client.database?.updateClientKeys(pickledOlmAccount, client.id);
+    return response['signed_curve25519'] == oneTimeKeysCount;
+  }
+
+  void handleDeviceOneTimeKeysCount(Map<String, int> countJson) {
+    if (!enabled) {
+      return;
+    }
+    // Check if there are at least half of max_number_of_one_time_keys left on the server
+    // and generate and upload more if not.
+    if (countJson.containsKey('signed_curve25519') &&
+        countJson['signed_curve25519'] <
+            (_olmAccount.max_number_of_one_time_keys() / 2)) {
+      uploadKeys(oldKeyCount: countJson['signed_curve25519']);
+    }
+  }
+
+  void storeOlmSession(String curve25519IdentityKey, olm.Session session) {
+    if (client.database == null) {
+      return;
+    }
+    if (!_olmSessions.containsKey(curve25519IdentityKey)) {
+      _olmSessions[curve25519IdentityKey] = [];
+    }
+    final ix = _olmSessions[curve25519IdentityKey]
+        .indexWhere((s) => s.session_id() == session.session_id());
+    if (ix == -1) {
+      // add a new session
+      _olmSessions[curve25519IdentityKey].add(session);
+    } else {
+      // update an existing session
+      _olmSessions[curve25519IdentityKey][ix] = session;
+    }
+    final pickle = session.pickle(client.userID);
+    client.database.storeOlmSession(
+        client.id, curve25519IdentityKey, session.session_id(), pickle);
+  }
+
+  ToDeviceEvent _decryptToDeviceEvent(ToDeviceEvent event) {
+    if (event.type != EventTypes.Encrypted) {
+      return event;
+    }
+    if (event.content['algorithm'] != 'm.olm.v1.curve25519-aes-sha2') {
+      throw ('Unknown algorithm: ${event.content}');
+    }
+    if (!event.content['ciphertext'].containsKey(identityKey)) {
+      throw ("The message isn't sent for this device");
+    }
+    String plaintext;
+    final String senderKey = event.content['sender_key'];
+    final String body = event.content['ciphertext'][identityKey]['body'];
+    final int type = event.content['ciphertext'][identityKey]['type'];
+    if (type != 0 && type != 1) {
+      throw ('Unknown message type');
+    }
+    var existingSessions = olmSessions[senderKey];
+    if (existingSessions != null) {
+      for (var session in existingSessions) {
+        if (type == 0 && session.matches_inbound(body) == true) {
+          plaintext = session.decrypt(type, body);
+          storeOlmSession(senderKey, session);
+          break;
+        } else if (type == 1) {
+          try {
+            plaintext = session.decrypt(type, body);
+            storeOlmSession(senderKey, session);
+            break;
+          } catch (_) {
+            plaintext = null;
+          }
+        }
+      }
+    }
+    if (plaintext == null && type != 0) {
+      return event;
+    }
+
+    if (plaintext == null) {
+      var newSession = olm.Session();
+      try {
+        newSession.create_inbound_from(_olmAccount, senderKey, body);
+        _olmAccount.remove_one_time_keys(newSession);
+        client.database?.updateClientKeys(pickledOlmAccount, client.id);
+        plaintext = newSession.decrypt(type, body);
+        storeOlmSession(senderKey, newSession);
+      } catch (_) {
+        newSession?.free();
+        rethrow;
+      }
+    }
+    final Map<String, dynamic> plainContent = json.decode(plaintext);
+    if (plainContent.containsKey('sender') &&
+        plainContent['sender'] != event.sender) {
+      throw ("Message was decrypted but sender doesn't match");
+    }
+    if (plainContent.containsKey('recipient') &&
+        plainContent['recipient'] != client.userID) {
+      throw ("Message was decrypted but recipient doesn't match");
+    }
+    if (plainContent['recipient_keys'] is Map &&
+        plainContent['recipient_keys']['ed25519'] is String &&
+        plainContent['recipient_keys']['ed25519'] != fingerprintKey) {
+      throw ("Message was decrypted but own fingerprint Key doesn't match");
+    }
+    return ToDeviceEvent(
+      content: plainContent['content'],
+      encryptedContent: event.content,
+      type: plainContent['type'],
+      sender: event.sender,
+    );
+  }
+
+  Future<ToDeviceEvent> decryptToDeviceEvent(ToDeviceEvent event) async {
+    if (event.type != EventTypes.Encrypted) {
+      return event;
+    }
+    final senderKey = event.content['sender_key'];
+    final loadFromDb = () async {
+      if (client.database == null) {
+        return false;
+      }
+      final sessions = await client.database
+          .getSingleOlmSessions(client.id, senderKey, client.userID);
+      if (sessions.isEmpty) {
+        return false; // okay, can't do anything
+      }
+      _olmSessions[senderKey] = sessions;
+      return true;
+    };
+    if (!_olmSessions.containsKey(senderKey)) {
+      await loadFromDb();
+    }
+    event = _decryptToDeviceEvent(event);
+    if (event.type != EventTypes.Encrypted || !(await loadFromDb())) {
+      return event;
+    }
+    // retry to decrypt!
+    return _decryptToDeviceEvent(event);
+  }
+
+  Future<void> startOutgoingOlmSessions(List<DeviceKeys> deviceKeys) async {
+    var requestingKeysFrom = <String, Map<String, String>>{};
+    for (var device in deviceKeys) {
+      if (requestingKeysFrom[device.userId] == null) {
+        requestingKeysFrom[device.userId] = {};
+      }
+      requestingKeysFrom[device.userId][device.deviceId] = 'signed_curve25519';
+    }
+
+    final response =
+        await client.api.requestOneTimeKeys(requestingKeysFrom, timeout: 10000);
+
+    for (var userKeysEntry in response.oneTimeKeys.entries) {
+      final userId = userKeysEntry.key;
+      for (var deviceKeysEntry in userKeysEntry.value.entries) {
+        final deviceId = deviceKeysEntry.key;
+        final fingerprintKey =
+            client.userDeviceKeys[userId].deviceKeys[deviceId].ed25519Key;
+        final identityKey =
+            client.userDeviceKeys[userId].deviceKeys[deviceId].curve25519Key;
+        for (Map<String, dynamic> deviceKey in deviceKeysEntry.value.values) {
+          if (!checkJsonSignature(
+              fingerprintKey, deviceKey, userId, deviceId)) {
+            continue;
+          }
+          try {
+            var session = olm.Session();
+            session.create_outbound(_olmAccount, identityKey, deviceKey['key']);
+            await storeOlmSession(identityKey, session);
+          } catch (e) {
+            print('[LibOlm] Could not create new outbound olm session: ' +
+                e.toString());
+          }
+        }
+      }
+    }
+  }
+
+  Future<Map<String, dynamic>> encryptToDeviceMessagePayload(
+      DeviceKeys device, String type, Map<String, dynamic> payload) async {
+    var sess = olmSessions[device.curve25519Key];
+    if (sess == null || sess.isEmpty) {
+      final sessions = await client.database
+          .getSingleOlmSessions(client.id, device.curve25519Key, client.userID);
+      if (sessions.isEmpty) {
+        throw ('No olm session found');
+      }
+      sess = _olmSessions[device.curve25519Key] = sessions;
+    }
+    sess.sort((a, b) => a.session_id().compareTo(b.session_id()));
+    final fullPayload = {
+      'type': type,
+      'content': payload,
+      'sender': client.userID,
+      'keys': {'ed25519': fingerprintKey},
+      'recipient': device.userId,
+      'recipient_keys': {'ed25519': device.ed25519Key},
+    };
+    final encryptResult = sess.first.encrypt(json.encode(fullPayload));
+    storeOlmSession(device.curve25519Key, sess.first);
+    final encryptedBody = <String, dynamic>{
+      'algorithm': 'm.olm.v1.curve25519-aes-sha2',
+      'sender_key': identityKey,
+      'ciphertext': <String, dynamic>{},
+    };
+    encryptedBody['ciphertext'][device.curve25519Key] = {
+      'type': encryptResult.type,
+      'body': encryptResult.body,
+    };
+    return encryptedBody;
+  }
+
+  Future<Map<String, dynamic>> encryptToDeviceMessage(
+      List<DeviceKeys> deviceKeys,
+      String type,
+      Map<String, dynamic> payload) async {
+    var data = <String, Map<String, Map<String, dynamic>>>{};
+    final deviceKeysWithoutSession = List<DeviceKeys>.from(deviceKeys);
+    deviceKeysWithoutSession.removeWhere((DeviceKeys deviceKeys) =>
+        olmSessions.containsKey(deviceKeys.curve25519Key));
+    if (deviceKeysWithoutSession.isNotEmpty) {
+      await startOutgoingOlmSessions(deviceKeysWithoutSession);
+    }
+    for (final device in deviceKeys) {
+      if (!data.containsKey(device.userId)) {
+        data[device.userId] = {};
+      }
+      try {
+        data[device.userId][device.deviceId] =
+            await encryptToDeviceMessagePayload(device, type, payload);
+      } catch (e) {
+        print('[LibOlm] Error encrypting to-device event: ' + e.toString());
+        continue;
+      }
+    }
+    return data;
+  }
+
+  void dispose() {
+    for (final sessions in olmSessions.values) {
+      for (final sess in sessions) {
+        sess.free();
+      }
+    }
+    _olmAccount?.free();
+    _olmAccount = null;
+  }
+}

lib/encryption/utils/key_verification.dart

@@ -1,11 +1,29 @@
+/*
+ *   Famedly Matrix SDK
+ *   Copyright (C) 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
 import 'dart:typed_data';
 import 'package:random_string/random_string.dart';
 import 'package:canonical_json/canonical_json.dart';
 import 'package:olm/olm.dart' as olm;
-import '../../matrix_api.dart';
+import 'package:famedlysdk/famedlysdk.dart';
-import 'device_keys_list.dart';
+import 'package:famedlysdk/matrix_api.dart';
-import '../client.dart';
+
-import '../room.dart';
+import '../encryption.dart';
 
 /*
     +-------------+                    +-----------+
@@ -53,6 +71,9 @@ enum KeyVerificationState {
 }
 
 List<String> _intersect(List<String> a, List<dynamic> b) {
+  if (b == null || a == null) {
+    return [];
+  }
   final res = <String>[];
   for (final v in a) {
     if (b.contains(v)) {
@@ -94,7 +115,8 @@ _KeyVerificationMethod _makeVerificationMethod(
 
 class KeyVerification {
   String transactionId;
-  final Client client;
+  final Encryption encryption;
+  Client get client => encryption.client;
   final Room room;
   final String userId;
   void Function() onUpdate;
@@ -114,7 +136,11 @@ class KeyVerification {
   String canceledReason;
 
   KeyVerification(
-      {this.client, this.room, this.userId, String deviceId, this.onUpdate}) {
+      {this.encryption,
+      this.room,
+      this.userId,
+      String deviceId,
+      this.onUpdate}) {
     lastActivity = DateTime.now();
     _deviceId ??= deviceId;
   }
@@ -384,7 +410,7 @@ class KeyVerification {
       final newTransactionId = await room.sendEvent(payload, type: type);
       if (transactionId == null) {
         transactionId = newTransactionId;
-        client.addKeyVerificationRequest(this);
+        encryption.keyVerificationManager.addRequest(this);
       }
     } else {
       await client.sendToDevice(
@@ -404,10 +430,9 @@ class KeyVerification {
 
 abstract class _KeyVerificationMethod {
   KeyVerification request;
-  Client client;
+  Encryption get encryption => request.encryption;
-  _KeyVerificationMethod({this.request}) {
+  Client get client => request.client;
-    client = request.client;
+  _KeyVerificationMethod({this.request});
-  }
 
   Future<void> handlePayload(String type, Map<String, dynamic> payload);
   bool validateStart(Map<String, dynamic> payload) {
@@ -662,7 +687,7 @@ class _KeyVerificationMethodSas extends _KeyVerificationMethod {
     // we would also add the cross signing key here
     final deviceKeyId = 'ed25519:${client.deviceID}';
     mac[deviceKeyId] =
-        _calculateMac(client.fingerprintKey, baseInfo + deviceKeyId);
+        _calculateMac(encryption.fingerprintKey, baseInfo + deviceKeyId);
     keyList.add(deviceKeyId);
 
     keyList.sort();

lib/encryption/utils/outbound_group_session.dart

@@ -0,0 +1,58 @@
+/*
+ *   Famedly Matrix SDK
+ *   Copyright (C) 2019, 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+import 'dart:convert';
+
+import 'package:olm/olm.dart' as olm;
+import '../../src/database/database.dart' show DbOutboundGroupSession;
+
+class OutboundGroupSession {
+  List<String> devices;
+  DateTime creationTime;
+  olm.OutboundGroupSession outboundGroupSession;
+  int sentMessages;
+  bool get isValid => outboundGroupSession != null;
+  final String key;
+
+  OutboundGroupSession(
+      {this.devices,
+      this.creationTime,
+      this.outboundGroupSession,
+      this.sentMessages,
+      this.key});
+
+  OutboundGroupSession.fromDb(DbOutboundGroupSession dbEntry, String key)
+      : key = key {
+    outboundGroupSession = olm.OutboundGroupSession();
+    try {
+      outboundGroupSession.unpickle(key, dbEntry.pickle);
+      devices = List<String>.from(json.decode(dbEntry.deviceIds));
+      creationTime = dbEntry.creationTime;
+      sentMessages = dbEntry.sentMessages;
+    } catch (e) {
+      dispose();
+      print(
+          '[LibOlm] Unable to unpickle outboundGroupSession: ' + e.toString());
+    }
+  }
+
+  void dispose() {
+    outboundGroupSession?.free();
+    outboundGroupSession = null;
+  }
+}

lib/encryption/utils/session_key.dart

@@ -0,0 +1,76 @@
+/*
+ *   Famedly Matrix SDK
+ *   Copyright (C) 2019, 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+import 'dart:convert';
+
+import 'package:olm/olm.dart' as olm;
+import 'package:famedlysdk/famedlysdk.dart';
+
+import '../../src/database/database.dart' show DbInboundGroupSession;
+
+class SessionKey {
+  Map<String, dynamic> content;
+  Map<String, int> indexes;
+  olm.InboundGroupSession inboundGroupSession;
+  final String key;
+  List<dynamic> get forwardingCurve25519KeyChain =>
+      content['forwarding_curve25519_key_chain'] ?? [];
+  String get senderClaimedEd25519Key =>
+      content['sender_claimed_ed25519_key'] ?? '';
+  String get senderKey => content['sender_key'] ?? '';
+  bool get isValid => inboundGroupSession != null;
+
+  SessionKey({this.content, this.inboundGroupSession, this.key, this.indexes});
+
+  SessionKey.fromDb(DbInboundGroupSession dbEntry, String key) : key = key {
+    final parsedContent = Event.getMapFromPayload(dbEntry.content);
+    final parsedIndexes = Event.getMapFromPayload(dbEntry.indexes);
+    content =
+        parsedContent != null ? Map<String, dynamic>.from(parsedContent) : null;
+    indexes = parsedIndexes != null
+        ? Map<String, int>.from(parsedIndexes)
+        : <String, int>{};
+    inboundGroupSession = olm.InboundGroupSession();
+    try {
+      inboundGroupSession.unpickle(key, dbEntry.pickle);
+    } catch (e) {
+      dispose();
+      print('[LibOlm] Unable to unpickle inboundGroupSession: ' + e.toString());
+    }
+  }
+
+  Map<String, dynamic> toJson() {
+    final data = <String, dynamic>{};
+    if (content != null) {
+      data['content'] = content;
+    }
+    if (indexes != null) {
+      data['indexes'] = indexes;
+    }
+    data['inboundGroupSession'] = inboundGroupSession.pickle(key);
+    return data;
+  }
+
+  void dispose() {
+    inboundGroupSession?.free();
+    inboundGroupSession = null;
+  }
+
+  @override
+  String toString() => json.encode(toJson());
+}

lib/famedlysdk.dart

@@ -22,7 +22,6 @@ export 'matrix_api.dart';
 export 'package:famedlysdk/src/utils/room_update.dart';
 export 'package:famedlysdk/src/utils/event_update.dart';
 export 'package:famedlysdk/src/utils/device_keys_list.dart';
-export 'package:famedlysdk/src/utils/key_verification.dart';
 export 'package:famedlysdk/src/utils/matrix_file.dart';
 export 'package:famedlysdk/src/utils/matrix_id_string_extension.dart';
 export 'package:famedlysdk/src/utils/uri_extension.dart';
@@ -32,7 +31,6 @@ export 'package:famedlysdk/src/utils/states_map.dart';
 export 'package:famedlysdk/src/utils/to_device_event.dart';
 export 'package:famedlysdk/src/client.dart';
 export 'package:famedlysdk/src/event.dart';
-export 'package:famedlysdk/src/key_manager.dart';
 export 'package:famedlysdk/src/room.dart';
 export 'package:famedlysdk/src/timeline.dart';
 export 'package:famedlysdk/src/user.dart';

lib/src/client.dart

@@ -20,16 +20,14 @@ import 'dart:async';
 import 'dart:convert';
 import 'dart:core';
 
-import 'package:canonical_json/canonical_json.dart';
 import 'package:famedlysdk/famedlysdk.dart';
 import 'package:famedlysdk/matrix_api.dart';
+import 'package:famedlysdk/encryption.dart';
 import 'package:famedlysdk/src/room.dart';
 import 'package:famedlysdk/src/utils/device_keys_list.dart';
 import 'package:famedlysdk/src/utils/matrix_file.dart';
-import 'package:famedlysdk/src/utils/session_key.dart';
 import 'package:famedlysdk/src/utils/to_device_event.dart';
 import 'package:http/http.dart' as http;
-import 'package:olm/olm.dart' as olm;
 import 'package:pedantic/pedantic.dart';
 
 import 'event.dart';
@@ -38,8 +36,6 @@ import 'utils/event_update.dart';
 import 'utils/room_update.dart';
 import 'user.dart';
 import 'database/database.dart' show Database;
-import 'utils/key_verification.dart';
-import 'key_manager.dart';
 
 typedef RoomSorter = int Function(Room a, Room b);
 
@@ -53,12 +49,13 @@ class Client {
   int get id => _id;
 
   Database database;
-  KeyManager keyManager;
 
   bool enableE2eeRecovery;
 
   MatrixApi api;
 
+  Encryption encryption;
+
   /// Create a client
   /// clientName = unique identifier of this client
   /// debug: Print debug output?
@@ -70,7 +67,6 @@ class Client {
       this.enableE2eeRecovery = false,
       http.Client httpClient}) {
     api = MatrixApi(debug: debug, httpClient: httpClient);
-    keyManager = KeyManager(this);
     onLoginStateChanged.stream.listen((loginState) {
       if (debug) {
         print('[LoginState]: ${loginState.toString()}');
@@ -106,18 +102,14 @@ class Client {
   List<Room> get rooms => _rooms;
   List<Room> _rooms = [];
 
-  olm.Account _olmAccount;
-
-  /// Returns the base64 encoded keys to store them in a store.
-  /// This String should **never** leave the device!
-  String get pickledOlmAccount =>
-      encryptionEnabled ? _olmAccount.pickle(userID) : null;
-
   /// Whether this client supports end-to-end encryption using olm.
-  bool get encryptionEnabled => _olmAccount != null;
+  bool get encryptionEnabled => encryption != null && encryption.enabled;
 
   /// Whether this client is able to encrypt and decrypt files.
-  bool get fileEncryptionEnabled => true;
+  bool get fileEncryptionEnabled => encryptionEnabled && true;
+
+  String get identityKey => encryption?.identityKey ?? '';
+  String get fingerprintKey => encryption?.fingerprintKey ?? '';
 
   /// Warning! This endpoint is for testing only!
   set rooms(List<Room> newList) {
@@ -529,8 +521,6 @@ class Client {
   final StreamController<KeyVerification> onKeyVerificationRequest =
       StreamController.broadcast();
 
-  final Map<String, KeyVerification> _keyVerificationRequests = {};
-
   /// Matrix synchronisation is done with https long polling. This needs a
   /// timeout which is usually 30 seconds.
   int syncTimeoutSec = 30;
@@ -604,31 +594,15 @@ class Client {
 
     if (api.accessToken == null || api.homeserver == null || _userID == null) {
       // we aren't logged in
+      encryption?.dispose();
+      encryption = null;
       onLoginStateChanged.add(LoginState.loggedOut);
       return;
     }
 
-    // Try to create a new olm account or restore a previous one.
+    encryption = Encryption(
-    if (olmAccount == null) {
+        debug: debug, client: this, enableE2eeRecovery: enableE2eeRecovery);
-      try {
+    await encryption.init(olmAccount);
-        await olm.init();
-        _olmAccount = olm.Account();
-        _olmAccount.create();
-        if (await _uploadKeys(uploadDeviceKeys: true) == false) {
-          throw ('Upload key failed');
-        }
-      } catch (_) {
-        _olmAccount = null;
-      }
-    } else {
-      try {
-        await olm.init();
-        _olmAccount = olm.Account();
-        _olmAccount.unpickle(userID, olmAccount);
-      } catch (_) {
-        _olmAccount = null;
-      }
-    }
 
     if (database != null) {
       if (id != null) {
@@ -639,7 +613,7 @@ class Client {
           _deviceID,
           _deviceName,
           prevBatch,
-          pickledOlmAccount,
+          encryption?.pickledOlmAccount,
           id,
         );
       } else {
@@ -651,11 +625,10 @@ class Client {
           _deviceID,
           _deviceName,
           prevBatch,
-          pickledOlmAccount,
+          encryption?.pickledOlmAccount,
         );
       }
       _userDeviceKeys = await database.getUserDeviceKeys(id);
-      _olmSessions = await database.getOlmSessions(id, _userID);
       _rooms = await database.getRoomList(this, onlyLeft: false);
       _sortRooms();
       accountData = await database.getAccountData(id);
@@ -674,20 +647,12 @@ class Client {
 
   /// Resets all settings and stops the synchronisation.
   void clear() {
-    olmSessions.values.forEach((List<olm.Session> sessions) {
-      sessions.forEach((olm.Session session) => session?.free());
-    });
-    rooms.forEach((Room room) {
-      room.clearOutboundGroupSession(wipe: true);
-      room.inboundGroupSessions.values.forEach((SessionKey sessionKey) {
-        sessionKey.inboundGroupSession?.free();
-      });
-    });
-    _olmAccount?.free();
     database?.clear(id);
     _id = api.accessToken =
         api.homeserver = _userID = _deviceID = _deviceName = prevBatch = null;
     _rooms = [];
+    encryption?.dispose();
+    encryption = null;
     onLoginStateChanged.add(LoginState.loggedOut);
   }
 
@@ -723,7 +688,9 @@ class Client {
       }
       prevBatch = syncResp.nextBatch;
       await _updateUserDeviceKeys();
-      _cleanupKeyVerificationRequests();
+      if (encryptionEnabled) {
+        encryption.onSync();
+      }
       if (hash == _syncRequest.hashCode) unawaited(_sync());
     } on MatrixException catch (exception) {
       onError.add(exception);
@@ -740,7 +707,7 @@ class Client {
   /// Use this method only for testing utilities!
   Future<void> handleSync(SyncUpdate sync) async {
     if (sync.toDevice != null) {
-      _handleToDeviceEvents(sync.toDevice);
+      await _handleToDeviceEvents(sync.toDevice);
     }
     if (sync.rooms != null) {
       if (sync.rooms.join != null) {
@@ -784,31 +751,12 @@ class Client {
     if (sync.deviceLists != null) {
       await _handleDeviceListsEvents(sync.deviceLists);
     }
-    if (sync.deviceOneTimeKeysCount != null) {
+    if (sync.deviceOneTimeKeysCount != null && encryptionEnabled) {
-      _handleDeviceOneTimeKeysCount(sync.deviceOneTimeKeysCount);
+      encryption.handleDeviceOneTimeKeysCount(sync.deviceOneTimeKeysCount);
-    }
-    while (_pendingToDeviceEvents.isNotEmpty) {
-      _updateRoomsByToDeviceEvent(
-        _pendingToDeviceEvents.removeLast(),
-        addToPendingIfNotFound: false,
-      );
     }
     onSync.add(sync);
   }
 
-  void _handleDeviceOneTimeKeysCount(Map<String, int> deviceOneTimeKeysCount) {
-    if (!encryptionEnabled) return;
-    // Check if there are at least half of max_number_of_one_time_keys left on the server
-    // and generate and upload more if not.
-    if (deviceOneTimeKeysCount['signed_curve25519'] != null) {
-      final oneTimeKeysCount = deviceOneTimeKeysCount['signed_curve25519'];
-      if (oneTimeKeysCount < (_olmAccount.max_number_of_one_time_keys() / 2)) {
-        // Generate and upload more one time keys:
-        _uploadKeys();
-      }
-    }
-  }
-
   Future<void> _handleDeviceListsEvents(DeviceListsUpdate deviceLists) async {
     if (deviceLists.changed is List) {
       for (final userId in deviceLists.changed) {
@@ -827,36 +775,12 @@ class Client {
     }
   }
 
-  void _cleanupKeyVerificationRequests() {
+  Future<void> _handleToDeviceEvents(List<BasicEventWithSender> events) async {
-    for (final entry in _keyVerificationRequests.entries) {
-      (() async {
-        var dispose = entry.value.canceled ||
-            entry.value.state == KeyVerificationState.done ||
-            entry.value.state == KeyVerificationState.error;
-        if (!dispose) {
-          dispose = !(await entry.value.verifyActivity());
-        }
-        if (dispose) {
-          entry.value.dispose();
-          _keyVerificationRequests.remove(entry.key);
-        }
-      })();
-    }
-  }
-
-  void addKeyVerificationRequest(KeyVerification request) {
-    if (request.transactionId == null) {
-      return;
-    }
-    _keyVerificationRequests[request.transactionId] = request;
-  }
-
-  void _handleToDeviceEvents(List<BasicEventWithSender> events) {
     for (var i = 0; i < events.length; i++) {
       var toDeviceEvent = ToDeviceEvent.fromJson(events[i].toJson());
-      if (toDeviceEvent.type == EventTypes.Encrypted) {
+      if (toDeviceEvent.type == EventTypes.Encrypted && encryptionEnabled) {
         try {
-          toDeviceEvent = decryptToDeviceEvent(toDeviceEvent);
+          toDeviceEvent = await encryption.decryptToDeviceEvent(toDeviceEvent);
         } catch (e, s) {
           print(
               '[LibOlm] Could not decrypt to device event from ${toDeviceEvent.sender} with content: ${toDeviceEvent.content}');
@@ -872,48 +796,13 @@ class Client {
           toDeviceEvent = ToDeviceEvent.fromJson(events[i].toJson());
         }
       }
-      _updateRoomsByToDeviceEvent(toDeviceEvent);
+      if (encryptionEnabled) {
-      if (toDeviceEvent.type.startsWith('m.key.verification.')) {
+        await encryption.handleToDeviceEvent(toDeviceEvent);
-        _handleToDeviceKeyVerificationRequest(toDeviceEvent);
-      }
-      if (['m.room_key_request', 'm.forwarded_room_key']
-          .contains(toDeviceEvent.type)) {
-        keyManager.handleToDeviceEvent(toDeviceEvent);
       }
       onToDeviceEvent.add(toDeviceEvent);
     }
   }
 
-  void _handleToDeviceKeyVerificationRequest(ToDeviceEvent toDeviceEvent) {
-    if (!toDeviceEvent.type.startsWith('m.key.verification.')) {
-      return;
-    }
-    // we have key verification going on!
-    final transactionId =
-        KeyVerification.getTransactionId(toDeviceEvent.content);
-    if (transactionId != null) {
-      if (_keyVerificationRequests.containsKey(transactionId)) {
-        _keyVerificationRequests[transactionId]
-            .handlePayload(toDeviceEvent.type, toDeviceEvent.content);
-      } else {
-        final newKeyRequest =
-            KeyVerification(client: this, userId: toDeviceEvent.sender);
-        newKeyRequest
-            .handlePayload(toDeviceEvent.type, toDeviceEvent.content)
-            .then((res) {
-          if (newKeyRequest.state != KeyVerificationState.askAccept) {
-            // okay, something went wrong (unknown transaction id?), just dispose it
-            newKeyRequest.dispose();
-          } else {
-            // we have a new request! Let's broadcast it!
-            _keyVerificationRequests[transactionId] = newKeyRequest;
-            onKeyVerificationRequest.add(newKeyRequest);
-          }
-        });
-      }
-    }
-  }
-
   Future<void> _handleRooms(
       Map<String, SyncRoomUpdate> rooms, Membership membership) async {
     for (final entry in rooms.entries) {
@@ -1056,14 +945,8 @@ class Client {
         content: event,
         sortOrder: sortOrder,
       );
-      if (event['type'] == EventTypes.Encrypted) {
+      if (event['type'] == EventTypes.Encrypted && encryptionEnabled) {
-        update = update.decrypt(room);
+        update = await update.decrypt(room);
-      }
-      if (update.eventType == EventTypes.Encrypted && database != null) {
-        // the event is still encrytped....let's try fetching the keys from the database!
-        await room.loadInboundGroupSessionKey(
-            event['content']['session_id'], event['content']['sender_key']);
-        update = update.decrypt(room);
       }
       if (type != 'ephemeral' && database != null) {
         await database.storeEventUpdate(id, update);
@@ -1187,42 +1070,6 @@ class Client {
     if (eventUpdate.type == 'timeline') _sortRooms();
   }
 
-  final List<ToDeviceEvent> _pendingToDeviceEvents = [];
-
-  void _updateRoomsByToDeviceEvent(ToDeviceEvent toDeviceEvent,
-      {addToPendingIfNotFound = true}) async {
-    try {
-      switch (toDeviceEvent.type) {
-        case 'm.room_key':
-          final roomId = toDeviceEvent.content['room_id'];
-          var room = getRoomById(roomId);
-          if (room == null && addToPendingIfNotFound) {
-            _pendingToDeviceEvents.add(toDeviceEvent);
-            break;
-          }
-          room ??= Room(client: this, id: roomId);
-          final String sessionId = toDeviceEvent.content['session_id'];
-          if (userDeviceKeys.containsKey(toDeviceEvent.sender) &&
-              userDeviceKeys[toDeviceEvent.sender]
-                  .deviceKeys
-                  .containsKey(toDeviceEvent.content['requesting_device_id'])) {
-            toDeviceEvent.content['sender_claimed_ed25519_key'] =
-                userDeviceKeys[toDeviceEvent.sender]
-                    .deviceKeys[toDeviceEvent.content['requesting_device_id']]
-                    .ed25519Key;
-          }
-          room.setInboundGroupSession(
-            sessionId,
-            toDeviceEvent.content,
-            forwarded: false,
-          );
-          break;
-      }
-    } catch (e) {
-      print('[Matrix] Error while processing to-device-event: ' + e.toString());
-    }
-  }
-
   bool _sortLock = false;
 
   /// The compare function how the rooms should be sorted internally. By default
@@ -1287,6 +1134,9 @@ class Client {
 
         for (final rawDeviceKeyListEntry in response.deviceKeys.entries) {
           final userId = rawDeviceKeyListEntry.key;
+          if (!userDeviceKeys.containsKey(userId)) {
+            _userDeviceKeys[userId] = DeviceKeysList(userId);
+          }
           final oldKeys =
               Map<String, DeviceKeys>.from(_userDeviceKeys[userId].deviceKeys);
           _userDeviceKeys[userId].deviceKeys = {};
@@ -1301,7 +1151,7 @@ class Client {
               if (entry.isValid) {
                 _userDeviceKeys[userId].deviceKeys[deviceId] = entry;
                 if (deviceId == deviceID &&
-                    entry.ed25519Key == fingerprintKey) {
+                    entry.ed25519Key == encryption?.fingerprintKey) {
                   // Always trust the own device
                   entry.verified = true;
                 }
@@ -1349,213 +1199,6 @@ class Client {
     }
   }
 
-  String get fingerprintKey => encryptionEnabled
-      ? json.decode(_olmAccount.identity_keys())['ed25519']
-      : null;
-  String get identityKey => encryptionEnabled
-      ? json.decode(_olmAccount.identity_keys())['curve25519']
-      : null;
-
-  /// Adds a signature to this json from this olm account.
-  Map<String, dynamic> signJson(Map<String, dynamic> payload) {
-    if (!encryptionEnabled) throw ('Encryption is disabled');
-    final Map<String, dynamic> unsigned = payload['unsigned'];
-    final Map<String, dynamic> signatures = payload['signatures'];
-    payload.remove('unsigned');
-    payload.remove('signatures');
-    final canonical = canonicalJson.encode(payload);
-    final signature = _olmAccount.sign(String.fromCharCodes(canonical));
-    if (signatures != null) {
-      payload['signatures'] = signatures;
-    } else {
-      payload['signatures'] = <String, dynamic>{};
-    }
-    payload['signatures'][userID] = <String, dynamic>{};
-    payload['signatures'][userID]['ed25519:$deviceID'] = signature;
-    if (unsigned != null) {
-      payload['unsigned'] = unsigned;
-    }
-    return payload;
-  }
-
-  /// Checks the signature of a signed json object.
-  bool checkJsonSignature(String key, Map<String, dynamic> signedJson,
-      String userId, String deviceId) {
-    if (!encryptionEnabled) throw ('Encryption is disabled');
-    final Map<String, dynamic> signatures = signedJson['signatures'];
-    if (signatures == null || !signatures.containsKey(userId)) return false;
-    signedJson.remove('unsigned');
-    signedJson.remove('signatures');
-    if (!signatures[userId].containsKey('ed25519:$deviceId')) return false;
-    final String signature = signatures[userId]['ed25519:$deviceId'];
-    final canonical = canonicalJson.encode(signedJson);
-    final message = String.fromCharCodes(canonical);
-    var isValid = true;
-    try {
-      olm.Utility()
-        ..ed25519_verify(key, message, signature)
-        ..free();
-    } catch (e) {
-      isValid = false;
-      print('[LibOlm] Signature check failed: ' + e.toString());
-    }
-    return isValid;
-  }
-
-  DateTime lastTimeKeysUploaded;
-
-  /// Generates new one time keys, signs everything and upload it to the server.
-  Future<bool> _uploadKeys({bool uploadDeviceKeys = false}) async {
-    if (!encryptionEnabled) return true;
-
-    final oneTimeKeysCount = _olmAccount.max_number_of_one_time_keys();
-    _olmAccount.generate_one_time_keys(oneTimeKeysCount);
-    final Map<String, dynamic> oneTimeKeys =
-        json.decode(_olmAccount.one_time_keys());
-
-    var signedOneTimeKeys = <String, dynamic>{};
-
-    for (String key in oneTimeKeys['curve25519'].keys) {
-      signedOneTimeKeys['signed_curve25519:$key'] = <String, dynamic>{};
-      signedOneTimeKeys['signed_curve25519:$key']['key'] =
-          oneTimeKeys['curve25519'][key];
-      signedOneTimeKeys['signed_curve25519:$key'] =
-          signJson(signedOneTimeKeys['signed_curve25519:$key']);
-    }
-
-    var keysContent = <String, dynamic>{
-      if (uploadDeviceKeys)
-        'device_keys': {
-          'user_id': userID,
-          'device_id': deviceID,
-          'algorithms': [
-            'm.olm.v1.curve25519-aes-sha2',
-            'm.megolm.v1.aes-sha2'
-          ],
-          'keys': <String, dynamic>{},
-        },
-    };
-    if (uploadDeviceKeys) {
-      final Map<String, dynamic> keys =
-          json.decode(_olmAccount.identity_keys());
-      for (var algorithm in keys.keys) {
-        keysContent['device_keys']['keys']['$algorithm:$deviceID'] =
-            keys[algorithm];
-      }
-      keysContent['device_keys'] =
-          signJson(keysContent['device_keys'] as Map<String, dynamic>);
-    }
-
-    _olmAccount.mark_keys_as_published();
-    final response = await api.uploadDeviceKeys(
-      deviceKeys: uploadDeviceKeys
-          ? MatrixDeviceKeys.fromJson(keysContent['device_keys'])
-          : null,
-      oneTimeKeys: signedOneTimeKeys,
-    );
-    if (response['signed_curve25519'] != oneTimeKeysCount) {
-      return false;
-    }
-    await database?.updateClientKeys(pickledOlmAccount, id);
-    lastTimeKeysUploaded = DateTime.now();
-    return true;
-  }
-
-  /// Try to decrypt a ToDeviceEvent encrypted with olm.
-  ToDeviceEvent decryptToDeviceEvent(ToDeviceEvent toDeviceEvent) {
-    if (toDeviceEvent.type != EventTypes.Encrypted) {
-      print(
-          '[LibOlm] Warning! Tried to decrypt a not-encrypted to-device-event');
-      return toDeviceEvent;
-    }
-    if (toDeviceEvent.content['algorithm'] != 'm.olm.v1.curve25519-aes-sha2') {
-      throw ('Unknown algorithm: ${toDeviceEvent.content}');
-    }
-    if (!toDeviceEvent.content['ciphertext'].containsKey(identityKey)) {
-      throw ("The message isn't sent for this device");
-    }
-    String plaintext;
-    final String senderKey = toDeviceEvent.content['sender_key'];
-    final String body =
-        toDeviceEvent.content['ciphertext'][identityKey]['body'];
-    final int type = toDeviceEvent.content['ciphertext'][identityKey]['type'];
-    if (type != 0 && type != 1) {
-      throw ('Unknown message type');
-    }
-    var existingSessions = olmSessions[senderKey];
-    if (existingSessions != null) {
-      for (var session in existingSessions) {
-        if (type == 0 && session.matches_inbound(body) == true) {
-          plaintext = session.decrypt(type, body);
-          storeOlmSession(senderKey, session);
-          break;
-        } else if (type == 1) {
-          try {
-            plaintext = session.decrypt(type, body);
-            storeOlmSession(senderKey, session);
-            break;
-          } catch (_) {
-            plaintext = null;
-          }
-        }
-      }
-    }
-    if (plaintext == null && type != 0) {
-      throw ('No existing sessions found');
-    }
-
-    if (plaintext == null) {
-      var newSession = olm.Session();
-      newSession.create_inbound_from(_olmAccount, senderKey, body);
-      _olmAccount.remove_one_time_keys(newSession);
-      database?.updateClientKeys(pickledOlmAccount, id);
-      plaintext = newSession.decrypt(type, body);
-      storeOlmSession(senderKey, newSession);
-    }
-    final Map<String, dynamic> plainContent = json.decode(plaintext);
-    if (plainContent.containsKey('sender') &&
-        plainContent['sender'] != toDeviceEvent.sender) {
-      throw ("Message was decrypted but sender doesn't match");
-    }
-    if (plainContent.containsKey('recipient') &&
-        plainContent['recipient'] != userID) {
-      throw ("Message was decrypted but recipient doesn't match");
-    }
-    if (plainContent['recipient_keys'] is Map &&
-        plainContent['recipient_keys']['ed25519'] is String &&
-        plainContent['recipient_keys']['ed25519'] != fingerprintKey) {
-      throw ("Message was decrypted but own fingerprint Key doesn't match");
-    }
-    return ToDeviceEvent(
-      content: plainContent['content'],
-      encryptedContent: toDeviceEvent.content,
-      type: plainContent['type'],
-      sender: toDeviceEvent.sender,
-    );
-  }
-
-  /// A map from Curve25519 identity keys to existing olm sessions.
-  Map<String, List<olm.Session>> get olmSessions => _olmSessions;
-  Map<String, List<olm.Session>> _olmSessions = {};
-
-  void storeOlmSession(String curve25519IdentityKey, olm.Session session) {
-    if (!_olmSessions.containsKey(curve25519IdentityKey)) {
-      _olmSessions[curve25519IdentityKey] = [];
-    }
-    final ix = _olmSessions[curve25519IdentityKey]
-        .indexWhere((s) => s.session_id() == session.session_id());
-    if (ix == -1) {
-      // add a new session
-      _olmSessions[curve25519IdentityKey].add(session);
-    } else {
-      // update an existing session
-      _olmSessions[curve25519IdentityKey][ix] = session;
-    }
-    final pickle = session.pickle(userID);
-    database?.storeOlmSession(
-        id, curve25519IdentityKey, session.session_id(), pickle);
-  }
-
   /// Sends an encrypted [message] of this [type] to these [deviceKeys]. To send
   /// the request to all devices of the current user, pass an empty list to [deviceKeys].
   Future<void> sendToDevice(
@@ -1589,96 +1232,22 @@ class Client {
       }
     } else {
       if (encrypted) {
-        // Create new sessions with devices if there is no existing session yet.
+        data =
-        var deviceKeysWithoutSession = List<DeviceKeys>.from(deviceKeys);
+            await encryption.encryptToDeviceMessage(deviceKeys, type, message);
-        deviceKeysWithoutSession.removeWhere((DeviceKeys deviceKeys) =>
+      } else {
-            olmSessions.containsKey(deviceKeys.curve25519Key));
+        for (final device in deviceKeys) {
-        if (deviceKeysWithoutSession.isNotEmpty) {
-          await startOutgoingOlmSessions(deviceKeysWithoutSession);
-        }
-      }
-      for (var i = 0; i < deviceKeys.length; i++) {
-        var device = deviceKeys[i];
           if (!data.containsKey(device.userId)) {
             data[device.userId] = {};
           }
-
-        if (encrypted) {
-          var existingSessions = olmSessions[device.curve25519Key];
-          if (existingSessions == null || existingSessions.isEmpty) continue;
-          existingSessions
-              .sort((a, b) => a.session_id().compareTo(b.session_id()));
-
-          final payload = {
-            'type': type,
-            'content': message,
-            'sender': userID,
-            'keys': {'ed25519': fingerprintKey},
-            'recipient': device.userId,
-            'recipient_keys': {'ed25519': device.ed25519Key},
-          };
-          final encryptResult =
-              existingSessions.first.encrypt(json.encode(payload));
-          storeOlmSession(device.curve25519Key, existingSessions.first);
-          sendToDeviceMessage = {
-            'algorithm': 'm.olm.v1.curve25519-aes-sha2',
-            'sender_key': identityKey,
-            'ciphertext': <String, dynamic>{},
-          };
-          sendToDeviceMessage['ciphertext'][device.curve25519Key] = {
-            'type': encryptResult.type,
-            'body': encryptResult.body,
-          };
-        }
-
           data[device.userId][device.deviceId] = sendToDeviceMessage;
         }
       }
+    }
     if (encrypted) type = EventTypes.Encrypted;
     final messageID = generateUniqueTransactionId();
     await api.sendToDevice(type, messageID, data);
   }
 
-  Future<void> startOutgoingOlmSessions(List<DeviceKeys> deviceKeys,
-      {bool checkSignature = true}) async {
-    var requestingKeysFrom = <String, Map<String, String>>{};
-    for (var device in deviceKeys) {
-      if (requestingKeysFrom[device.userId] == null) {
-        requestingKeysFrom[device.userId] = {};
-      }
-      requestingKeysFrom[device.userId][device.deviceId] = 'signed_curve25519';
-    }
-
-    final response =
-        await api.requestOneTimeKeys(requestingKeysFrom, timeout: 10000);
-
-    for (var userKeysEntry in response.oneTimeKeys.entries) {
-      final userId = userKeysEntry.key;
-      for (var deviceKeysEntry in userKeysEntry.value.entries) {
-        final deviceId = deviceKeysEntry.key;
-        final fingerprintKey =
-            userDeviceKeys[userId].deviceKeys[deviceId].ed25519Key;
-        final identityKey =
-            userDeviceKeys[userId].deviceKeys[deviceId].curve25519Key;
-        for (Map<String, dynamic> deviceKey in deviceKeysEntry.value.values) {
-          if (checkSignature &&
-              checkJsonSignature(fingerprintKey, deviceKey, userId, deviceId) ==
-                  false) {
-            continue;
-          }
-          try {
-            var session = olm.Session();
-            session.create_outbound(_olmAccount, identityKey, deviceKey['key']);
-            await storeOlmSession(identityKey, session);
-          } catch (e) {
-            print('[LibOlm] Could not create new outbound olm session: ' +
-                e.toString());
-          }
-        }
-      }
-    }
-  }
-
   /// Whether all push notifications are muted using the [.m.rule.master]
   /// rule of the push rules: https://matrix.org/docs/spec/client_server/r0.6.0#m-rule-master
   bool get allPushNotificationsMuted {

lib/src/database/database.dart

@@ -91,6 +91,22 @@ class Database extends _$Database {
     return res;
   }
 
+  Future<List<olm.Session>> getSingleOlmSessions(
+      int clientId, String identityKey, String userId) async {
+    final rows = await dbGetOlmSessions(clientId, identityKey).get();
+    final res = <olm.Session>[];
+    for (final row in rows) {
+      try {
+        var session = olm.Session();
+        session.unpickle(userId, row.pickle);
+        res.add(session);
+      } catch (e) {
+        print('[LibOlm] Could not unpickle olm session: ' + e.toString());
+      }
+    }
+    return res;
+  }
+
   Future<DbOutboundGroupSession> getDbOutboundGroupSession(
       int clientId, String roomId) async {
     final res = await dbGetOutboundGroupSession(clientId, roomId).get();

lib/src/database/database.g.dart

@@ -4851,6 +4851,19 @@ abstract class _$Database extends GeneratedDatabase {
         readsFrom: {olmSessions}).map(_rowToDbOlmSessions);
   }
 
+  Selectable<DbOlmSessions> dbGetOlmSessions(
+      int client_id, String identity_key) {
+    return customSelect(
+        'SELECT * FROM olm_sessions WHERE client_id = :client_id AND identity_key = :identity_key',
+        variables: [
+          Variable.withInt(client_id),
+          Variable.withString(identity_key)
+        ],
+        readsFrom: {
+          olmSessions
+        }).map(_rowToDbOlmSessions);
+  }
+
   Future<int> storeOlmSession(
       int client_id, String identitiy_key, String session_id, String pickle) {
     return customInsert(

lib/src/database/database.moor

@@ -155,6 +155,7 @@ storePrevBatch: UPDATE clients SET prev_batch = :prev_batch WHERE client_id = :c
 getAllUserDeviceKeys: SELECT * FROM user_device_keys WHERE client_id = :client_id;
 getAllUserDeviceKeysKeys: SELECT * FROM user_device_keys_key WHERE client_id = :client_id;
 getAllOlmSessions: SELECT * FROM olm_sessions WHERE client_id = :client_id;
+dbGetOlmSessions: SELECT * FROM olm_sessions WHERE client_id = :client_id AND identity_key = :identity_key;
 storeOlmSession: INSERT OR REPLACE INTO olm_sessions (client_id, identity_key, session_id, pickle) VALUES (:client_id, :identitiy_key, :session_id, :pickle);
 getAllOutboundGroupSessions: SELECT * FROM outbound_group_sessions WHERE client_id = :client_id;
 dbGetOutboundGroupSession: SELECT * FROM outbound_group_sessions WHERE client_id = :client_id AND room_id = :room_id;

lib/src/event.dart

@@ -19,6 +19,7 @@
 import 'dart:convert';
 import 'dart:typed_data';
 import 'package:famedlysdk/famedlysdk.dart';
+import 'package:famedlysdk/encryption.dart';
 import 'package:famedlysdk/src/utils/receipt.dart';
 import 'package:http/http.dart' as http;
 import 'package:matrix_file_e2ee/matrix_file_e2ee.dart';
@@ -333,36 +334,6 @@ class Event extends MatrixEvent {
     return await timeline.getEventById(replyEventId);
   }
 
-  Future<void> loadSession() {
-    return room.loadInboundGroupSessionKeyForEvent(this);
-  }
-
-  /// Trys to decrypt this event. Returns a m.bad.encrypted event
-  /// if it fails and does nothing if the event was not encrypted.
-  Event get decrypted => room.decryptGroupMessage(this);
-
-  /// Trys to decrypt this event and persists it in the database afterwards
-  Future<Event> decryptAndStore([String updateType = 'timeline']) async {
-    final newEvent = decrypted;
-    if (newEvent.type == EventTypes.Encrypted) {
-      return newEvent; // decryption failed
-    }
-    await room.client.database?.storeEventUpdate(
-      room.client.id,
-      EventUpdate(
-        eventType: newEvent.type,
-        content: newEvent.toJson(),
-        roomID: newEvent.roomId,
-        type: updateType,
-        sortOrder: newEvent.sortOrder,
-      ),
-    );
-    if (updateType != 'history') {
-      room.setState(newEvent);
-    }
-    return newEvent;
-  }
-
   /// If this event is encrypted and the decryption was not successful because
   /// the session is unknown, this requests the session key from other devices
   /// in the room. If the event is not encrypted or the decryption failed because

lib/src/key_manager.dart

@@ -1,214 +0,0 @@
-import 'client.dart';
-import 'room.dart';
-import 'utils/to_device_event.dart';
-import 'utils/device_keys_list.dart';
-
-class KeyManager {
-  final Client client;
-  final outgoingShareRequests = <String, KeyManagerKeyShareRequest>{};
-  final incomingShareRequests = <String, KeyManagerKeyShareRequest>{};
-
-  KeyManager(this.client);
-
-  /// Request a certain key from another device
-  Future<void> request(Room room, String sessionId, String senderKey) async {
-    // while we just send the to-device event to '*', we still need to save the
-    // devices themself to know where to send the cancel to after receiving a reply
-    final devices = await room.getUserDeviceKeys();
-    final requestId = client.generateUniqueTransactionId();
-    final request = KeyManagerKeyShareRequest(
-      requestId: requestId,
-      devices: devices,
-      room: room,
-      sessionId: sessionId,
-      senderKey: senderKey,
-    );
-    await client.sendToDevice(
-        [],
-        'm.room_key_request',
-        {
-          'action': 'request',
-          'body': {
-            'algorithm': 'm.megolm.v1.aes-sha2',
-            'room_id': room.id,
-            'sender_key': senderKey,
-            'session_id': sessionId,
-          },
-          'request_id': requestId,
-          'requesting_device_id': client.deviceID,
-        },
-        encrypted: false,
-        toUsers: await room.requestParticipants());
-    outgoingShareRequests[request.requestId] = request;
-  }
-
-  /// Handle an incoming to_device event that is related to key sharing
-  Future<void> handleToDeviceEvent(ToDeviceEvent event) async {
-    if (event.type == 'm.room_key_request') {
-      if (!event.content.containsKey('request_id')) {
-        return; // invalid event
-      }
-      if (event.content['action'] == 'request') {
-        // we are *receiving* a request
-        if (!event.content.containsKey('body')) {
-          return; // no body
-        }
-        if (!client.userDeviceKeys.containsKey(event.sender) ||
-            !client.userDeviceKeys[event.sender].deviceKeys
-                .containsKey(event.content['requesting_device_id'])) {
-          return; // device not found
-        }
-        final device = client.userDeviceKeys[event.sender]
-            .deviceKeys[event.content['requesting_device_id']];
-        if (device.userId == client.userID &&
-            device.deviceId == client.deviceID) {
-          return; // ignore requests by ourself
-        }
-        final room = client.getRoomById(event.content['body']['room_id']);
-        if (room == null) {
-          return; // unknown room
-        }
-        final sessionId = event.content['body']['session_id'];
-        // okay, let's see if we have this session at all
-        await room.loadInboundGroupSessionKey(sessionId);
-        if (!room.inboundGroupSessions.containsKey(sessionId)) {
-          return; // we don't have this session anyways
-        }
-        final request = KeyManagerKeyShareRequest(
-          requestId: event.content['request_id'],
-          devices: [device],
-          room: room,
-          sessionId: event.content['body']['session_id'],
-          senderKey: event.content['body']['sender_key'],
-        );
-        if (incomingShareRequests.containsKey(request.requestId)) {
-          return; // we don't want to process one and the same request multiple times
-        }
-        incomingShareRequests[request.requestId] = request;
-        final roomKeyRequest =
-            RoomKeyRequest.fromToDeviceEvent(event, this, request);
-        if (device.userId == client.userID &&
-            device.verified &&
-            !device.blocked) {
-          // alright, we can forward the key
-          await roomKeyRequest.forwardKey();
-        } else {
-          client.onRoomKeyRequest
-              .add(roomKeyRequest); // let the client handle this
-        }
-      } else if (event.content['action'] == 'request_cancellation') {
-        // we got told to cancel an incoming request
-        if (!incomingShareRequests.containsKey(event.content['request_id'])) {
-          return; // we don't know this request anyways
-        }
-        // alright, let's just cancel this request
-        final request = incomingShareRequests[event.content['request_id']];
-        request.canceled = true;
-        incomingShareRequests.remove(request.requestId);
-      }
-    } else if (event.type == 'm.forwarded_room_key') {
-      // we *received* an incoming key request
-      if (event.encryptedContent == null) {
-        return; // event wasn't encrypted, this is a security risk
-      }
-      final request = outgoingShareRequests.values.firstWhere(
-          (r) =>
-              r.room.id == event.content['room_id'] &&
-              r.sessionId == event.content['session_id'] &&
-              r.senderKey == event.content['sender_key'],
-          orElse: () => null);
-      if (request == null || request.canceled) {
-        return; // no associated request found or it got canceled
-      }
-      final device = request.devices.firstWhere(
-          (d) =>
-              d.userId == event.sender &&
-              d.curve25519Key == event.encryptedContent['sender_key'],
-          orElse: () => null);
-      if (device == null) {
-        return; // someone we didn't send our request to replied....better ignore this
-      }
-      // TODO: verify that the keys work to decrypt a message
-      // alright, all checks out, let's go ahead and store this session
-      request.room.setInboundGroupSession(request.sessionId, event.content,
-          forwarded: true);
-      request.devices.removeWhere(
-          (k) => k.userId == device.userId && k.deviceId == device.deviceId);
-      outgoingShareRequests.remove(request.requestId);
-      // send cancel to all other devices
-      if (request.devices.isEmpty) {
-        return; // no need to send any cancellation
-      }
-      await client.sendToDevice(
-          request.devices,
-          'm.room_key_request',
-          {
-            'action': 'request_cancellation',
-            'request_id': request.requestId,
-            'requesting_device_id': client.deviceID,
-          },
-          encrypted: false);
-    }
-  }
-}
-
-class KeyManagerKeyShareRequest {
-  final String requestId;
-  final List<DeviceKeys> devices;
-  final Room room;
-  final String sessionId;
-  final String senderKey;
-  bool canceled;
-
-  KeyManagerKeyShareRequest(
-      {this.requestId,
-      this.devices,
-      this.room,
-      this.sessionId,
-      this.senderKey,
-      this.canceled = false});
-}
-
-class RoomKeyRequest extends ToDeviceEvent {
-  KeyManager keyManager;
-  KeyManagerKeyShareRequest request;
-  RoomKeyRequest.fromToDeviceEvent(ToDeviceEvent toDeviceEvent,
-      KeyManager keyManager, KeyManagerKeyShareRequest request) {
-    this.keyManager = keyManager;
-    this.request = request;
-    sender = toDeviceEvent.sender;
-    content = toDeviceEvent.content;
-    type = toDeviceEvent.type;
-  }
-
-  Room get room => request.room;
-
-  DeviceKeys get requestingDevice => request.devices.first;
-
-  Future<void> forwardKey() async {
-    if (request.canceled) {
-      keyManager.incomingShareRequests.remove(request.requestId);
-      return; // request is canceled, don't send anything
-    }
-    var room = this.room;
-    await room.loadInboundGroupSessionKey(request.sessionId);
-    final session = room.inboundGroupSessions[request.sessionId];
-    var forwardedKeys = <dynamic>[keyManager.client.identityKey];
-    for (final key in session.forwardingCurve25519KeyChain) {
-      forwardedKeys.add(key);
-    }
-    await requestingDevice.setVerified(true, keyManager.client);
-    var message = session.content;
-    message['forwarding_curve25519_key_chain'] = forwardedKeys;
-
-    message['session_key'] = session.inboundGroupSession
-        .export_session(session.inboundGroupSession.first_known_index());
-    // send the actual reply of the key back to the requester
-    await keyManager.client.sendToDevice(
-      [requestingDevice],
-      'm.forwarded_room_key',
-      message,
-    );
-    keyManager.incomingShareRequests.remove(request.requestId);
-  }
-}

lib/src/room.dart

@@ -17,21 +17,18 @@
  */
 
 import 'dart:async';
-import 'dart:convert';
 
 import 'package:famedlysdk/matrix_api.dart';
-import 'package:pedantic/pedantic.dart';
+import 'package:famedlysdk/encryption.dart';
 import 'package:famedlysdk/famedlysdk.dart';
 import 'package:famedlysdk/src/client.dart';
 import 'package:famedlysdk/src/event.dart';
 import 'package:famedlysdk/src/utils/event_update.dart';
 import 'package:famedlysdk/src/utils/room_update.dart';
 import 'package:famedlysdk/src/utils/matrix_file.dart';
-import 'package:famedlysdk/src/utils/session_key.dart';
 import 'package:image/image.dart';
 import 'package:matrix_file_e2ee/matrix_file_e2ee.dart';
 import 'package:mime_type/mime_type.dart';
-import 'package:olm/olm.dart' as olm;
 import 'package:html_unescape/html_unescape.dart';
 
 import './user.dart';
@@ -81,13 +78,6 @@ class Room {
   /// Key-Value store for private account data only visible for this user.
   Map<String, BasicRoomEvent> roomAccountData = {};
 
-  olm.OutboundGroupSession get outboundGroupSession => _outboundGroupSession;
-  olm.OutboundGroupSession _outboundGroupSession;
-
-  List<String> _outboundGroupSessionDevices;
-  DateTime _outboundGroupSessionCreationTime;
-  int _outboundGroupSessionSentMessages;
-
   double _newestSortOrder;
   double _oldestSortOrder;
 
@@ -110,168 +100,6 @@ class Room {
         _oldestSortOrder, _newestSortOrder, client.id, id);
   }
 
-  /// Clears the existing outboundGroupSession, tries to create a new one and
-  /// stores it as an ingoingGroupSession in the [sessionKeys]. Then sends the
-  /// new session encrypted with olm to all non-blocked devices using
-  /// to-device-messaging.
-  Future<void> createOutboundGroupSession() async {
-    await clearOutboundGroupSession(wipe: true);
-    var deviceKeys = await getUserDeviceKeys();
-    olm.OutboundGroupSession outboundGroupSession;
-    var outboundGroupSessionDevices = <String>[];
-    for (var keys in deviceKeys) {
-      if (!keys.blocked) outboundGroupSessionDevices.add(keys.deviceId);
-    }
-    outboundGroupSessionDevices.sort();
-    try {
-      outboundGroupSession = olm.OutboundGroupSession();
-      outboundGroupSession.create();
-    } catch (e) {
-      outboundGroupSession = null;
-      print('[LibOlm] Unable to create new outboundGroupSession: ' +
-          e.toString());
-    }
-
-    if (outboundGroupSession == null) return;
-    // Add as an inboundSession to the [sessionKeys].
-    var rawSession = <String, dynamic>{
-      'algorithm': 'm.megolm.v1.aes-sha2',
-      'room_id': id,
-      'session_id': outboundGroupSession.session_id(),
-      'session_key': outboundGroupSession.session_key(),
-    };
-    setInboundGroupSession(rawSession['session_id'], rawSession);
-    try {
-      await client.sendToDevice(deviceKeys, 'm.room_key', rawSession);
-      _outboundGroupSession = outboundGroupSession;
-      _outboundGroupSessionDevices = outboundGroupSessionDevices;
-      _outboundGroupSessionCreationTime = DateTime.now();
-      _outboundGroupSessionSentMessages = 0;
-      await _storeOutboundGroupSession();
-    } catch (e, s) {
-      print(
-          '[LibOlm] Unable to send the session key to the participating devices: ' +
-              e.toString());
-      print(s);
-      await clearOutboundGroupSession();
-    }
-    return;
-  }
-
-  Future<void> _storeOutboundGroupSession() async {
-    if (_outboundGroupSession == null) return;
-    await client.database?.storeOutboundGroupSession(
-        client.id,
-        id,
-        _outboundGroupSession.pickle(client.userID),
-        json.encode(_outboundGroupSessionDevices),
-        _outboundGroupSessionCreationTime,
-        _outboundGroupSessionSentMessages);
-    return;
-  }
-
-  /// Clears the existing outboundGroupSession but first checks if the participating
-  /// devices have been changed. Returns false if the session has not been cleared because
-  /// it wasn't necessary.
-  Future<bool> clearOutboundGroupSession({bool wipe = false}) async {
-    if (!wipe && _outboundGroupSessionDevices != null) {
-      // first check if the devices in the room changed
-      var deviceKeys = await getUserDeviceKeys();
-      var outboundGroupSessionDevices = <String>[];
-      for (var keys in deviceKeys) {
-        if (!keys.blocked) outboundGroupSessionDevices.add(keys.deviceId);
-      }
-      outboundGroupSessionDevices.sort();
-      if (outboundGroupSessionDevices.toString() !=
-          _outboundGroupSessionDevices.toString()) {
-        wipe = true;
-      }
-      // next check if it needs to be rotated
-      final encryptionContent = getState(EventTypes.Encryption)?.content;
-      final maxMessages = encryptionContent != null &&
-              encryptionContent['rotation_period_msgs'] is int
-          ? encryptionContent['rotation_period_msgs']
-          : 100;
-      final maxAge = encryptionContent != null &&
-              encryptionContent['rotation_period_ms'] is int
-          ? encryptionContent['rotation_period_ms']
-          : 604800000; // default of one week
-      if (_outboundGroupSessionSentMessages >= maxMessages ||
-          _outboundGroupSessionCreationTime
-              .add(Duration(milliseconds: maxAge))
-              .isBefore(DateTime.now())) {
-        wipe = true;
-      }
-      if (!wipe) {
-        return false;
-      }
-    }
-    if (!wipe &&
-        _outboundGroupSessionDevices == null &&
-        _outboundGroupSession == null) {
-      return true; // let's just short-circuit out of here, no need to do DB stuff
-    }
-    _outboundGroupSessionDevices = null;
-    await client.database?.removeOutboundGroupSession(client.id, id);
-    _outboundGroupSession?.free();
-    _outboundGroupSession = null;
-    return true;
-  }
-
-  /// Key-Value store of session ids to the session keys. Only m.megolm.v1.aes-sha2
-  /// session keys are supported. They are stored as a Map with the following keys:
-  /// {
-  ///   "algorithm": "m.megolm.v1.aes-sha2",
-  ///   "room_id": "!Cuyf34gef24t:localhost",
-  ///   "session_id": "X3lUlvLELLYxeTx4yOVu6UDpasGEVO0Jbu+QFnm0cKQ",
-  ///   "session_key": "AgAAAADxKHa9uFxcXzwYoNueL5Xqi69IkD4sni8LlfJL7qNBEY..."
-  /// }
-  Map<String, SessionKey> get inboundGroupSessions => _inboundGroupSessions;
-  final _inboundGroupSessions = <String, SessionKey>{};
-
-  /// Add a new session key to the [sessionKeys].
-  void setInboundGroupSession(String sessionId, Map<String, dynamic> content,
-      {bool forwarded = false}) {
-    if (inboundGroupSessions.containsKey(sessionId)) return;
-    olm.InboundGroupSession inboundGroupSession;
-    if (content['algorithm'] == 'm.megolm.v1.aes-sha2') {
-      try {
-        inboundGroupSession = olm.InboundGroupSession();
-        if (forwarded) {
-          inboundGroupSession.import_session(content['session_key']);
-        } else {
-          inboundGroupSession.create(content['session_key']);
-        }
-      } catch (e) {
-        inboundGroupSession = null;
-        print('[LibOlm] Could not create new InboundGroupSession: ' +
-            e.toString());
-      }
-    }
-    _inboundGroupSessions[sessionId] = SessionKey(
-      content: content,
-      inboundGroupSession: inboundGroupSession,
-      indexes: {},
-      key: client.userID,
-    );
-    client.database?.storeInboundGroupSession(
-      client.id,
-      id,
-      sessionId,
-      inboundGroupSession.pickle(client.userID),
-      json.encode(content),
-      json.encode({}),
-    );
-    _tryAgainDecryptLastMessage();
-    onSessionKeyReceived.add(sessionId);
-  }
-
-  Future<void> _tryAgainDecryptLastMessage() async {
-    if (getState(EventTypes.Encrypted) != null) {
-      await getState(EventTypes.Encrypted).decryptAndStore();
-    }
-  }
-
   /// Returns the [Event] for the given [typeKey] and optional [stateKey].
   /// If no [stateKey] is provided, it defaults to an empty string.
   Event getState(String typeKey, [String stateKey = '']) =>
@@ -281,23 +109,13 @@ class Room {
   /// typeKey/stateKey key pair if there is one.
   void setState(Event state) {
     // Decrypt if necessary
-    if (state.type == EventTypes.Encrypted) {
+    if (state.type == EventTypes.Encrypted && client.encryptionEnabled) {
       try {
-        state = decryptGroupMessage(state);
+        state = client.encryption.decryptRoomEventSync(id, state);
       } catch (e) {
         print('[LibOlm] Could not decrypt room state: ' + e.toString());
       }
     }
-    // Check if this is a member change and we need to clear the outboundGroupSession.
-    if (encrypted &&
-        outboundGroupSession != null &&
-        state.type == EventTypes.RoomMember) {
-      var newUser = state.asUser;
-      var oldUser = getState(EventTypes.RoomMember, newUser.id)?.asUser;
-      if (oldUser == null || oldUser.membership != newUser.membership) {
-        clearOutboundGroupSession();
-      }
-    }
     if ((getState(state.type)?.originServerTs?.millisecondsSinceEpoch ?? 0) >
         (state.originServerTs?.millisecondsSinceEpoch ?? 1)) {
       return;
@@ -883,7 +701,8 @@ class Room {
     // Send the text and on success, store and display a *sent* event.
     try {
       final sendMessageContent = encrypted && client.encryptionEnabled
-          ? await encryptGroupMessagePayload(content, type: type)
+          ? await client.encryption
+              .encryptGroupMessagePayload(id, content, type: type)
           : content;
       final res = await client.api.sendMessage(
         id,
@@ -999,55 +818,42 @@ class Room {
     if (onHistoryReceived != null) onHistoryReceived();
     prev_batch = resp.end;
 
-    final dbActions = <Future<dynamic> Function()>[];
+    final loadFn = () async {
-    if (client.database != null) {
-      dbActions.add(
-          () => client.database.setRoomPrevBatch(prev_batch, client.id, id));
-    }
-
       if (!((resp.chunk?.isNotEmpty ?? false) && resp.end != null)) return;
 
       if (resp.state != null) {
         for (final state in resp.state) {
-        var eventUpdate = EventUpdate(
+          await EventUpdate(
             type: 'state',
             roomID: id,
             eventType: state.type,
             content: state.toJson(),
             sortOrder: oldSortOrder,
-        ).decrypt(this);
+          ).decrypt(this, store: true);
-        client.onEvent.add(eventUpdate);
-        if (client.database != null) {
-          dbActions.add(
-              () => client.database.storeEventUpdate(client.id, eventUpdate));
-        }
         }
       }
 
       for (final hist in resp.chunk) {
-      var eventUpdate = EventUpdate(
+        final eventUpdate = await EventUpdate(
           type: 'history',
           roomID: id,
           eventType: hist.type,
           content: hist.toJson(),
           sortOrder: oldSortOrder,
-      ).decrypt(this);
+        ).decrypt(this, store: true);
         client.onEvent.add(eventUpdate);
+      }
+    };
+
     if (client.database != null) {
-        dbActions.add(
+      await client.database.transaction(() async {
-            () => client.database.storeEventUpdate(client.id, eventUpdate));
+        await client.database.setRoomPrevBatch(resp.end, client.id, id);
-      }
+        await loadFn();
-    }
-    if (client.database != null) {
-      dbActions
-          .add(() => client.database.setRoomPrevBatch(resp.end, client.id, id));
-    }
-    await client.database?.transaction(() async {
-      for (final f in dbActions) {
-        await f();
-      }
         await updateSortOrder();
       });
+    } else {
+      await loadFn();
+    }
     client.onRoomUpdate.add(
       RoomUpdate(
         id: id,
@@ -1147,7 +953,6 @@ class Room {
       }
       for (final rawState in rawStates) {
         final newState = Event.fromDb(rawState, newRoom);
-        ;
         newRoom.setState(newState);
       }
     }
@@ -1187,13 +992,13 @@ class Room {
     }
 
     // Try again to decrypt encrypted events and update the database.
-    if (encrypted && client.database != null) {
+    if (encrypted && client.database != null && client.encryptionEnabled) {
       await client.database.transaction(() async {
         for (var i = 0; i < events.length; i++) {
           if (events[i].type == EventTypes.Encrypted &&
               events[i].content['body'] == DecryptError.UNKNOWN_SESSION) {
-            await events[i].loadSession();
+            events[i] = await client.encryption
-            events[i] = await events[i].decryptAndStore();
+                .decryptRoomEvent(id, events[i], store: true);
           }
         }
       });
@@ -1746,209 +1551,10 @@ class Room {
     return deviceKeys;
   }
 
-  bool _restoredOutboundGroupSession = false;
-
-  Future<void> restoreOutboundGroupSession() async {
-    if (_restoredOutboundGroupSession || client.database == null) {
-      return;
-    }
-    final outboundSession =
-        await client.database.getDbOutboundGroupSession(client.id, id);
-    if (outboundSession != null) {
-      try {
-        _outboundGroupSession = olm.OutboundGroupSession();
-        _outboundGroupSession.unpickle(client.userID, outboundSession.pickle);
-        _outboundGroupSessionDevices =
-            List<String>.from(json.decode(outboundSession.deviceIds));
-        _outboundGroupSessionCreationTime = outboundSession.creationTime;
-        _outboundGroupSessionSentMessages = outboundSession.sentMessages;
-      } catch (e) {
-        _outboundGroupSession = null;
-        _outboundGroupSessionDevices = null;
-        print('[LibOlm] Unable to unpickle outboundGroupSession: ' +
-            e.toString());
-      }
-    }
-    _restoredOutboundGroupSession = true;
-  }
-
-  /// Encrypts the given json payload and creates a send-ready m.room.encrypted
-  /// payload. This will create a new outgoingGroupSession if necessary.
-  Future<Map<String, dynamic>> encryptGroupMessagePayload(
-      Map<String, dynamic> payload,
-      {String type = EventTypes.Message}) async {
-    if (!encrypted || !client.encryptionEnabled) return payload;
-    if (encryptionAlgorithm != 'm.megolm.v1.aes-sha2') {
-      throw ('Unknown encryption algorithm');
-    }
-    if (!_restoredOutboundGroupSession && client.database != null) {
-      // try to restore an outbound group session from the database
-      await restoreOutboundGroupSession();
-    }
-    // and clear the outbound session, if it needs clearing
-    await clearOutboundGroupSession();
-    // create a new one if none exists...
-    if (_outboundGroupSession == null) {
-      await createOutboundGroupSession();
-    }
-    final Map<String, dynamic> mRelatesTo = payload.remove('m.relates_to');
-    final payloadContent = {
-      'content': payload,
-      'type': type,
-      'room_id': id,
-    };
-    var encryptedPayload = <String, dynamic>{
-      'algorithm': 'm.megolm.v1.aes-sha2',
-      'ciphertext': _outboundGroupSession.encrypt(json.encode(payloadContent)),
-      'device_id': client.deviceID,
-      'sender_key': client.identityKey,
-      'session_id': _outboundGroupSession.session_id(),
-      if (mRelatesTo != null) 'm.relates_to': mRelatesTo,
-    };
-    _outboundGroupSessionSentMessages++;
-    await _storeOutboundGroupSession();
-    return encryptedPayload;
-  }
-
-  final Set<String> _requestedSessionIds = <String>{};
-
   Future<void> requestSessionKey(String sessionId, String senderKey) async {
-    await client.keyManager.request(this, sessionId, senderKey);
+    if (!client.encryptionEnabled) {
-  }
-
-  Future<void> loadInboundGroupSessionKey(String sessionId,
-      [String senderKey]) async {
-    if (sessionId == null || inboundGroupSessions.containsKey(sessionId)) {
-      return;
-    } // nothing to do
-    final session = await client.database
-        .getDbInboundGroupSession(client.id, id, sessionId);
-    if (session == null) {
-      // no session found, let's request it!
-      if (client.enableE2eeRecovery &&
-          !_requestedSessionIds.contains(sessionId) &&
-          senderKey != null) {
-        unawaited(requestSessionKey(sessionId, senderKey));
-        _requestedSessionIds.add(sessionId);
-      }
       return;
     }
-    try {
+    await client.encryption.keyManager.request(this, sessionId, senderKey);
-      _inboundGroupSessions[sessionId] =
-          SessionKey.fromDb(session, client.userID);
-    } catch (e) {
-      print('[LibOlm] Could not unpickle inboundGroupSession: ' + e.toString());
   }
 }
-
-  Future<void> loadInboundGroupSessionKeyForEvent(Event event) async {
-    if (client.database == null) return; // nothing to do, no database
-    if (event.type != EventTypes.Encrypted) return;
-    if (!client.encryptionEnabled) {
-      throw (DecryptError.NOT_ENABLED);
-    }
-    if (event.content['algorithm'] != 'm.megolm.v1.aes-sha2') {
-      throw (DecryptError.UNKNOWN_ALGORITHM);
-    }
-    final String sessionId = event.content['session_id'];
-    return loadInboundGroupSessionKey(sessionId, event.content['sender_key']);
-  }
-
-  /// Decrypts the given [event] with one of the available ingoingGroupSessions.
-  /// Returns a m.bad.encrypted event if it fails and does nothing if the event
-  /// was not encrypted.
-  Event decryptGroupMessage(Event event) {
-    if (event.type != EventTypes.Encrypted ||
-        event.content['ciphertext'] == null) return event;
-    Map<String, dynamic> decryptedPayload;
-    try {
-      if (!client.encryptionEnabled) {
-        throw (DecryptError.NOT_ENABLED);
-      }
-      if (event.content['algorithm'] != 'm.megolm.v1.aes-sha2') {
-        throw (DecryptError.UNKNOWN_ALGORITHM);
-      }
-      final String sessionId = event.content['session_id'];
-      if (!inboundGroupSessions.containsKey(sessionId)) {
-        throw (DecryptError.UNKNOWN_SESSION);
-      }
-      final decryptResult = inboundGroupSessions[sessionId]
-          .inboundGroupSession
-          .decrypt(event.content['ciphertext']);
-      final messageIndexKey = event.eventId +
-          event.originServerTs.millisecondsSinceEpoch.toString();
-      if (inboundGroupSessions[sessionId]
-              .indexes
-              .containsKey(messageIndexKey) &&
-          inboundGroupSessions[sessionId].indexes[messageIndexKey] !=
-              decryptResult.message_index) {
-        if ((_outboundGroupSession?.session_id() ?? '') == sessionId) {
-          clearOutboundGroupSession();
-        }
-        throw (DecryptError.CHANNEL_CORRUPTED);
-      }
-      inboundGroupSessions[sessionId].indexes[messageIndexKey] =
-          decryptResult.message_index;
-      // now we persist the udpated indexes into the database.
-      // the entry should always exist. In the case it doesn't, the following
-      // line *could* throw an error. As that is a future, though, and we call
-      // it un-awaited here, nothing happens, which is exactly the result we want
-      client.database?.updateInboundGroupSessionIndexes(
-          json.encode(inboundGroupSessions[sessionId].indexes),
-          client.id,
-          id,
-          sessionId);
-      decryptedPayload = json.decode(decryptResult.plaintext);
-    } catch (exception) {
-      // alright, if this was actually by our own outbound group session, we might as well clear it
-      if (client.enableE2eeRecovery &&
-          (_outboundGroupSession?.session_id() ?? '') ==
-              event.content['session_id']) {
-        clearOutboundGroupSession(wipe: true);
-      }
-      if (exception.toString() == DecryptError.UNKNOWN_SESSION) {
-        decryptedPayload = {
-          'content': event.content,
-          'type': EventTypes.Encrypted,
-        };
-        decryptedPayload['content']['body'] = exception.toString();
-        decryptedPayload['content']['msgtype'] = 'm.bad.encrypted';
-      } else {
-        decryptedPayload = {
-          'content': <String, dynamic>{
-            'msgtype': 'm.bad.encrypted',
-            'body': exception.toString(),
-          },
-          'type': EventTypes.Encrypted,
-        };
-      }
-    }
-    if (event.content['m.relates_to'] != null) {
-      decryptedPayload['content']['m.relates_to'] =
-          event.content['m.relates_to'];
-    }
-    return Event(
-      content: decryptedPayload['content'],
-      type: decryptedPayload['type'],
-      senderId: event.senderId,
-      eventId: event.eventId,
-      roomId: event.roomId,
-      room: event.room,
-      originServerTs: event.originServerTs,
-      unsigned: event.unsigned,
-      stateKey: event.stateKey,
-      prevContent: event.prevContent,
-      status: event.status,
-      sortOrder: event.sortOrder,
-    );
-  }
-}
-
-abstract class DecryptError {
-  static const String NOT_ENABLED = 'Encryption is not enabled in your client.';
-  static const String UNKNOWN_ALGORITHM = 'Unknown encryption algorithm.';
-  static const String UNKNOWN_SESSION =
-      'The sender has not sent us the session key.';
-  static const String CHANNEL_CORRUPTED =
-      'The secure channel with the sender was corrupted.';
-}

lib/src/timeline.dart

@@ -19,6 +19,7 @@
 import 'dart:async';
 
 import 'package:famedlysdk/matrix_api.dart';
+import 'package:famedlysdk/encryption.dart';
 
 import 'event.dart';
 import 'room.dart';
@@ -97,12 +98,16 @@ class Timeline {
   void _sessionKeyReceived(String sessionId) async {
     var decryptAtLeastOneEvent = false;
     final decryptFn = () async {
+      if (!room.client.encryptionEnabled) {
+        return;
+      }
       for (var i = 0; i < events.length; i++) {
         if (events[i].type == EventTypes.Encrypted &&
             events[i].messageType == MessageTypes.BadEncrypted &&
             events[i].content['body'] == DecryptError.UNKNOWN_SESSION &&
             events[i].content['session_id'] == sessionId) {
-          events[i] = await events[i].decryptAndStore();
+          events[i] = await room.client.encryption
+              .decryptRoomEvent(room.id, events[i], store: true);
           if (events[i].type != EventTypes.Encrypted) {
             decryptAtLeastOneEvent = true;
           }

lib/src/utils/device_keys_list.dart

@@ -1,11 +1,11 @@
 import 'dart:convert';
 
 import 'package:famedlysdk/matrix_api.dart';
+import 'package:famedlysdk/encryption.dart';
 
 import '../client.dart';
 import '../database/database.dart' show DbUserDeviceKey, DbUserDeviceKeysKey;
 import '../event.dart';
-import 'key_verification.dart';
 
 class DeviceKeysList {
   String userId;
@@ -78,12 +78,6 @@ class DeviceKeys extends MatrixDeviceKeys {
 
   Future<void> setBlocked(bool newBlocked, Client client) {
     blocked = newBlocked;
-    for (var room in client.rooms) {
-      if (!room.encrypted) continue;
-      if (room.getParticipants().indexWhere((u) => u.id == userId) != -1) {
-        room.clearOutboundGroupSession();
-      }
-    }
     return client.database
         ?.setBlockedUserDeviceKey(newBlocked, client.id, userId, deviceId);
   }
@@ -157,10 +151,10 @@ class DeviceKeys extends MatrixDeviceKeys {
   }
 
   KeyVerification startVerification(Client client) {
-    final request =
+    final request = KeyVerification(
-        KeyVerification(client: client, userId: userId, deviceId: deviceId);
+        encryption: client.encryption, userId: userId, deviceId: deviceId);
     request.start();
-    client.addKeyVerificationRequest(request);
+    client.encryption.keyVerificationManager.addRequest(request);
     return request;
   }
 }

lib/src/utils/event_update.dart

@@ -42,13 +42,14 @@ class EventUpdate {
   EventUpdate(
       {this.eventType, this.roomID, this.type, this.content, this.sortOrder});
 
-  EventUpdate decrypt(Room room) {
+  Future<EventUpdate> decrypt(Room room, {bool store = false}) async {
-    if (eventType != EventTypes.Encrypted) {
+    if (eventType != EventTypes.Encrypted || !room.client.encryptionEnabled) {
       return this;
     }
     try {
-      var decrpytedEvent =
+      var decrpytedEvent = await room.client.encryption.decryptRoomEvent(
-          room.decryptGroupMessage(Event.fromJson(content, room, sortOrder));
+          room.id, Event.fromJson(content, room, sortOrder),
+          store: store, updateType: type);
       return EventUpdate(
         eventType: decrpytedEvent.type,
         roomID: roomID,

lib/src/utils/session_key.dart

@@ -1,59 +0,0 @@
-import 'dart:convert';
-
-import 'package:olm/olm.dart';
-
-import '../database/database.dart' show DbInboundGroupSession;
-import '../event.dart';
-
-class SessionKey {
-  Map<String, dynamic> content;
-  Map<String, int> indexes;
-  InboundGroupSession inboundGroupSession;
-  final String key;
-  List<dynamic> get forwardingCurve25519KeyChain =>
-      content['forwarding_curve25519_key_chain'] ?? [];
-  String get senderClaimedEd25519Key =>
-      content['sender_claimed_ed25519_key'] ?? '';
-
-  SessionKey({this.content, this.inboundGroupSession, this.key, this.indexes});
-
-  SessionKey.fromDb(DbInboundGroupSession dbEntry, String key) : key = key {
-    final parsedContent = Event.getMapFromPayload(dbEntry.content);
-    final parsedIndexes = Event.getMapFromPayload(dbEntry.indexes);
-    content =
-        parsedContent != null ? Map<String, dynamic>.from(parsedContent) : null;
-    indexes = parsedIndexes != null
-        ? Map<String, int>.from(parsedIndexes)
-        : <String, int>{};
-    var newInboundGroupSession = InboundGroupSession();
-    newInboundGroupSession.unpickle(key, dbEntry.pickle);
-    inboundGroupSession = newInboundGroupSession;
-  }
-
-  SessionKey.fromJson(Map<String, dynamic> json, String key) : key = key {
-    content = json['content'] != null
-        ? Map<String, dynamic>.from(json['content'])
-        : null;
-    indexes = json['indexes'] != null
-        ? Map<String, int>.from(json['indexes'])
-        : <String, int>{};
-    var newInboundGroupSession = InboundGroupSession();
-    newInboundGroupSession.unpickle(key, json['inboundGroupSession']);
-    inboundGroupSession = newInboundGroupSession;
-  }
-
-  Map<String, dynamic> toJson() {
-    final data = <String, dynamic>{};
-    if (content != null) {
-      data['content'] = content;
-    }
-    if (indexes != null) {
-      data['indexes'] = indexes;
-    }
-    data['inboundGroupSession'] = inboundGroupSession.pickle(key);
-    return data;
-  }
-
-  @override
-  String toString() => json.encode(toJson());
-}

test/client_test.dart

@@ -17,7 +17,6 @@
  */
 
 import 'dart:async';
-import 'dart:convert';
 import 'dart:typed_data';
 
 import 'package:famedlysdk/famedlysdk.dart';
@@ -39,8 +38,9 @@ void main() {
   Future<List<EventUpdate>> eventUpdateListFuture;
   Future<List<ToDeviceEvent>> toDeviceUpdateListFuture;
 
+  // key @test:fakeServer.notExisting
   const pickledOlmAccount =
-      'N2v1MkIFGcl0mQpo2OCwSopxPQJ0wnl7oe7PKiT4141AijfdTIhRu+ceXzXKy3Kr00nLqXtRv7kid6hU4a+V0rfJWLL0Y51+3Rp/ORDVnQy+SSeo6Fn4FHcXrxifJEJ0djla5u98fBcJ8BSkhIDmtXRPi5/oJAvpiYn+8zMjFHobOeZUAxYR0VfQ9JzSYBsSovoQ7uFkNks1M4EDUvHtuweStA+EKZvvHZO0SnwRp0Hw7sv8UMYvXw';
+      'N2v1MkIFGcl0mQpo2OCwSopxPQJ0wnl7oe7PKiT4141AijfdTIhRu+ceXzXKy3Kr00nLqXtRv7kid6hU4a+V0rfJWLL0Y51+3Rp/ORDVnQy+SSeo6Fn4FHcXrxifJEJ0djla5u98fBcJ8BSkhIDmtXRPi5/oJAvpiYn+8zMjFHobOeZUAxYR0VfQ9JzSYBsSovoQ7uFkNks1M4EDUvHtuyg3RxViwdNxs3718fyAqQ/VSwbXsY0Nl+qQbF+nlVGHenGqk5SuNl1P6e1PzZxcR0IfXA94Xij1Ob5gDv5YH4UCn9wRMG0abZsQP0YzpDM0FLaHSCyo9i5JD/vMlhH+nZWrgAzPPCTNGYewNV8/h3c+VyJh8ZTx/fVi6Yq46Fv+27Ga2ETRZ3Qn+Oyx6dLBjnBZ9iUvIhqpe2XqaGA1PopOz8iDnaZitw';
   const identityKey = '7rvl3jORJkBiK4XX1e5TnGnqz068XfYJ0W++Ml63rgk';
   const fingerprintKey = 'gjL//fyaFHADt9KBADGag8g7F8Up78B/K1zXeiEPLJo';
 
@@ -134,24 +134,6 @@ void main() {
       expect(matrix.directChats, matrix.accountData['m.direct'].content);
       expect(matrix.presences.length, 1);
       expect(matrix.rooms[1].ephemerals.length, 2);
-      expect(matrix.rooms[1].inboundGroupSessions.length, 1);
-      expect(
-          matrix
-              .rooms[1]
-              .inboundGroupSessions[
-                  'ciM/JWTPrmiWPPZNkRLDPQYf9AW/I46bxyLSr+Bx5oU']
-              .content['session_key'],
-          'AgAAAAAQcQ6XrFJk6Prm8FikZDqfry/NbDz8Xw7T6e+/9Yf/q3YHIPEQlzv7IZMNcYb51ifkRzFejVvtphS7wwG2FaXIp4XS2obla14iKISR0X74ugB2vyb1AydIHE/zbBQ1ic5s3kgjMFlWpu/S3FQCnCrv+DPFGEt3ERGWxIl3Bl5X53IjPyVkz65oljz2TZESwz0GH/QFvyOOm8ci0q/gceaF3S7Dmafg3dwTKYwcA5xkcc+BLyrLRzB6Hn+oMAqSNSscnm4mTeT5zYibIhrzqyUTMWr32spFtI9dNR/RFSzfCw');
-      if (olmEnabled) {
-        expect(
-            matrix
-                    .rooms[1]
-                    .inboundGroupSessions[
-                        'ciM/JWTPrmiWPPZNkRLDPQYf9AW/I46bxyLSr+Bx5oU']
-                    .inboundGroupSession !=
-                null,
-            true);
-      }
       expect(matrix.rooms[1].typingUsers.length, 1);
       expect(matrix.rooms[1].typingUsers[0].id, '@alice:example.com');
       expect(matrix.rooms[1].roomAccountData.length, 3);
@@ -177,7 +159,7 @@ void main() {
       expect(presenceCounter, 1);
       expect(accountDataCounter, 3);
       await Future.delayed(Duration(milliseconds: 50));
-      expect(matrix.userDeviceKeys.length, 3);
+      expect(matrix.userDeviceKeys.length, 4);
       expect(matrix.userDeviceKeys['@alice:example.com'].outdated, false);
       expect(matrix.userDeviceKeys['@alice:example.com'].deviceKeys.length, 2);
       expect(
@@ -196,7 +178,7 @@ void main() {
         }
       }));
       await Future.delayed(Duration(milliseconds: 50));
-      expect(matrix.userDeviceKeys.length, 2);
+      expect(matrix.userDeviceKeys.length, 3);
       expect(matrix.userDeviceKeys['@alice:example.com'].outdated, true);
 
       await matrix.handleSync(SyncUpdate.fromJson({
@@ -335,7 +317,11 @@ void main() {
       expect(eventUpdateList.length, 2);
 
       expect(eventUpdateList[0].type, 'm.new_device');
+      if (olmEnabled) {
         expect(eventUpdateList[1].type, 'm.room_key');
+      } else {
+        expect(eventUpdateList[1].type, 'm.room.encrypted');
+      }
     });
 
     test('Login', () async {
@@ -388,115 +374,6 @@ void main() {
           'mxc://example.org/SEsfnsuifSDFSSEF');
       expect(aliceProfile.displayname, 'Alice Margatroid');
     });
-
-    test('signJson', () {
-      if (matrix.encryptionEnabled) {
-        expect(matrix.fingerprintKey.isNotEmpty, true);
-        expect(matrix.identityKey.isNotEmpty, true);
-        var payload = <String, dynamic>{
-          'unsigned': {
-            'foo': 'bar',
-          },
-          'auth': {
-            'success': true,
-            'mxid': '@john.doe:example.com',
-            'profile': {
-              'display_name': 'John Doe',
-              'three_pids': [
-                {'medium': 'email', 'address': 'john.doe@example.org'},
-                {'medium': 'msisdn', 'address': '123456789'}
-              ]
-            }
-          }
-        };
-        var payloadWithoutUnsigned = Map<String, dynamic>.from(payload);
-        payloadWithoutUnsigned.remove('unsigned');
-
-        expect(
-            matrix.checkJsonSignature(
-                matrix.fingerprintKey, payload, matrix.userID, matrix.deviceID),
-            false);
-        expect(
-            matrix.checkJsonSignature(matrix.fingerprintKey,
-                payloadWithoutUnsigned, matrix.userID, matrix.deviceID),
-            false);
-        payload = matrix.signJson(payload);
-        payloadWithoutUnsigned = matrix.signJson(payloadWithoutUnsigned);
-        expect(payload['signatures'], payloadWithoutUnsigned['signatures']);
-        print(payload['signatures']);
-        expect(
-            matrix.checkJsonSignature(
-                matrix.fingerprintKey, payload, matrix.userID, matrix.deviceID),
-            true);
-        expect(
-            matrix.checkJsonSignature(matrix.fingerprintKey,
-                payloadWithoutUnsigned, matrix.userID, matrix.deviceID),
-            true);
-      }
-    });
-    test('Track oneTimeKeys', () async {
-      if (matrix.encryptionEnabled) {
-        var last = matrix.lastTimeKeysUploaded ?? DateTime.now();
-        await matrix.handleSync(SyncUpdate.fromJson({
-          'device_one_time_keys_count': {'signed_curve25519': 49}
-        }));
-        await Future.delayed(Duration(milliseconds: 50));
-        expect(
-            matrix.lastTimeKeysUploaded.millisecondsSinceEpoch >
-                last.millisecondsSinceEpoch,
-            true);
-      }
-    });
-    test('Test invalidate outboundGroupSessions', () async {
-      if (matrix.encryptionEnabled) {
-        expect(matrix.rooms[1].outboundGroupSession == null, true);
-        await matrix.rooms[1].createOutboundGroupSession();
-        expect(matrix.rooms[1].outboundGroupSession != null, true);
-        await matrix.handleSync(SyncUpdate.fromJson({
-          'device_lists': {
-            'changed': [
-              '@alice:example.com',
-            ],
-            'left': [
-              '@bob:example.com',
-            ],
-          }
-        }));
-        await Future.delayed(Duration(milliseconds: 50));
-        expect(matrix.rooms[1].outboundGroupSession != null, true);
-      }
-    });
-    test('Test invalidate outboundGroupSessions', () async {
-      if (matrix.encryptionEnabled) {
-        await matrix.rooms[1].clearOutboundGroupSession(wipe: true);
-        expect(matrix.rooms[1].outboundGroupSession == null, true);
-        await matrix.rooms[1].createOutboundGroupSession();
-        expect(matrix.rooms[1].outboundGroupSession != null, true);
-        await matrix.handleSync(SyncUpdate.fromJson({
-          'rooms': {
-            'join': {
-              '!726s6s6q:example.com': {
-                'state': {
-                  'events': [
-                    {
-                      'content': {'membership': 'leave'},
-                      'event_id': '143273582443PhrSn:example.org',
-                      'origin_server_ts': 1432735824653,
-                      'room_id': '!726s6s6q:example.com',
-                      'sender': '@alice:example.com',
-                      'state_key': '@alice:example.com',
-                      'type': 'm.room.member'
-                    }
-                  ]
-                }
-              }
-            }
-          }
-        }));
-        await Future.delayed(Duration(milliseconds: 50));
-        expect(matrix.rooms[1].outboundGroupSession != null, true);
-      }
-    });
     var deviceKeys = DeviceKeys.fromJson({
       'user_id': '@alice:example.com',
       'device_id': 'JLAFKJWSCS',
@@ -512,16 +389,6 @@ void main() {
         }
       }
     });
-    test('startOutgoingOlmSessions', () async {
-      expect(matrix.olmSessions.length, 0);
-      if (olmEnabled) {
-        await matrix
-            .startOutgoingOlmSessions([deviceKeys], checkSignature: false);
-        expect(matrix.olmSessions.length, 1);
-        expect(matrix.olmSessions.entries.first.key,
-            '3C5BFWi2Y8MaVvjM8M22DBmh24PmgR0nPvJOIArzgyI');
-      }
-    });
     test('sendToDevice', () async {
       await matrix.sendToDevice(
           [deviceKeys],
@@ -547,13 +414,6 @@ void main() {
 
       await Future.delayed(Duration(milliseconds: 50));
 
-      String sessionKey;
-      if (client1.encryptionEnabled) {
-        await client1.rooms[1].createOutboundGroupSession();
-
-        sessionKey = client1.rooms[1].outboundGroupSession.session_key();
-      }
-
       expect(client1.isLogged(), true);
       expect(client1.rooms.length, 2);
 
@@ -571,12 +431,9 @@ void main() {
       expect(client2.deviceID, client1.deviceID);
       expect(client2.deviceName, client1.deviceName);
       if (client2.encryptionEnabled) {
-        await client2.rooms[1].restoreOutboundGroupSession();
+        expect(client2.encryption.pickledOlmAccount,
-        expect(client2.pickledOlmAccount, client1.pickledOlmAccount);
+            client1.encryption.pickledOlmAccount);
-        expect(json.encode(client2.rooms[1].inboundGroupSessions[sessionKey]),
-            json.encode(client1.rooms[1].inboundGroupSessions[sessionKey]));
         expect(client2.rooms[1].id, client1.rooms[1].id);
-        expect(client2.rooms[1].outboundGroupSession.session_key(), sessionKey);
       }
 
       await client1.logout();

test/encryption/encrypt_decrypt_room_message_test.dart

@@ -0,0 +1,99 @@
+/*
+ *   Ansible inventory script used at Famedly GmbH for managing many hosts
+ *   Copyright (C) 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+import 'package:famedlysdk/famedlysdk.dart';
+import 'package:test/test.dart';
+import 'package:olm/olm.dart' as olm;
+
+import '../fake_client.dart';
+
+void main() {
+  group('Encrypt/Decrypt room message', () {
+    var olmEnabled = true;
+    try {
+      olm.init();
+      olm.Account();
+    } catch (_) {
+      olmEnabled = false;
+      print('[LibOlm] Failed to load LibOlm: ' + _.toString());
+    }
+    print('[LibOlm] Enabled: $olmEnabled');
+
+    if (!olmEnabled) return;
+
+    Client client;
+    final roomId = '!726s6s6q:example.com';
+    Room room;
+    Map<String, dynamic> payload;
+    final now = DateTime.now();
+
+    test('setupClient', () async {
+      client = await getClient();
+      room = client.getRoomById(roomId);
+    });
+
+    test('encrypt payload', () async {
+      payload = await client.encryption.encryptGroupMessagePayload(roomId, {
+        'msgtype': 'm.text',
+        'text': 'Hello foxies!',
+      });
+      expect(payload['algorithm'], 'm.megolm.v1.aes-sha2');
+      expect(payload['ciphertext'] is String, true);
+      expect(payload['device_id'], client.deviceID);
+      expect(payload['sender_key'], client.identityKey);
+      expect(payload['session_id'] is String, true);
+    });
+
+    test('decrypt payload', () async {
+      final encryptedEvent = Event(
+        type: EventTypes.Encrypted,
+        content: payload,
+        roomId: roomId,
+        room: room,
+        originServerTs: now,
+        eventId: '\$event',
+      );
+      final decryptedEvent =
+          await client.encryption.decryptRoomEvent(roomId, encryptedEvent);
+      expect(decryptedEvent.type, 'm.room.message');
+      expect(decryptedEvent.content['msgtype'], 'm.text');
+      expect(decryptedEvent.content['text'], 'Hello foxies!');
+    });
+
+    test('decrypt payload nocache', () async {
+      client.encryption.keyManager.clearInboundGroupSessions();
+      final encryptedEvent = Event(
+        type: EventTypes.Encrypted,
+        content: payload,
+        roomId: roomId,
+        room: room,
+        originServerTs: now,
+        eventId: '\$event',
+      );
+      final decryptedEvent =
+          await client.encryption.decryptRoomEvent(roomId, encryptedEvent);
+      expect(decryptedEvent.type, 'm.room.message');
+      expect(decryptedEvent.content['msgtype'], 'm.text');
+      expect(decryptedEvent.content['text'], 'Hello foxies!');
+    });
+
+    test('dispose client', () async {
+      await client.dispose(closeDatabase: true);
+    });
+  });
+}

test/encryption/encrypt_decrypt_to_device_test.dart

@@ -0,0 +1,120 @@
+/*
+ *   Ansible inventory script used at Famedly GmbH for managing many hosts
+ *   Copyright (C) 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+import 'package:famedlysdk/famedlysdk.dart';
+import 'package:test/test.dart';
+import 'package:olm/olm.dart' as olm;
+
+import '../fake_client.dart';
+import '../fake_matrix_api.dart';
+
+void main() {
+  // key @othertest:fakeServer.notExisting
+  const otherPickledOlmAccount =
+      'VWhVApbkcilKAEGppsPDf9nNVjaK8/IxT3asSR0sYg0S5KgbfE8vXEPwoiKBX2cEvwX3OessOBOkk+ZE7TTbjlrh/KEd31p8Wo+47qj0AP+Ky+pabnhi+/rTBvZy+gfzTqUfCxZrkzfXI9Op4JnP6gYmy7dVX2lMYIIs9WCO1jcmIXiXum5jnfXu1WLfc7PZtO2hH+k9CDKosOFaXRBmsu8k/BGXPSoWqUpvu6WpEG9t5STk4FeAzA';
+
+  group('Encrypt/Decrypt to-device messages', () {
+    var olmEnabled = true;
+    try {
+      olm.init();
+      olm.Account();
+    } catch (_) {
+      olmEnabled = false;
+      print('[LibOlm] Failed to load LibOlm: ' + _.toString());
+    }
+    print('[LibOlm] Enabled: $olmEnabled');
+
+    if (!olmEnabled) return;
+
+    Client client;
+    var otherClient =
+        Client('othertestclient', debug: true, httpClient: FakeMatrixApi());
+    DeviceKeys device;
+    Map<String, dynamic> payload;
+
+    test('setupClient', () async {
+      client = await getClient();
+      otherClient.database = client.database;
+      await otherClient.checkServer('https://fakeServer.notExisting');
+      otherClient.connect(
+        newToken: 'abc',
+        newUserID: '@othertest:fakeServer.notExisting',
+        newHomeserver: otherClient.api.homeserver,
+        newDeviceName: 'Text Matrix Client',
+        newDeviceID: 'FOXDEVICE',
+        newOlmAccount: otherPickledOlmAccount,
+      );
+
+      await Future.delayed(Duration(milliseconds: 10));
+      device = DeviceKeys(
+        userId: client.userID,
+        deviceId: client.deviceID,
+        algorithms: ['m.olm.v1.curve25519-aes-sha2', 'm.megolm.v1.aes-sha2'],
+        keys: {
+          'curve25519:${client.deviceID}': client.identityKey,
+          'ed25519:${client.deviceID}': client.fingerprintKey,
+        },
+        verified: true,
+        blocked: false,
+      );
+    });
+
+    test('encryptToDeviceMessage', () async {
+      payload = await otherClient.encryption
+          .encryptToDeviceMessage([device], 'm.to_device', {'hello': 'foxies'});
+    });
+
+    test('encryptToDeviceMessagePayload', () async {
+      // just a hard test if nothing errors
+      await otherClient.encryption.encryptToDeviceMessagePayload(
+          device, 'm.to_device', {'hello': 'foxies'});
+    });
+
+    test('decryptToDeviceEvent', () async {
+      final encryptedEvent = ToDeviceEvent(
+        sender: '@othertest:fakeServer.notExisting',
+        type: EventTypes.Encrypted,
+        content: payload[client.userID][client.deviceID],
+      );
+      final decryptedEvent =
+          await client.encryption.decryptToDeviceEvent(encryptedEvent);
+      expect(decryptedEvent.type, 'm.to_device');
+      expect(decryptedEvent.content['hello'], 'foxies');
+    });
+
+    test('decryptToDeviceEvent nocache', () async {
+      client.encryption.olmManager.olmSessions.clear();
+      payload = await otherClient.encryption.encryptToDeviceMessage(
+          [device], 'm.to_device', {'hello': 'superfoxies'});
+      final encryptedEvent = ToDeviceEvent(
+        sender: '@othertest:fakeServer.notExisting',
+        type: EventTypes.Encrypted,
+        content: payload[client.userID][client.deviceID],
+      );
+      final decryptedEvent =
+          await client.encryption.decryptToDeviceEvent(encryptedEvent);
+      expect(decryptedEvent.type, 'm.to_device');
+      expect(decryptedEvent.content['hello'], 'superfoxies');
+    });
+
+    test('dispose client', () async {
+      await client.dispose(closeDatabase: true);
+      await otherClient.dispose(closeDatabase: true);
+    });
+  });
+}

test/encryption/key_manager_test.dart

@@ -0,0 +1,223 @@
+/*
+ *   Ansible inventory script used at Famedly GmbH for managing many hosts
+ *   Copyright (C) 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+import 'package:famedlysdk/famedlysdk.dart';
+import 'package:test/test.dart';
+import 'package:olm/olm.dart' as olm;
+
+import '../fake_client.dart';
+
+void main() {
+  group('Key Manager', () {
+    var olmEnabled = true;
+    try {
+      olm.init();
+      olm.Account();
+    } catch (_) {
+      olmEnabled = false;
+      print('[LibOlm] Failed to load LibOlm: ' + _.toString());
+    }
+    print('[LibOlm] Enabled: $olmEnabled');
+
+    if (!olmEnabled) return;
+
+    Client client;
+
+    test('setupClient', () async {
+      client = await getClient();
+    });
+
+    test('handle new m.room_key', () async {
+      final validSessionId = 'ciM/JWTPrmiWPPZNkRLDPQYf9AW/I46bxyLSr+Bx5oU';
+      final validSenderKey = 'JBG7ZaPn54OBC7TuIEiylW3BZ+7WcGQhFBPB9pogbAg';
+      final sessionKey =
+          'AgAAAAAQcQ6XrFJk6Prm8FikZDqfry/NbDz8Xw7T6e+/9Yf/q3YHIPEQlzv7IZMNcYb51ifkRzFejVvtphS7wwG2FaXIp4XS2obla14iKISR0X74ugB2vyb1AydIHE/zbBQ1ic5s3kgjMFlWpu/S3FQCnCrv+DPFGEt3ERGWxIl3Bl5X53IjPyVkz65oljz2TZESwz0GH/QFvyOOm8ci0q/gceaF3S7Dmafg3dwTKYwcA5xkcc+BLyrLRzB6Hn+oMAqSNSscnm4mTeT5zYibIhrzqyUTMWr32spFtI9dNR/RFSzfCw';
+
+      client.encryption.keyManager.clearInboundGroupSessions();
+      var event = ToDeviceEvent(
+          sender: '@alice:example.com',
+          type: 'm.room_key',
+          content: {
+            'algorithm': 'm.megolm.v1.aes-sha2',
+            'room_id': '!726s6s6q:example.com',
+            'session_id': validSessionId,
+            'session_key': sessionKey,
+          },
+          encryptedContent: {
+            'sender_key': validSessionId,
+          });
+      await client.encryption.keyManager.handleToDeviceEvent(event);
+      expect(
+          client.encryption.keyManager.getInboundGroupSession(
+                  '!726s6s6q:example.com', validSessionId, validSenderKey) !=
+              null,
+          true);
+
+      // now test a few invalid scenarios
+
+      // not encrypted
+      client.encryption.keyManager.clearInboundGroupSessions();
+      event = ToDeviceEvent(
+          sender: '@alice:example.com',
+          type: 'm.room_key',
+          content: {
+            'algorithm': 'm.megolm.v1.aes-sha2',
+            'room_id': '!726s6s6q:example.com',
+            'session_id': validSessionId,
+            'session_key': sessionKey,
+          });
+      await client.encryption.keyManager.handleToDeviceEvent(event);
+      expect(
+          client.encryption.keyManager.getInboundGroupSession(
+                  '!726s6s6q:example.com', validSessionId, validSenderKey) !=
+              null,
+          false);
+    });
+
+    test('outbound group session', () async {
+      final roomId = '!726s6s6q:example.com';
+      expect(
+          client.encryption.keyManager.getOutboundGroupSession(roomId) != null,
+          false);
+      var sess =
+          await client.encryption.keyManager.createOutboundGroupSession(roomId);
+      expect(
+          client.encryption.keyManager.getOutboundGroupSession(roomId) != null,
+          true);
+      await client.encryption.keyManager.clearOutboundGroupSession(roomId);
+      expect(
+          client.encryption.keyManager.getOutboundGroupSession(roomId) != null,
+          true);
+      expect(
+          client.encryption.keyManager.getInboundGroupSession(roomId,
+                  sess.outboundGroupSession.session_id(), client.identityKey) !=
+              null,
+          true);
+
+      // rotate after too many messages
+      sess.sentMessages = 300;
+      await client.encryption.keyManager.clearOutboundGroupSession(roomId);
+      expect(
+          client.encryption.keyManager.getOutboundGroupSession(roomId) != null,
+          false);
+
+      // rotate if devices in room change
+      sess =
+          await client.encryption.keyManager.createOutboundGroupSession(roomId);
+      client.userDeviceKeys['@alice:example.com'].deviceKeys['JLAFKJWSCS']
+          .blocked = true;
+      await client.encryption.keyManager.clearOutboundGroupSession(roomId);
+      expect(
+          client.encryption.keyManager.getOutboundGroupSession(roomId) != null,
+          false);
+      client.userDeviceKeys['@alice:example.com'].deviceKeys['JLAFKJWSCS']
+          .blocked = false;
+
+      // rotate if too far in the past
+      sess =
+          await client.encryption.keyManager.createOutboundGroupSession(roomId);
+      sess.creationTime = DateTime.now().subtract(Duration(days: 30));
+      await client.encryption.keyManager.clearOutboundGroupSession(roomId);
+      expect(
+          client.encryption.keyManager.getOutboundGroupSession(roomId) != null,
+          false);
+
+      // force wipe
+      sess =
+          await client.encryption.keyManager.createOutboundGroupSession(roomId);
+      await client.encryption.keyManager
+          .clearOutboundGroupSession(roomId, wipe: true);
+      expect(
+          client.encryption.keyManager.getOutboundGroupSession(roomId) != null,
+          false);
+
+      // load from database
+      sess =
+          await client.encryption.keyManager.createOutboundGroupSession(roomId);
+      client.encryption.keyManager.clearOutboundGroupSessions();
+      expect(
+          client.encryption.keyManager.getOutboundGroupSession(roomId) != null,
+          false);
+      await client.encryption.keyManager.loadOutboundGroupSession(roomId);
+      expect(
+          client.encryption.keyManager.getOutboundGroupSession(roomId) != null,
+          true);
+    });
+
+    test('inbound group session', () async {
+      final roomId = '!726s6s6q:example.com';
+      final sessionId = 'ciM/JWTPrmiWPPZNkRLDPQYf9AW/I46bxyLSr+Bx5oU';
+      final senderKey = 'JBG7ZaPn54OBC7TuIEiylW3BZ+7WcGQhFBPB9pogbAg';
+      final sessionContent = <String, dynamic>{
+        'algorithm': 'm.megolm.v1.aes-sha2',
+        'room_id': '!726s6s6q:example.com',
+        'session_id': 'ciM/JWTPrmiWPPZNkRLDPQYf9AW/I46bxyLSr+Bx5oU',
+        'session_key':
+            'AgAAAAAQcQ6XrFJk6Prm8FikZDqfry/NbDz8Xw7T6e+/9Yf/q3YHIPEQlzv7IZMNcYb51ifkRzFejVvtphS7wwG2FaXIp4XS2obla14iKISR0X74ugB2vyb1AydIHE/zbBQ1ic5s3kgjMFlWpu/S3FQCnCrv+DPFGEt3ERGWxIl3Bl5X53IjPyVkz65oljz2TZESwz0GH/QFvyOOm8ci0q/gceaF3S7Dmafg3dwTKYwcA5xkcc+BLyrLRzB6Hn+oMAqSNSscnm4mTeT5zYibIhrzqyUTMWr32spFtI9dNR/RFSzfCw'
+      };
+      client.encryption.keyManager.clearInboundGroupSessions();
+      expect(
+          client.encryption.keyManager
+                  .getInboundGroupSession(roomId, sessionId, senderKey) !=
+              null,
+          false);
+      client.encryption.keyManager
+          .setInboundGroupSession(roomId, sessionId, senderKey, sessionContent);
+      await Future.delayed(Duration(milliseconds: 10));
+      expect(
+          client.encryption.keyManager
+                  .getInboundGroupSession(roomId, sessionId, senderKey) !=
+              null,
+          true);
+
+      expect(
+          client.encryption.keyManager
+                  .getInboundGroupSession(roomId, sessionId, senderKey) !=
+              null,
+          true);
+      expect(
+          client.encryption.keyManager
+                  .getInboundGroupSession('otherroom', sessionId, senderKey) !=
+              null,
+          true);
+      expect(
+          client.encryption.keyManager
+                  .getInboundGroupSession('otherroom', 'invalid', senderKey) !=
+              null,
+          false);
+
+      client.encryption.keyManager.clearInboundGroupSessions();
+      expect(
+          client.encryption.keyManager
+                  .getInboundGroupSession(roomId, sessionId, senderKey) !=
+              null,
+          false);
+      await client.encryption.keyManager
+          .loadInboundGroupSession(roomId, sessionId, senderKey);
+      expect(
+          client.encryption.keyManager
+                  .getInboundGroupSession(roomId, sessionId, senderKey) !=
+              null,
+          true);
+    });
+
+    test('dispose client', () async {
+      await client.dispose(closeDatabase: true);
+    });
+  });
+}

test/encryption/key_request_test.dart

@@ -0,0 +1,331 @@
+/*
+ *   Ansible inventory script used at Famedly GmbH for managing many hosts
+ *   Copyright (C) 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+import 'dart:convert';
+import 'package:famedlysdk/famedlysdk.dart';
+import 'package:test/test.dart';
+import 'package:olm/olm.dart' as olm;
+
+import '../fake_client.dart';
+import '../fake_matrix_api.dart';
+
+Map<String, dynamic> jsonDecode(dynamic payload) {
+  if (payload is String) {
+    try {
+      return json.decode(payload);
+    } catch (e) {
+      return {};
+    }
+  }
+  if (payload is Map<String, dynamic>) return payload;
+  return {};
+}
+
+void main() {
+  /// All Tests related to device keys
+  group('Key Request', () {
+    var olmEnabled = true;
+    try {
+      olm.init();
+      olm.Account();
+    } catch (_) {
+      olmEnabled = false;
+      print('[LibOlm] Failed to load LibOlm: ' + _.toString());
+    }
+    print('[LibOlm] Enabled: $olmEnabled');
+
+    if (!olmEnabled) return;
+
+    final validSessionId = 'ciM/JWTPrmiWPPZNkRLDPQYf9AW/I46bxyLSr+Bx5oU';
+    final validSenderKey = '3C5BFWi2Y8MaVvjM8M22DBmh24PmgR0nPvJOIArzgyI';
+    test('Create Request', () async {
+      var matrix = await getClient();
+      final requestRoom = matrix.getRoomById('!726s6s6q:example.com');
+      await matrix.encryption.keyManager
+          .request(requestRoom, 'sessionId', validSenderKey);
+      var foundEvent = false;
+      for (var entry in FakeMatrixApi.calledEndpoints.entries) {
+        final payload = jsonDecode(entry.value.first);
+        if (entry.key
+                .startsWith('/client/r0/sendToDevice/m.room_key_request') &&
+            (payload['messages'] is Map) &&
+            (payload['messages']['@alice:example.com'] is Map) &&
+            (payload['messages']['@alice:example.com']['*'] is Map)) {
+          final content = payload['messages']['@alice:example.com']['*'];
+          if (content['action'] == 'request' &&
+              content['body']['room_id'] == '!726s6s6q:example.com' &&
+              content['body']['sender_key'] == validSenderKey &&
+              content['body']['session_id'] == 'sessionId') {
+            foundEvent = true;
+            break;
+          }
+        }
+      }
+      expect(foundEvent, true);
+      await matrix.dispose(closeDatabase: true);
+    });
+    test('Reply To Request', () async {
+      var matrix = await getClient();
+      matrix.setUserId('@alice:example.com'); // we need to pretend to be alice
+      FakeMatrixApi.calledEndpoints.clear();
+      await matrix
+          .userDeviceKeys['@alice:example.com'].deviceKeys['OTHERDEVICE']
+          .setBlocked(false, matrix);
+      await matrix
+          .userDeviceKeys['@alice:example.com'].deviceKeys['OTHERDEVICE']
+          .setVerified(true, matrix);
+      // test a successful share
+      var event = ToDeviceEvent(
+          sender: '@alice:example.com',
+          type: 'm.room_key_request',
+          content: {
+            'action': 'request',
+            'body': {
+              'algorithm': 'm.megolm.v1.aes-sha2',
+              'room_id': '!726s6s6q:example.com',
+              'sender_key': validSenderKey,
+              'session_id': validSessionId,
+            },
+            'request_id': 'request_1',
+            'requesting_device_id': 'OTHERDEVICE',
+          });
+      await matrix.encryption.keyManager.handleToDeviceEvent(event);
+      print(FakeMatrixApi.calledEndpoints.keys.toString());
+      expect(
+          FakeMatrixApi.calledEndpoints.keys.any(
+              (k) => k.startsWith('/client/r0/sendToDevice/m.room.encrypted')),
+          true);
+
+      // test various fail scenarios
+
+      // no body
+      FakeMatrixApi.calledEndpoints.clear();
+      event = ToDeviceEvent(
+          sender: '@alice:example.com',
+          type: 'm.room_key_request',
+          content: {
+            'action': 'request',
+            'request_id': 'request_2',
+            'requesting_device_id': 'OTHERDEVICE',
+          });
+      await matrix.encryption.keyManager.handleToDeviceEvent(event);
+      expect(
+          FakeMatrixApi.calledEndpoints.keys.any(
+              (k) => k.startsWith('/client/r0/sendToDevice/m.room.encrypted')),
+          false);
+
+      // request by ourself
+      FakeMatrixApi.calledEndpoints.clear();
+      event = ToDeviceEvent(
+          sender: '@alice:example.com',
+          type: 'm.room_key_request',
+          content: {
+            'action': 'request',
+            'body': {
+              'algorithm': 'm.megolm.v1.aes-sha2',
+              'room_id': '!726s6s6q:example.com',
+              'sender_key': validSenderKey,
+              'session_id': validSessionId,
+            },
+            'request_id': 'request_3',
+            'requesting_device_id': 'JLAFKJWSCS',
+          });
+      await matrix.encryption.keyManager.handleToDeviceEvent(event);
+      expect(
+          FakeMatrixApi.calledEndpoints.keys.any(
+              (k) => k.startsWith('/client/r0/sendToDevice/m.room.encrypted')),
+          false);
+
+      // device not found
+      FakeMatrixApi.calledEndpoints.clear();
+      event = ToDeviceEvent(
+          sender: '@alice:example.com',
+          type: 'm.room_key_request',
+          content: {
+            'action': 'request',
+            'body': {
+              'algorithm': 'm.megolm.v1.aes-sha2',
+              'room_id': '!726s6s6q:example.com',
+              'sender_key': validSenderKey,
+              'session_id': validSessionId,
+            },
+            'request_id': 'request_4',
+            'requesting_device_id': 'blubb',
+          });
+      await matrix.encryption.keyManager.handleToDeviceEvent(event);
+      expect(
+          FakeMatrixApi.calledEndpoints.keys.any(
+              (k) => k.startsWith('/client/r0/sendToDevice/m.room.encrypted')),
+          false);
+
+      // unknown room
+      FakeMatrixApi.calledEndpoints.clear();
+      event = ToDeviceEvent(
+          sender: '@alice:example.com',
+          type: 'm.room_key_request',
+          content: {
+            'action': 'request',
+            'body': {
+              'algorithm': 'm.megolm.v1.aes-sha2',
+              'room_id': '!invalid:example.com',
+              'sender_key': validSenderKey,
+              'session_id': validSessionId,
+            },
+            'request_id': 'request_5',
+            'requesting_device_id': 'OTHERDEVICE',
+          });
+      await matrix.encryption.keyManager.handleToDeviceEvent(event);
+      expect(
+          FakeMatrixApi.calledEndpoints.keys.any(
+              (k) => k.startsWith('/client/r0/sendToDevice/m.room.encrypted')),
+          false);
+
+      // unknwon session
+      FakeMatrixApi.calledEndpoints.clear();
+      event = ToDeviceEvent(
+          sender: '@alice:example.com',
+          type: 'm.room_key_request',
+          content: {
+            'action': 'request',
+            'body': {
+              'algorithm': 'm.megolm.v1.aes-sha2',
+              'room_id': '!726s6s6q:example.com',
+              'sender_key': validSenderKey,
+              'session_id': 'invalid',
+            },
+            'request_id': 'request_6',
+            'requesting_device_id': 'OTHERDEVICE',
+          });
+      await matrix.encryption.keyManager.handleToDeviceEvent(event);
+      expect(
+          FakeMatrixApi.calledEndpoints.keys.any(
+              (k) => k.startsWith('/client/r0/sendToDevice/m.room.encrypted')),
+          false);
+
+      FakeMatrixApi.calledEndpoints.clear();
+      await matrix.dispose(closeDatabase: true);
+    });
+    test('Receive shared keys', () async {
+      var matrix = await getClient();
+      final requestRoom = matrix.getRoomById('!726s6s6q:example.com');
+      await matrix.encryption.keyManager
+          .request(requestRoom, validSessionId, validSenderKey);
+
+      final session = await matrix.encryption.keyManager
+          .loadInboundGroupSession(
+              requestRoom.id, validSessionId, validSenderKey);
+      final sessionKey = session.inboundGroupSession
+          .export_session(session.inboundGroupSession.first_known_index());
+      matrix.encryption.keyManager.clearInboundGroupSessions();
+      var event = ToDeviceEvent(
+          sender: '@alice:example.com',
+          type: 'm.forwarded_room_key',
+          content: {
+            'algorithm': 'm.megolm.v1.aes-sha2',
+            'room_id': '!726s6s6q:example.com',
+            'session_id': validSessionId,
+            'session_key': sessionKey,
+            'sender_key': validSenderKey,
+            'forwarding_curve25519_key_chain': [],
+          },
+          encryptedContent: {
+            'sender_key': '3C5BFWi2Y8MaVvjM8M22DBmh24PmgR0nPvJOIArzgyI',
+          });
+      await matrix.encryption.keyManager.handleToDeviceEvent(event);
+      expect(
+          matrix.encryption.keyManager.getInboundGroupSession(
+                  requestRoom.id, validSessionId, validSenderKey) !=
+              null,
+          true);
+
+      // now test a few invalid scenarios
+
+      // request not found
+      matrix.encryption.keyManager.clearInboundGroupSessions();
+      event = ToDeviceEvent(
+          sender: '@alice:example.com',
+          type: 'm.forwarded_room_key',
+          content: {
+            'algorithm': 'm.megolm.v1.aes-sha2',
+            'room_id': '!726s6s6q:example.com',
+            'session_id': validSessionId,
+            'session_key': sessionKey,
+            'sender_key': validSenderKey,
+            'forwarding_curve25519_key_chain': [],
+          },
+          encryptedContent: {
+            'sender_key': '3C5BFWi2Y8MaVvjM8M22DBmh24PmgR0nPvJOIArzgyI',
+          });
+      await matrix.encryption.keyManager.handleToDeviceEvent(event);
+      expect(
+          matrix.encryption.keyManager.getInboundGroupSession(
+                  requestRoom.id, validSessionId, validSenderKey) !=
+              null,
+          false);
+
+      // unknown device
+      await matrix.encryption.keyManager
+          .request(requestRoom, validSessionId, validSenderKey);
+      matrix.encryption.keyManager.clearInboundGroupSessions();
+      event = ToDeviceEvent(
+          sender: '@alice:example.com',
+          type: 'm.forwarded_room_key',
+          content: {
+            'algorithm': 'm.megolm.v1.aes-sha2',
+            'room_id': '!726s6s6q:example.com',
+            'session_id': validSessionId,
+            'session_key': sessionKey,
+            'sender_key': validSenderKey,
+            'forwarding_curve25519_key_chain': [],
+          },
+          encryptedContent: {
+            'sender_key': 'invalid',
+          });
+      await matrix.encryption.keyManager.handleToDeviceEvent(event);
+      expect(
+          matrix.encryption.keyManager.getInboundGroupSession(
+                  requestRoom.id, validSessionId, validSenderKey) !=
+              null,
+          false);
+
+      // no encrypted content
+      await matrix.encryption.keyManager
+          .request(requestRoom, validSessionId, validSenderKey);
+      matrix.encryption.keyManager.clearInboundGroupSessions();
+      event = ToDeviceEvent(
+          sender: '@alice:example.com',
+          type: 'm.forwarded_room_key',
+          content: {
+            'algorithm': 'm.megolm.v1.aes-sha2',
+            'room_id': '!726s6s6q:example.com',
+            'session_id': validSessionId,
+            'session_key': sessionKey,
+            'sender_key': validSenderKey,
+            'forwarding_curve25519_key_chain': [],
+          });
+      await matrix.encryption.keyManager.handleToDeviceEvent(event);
+      expect(
+          matrix.encryption.keyManager.getInboundGroupSession(
+                  requestRoom.id, validSessionId, validSenderKey) !=
+              null,
+          false);
+
+      await matrix.dispose(closeDatabase: true);
+    });
+  });
+}

test/encryption/key_verification_test.dart

@@ -1,6 +1,6 @@
 /*
  *   Ansible inventory script used at Famedly GmbH for managing many hosts
- *   Copyright (C) 2019, 2020 Famedly GmbH
+ *   Copyright (C) 2020 Famedly GmbH
  *
  *   This program is free software: you can redistribute it and/or modify
  *   it under the terms of the GNU Affero General Public License as
@@ -17,10 +17,11 @@
  */
 
 import 'package:famedlysdk/famedlysdk.dart';
+import 'package:famedlysdk/encryption.dart';
 import 'package:test/test.dart';
 import 'package:olm/olm.dart' as olm;
 
-import 'fake_matrix_api.dart';
+import '../fake_client.dart';
 
 void main() {
   /// All Tests related to the ChatTime
@@ -35,19 +36,24 @@ void main() {
     }
     print('[LibOlm] Enabled: $olmEnabled');
 
-    var client = Client('testclient', debug: true, httpClient: FakeMatrixApi());
+    if (!olmEnabled) return;
-    client.api.homeserver = Uri.parse('https://fakeserver.notexisting');
+
-    var room = Room(id: '!localpart:server.abc', client: client);
+    Client client;
+    Room room;
     var updateCounter = 0;
-    final keyVerification = KeyVerification(
+    KeyVerification keyVerification;
-      client: client,
+
+    test('setupClient', () async {
+      client = await getClient();
+      room = Room(id: '!localpart:server.abc', client: client);
+      keyVerification = KeyVerification(
+        encryption: client.encryption,
         room: room,
         userId: '@alice:example.com',
         deviceId: 'ABCD',
         onUpdate: () => updateCounter++,
       );
-
+    });
-    if (!olmEnabled) return;
 
     test('acceptSas', () async {
       await keyVerification.acceptSas();
@@ -91,7 +97,11 @@ void main() {
     test('verifyActivity', () async {
       final verified = await keyVerification.verifyActivity();
       expect(verified, true);
+      keyVerification?.dispose();
+    });
+
+    test('dispose client', () async {
+      await client.dispose(closeDatabase: true);
     });
-    keyVerification.dispose();
   });
 }

test/encryption/olm_manager_test.dart

@@ -0,0 +1,116 @@
+/*
+ *   Ansible inventory script used at Famedly GmbH for managing many hosts
+ *   Copyright (C) 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+import 'dart:convert';
+import 'package:famedlysdk/famedlysdk.dart';
+import 'package:test/test.dart';
+import 'package:olm/olm.dart' as olm;
+
+import '../fake_client.dart';
+import '../fake_matrix_api.dart';
+
+void main() {
+  group('Olm Manager', () {
+    var olmEnabled = true;
+    try {
+      olm.init();
+      olm.Account();
+    } catch (_) {
+      olmEnabled = false;
+      print('[LibOlm] Failed to load LibOlm: ' + _.toString());
+    }
+    print('[LibOlm] Enabled: $olmEnabled');
+
+    if (!olmEnabled) return;
+
+    Client client;
+
+    test('setupClient', () async {
+      client = await getClient();
+    });
+
+    test('signatures', () async {
+      final payload = <String, dynamic>{
+        'fox': 'floof',
+      };
+      final signedPayload = client.encryption.olmManager.signJson(payload);
+      expect(
+          client.encryption.olmManager.checkJsonSignature(client.fingerprintKey,
+              signedPayload, client.userID, client.deviceID),
+          true);
+      expect(
+          client.encryption.olmManager.checkJsonSignature(
+              client.fingerprintKey, payload, client.userID, client.deviceID),
+          false);
+    });
+
+    test('uploadKeys', () async {
+      FakeMatrixApi.calledEndpoints.clear();
+      final res =
+          await client.encryption.olmManager.uploadKeys(uploadDeviceKeys: true);
+      expect(res, true);
+      var sent = json.decode(
+          FakeMatrixApi.calledEndpoints['/client/r0/keys/upload'].first);
+      expect(sent['device_keys'] != null, true);
+      expect(sent['one_time_keys'] != null, true);
+      expect(sent['one_time_keys'].keys.length, 66);
+      FakeMatrixApi.calledEndpoints.clear();
+      await client.encryption.olmManager.uploadKeys();
+      sent = json.decode(
+          FakeMatrixApi.calledEndpoints['/client/r0/keys/upload'].first);
+      expect(sent['device_keys'] != null, false);
+      FakeMatrixApi.calledEndpoints.clear();
+      await client.encryption.olmManager.uploadKeys(oldKeyCount: 20);
+      sent = json.decode(
+          FakeMatrixApi.calledEndpoints['/client/r0/keys/upload'].first);
+      expect(sent['one_time_keys'].keys.length, 46);
+    });
+
+    test('handleDeviceOneTimeKeysCount', () async {
+      FakeMatrixApi.calledEndpoints.clear();
+      client.encryption.olmManager
+          .handleDeviceOneTimeKeysCount({'signed_curve25519': 20});
+      await Future.delayed(Duration(milliseconds: 50));
+      expect(
+          FakeMatrixApi.calledEndpoints.containsKey('/client/r0/keys/upload'),
+          true);
+
+      FakeMatrixApi.calledEndpoints.clear();
+      client.encryption.olmManager
+          .handleDeviceOneTimeKeysCount({'signed_curve25519': 70});
+      await Future.delayed(Duration(milliseconds: 50));
+      expect(
+          FakeMatrixApi.calledEndpoints.containsKey('/client/r0/keys/upload'),
+          false);
+    });
+
+    test('startOutgoingOlmSessions', () async {
+      // start an olm session.....with ourself!
+      await client.encryption.olmManager.startOutgoingOlmSessions(
+          [client.userDeviceKeys[client.userID].deviceKeys[client.deviceID]]);
+      expect(
+          client.encryption.olmManager.olmSessions
+              .containsKey(client.identityKey),
+          true);
+    });
+
+    test('dispose client', () async {
+      await client.dispose(closeDatabase: true);
+    });
+  });
+}

test/event_test.dart

@@ -20,6 +20,7 @@ import 'dart:convert';
 
 import 'package:famedlysdk/famedlysdk.dart';
 import 'package:famedlysdk/matrix_api.dart';
+import 'package:famedlysdk/encryption.dart';
 import 'package:famedlysdk/src/event.dart';
 import 'package:test/test.dart';
 
@@ -219,7 +220,7 @@ void main() {
       event.status = -1;
       final resp2 = await event.sendAgain(txid: '1234');
       expect(resp1, null);
-      expect(resp2, '42');
+      expect(resp2.startsWith('\$event'), true);
 
       await matrix.dispose(closeDatabase: true);
     });

test/fake_client.dart

@@ -0,0 +1,48 @@
+/*
+ *   Ansible inventory script used at Famedly GmbH for managing many hosts
+ *   Copyright (C) 2020 Famedly GmbH
+ *
+ *   This program is free software: you can redistribute it and/or modify
+ *   it under the terms of the GNU Affero General Public License as
+ *   published by the Free Software Foundation, either version 3 of the
+ *   License, or (at your option) any later version.
+ *
+ *   This program is distributed in the hope that it will be useful,
+ *   but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ *   GNU Affero General Public License for more details.
+ *
+ *   You should have received a copy of the GNU Affero General Public License
+ *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+import 'package:famedlysdk/famedlysdk.dart';
+
+import 'fake_matrix_api.dart';
+import 'fake_database.dart';
+
+// key @test:fakeServer.notExisting
+const pickledOlmAccount =
+    'N2v1MkIFGcl0mQpo2OCwSopxPQJ0wnl7oe7PKiT4141AijfdTIhRu+ceXzXKy3Kr00nLqXtRv7kid6hU4a+V0rfJWLL0Y51+3Rp/ORDVnQy+SSeo6Fn4FHcXrxifJEJ0djla5u98fBcJ8BSkhIDmtXRPi5/oJAvpiYn+8zMjFHobOeZUAxYR0VfQ9JzSYBsSovoQ7uFkNks1M4EDUvHtuyg3RxViwdNxs3718fyAqQ/VSwbXsY0Nl+qQbF+nlVGHenGqk5SuNl1P6e1PzZxcR0IfXA94Xij1Ob5gDv5YH4UCn9wRMG0abZsQP0YzpDM0FLaHSCyo9i5JD/vMlhH+nZWrgAzPPCTNGYewNV8/h3c+VyJh8ZTx/fVi6Yq46Fv+27Ga2ETRZ3Qn+Oyx6dLBjnBZ9iUvIhqpe2XqaGA1PopOz8iDnaZitw';
+
+Future<Client> getClient() async {
+  final client = Client('testclient', debug: true, httpClient: FakeMatrixApi());
+  client.database = getDatabase();
+  await client.checkServer('https://fakeServer.notExisting');
+  final resp = await client.api.login(
+    type: 'm.login.password',
+    user: 'test',
+    password: '1234',
+    initialDeviceDisplayName: 'Fluffy Matrix Client',
+  );
+  client.connect(
+    newToken: resp.accessToken,
+    newUserID: resp.userId,
+    newHomeserver: client.api.homeserver,
+    newDeviceName: 'Text Matrix Client',
+    newDeviceID: resp.deviceId,
+    newOlmAccount: pickledOlmAccount,
+  );
+  await Future.delayed(Duration(milliseconds: 10));
+  return client;
+}

test/fake_matrix_api.dart

@@ -25,6 +25,7 @@ import 'package:http/testing.dart';
 
 class FakeMatrixApi extends MockClient {
   static final calledEndpoints = <String, List<dynamic>>{};
+  static int eventCounter = 0;
 
   FakeMatrixApi()
       : super((request) async {
@@ -527,16 +528,32 @@ class FakeMatrixApi extends MockClient {
             'rooms': ['!726s6s6q:example.com']
           }
         },
+//        {
+//          'sender': '@othertest:fakeServer.notExisting',
+//          'content': {
+//            'algorithm': 'm.megolm.v1.aes-sha2',
+//            'room_id': '!726s6s6q:example.com',
+//            'session_id': 'ciM/JWTPrmiWPPZNkRLDPQYf9AW/I46bxyLSr+Bx5oU',
+//            'session_key':
+//                'AgAAAAAQcQ6XrFJk6Prm8FikZDqfry/NbDz8Xw7T6e+/9Yf/q3YHIPEQlzv7IZMNcYb51ifkRzFejVvtphS7wwG2FaXIp4XS2obla14iKISR0X74ugB2vyb1AydIHE/zbBQ1ic5s3kgjMFlWpu/S3FQCnCrv+DPFGEt3ERGWxIl3Bl5X53IjPyVkz65oljz2TZESwz0GH/QFvyOOm8ci0q/gceaF3S7Dmafg3dwTKYwcA5xkcc+BLyrLRzB6Hn+oMAqSNSscnm4mTeT5zYibIhrzqyUTMWr32spFtI9dNR/RFSzfCw'
+//          },
+//          'type': 'm.room_key'
+//        },
         {
-          'sender': '@alice:example.com',
+          // this is the commented out m.room_key event - only encrypted
+          'sender': '@othertest:fakeServer.notExisting',
           'content': {
-            'algorithm': 'm.megolm.v1.aes-sha2',
+            'algorithm': 'm.olm.v1.curve25519-aes-sha2',
-            'room_id': '!726s6s6q:example.com',
+            'sender_key': 'JBG7ZaPn54OBC7TuIEiylW3BZ+7WcGQhFBPB9pogbAg',
-            'session_id': 'ciM/JWTPrmiWPPZNkRLDPQYf9AW/I46bxyLSr+Bx5oU',
+            'ciphertext': {
-            'session_key':
+              '7rvl3jORJkBiK4XX1e5TnGnqz068XfYJ0W++Ml63rgk': {
-                'AgAAAAAQcQ6XrFJk6Prm8FikZDqfry/NbDz8Xw7T6e+/9Yf/q3YHIPEQlzv7IZMNcYb51ifkRzFejVvtphS7wwG2FaXIp4XS2obla14iKISR0X74ugB2vyb1AydIHE/zbBQ1ic5s3kgjMFlWpu/S3FQCnCrv+DPFGEt3ERGWxIl3Bl5X53IjPyVkz65oljz2TZESwz0GH/QFvyOOm8ci0q/gceaF3S7Dmafg3dwTKYwcA5xkcc+BLyrLRzB6Hn+oMAqSNSscnm4mTeT5zYibIhrzqyUTMWr32spFtI9dNR/RFSzfCw'
+                'type': 0,
+                'body':
+                    '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',
               },
-          'type': 'm.room_key'
+            },
+          },
+          'type': 'm.room.encrypted',
         },
       ]
     },
@@ -1567,7 +1584,20 @@ class FakeMatrixApi extends MockClient {
                     }
                   }
                 }
-              }
+              },
+              '@test:fakeServer.notExisting': {
+                'GHTYAJCE': {
+                  'signed_curve25519:AAAAAQ': {
+                    'key': 'qc72ve94cA28iuE0fXa98QO3uls39DHWdQlYyvvhGh0',
+                    'signatures': {
+                      '@test:fakeServer.notExisting': {
+                        'ed25519:GHTYAJCE':
+                            'dFwffr5kTKefO7sjnWLMhTzw7oV31nkPIDRxFy5OQT2OP5++Ao0KRbaBZ6qfuT7lW1owKK0Xk3s7QTBvc/eNDA',
+                      },
+                    },
+                  },
+                },
+              },
             }
           },
       '/client/r0/rooms/!localpart%3Aexample.com/invite': (var req) => {},
@@ -1584,7 +1614,8 @@ class FakeMatrixApi extends MockClient {
       '/client/r0/keys/upload': (var req) => {
             'one_time_key_counts': {
               'curve25519': 10,
-              'signed_curve25519': 100,
+              'signed_curve25519':
+                  json.decode(req)['one_time_keys']?.keys?.length ?? 0,
             }
           },
       '/client/r0/keys/query': (var req) => {
@@ -1625,8 +1656,42 @@ class FakeMatrixApi extends MockClient {
                   },
                   'signatures': {},
                 },
-              }
+              },
-            }
+              '@test:fakeServer.notExisting': {
+                'GHTYAJCE': {
+                  'user_id': '@test:fakeServer.notExisting',
+                  'device_id': 'GHTYAJCE',
+                  'algorithms': [
+                    'm.olm.v1.curve25519-aes-sha2',
+                    'm.megolm.v1.aes-sha2'
+                  ],
+                  'keys': {
+                    'curve25519:GHTYAJCE':
+                        '7rvl3jORJkBiK4XX1e5TnGnqz068XfYJ0W++Ml63rgk',
+                    'ed25519:GHTYAJCE':
+                        'gjL//fyaFHADt9KBADGag8g7F8Up78B/K1zXeiEPLJo'
+                  },
+                  'signatures': {},
+                },
+              },
+              '@othertest:fakeServer.notExisting': {
+                'FOXDEVICE': {
+                  'user_id': '@othertest:fakeServer.notExisting',
+                  'device_id': 'FOXDEVICE',
+                  'algorithms': [
+                    'm.olm.v1.curve25519-aes-sha2',
+                    'm.megolm.v1.aes-sha2'
+                  ],
+                  'keys': {
+                    'curve25519:FOXDEVICE':
+                        'JBG7ZaPn54OBC7TuIEiylW3BZ+7WcGQhFBPB9pogbAg',
+                    'ed25519:FOXDEVICE':
+                        'R5/p04tticvdlNIxiiBIP0j9OQWv8ep6eEU6/lWKDxw',
+                  },
+                  'signatures': {},
+                },
+              },
+            },
           },
       '/client/r0/register': (var req) => {
             'user_id': '@testuser:example.com',
@@ -1706,13 +1771,13 @@ class FakeMatrixApi extends MockClient {
       '/client/r0/directory/room/%23testalias%3Aexample.com': (var reqI) => {},
       '/client/r0/rooms/%21localpart%3Aserver.abc/send/m.room.message/testtxid':
           (var reqI) => {
-                'event_id': '42',
+                'event_id': '\$event${FakeMatrixApi.eventCounter++}',
               },
       '/client/r0/rooms/!localpart%3Aexample.com/typing/%40alice%3Aexample.com':
           (var req) => {},
       '/client/r0/rooms/%211234%3Aexample.com/send/m.room.message/1234':
           (var reqI) => {
-                'event_id': '42',
+                'event_id': '\$event${FakeMatrixApi.eventCounter++}',
               },
       '/client/r0/user/%40alice%3Aexample.com/rooms/%21localpart%3Aexample.com/tags/testtag':
           (var req) => {},

test/room_key_request_test.dart

@@ -1,367 +0,0 @@
-/*
- *   Ansible inventory script used at Famedly GmbH for managing many hosts
- *   Copyright (C) 2019, 2020 Famedly GmbH
- *
- *   This program is free software: you can redistribute it and/or modify
- *   it under the terms of the GNU Affero General Public License as
- *   published by the Free Software Foundation, either version 3 of the
- *   License, or (at your option) any later version.
- *
- *   This program is distributed in the hope that it will be useful,
- *   but WITHOUT ANY WARRANTY; without even the implied warranty of
- *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
- *   GNU Affero General Public License for more details.
- *
- *   You should have received a copy of the GNU Affero General Public License
- *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
- */
-
-import 'dart:convert';
-import 'package:famedlysdk/famedlysdk.dart';
-import 'package:test/test.dart';
-
-import 'fake_matrix_api.dart';
-import 'fake_database.dart';
-
-Map<String, dynamic> jsonDecode(dynamic payload) {
-  if (payload is String) {
-    try {
-      return json.decode(payload);
-    } catch (e) {
-      return {};
-    }
-  }
-  if (payload is Map<String, dynamic>) return payload;
-  return {};
-}
-
-void main() {
-  /// All Tests related to device keys
-  test('fromJson', () async {
-    var rawJson = <String, dynamic>{
-      'content': {
-        'action': 'request',
-        'body': {
-          'algorithm': 'm.megolm.v1.aes-sha2',
-          'room_id': '!726s6s6q:example.com',
-          'sender_key': 'RF3s+E7RkTQTGF2d8Deol0FkQvgII2aJDf3/Jp5mxVU',
-          'session_id': 'X3lUlvLELLYxeTx4yOVu6UDpasGEVO0Jbu+QFnm0cKQ'
-        },
-        'request_id': '1495474790150.19',
-        'requesting_device_id': 'JLAFKJWSCS'
-      },
-      'type': 'm.room_key_request',
-      'sender': '@alice:example.com'
-    };
-    var toDeviceEvent = ToDeviceEvent.fromJson(rawJson);
-    expect(toDeviceEvent.content, rawJson['content']);
-    expect(toDeviceEvent.sender, rawJson['sender']);
-    expect(toDeviceEvent.type, rawJson['type']);
-    expect(
-      ToDeviceEventDecryptionError(
-              exception: Exception('test'),
-              stackTrace: null,
-              toDeviceEvent: toDeviceEvent)
-          .sender,
-      rawJson['sender'],
-    );
-
-    var matrix = Client('testclient', debug: true, httpClient: FakeMatrixApi());
-    matrix.database = getDatabase();
-    await matrix.checkServer('https://fakeServer.notExisting');
-    await matrix.login('test', '1234');
-    var room = matrix.getRoomById('!726s6s6q:example.com');
-    if (matrix.encryptionEnabled) {
-      await room.createOutboundGroupSession();
-      rawJson['content']['body']['session_id'] =
-          room.inboundGroupSessions.keys.first;
-
-      var roomKeyRequest = RoomKeyRequest.fromToDeviceEvent(
-          ToDeviceEvent.fromJson(rawJson),
-          matrix.keyManager,
-          KeyManagerKeyShareRequest(
-            room: room,
-            sessionId: rawJson['content']['body']['session_id'],
-            senderKey: rawJson['content']['body']['sender_key'],
-            devices: [
-              matrix.userDeviceKeys[rawJson['sender']]
-                  .deviceKeys[rawJson['content']['requesting_device_id']]
-            ],
-          ));
-      await roomKeyRequest.forwardKey();
-    }
-    await matrix.dispose(closeDatabase: true);
-  });
-  test('Create Request', () async {
-    var matrix = Client('testclient', debug: true, httpClient: FakeMatrixApi());
-    matrix.database = getDatabase();
-    await matrix.checkServer('https://fakeServer.notExisting');
-    await matrix.login('test', '1234');
-    if (!matrix.encryptionEnabled) {
-      await matrix.dispose(closeDatabase: true);
-      return;
-    }
-    final requestRoom = matrix.getRoomById('!726s6s6q:example.com');
-    await matrix.keyManager.request(requestRoom, 'sessionId', 'senderKey');
-    var foundEvent = false;
-    for (var entry in FakeMatrixApi.calledEndpoints.entries) {
-      final payload = jsonDecode(entry.value.first);
-      if (entry.key.startsWith('/client/r0/sendToDevice/m.room_key_request') &&
-          (payload['messages'] is Map) &&
-          (payload['messages']['@alice:example.com'] is Map) &&
-          (payload['messages']['@alice:example.com']['*'] is Map)) {
-        final content = payload['messages']['@alice:example.com']['*'];
-        if (content['action'] == 'request' &&
-            content['body']['room_id'] == '!726s6s6q:example.com' &&
-            content['body']['sender_key'] == 'senderKey' &&
-            content['body']['session_id'] == 'sessionId') {
-          foundEvent = true;
-          break;
-        }
-      }
-    }
-    expect(foundEvent, true);
-    await matrix.dispose(closeDatabase: true);
-  });
-  final validSessionId = 'ciM/JWTPrmiWPPZNkRLDPQYf9AW/I46bxyLSr+Bx5oU';
-  test('Reply To Request', () async {
-    var matrix = Client('testclient', debug: true, httpClient: FakeMatrixApi());
-    matrix.database = getDatabase();
-    await matrix.checkServer('https://fakeServer.notExisting');
-    await matrix.login('test', '1234');
-    if (!matrix.encryptionEnabled) {
-      await matrix.dispose(closeDatabase: true);
-      return;
-    }
-    matrix.setUserId('@alice:example.com'); // we need to pretend to be alice
-    FakeMatrixApi.calledEndpoints.clear();
-    await matrix.userDeviceKeys['@alice:example.com'].deviceKeys['OTHERDEVICE']
-        .setBlocked(false, matrix);
-    await matrix.userDeviceKeys['@alice:example.com'].deviceKeys['OTHERDEVICE']
-        .setVerified(true, matrix);
-    await matrix.userDeviceKeys['@alice:example.com'].deviceKeys['OTHERDEVICE']
-        .startVerification(matrix);
-    // test a successful share
-    var event = ToDeviceEvent(
-        sender: '@alice:example.com',
-        type: 'm.room_key_request',
-        content: {
-          'action': 'request',
-          'body': {
-            'algorithm': 'm.megolm.v1.aes-sha2',
-            'room_id': '!726s6s6q:example.com',
-            'sender_key': 'senderKey',
-            'session_id': validSessionId,
-          },
-          'request_id': 'request_1',
-          'requesting_device_id': 'OTHERDEVICE',
-        });
-    await matrix.keyManager.handleToDeviceEvent(event);
-    expect(
-        FakeMatrixApi.calledEndpoints.keys.any(
-            (k) => k.startsWith('/client/r0/sendToDevice/m.room.encrypted')),
-        true);
-
-    // test various fail scenarios
-
-    // no body
-    FakeMatrixApi.calledEndpoints.clear();
-    event = ToDeviceEvent(
-        sender: '@alice:example.com',
-        type: 'm.room_key_request',
-        content: {
-          'action': 'request',
-          'request_id': 'request_2',
-          'requesting_device_id': 'OTHERDEVICE',
-        });
-    await matrix.keyManager.handleToDeviceEvent(event);
-    expect(
-        FakeMatrixApi.calledEndpoints.keys.any(
-            (k) => k.startsWith('/client/r0/sendToDevice/m.room.encrypted')),
-        false);
-
-    // request by ourself
-    FakeMatrixApi.calledEndpoints.clear();
-    event = ToDeviceEvent(
-        sender: '@alice:example.com',
-        type: 'm.room_key_request',
-        content: {
-          'action': 'request',
-          'body': {
-            'algorithm': 'm.megolm.v1.aes-sha2',
-            'room_id': '!726s6s6q:example.com',
-            'sender_key': 'senderKey',
-            'session_id': validSessionId,
-          },
-          'request_id': 'request_3',
-          'requesting_device_id': 'JLAFKJWSCS',
-        });
-    await matrix.keyManager.handleToDeviceEvent(event);
-    expect(
-        FakeMatrixApi.calledEndpoints.keys.any(
-            (k) => k.startsWith('/client/r0/sendToDevice/m.room.encrypted')),
-        false);
-
-    // device not found
-    FakeMatrixApi.calledEndpoints.clear();
-    event = ToDeviceEvent(
-        sender: '@alice:example.com',
-        type: 'm.room_key_request',
-        content: {
-          'action': 'request',
-          'body': {
-            'algorithm': 'm.megolm.v1.aes-sha2',
-            'room_id': '!726s6s6q:example.com',
-            'sender_key': 'senderKey',
-            'session_id': validSessionId,
-          },
-          'request_id': 'request_4',
-          'requesting_device_id': 'blubb',
-        });
-    await matrix.keyManager.handleToDeviceEvent(event);
-    expect(
-        FakeMatrixApi.calledEndpoints.keys.any(
-            (k) => k.startsWith('/client/r0/sendToDevice/m.room.encrypted')),
-        false);
-
-    // unknown room
-    FakeMatrixApi.calledEndpoints.clear();
-    event = ToDeviceEvent(
-        sender: '@alice:example.com',
-        type: 'm.room_key_request',
-        content: {
-          'action': 'request',
-          'body': {
-            'algorithm': 'm.megolm.v1.aes-sha2',
-            'room_id': '!invalid:example.com',
-            'sender_key': 'senderKey',
-            'session_id': validSessionId,
-          },
-          'request_id': 'request_5',
-          'requesting_device_id': 'OTHERDEVICE',
-        });
-    await matrix.keyManager.handleToDeviceEvent(event);
-    expect(
-        FakeMatrixApi.calledEndpoints.keys.any(
-            (k) => k.startsWith('/client/r0/sendToDevice/m.room.encrypted')),
-        false);
-
-    // unknwon session
-    FakeMatrixApi.calledEndpoints.clear();
-    event = ToDeviceEvent(
-        sender: '@alice:example.com',
-        type: 'm.room_key_request',
-        content: {
-          'action': 'request',
-          'body': {
-            'algorithm': 'm.megolm.v1.aes-sha2',
-            'room_id': '!726s6s6q:example.com',
-            'sender_key': 'senderKey',
-            'session_id': 'invalid',
-          },
-          'request_id': 'request_6',
-          'requesting_device_id': 'OTHERDEVICE',
-        });
-    await matrix.keyManager.handleToDeviceEvent(event);
-    expect(
-        FakeMatrixApi.calledEndpoints.keys.any(
-            (k) => k.startsWith('/client/r0/sendToDevice/m.room.encrypted')),
-        false);
-
-    FakeMatrixApi.calledEndpoints.clear();
-    await matrix.dispose(closeDatabase: true);
-  });
-  test('Receive shared keys', () async {
-    var matrix = Client('testclient', debug: true, httpClient: FakeMatrixApi());
-    matrix.database = getDatabase();
-    await matrix.checkServer('https://fakeServer.notExisting');
-    await matrix.login('test', '1234');
-    if (!matrix.encryptionEnabled) {
-      await matrix.dispose(closeDatabase: true);
-      return;
-    }
-    final requestRoom = matrix.getRoomById('!726s6s6q:example.com');
-    await matrix.keyManager.request(requestRoom, validSessionId, 'senderKey');
-
-    final session = requestRoom.inboundGroupSessions[validSessionId];
-    final sessionKey = session.inboundGroupSession
-        .export_session(session.inboundGroupSession.first_known_index());
-    requestRoom.inboundGroupSessions.clear();
-    var event = ToDeviceEvent(
-        sender: '@alice:example.com',
-        type: 'm.forwarded_room_key',
-        content: {
-          'algorithm': 'm.megolm.v1.aes-sha2',
-          'room_id': '!726s6s6q:example.com',
-          'session_id': validSessionId,
-          'session_key': sessionKey,
-          'sender_key': 'senderKey',
-          'forwarding_curve25519_key_chain': [],
-        },
-        encryptedContent: {
-          'sender_key': '3C5BFWi2Y8MaVvjM8M22DBmh24PmgR0nPvJOIArzgyI',
-        });
-    await matrix.keyManager.handleToDeviceEvent(event);
-    expect(requestRoom.inboundGroupSessions.containsKey(validSessionId), true);
-
-    // now test a few invalid scenarios
-
-    // request not found
-    requestRoom.inboundGroupSessions.clear();
-    event = ToDeviceEvent(
-        sender: '@alice:example.com',
-        type: 'm.forwarded_room_key',
-        content: {
-          'algorithm': 'm.megolm.v1.aes-sha2',
-          'room_id': '!726s6s6q:example.com',
-          'session_id': validSessionId,
-          'session_key': sessionKey,
-          'sender_key': 'senderKey',
-          'forwarding_curve25519_key_chain': [],
-        },
-        encryptedContent: {
-          'sender_key': '3C5BFWi2Y8MaVvjM8M22DBmh24PmgR0nPvJOIArzgyI',
-        });
-    await matrix.keyManager.handleToDeviceEvent(event);
-    expect(requestRoom.inboundGroupSessions.containsKey(validSessionId), false);
-
-    // unknown device
-    await matrix.keyManager.request(requestRoom, validSessionId, 'senderKey');
-    requestRoom.inboundGroupSessions.clear();
-    event = ToDeviceEvent(
-        sender: '@alice:example.com',
-        type: 'm.forwarded_room_key',
-        content: {
-          'algorithm': 'm.megolm.v1.aes-sha2',
-          'room_id': '!726s6s6q:example.com',
-          'session_id': validSessionId,
-          'session_key': sessionKey,
-          'sender_key': 'senderKey',
-          'forwarding_curve25519_key_chain': [],
-        },
-        encryptedContent: {
-          'sender_key': 'invalid',
-        });
-    await matrix.keyManager.handleToDeviceEvent(event);
-    expect(requestRoom.inboundGroupSessions.containsKey(validSessionId), false);
-
-    // no encrypted content
-    await matrix.keyManager.request(requestRoom, validSessionId, 'senderKey');
-    requestRoom.inboundGroupSessions.clear();
-    event = ToDeviceEvent(
-        sender: '@alice:example.com',
-        type: 'm.forwarded_room_key',
-        content: {
-          'algorithm': 'm.megolm.v1.aes-sha2',
-          'room_id': '!726s6s6q:example.com',
-          'session_id': validSessionId,
-          'session_key': sessionKey,
-          'sender_key': 'senderKey',
-          'forwarding_curve25519_key_chain': [],
-        });
-    await matrix.keyManager.handleToDeviceEvent(event);
-    expect(requestRoom.inboundGroupSessions.containsKey(validSessionId), false);
-
-    await matrix.dispose(closeDatabase: true);
-  });
-}

test/room_test.dart

@@ -26,7 +26,7 @@ import 'package:famedlysdk/src/database/database.dart'
     show DbRoom, DbRoomState, DbRoomAccountData;
 import 'package:test/test.dart';
 
-import 'fake_matrix_api.dart';
+import 'fake_client.dart';
 
 import 'dart:typed_data';
 
@@ -37,15 +37,7 @@ void main() {
   /// All Tests related to the Event
   group('Room', () {
     test('Login', () async {
-      matrix = Client('testclient', debug: true, httpClient: FakeMatrixApi());
+      matrix = await getClient();
-
-      final checkResp =
-          await matrix.checkServer('https://fakeServer.notExisting');
-
-      final loginResp = await matrix.login('test', '1234');
-
-      expect(checkResp, true);
-      expect(loginResp, true);
     });
 
     test('Create from json', () async {
@@ -315,7 +307,7 @@ void main() {
 
     test('getTimeline', () async {
       final timeline = await room.getTimeline();
-      expect(timeline.events, []);
+      expect(timeline.events.length, 0);
     });
 
     test('getUserByMXID', () async {
@@ -338,13 +330,13 @@ void main() {
       final dynamic resp = await room.sendEvent(
           {'msgtype': 'm.text', 'body': 'hello world'},
           txid: 'testtxid');
-      expect(resp, '42');
+      expect(resp.startsWith('\$event'), true);
     });
 
     test('sendEvent', () async {
       final dynamic resp =
           await room.sendTextEvent('Hello world', txid: 'testtxid');
-      expect(resp, '42');
+      expect(resp.startsWith('\$event'), true);
     });
 
     // Not working because there is no real file to test it...
@@ -388,60 +380,6 @@ void main() {
       );
       expect(room.encrypted, true);
       expect(room.encryptionAlgorithm, 'm.megolm.v1.aes-sha2');
-      expect(room.outboundGroupSession, null);
-    });
-
-    test('createOutboundGroupSession', () async {
-      if (!room.client.encryptionEnabled) return;
-      await room.createOutboundGroupSession();
-      expect(room.outboundGroupSession != null, true);
-      expect(room.outboundGroupSession.session_id().isNotEmpty, true);
-      expect(
-          room.inboundGroupSessions
-              .containsKey(room.outboundGroupSession.session_id()),
-          true);
-      expect(
-          room.inboundGroupSessions[room.outboundGroupSession.session_id()]
-              .content['session_key'],
-          room.outboundGroupSession.session_key());
-      expect(
-          room.inboundGroupSessions[room.outboundGroupSession.session_id()]
-              .indexes.length,
-          0);
-    });
-
-    test('clearOutboundGroupSession', () async {
-      if (!room.client.encryptionEnabled) return;
-      await room.clearOutboundGroupSession(wipe: true);
-      expect(room.outboundGroupSession == null, true);
-    });
-
-    test('encryptGroupMessagePayload and decryptGroupMessage', () async {
-      if (!room.client.encryptionEnabled) return;
-      final payload = {
-        'msgtype': 'm.text',
-        'body': 'Hello world',
-      };
-      final encryptedPayload = await room.encryptGroupMessagePayload(payload);
-      expect(encryptedPayload['algorithm'], 'm.megolm.v1.aes-sha2');
-      expect(encryptedPayload['ciphertext'].isNotEmpty, true);
-      expect(encryptedPayload['device_id'], room.client.deviceID);
-      expect(encryptedPayload['sender_key'], room.client.identityKey);
-      expect(encryptedPayload['session_id'],
-          room.outboundGroupSession.session_id());
-
-      var encryptedEvent = Event(
-        content: encryptedPayload,
-        type: 'm.room.encrypted',
-        senderId: room.client.userID,
-        eventId: '1234',
-        roomId: room.id,
-        room: room,
-        originServerTs: DateTime.now(),
-      );
-      var decryptedEvent = room.decryptGroupMessage(encryptedEvent);
-      expect(decryptedEvent.type, 'm.room.message');
-      expect(decryptedEvent.content, payload);
     });
 
     test('setPushRuleState', () async {

test/session_key_test.dart

@@ -1,56 +0,0 @@
-/*
- *   Ansible inventory script used at Famedly GmbH for managing many hosts
- *   Copyright (C) 2019, 2020 Famedly GmbH
- *
- *   This program is free software: you can redistribute it and/or modify
- *   it under the terms of the GNU Affero General Public License as
- *   published by the Free Software Foundation, either version 3 of the
- *   License, or (at your option) any later version.
- *
- *   This program is distributed in the hope that it will be useful,
- *   but WITHOUT ANY WARRANTY; without even the implied warranty of
- *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
- *   GNU Affero General Public License for more details.
- *
- *   You should have received a copy of the GNU Affero General Public License
- *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
- */
-import 'dart:convert';
-import 'package:famedlysdk/src/utils/session_key.dart';
-import 'package:olm/olm.dart' as olm;
-import 'package:test/test.dart';
-
-void main() {
-  /// All Tests related to the ChatTime
-  group('SessionKey', () {
-    var olmEnabled = true;
-    try {
-      olm.init();
-      olm.Account();
-    } catch (_) {
-      olmEnabled = false;
-      print('[LibOlm] Failed to load LibOlm: ' + _.toString());
-    }
-    print('[LibOlm] Enabled: $olmEnabled');
-    test('SessionKey test', () {
-      if (olmEnabled) {
-        final sessionKey = SessionKey(
-          content: {
-            'algorithm': 'm.megolm.v1.aes-sha2',
-            'room_id': '!Cuyf34gef24t:localhost',
-            'session_id': 'X3lUlvLELLYxeTx4yOVu6UDpasGEVO0Jbu+QFnm0cKQ',
-            'session_key':
-                'AgAAAADxKHa9uFxcXzwYoNueL5Xqi69IkD4sni8LlfJL7qNBEY...'
-          },
-          inboundGroupSession: olm.InboundGroupSession(),
-          key: '1234',
-          indexes: {},
-        );
-        expect(sessionKey.senderClaimedEd25519Key, '');
-        expect(sessionKey.toJson(),
-            SessionKey.fromJson(sessionKey.toJson(), '1234').toJson());
-        expect(sessionKey.toString(), json.encode(sessionKey.toJson()));
-      }
-    });
-  });
-}

test/timeline_test.dart

@@ -143,7 +143,8 @@ void main() {
       expect(updateCount, 5);
       expect(insertList, [0, 0, 0]);
       expect(insertList.length, timeline.events.length);
-      expect(timeline.events[0].eventId, '42');
+      final eventId = timeline.events[0].eventId;
+      expect(eventId.startsWith('\$event'), true);
       expect(timeline.events[0].status, 1);
 
       client.onEvent.add(EventUpdate(
@@ -155,7 +156,7 @@ void main() {
             'content': {'msgtype': 'm.text', 'body': 'test'},
             'sender': '@alice:example.com',
             'status': 2,
-            'event_id': '42',
+            'event_id': eventId,
             'unsigned': {'transaction_id': '1234'},
             'origin_server_ts': DateTime.now().millisecondsSinceEpoch
           },
@@ -166,7 +167,7 @@ void main() {
       expect(updateCount, 6);
       expect(insertList, [0, 0, 0]);
       expect(insertList.length, timeline.events.length);
-      expect(timeline.events[0].eventId, '42');
+      expect(timeline.events[0].eventId, eventId);
       expect(timeline.events[0].status, 2);
     });
 

test_driver/famedlysdk_test.dart

@@ -88,7 +88,8 @@ void test() async {
   await room.enableEncryption();
   await Future.delayed(Duration(seconds: 5));
   assert(room.encrypted == true);
-  assert(room.outboundGroupSession == null);
+  assert(room.client.encryption.keyManager.getOutboundGroupSession(room.id) ==
+      null);
 
   print('++++ ($testUserA) Check known olm devices ++++');
   assert(testClientA.userDeviceKeys.containsKey(testUserB));
@@ -123,16 +124,30 @@ void test() async {
   print("++++ ($testUserA) Send encrypted message: '$testMessage' ++++");
   await room.sendTextEvent(testMessage);
   await Future.delayed(Duration(seconds: 5));
-  assert(room.outboundGroupSession != null);
+  assert(room.client.encryption.keyManager.getOutboundGroupSession(room.id) !=
-  var currentSessionIdA = room.outboundGroupSession.session_id();
+      null);
-  assert(room.inboundGroupSessions
+  var currentSessionIdA = room.client.encryption.keyManager
-      .containsKey(room.outboundGroupSession.session_id()));
+      .getOutboundGroupSession(room.id)
-  assert(testClientA.olmSessions[testClientB.identityKey].length == 1);
+      .outboundGroupSession
-  assert(testClientB.olmSessions[testClientA.identityKey].length == 1);
+      .session_id();
-  assert(testClientA.olmSessions[testClientB.identityKey].first.session_id() ==
+  assert(room.client.encryption.keyManager
-      testClientB.olmSessions[testClientA.identityKey].first.session_id());
+          .getInboundGroupSession(room.id, currentSessionIdA, '') !=
-  assert(inviteRoom.inboundGroupSessions
+      null);
-      .containsKey(room.outboundGroupSession.session_id()));
+  assert(testClientA
+          .encryption.olmManager.olmSessions[testClientB.identityKey].length ==
+      1);
+  assert(testClientB
+          .encryption.olmManager.olmSessions[testClientA.identityKey].length ==
+      1);
+  assert(testClientA
+          .encryption.olmManager.olmSessions[testClientB.identityKey].first
+          .session_id() ==
+      testClientB
+          .encryption.olmManager.olmSessions[testClientA.identityKey].first
+          .session_id());
+  assert(inviteRoom.client.encryption.keyManager
+          .getInboundGroupSession(inviteRoom.id, currentSessionIdA, '') !=
+      null);
   assert(room.lastMessage == testMessage);
   assert(inviteRoom.lastMessage == testMessage);
   print(
@@ -141,14 +156,27 @@ void test() async {
   print("++++ ($testUserA) Send again encrypted message: '$testMessage2' ++++");
   await room.sendTextEvent(testMessage2);
   await Future.delayed(Duration(seconds: 5));
-  assert(testClientA.olmSessions[testClientB.identityKey].length == 1);
+  assert(testClientA
-  assert(testClientB.olmSessions[testClientA.identityKey].length == 1);
+          .encryption.olmManager.olmSessions[testClientB.identityKey].length ==
-  assert(testClientA.olmSessions[testClientB.identityKey].first.session_id() ==
+      1);
-      testClientB.olmSessions[testClientA.identityKey].first.session_id());
+  assert(testClientB
+          .encryption.olmManager.olmSessions[testClientA.identityKey].length ==
+      1);
+  assert(testClientA
+          .encryption.olmManager.olmSessions[testClientB.identityKey].first
+          .session_id() ==
+      testClientB
+          .encryption.olmManager.olmSessions[testClientA.identityKey].first
+          .session_id());
 
-  assert(room.outboundGroupSession.session_id() == currentSessionIdA);
+  assert(room.client.encryption.keyManager
-  assert(inviteRoom.inboundGroupSessions
+          .getOutboundGroupSession(room.id)
-      .containsKey(room.outboundGroupSession.session_id()));
+          .outboundGroupSession
+          .session_id() ==
+      currentSessionIdA);
+  assert(room.client.encryption.keyManager
+          .getInboundGroupSession(room.id, currentSessionIdA, '') !=
+      null);
   assert(room.lastMessage == testMessage2);
   assert(inviteRoom.lastMessage == testMessage2);
   print(
@@ -157,14 +185,31 @@ void test() async {
   print("++++ ($testUserB) Send again encrypted message: '$testMessage3' ++++");
   await inviteRoom.sendTextEvent(testMessage3);
   await Future.delayed(Duration(seconds: 5));
-  assert(testClientA.olmSessions[testClientB.identityKey].length == 1);
+  assert(testClientA
-  assert(testClientB.olmSessions[testClientA.identityKey].length == 1);
+          .encryption.olmManager.olmSessions[testClientB.identityKey].length ==
-  assert(room.outboundGroupSession.session_id() == currentSessionIdA);
+      1);
-  assert(inviteRoom.outboundGroupSession != null);
+  assert(testClientB
-  assert(inviteRoom.inboundGroupSessions
+          .encryption.olmManager.olmSessions[testClientA.identityKey].length ==
-      .containsKey(inviteRoom.outboundGroupSession.session_id()));
+      1);
-  assert(room.inboundGroupSessions
+  assert(room.client.encryption.keyManager
-      .containsKey(inviteRoom.outboundGroupSession.session_id()));
+          .getOutboundGroupSession(room.id)
+          .outboundGroupSession
+          .session_id() ==
+      currentSessionIdA);
+  var inviteRoomOutboundGroupSession = inviteRoom.client.encryption.keyManager
+      .getOutboundGroupSession(inviteRoom.id);
+
+  assert(inviteRoomOutboundGroupSession != null);
+  assert(inviteRoom.client.encryption.keyManager.getInboundGroupSession(
+          inviteRoom.id,
+          inviteRoomOutboundGroupSession.outboundGroupSession.session_id(),
+          '') !=
+      null);
+  assert(room.client.encryption.keyManager.getInboundGroupSession(
+          room.id,
+          inviteRoomOutboundGroupSession.outboundGroupSession.session_id(),
+          '') !=
+      null);
   assert(inviteRoom.lastMessage == testMessage3);
   assert(room.lastMessage == testMessage3);
   print(
@@ -180,18 +225,42 @@ void test() async {
   print("++++ ($testUserA) Send again encrypted message: '$testMessage4' ++++");
   await room.sendTextEvent(testMessage4);
   await Future.delayed(Duration(seconds: 5));
-  assert(testClientA.olmSessions[testClientB.identityKey].length == 1);
+  assert(testClientA
-  assert(testClientB.olmSessions[testClientA.identityKey].length == 1);
+          .encryption.olmManager.olmSessions[testClientB.identityKey].length ==
-  assert(testClientA.olmSessions[testClientB.identityKey].first.session_id() ==
+      1);
-      testClientB.olmSessions[testClientA.identityKey].first.session_id());
+  assert(testClientB
-  assert(testClientA.olmSessions[testClientC.identityKey].length == 1);
+          .encryption.olmManager.olmSessions[testClientA.identityKey].length ==
-  assert(testClientC.olmSessions[testClientA.identityKey].length == 1);
+      1);
-  assert(testClientA.olmSessions[testClientC.identityKey].first.session_id() ==
+  assert(testClientA
-      testClientC.olmSessions[testClientA.identityKey].first.session_id());
+          .encryption.olmManager.olmSessions[testClientB.identityKey].first
-  assert(room.outboundGroupSession.session_id() != currentSessionIdA);
+          .session_id() ==
-  currentSessionIdA = room.outboundGroupSession.session_id();
+      testClientB
-  assert(inviteRoom.inboundGroupSessions
+          .encryption.olmManager.olmSessions[testClientA.identityKey].first
-      .containsKey(room.outboundGroupSession.session_id()));
+          .session_id());
+  assert(testClientA
+          .encryption.olmManager.olmSessions[testClientC.identityKey].length ==
+      1);
+  assert(testClientC
+          .encryption.olmManager.olmSessions[testClientA.identityKey].length ==
+      1);
+  assert(testClientA
+          .encryption.olmManager.olmSessions[testClientC.identityKey].first
+          .session_id() ==
+      testClientC
+          .encryption.olmManager.olmSessions[testClientA.identityKey].first
+          .session_id());
+  assert(room.client.encryption.keyManager
+          .getOutboundGroupSession(room.id)
+          .outboundGroupSession
+          .session_id() !=
+      currentSessionIdA);
+  currentSessionIdA = room.client.encryption.keyManager
+      .getOutboundGroupSession(room.id)
+      .outboundGroupSession
+      .session_id();
+  assert(inviteRoom.client.encryption.keyManager
+          .getInboundGroupSession(inviteRoom.id, currentSessionIdA, '') !=
+      null);
   assert(room.lastMessage == testMessage4);
   assert(inviteRoom.lastMessage == testMessage4);
   print(
@@ -206,14 +275,30 @@ void test() async {
   print("++++ ($testUserA) Send again encrypted message: '$testMessage6' ++++");
   await room.sendTextEvent(testMessage6);
   await Future.delayed(Duration(seconds: 5));
-  assert(testClientA.olmSessions[testClientB.identityKey].length == 1);
+  assert(testClientA
-  assert(testClientB.olmSessions[testClientA.identityKey].length == 1);
+          .encryption.olmManager.olmSessions[testClientB.identityKey].length ==
-  assert(testClientA.olmSessions[testClientB.identityKey].first.session_id() ==
+      1);
-      testClientB.olmSessions[testClientA.identityKey].first.session_id());
+  assert(testClientB
-  assert(room.outboundGroupSession.session_id() != currentSessionIdA);
+          .encryption.olmManager.olmSessions[testClientA.identityKey].length ==
-  currentSessionIdA = room.outboundGroupSession.session_id();
+      1);
-  assert(inviteRoom.inboundGroupSessions
+  assert(testClientA
-      .containsKey(room.outboundGroupSession.session_id()));
+          .encryption.olmManager.olmSessions[testClientB.identityKey].first
+          .session_id() ==
+      testClientB
+          .encryption.olmManager.olmSessions[testClientA.identityKey].first
+          .session_id());
+  assert(room.client.encryption.keyManager
+          .getOutboundGroupSession(room.id)
+          .outboundGroupSession
+          .session_id() !=
+      currentSessionIdA);
+  currentSessionIdA = room.client.encryption.keyManager
+      .getOutboundGroupSession(room.id)
+      .outboundGroupSession
+      .session_id();
+  assert(inviteRoom.client.encryption.keyManager
+          .getInboundGroupSession(inviteRoom.id, currentSessionIdA, '') !=
+      null);
   assert(room.lastMessage == testMessage6);
   assert(inviteRoom.lastMessage == testMessage6);
   print(
@@ -241,18 +326,18 @@ void test() async {
     assert(restoredRoom.inboundGroupSessions.keys.toList()[i] ==
         room.inboundGroupSessions.keys.toList()[i]);
   }
-  assert(testClientA.olmSessions[testClientB.identityKey].length == 1);
+  assert(testClientA.encryption.olmManager.olmSessions[testClientB.identityKey].length == 1);
-  assert(testClientB.olmSessions[testClientA.identityKey].length == 1);
+  assert(testClientB.encryption.olmManager.olmSessions[testClientA.identityKey].length == 1);
-  assert(testClientA.olmSessions[testClientB.identityKey].first.session_id() ==
+  assert(testClientA.encryption.olmManager.olmSessions[testClientB.identityKey].first.session_id() ==
-      testClientB.olmSessions[testClientA.identityKey].first.session_id());
+      testClientB.encryption.olmManager.olmSessions[testClientA.identityKey].first.session_id());
 
   print("++++ ($testUserA) Send again encrypted message: '$testMessage5' ++++");
   await restoredRoom.sendTextEvent(testMessage5);
   await Future.delayed(Duration(seconds: 5));
-  assert(testClientA.olmSessions[testClientB.identityKey].length == 1);
+  assert(testClientA.encryption.olmManager.olmSessions[testClientB.identityKey].length == 1);
-  assert(testClientB.olmSessions[testClientA.identityKey].length == 1);
+  assert(testClientB.encryption.olmManager.olmSessions[testClientA.identityKey].length == 1);
-  assert(testClientA.olmSessions[testClientB.identityKey].first.session_id() ==
+  assert(testClientA.encryption.olmManager.olmSessions[testClientB.identityKey].first.session_id() ==
-      testClientB.olmSessions[testClientA.identityKey].first.session_id());
+      testClientB.encryption.olmManager.olmSessions[testClientA.identityKey].first.session_id());
   assert(restoredRoom.lastMessage == testMessage5);
   assert(inviteRoom.lastMessage == testMessage5);
   assert(testClientB.getRoomById(roomId).lastMessage == testMessage5);