LCOV - code coverage report
Current view: top level - lib/encryption - olm_manager.dart (source / functions) Hit Total Coverage
Test: merged.info Lines: 302 362 83.4 %
Date: 2025-01-06 12:44:40 Functions: 0 0 -

          Line data    Source code
       1             : /*
       2             :  *   Famedly Matrix SDK
       3             :  *   Copyright (C) 2019, 2020, 2021 Famedly GmbH
       4             :  *
       5             :  *   This program is free software: you can redistribute it and/or modify
       6             :  *   it under the terms of the GNU Affero General Public License as
       7             :  *   published by the Free Software Foundation, either version 3 of the
       8             :  *   License, or (at your option) any later version.
       9             :  *
      10             :  *   This program is distributed in the hope that it will be useful,
      11             :  *   but WITHOUT ANY WARRANTY; without even the implied warranty of
      12             :  *   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
      13             :  *   GNU Affero General Public License for more details.
      14             :  *
      15             :  *   You should have received a copy of the GNU Affero General Public License
      16             :  *   along with this program.  If not, see <https://www.gnu.org/licenses/>.
      17             :  */
      18             : 
      19             : import 'dart:convert';
      20             : 
      21             : import 'package:async/async.dart';
      22             : import 'package:canonical_json/canonical_json.dart';
      23             : import 'package:collection/collection.dart';
      24             : import 'package:olm/olm.dart' as olm;
      25             : 
      26             : import 'package:matrix/encryption/encryption.dart';
      27             : import 'package:matrix/encryption/utils/json_signature_check_extension.dart';
      28             : import 'package:matrix/encryption/utils/olm_session.dart';
      29             : import 'package:matrix/matrix.dart';
      30             : import 'package:matrix/msc_extensions/msc_3814_dehydrated_devices/api.dart';
      31             : import 'package:matrix/src/utils/run_benchmarked.dart';
      32             : import 'package:matrix/src/utils/run_in_root.dart';
      33             : 
      34             : class OlmManager {
      35             :   final Encryption encryption;
      36          75 :   Client get client => encryption.client;
      37             :   olm.Account? _olmAccount;
      38             :   String? ourDeviceId;
      39             : 
      40             :   /// Returns the base64 encoded keys to store them in a store.
      41             :   /// This String should **never** leave the device!
      42          24 :   String? get pickledOlmAccount =>
      43         120 :       enabled ? _olmAccount!.pickle(client.userID!) : null;
      44          24 :   String? get fingerprintKey =>
      45         120 :       enabled ? json.decode(_olmAccount!.identity_keys())['ed25519'] : null;
      46          25 :   String? get identityKey =>
      47         125 :       enabled ? json.decode(_olmAccount!.identity_keys())['curve25519'] : null;
      48             : 
      49           0 :   String? pickleOlmAccountWithKey(String key) =>
      50           0 :       enabled ? _olmAccount!.pickle(key) : null;
      51             : 
      52          50 :   bool get enabled => _olmAccount != null;
      53             : 
      54          25 :   OlmManager(this.encryption);
      55             : 
      56             :   /// A map from Curve25519 identity keys to existing olm sessions.
      57          50 :   Map<String, List<OlmSession>> get olmSessions => _olmSessions;
      58             :   final Map<String, List<OlmSession>> _olmSessions = {};
      59             : 
      60             :   // NOTE(Nico): On initial login we pass null to create a new account
      61          25 :   Future<void> init({
      62             :     String? olmAccount,
      63             :     required String? deviceId,
      64             :     String? pickleKey,
      65             :     String? dehydratedDeviceAlgorithm,
      66             :   }) async {
      67          25 :     ourDeviceId = deviceId;
      68             :     if (olmAccount == null) {
      69             :       try {
      70           4 :         await olm.init();
      71           8 :         _olmAccount = olm.Account();
      72           8 :         _olmAccount!.create();
      73           4 :         if (!await uploadKeys(
      74             :           uploadDeviceKeys: true,
      75             :           updateDatabase: false,
      76             :           dehydratedDeviceAlgorithm: dehydratedDeviceAlgorithm,
      77             :           dehydratedDevicePickleKey:
      78             :               dehydratedDeviceAlgorithm != null ? pickleKey : null,
      79             :         )) {
      80             :           throw ('Upload key failed');
      81             :         }
      82             :       } catch (_) {
      83           0 :         _olmAccount?.free();
      84           0 :         _olmAccount = null;
      85             :         rethrow;
      86             :       }
      87             :     } else {
      88             :       try {
      89          24 :         await olm.init();
      90          48 :         _olmAccount = olm.Account();
      91          96 :         _olmAccount!.unpickle(pickleKey ?? client.userID!, olmAccount);
      92             :       } catch (_) {
      93           2 :         _olmAccount?.free();
      94           1 :         _olmAccount = null;
      95             :         rethrow;
      96             :       }
      97             :     }
      98             :   }
      99             : 
     100             :   /// Adds a signature to this json from this olm account and returns the signed
     101             :   /// json.
     102           5 :   Map<String, dynamic> signJson(Map<String, dynamic> payload) {
     103           5 :     if (!enabled) throw ('Encryption is disabled');
     104           5 :     final Map<String, dynamic>? unsigned = payload['unsigned'];
     105           5 :     final Map<String, dynamic>? signatures = payload['signatures'];
     106           5 :     payload.remove('unsigned');
     107           5 :     payload.remove('signatures');
     108           5 :     final canonical = canonicalJson.encode(payload);
     109          15 :     final signature = _olmAccount!.sign(String.fromCharCodes(canonical));
     110             :     if (signatures != null) {
     111           0 :       payload['signatures'] = signatures;
     112             :     } else {
     113          10 :       payload['signatures'] = <String, dynamic>{};
     114             :     }
     115          20 :     if (!payload['signatures'].containsKey(client.userID)) {
     116          25 :       payload['signatures'][client.userID] = <String, dynamic>{};
     117             :     }
     118          35 :     payload['signatures'][client.userID]['ed25519:$ourDeviceId'] = signature;
     119             :     if (unsigned != null) {
     120           0 :       payload['unsigned'] = unsigned;
     121             :     }
     122             :     return payload;
     123             :   }
     124             : 
     125           4 :   String signString(String s) {
     126           8 :     return _olmAccount!.sign(s);
     127             :   }
     128             : 
     129             :   bool _uploadKeysLock = false;
     130             :   CancelableOperation<Map<String, int>>? currentUpload;
     131             : 
     132          45 :   int? get maxNumberOfOneTimeKeys => _olmAccount?.max_number_of_one_time_keys();
     133             : 
     134             :   /// Generates new one time keys, signs everything and upload it to the server.
     135             :   /// If `retry` is > 0, the request will be retried with new OTKs on upload failure.
     136           5 :   Future<bool> uploadKeys({
     137             :     bool uploadDeviceKeys = false,
     138             :     int? oldKeyCount = 0,
     139             :     bool updateDatabase = true,
     140             :     bool? unusedFallbackKey = false,
     141             :     String? dehydratedDeviceAlgorithm,
     142             :     String? dehydratedDevicePickleKey,
     143             :     int retry = 1,
     144             :   }) async {
     145           5 :     final olmAccount = _olmAccount;
     146             :     if (olmAccount == null) {
     147             :       return true;
     148             :     }
     149             : 
     150           5 :     if (_uploadKeysLock) {
     151             :       return false;
     152             :     }
     153           5 :     _uploadKeysLock = true;
     154             : 
     155           5 :     final signedOneTimeKeys = <String, Map<String, Object?>>{};
     156             :     try {
     157             :       int? uploadedOneTimeKeysCount;
     158             :       if (oldKeyCount != null) {
     159             :         // check if we have OTKs that still need uploading. If we do, we don't try to generate new ones,
     160             :         // instead we try to upload the old ones first
     161             :         final oldOTKsNeedingUpload = json
     162          15 :             .decode(olmAccount.one_time_keys())['curve25519']
     163           5 :             .entries
     164           5 :             .length as int;
     165             :         // generate one-time keys
     166             :         // we generate 2/3rds of max, so that other keys people may still have can
     167             :         // still be used
     168             :         final oneTimeKeysCount =
     169          25 :             (olmAccount.max_number_of_one_time_keys() * 2 / 3).floor() -
     170           5 :                 oldKeyCount -
     171             :                 oldOTKsNeedingUpload;
     172           5 :         if (oneTimeKeysCount > 0) {
     173           5 :           olmAccount.generate_one_time_keys(oneTimeKeysCount);
     174             :         }
     175           5 :         uploadedOneTimeKeysCount = oneTimeKeysCount + oldOTKsNeedingUpload;
     176             :       }
     177             : 
     178          15 :       if (encryption.isMinOlmVersion(3, 2, 7) && unusedFallbackKey == false) {
     179             :         // we don't have an unused fallback key uploaded....so let's change that!
     180           5 :         olmAccount.generate_fallback_key();
     181             :       }
     182             : 
     183             :       // we save the generated OTKs into the database.
     184             :       // in case the app gets killed during upload or the upload fails due to bad network
     185             :       // we can still re-try later
     186             :       if (updateDatabase) {
     187           4 :         await encryption.olmDatabase?.updateClientKeys(pickledOlmAccount!);
     188             :       }
     189             : 
     190             :       // and now generate the payload to upload
     191           5 :       var deviceKeys = <String, dynamic>{
     192          10 :         'user_id': client.userID,
     193           5 :         'device_id': ourDeviceId,
     194           5 :         'algorithms': [
     195             :           AlgorithmTypes.olmV1Curve25519AesSha2,
     196             :           AlgorithmTypes.megolmV1AesSha2,
     197             :         ],
     198           5 :         'keys': <String, dynamic>{},
     199             :       };
     200             : 
     201             :       if (uploadDeviceKeys) {
     202             :         final Map<String, dynamic> keys =
     203          10 :             json.decode(olmAccount.identity_keys());
     204          10 :         for (final entry in keys.entries) {
     205           5 :           final algorithm = entry.key;
     206           5 :           final value = entry.value;
     207          20 :           deviceKeys['keys']['$algorithm:$ourDeviceId'] = value;
     208             :         }
     209           5 :         deviceKeys = signJson(deviceKeys);
     210             :       }
     211             : 
     212             :       // now sign all the one-time keys
     213             :       for (final entry
     214          25 :           in json.decode(olmAccount.one_time_keys())['curve25519'].entries) {
     215           5 :         final key = entry.key;
     216           5 :         final value = entry.value;
     217          20 :         signedOneTimeKeys['signed_curve25519:$key'] = signJson({
     218             :           'key': value,
     219             :         });
     220             :       }
     221             : 
     222           5 :       final signedFallbackKeys = <String, dynamic>{};
     223          10 :       if (encryption.isMinOlmVersion(3, 2, 7)) {
     224          10 :         final fallbackKey = json.decode(olmAccount.unpublished_fallback_key());
     225             :         // now sign all the fallback keys
     226          15 :         for (final entry in fallbackKey['curve25519'].entries) {
     227           5 :           final key = entry.key;
     228           5 :           final value = entry.value;
     229          20 :           signedFallbackKeys['signed_curve25519:$key'] = signJson({
     230             :             'key': value,
     231             :             'fallback': true,
     232             :           });
     233             :         }
     234             :       }
     235             : 
     236           5 :       if (signedFallbackKeys.isEmpty &&
     237           1 :           signedOneTimeKeys.isEmpty &&
     238             :           !uploadDeviceKeys) {
     239           0 :         _uploadKeysLock = false;
     240             :         return true;
     241             :       }
     242             : 
     243             :       // Workaround: Make sure we stop if we got logged out in the meantime.
     244          10 :       if (!client.isLogged()) return true;
     245             : 
     246          20 :       if (ourDeviceId != client.deviceID) {
     247             :         if (dehydratedDeviceAlgorithm == null ||
     248             :             dehydratedDevicePickleKey == null) {
     249           0 :           throw Exception(
     250             :             'You need to provide both the pickle key and the algorithm to use dehydrated devices!',
     251             :           );
     252             :         }
     253             : 
     254           0 :         await client.uploadDehydratedDevice(
     255           0 :           deviceId: ourDeviceId!,
     256             :           initialDeviceDisplayName: 'Dehydrated Device',
     257             :           deviceKeys:
     258           0 :               uploadDeviceKeys ? MatrixDeviceKeys.fromJson(deviceKeys) : null,
     259             :           oneTimeKeys: signedOneTimeKeys,
     260             :           fallbackKeys: signedFallbackKeys,
     261           0 :           deviceData: {
     262             :             'algorithm': dehydratedDeviceAlgorithm,
     263           0 :             'device': encryption.olmManager
     264           0 :                 .pickleOlmAccountWithKey(dehydratedDevicePickleKey),
     265             :           },
     266             :         );
     267             :         return true;
     268             :       }
     269          10 :       final currentUpload = this.currentUpload = CancelableOperation.fromFuture(
     270          10 :         client.uploadKeys(
     271             :           deviceKeys:
     272           5 :               uploadDeviceKeys ? MatrixDeviceKeys.fromJson(deviceKeys) : null,
     273             :           oneTimeKeys: signedOneTimeKeys,
     274             :           fallbackKeys: signedFallbackKeys,
     275             :         ),
     276             :       );
     277           5 :       final response = await currentUpload.valueOrCancellation();
     278             :       if (response == null) {
     279           0 :         _uploadKeysLock = false;
     280             :         return false;
     281             :       }
     282             : 
     283             :       // mark the OTKs as published and save that to datbase
     284           5 :       olmAccount.mark_keys_as_published();
     285             :       if (updateDatabase) {
     286           4 :         await encryption.olmDatabase?.updateClientKeys(pickledOlmAccount!);
     287             :       }
     288             :       return (uploadedOneTimeKeysCount != null &&
     289          10 :               response['signed_curve25519'] == uploadedOneTimeKeysCount) ||
     290             :           uploadedOneTimeKeysCount == null;
     291           0 :     } on MatrixException catch (exception) {
     292           0 :       _uploadKeysLock = false;
     293             : 
     294             :       // we failed to upload the keys. If we only tried to upload one time keys, try to recover by removing them and generating new ones.
     295             :       if (!uploadDeviceKeys &&
     296           0 :           unusedFallbackKey != false &&
     297           0 :           retry > 0 &&
     298             :           dehydratedDeviceAlgorithm != null &&
     299           0 :           signedOneTimeKeys.isNotEmpty &&
     300           0 :           exception.error == MatrixError.M_UNKNOWN) {
     301           0 :         Logs().w('Rotating otks because upload failed', exception);
     302           0 :         for (final otk in signedOneTimeKeys.values) {
     303             :           // Keys can only be removed by creating a session...
     304           0 :           final session = olm.Session();
     305             :           try {
     306             :             final String identity =
     307           0 :                 json.decode(olmAccount.identity_keys())['curve25519'];
     308           0 :             final key = otk.tryGet<String>('key');
     309             :             if (key != null) {
     310           0 :               session.create_outbound(_olmAccount!, identity, key);
     311           0 :               olmAccount.remove_one_time_keys(session);
     312             :             }
     313             :           } finally {
     314           0 :             session.free();
     315             :           }
     316             :         }
     317             : 
     318           0 :         await uploadKeys(
     319             :           uploadDeviceKeys: uploadDeviceKeys,
     320             :           oldKeyCount: oldKeyCount,
     321             :           updateDatabase: updateDatabase,
     322             :           unusedFallbackKey: unusedFallbackKey,
     323           0 :           retry: retry - 1,
     324             :         );
     325             :       }
     326             :     } finally {
     327           5 :       _uploadKeysLock = false;
     328             :     }
     329             : 
     330             :     return false;
     331             :   }
     332             : 
     333             :   final _otkUpdateDedup = AsyncCache<void>.ephemeral();
     334             : 
     335          25 :   Future<void> handleDeviceOneTimeKeysCount(
     336             :     Map<String, int>? countJson,
     337             :     List<String>? unusedFallbackKeyTypes,
     338             :   ) async {
     339          25 :     if (!enabled) {
     340             :       return;
     341             :     }
     342             : 
     343          50 :     await _otkUpdateDedup.fetch(
     344          75 :       () => runBenchmarked('handleOtkUpdate', () async {
     345          50 :         final haveFallbackKeys = encryption.isMinOlmVersion(3, 2, 0);
     346             :         // Check if there are at least half of max_number_of_one_time_keys left on the server
     347             :         // and generate and upload more if not.
     348             : 
     349             :         // If the server did not send us a count, assume it is 0
     350          25 :         final keyCount = countJson?.tryGet<int>('signed_curve25519') ?? 0;
     351             : 
     352             :         // If the server does not support fallback keys, it will not tell us about them.
     353             :         // If the server supports them but has no key, upload a new one.
     354             :         var unusedFallbackKey = true;
     355          27 :         if (unusedFallbackKeyTypes?.contains('signed_curve25519') == false) {
     356             :           unusedFallbackKey = false;
     357             :         }
     358             : 
     359             :         // fixup accidental too many uploads. We delete only one of them so that the server has time to update the counts and because we will get rate limited anyway.
     360          75 :         if (keyCount > _olmAccount!.max_number_of_one_time_keys()) {
     361           0 :           final requestingKeysFrom = {
     362           0 :             client.userID!: {ourDeviceId!: 'signed_curve25519'},
     363             :           };
     364           0 :           await client.claimKeys(requestingKeysFrom, timeout: 10000);
     365             :         }
     366             : 
     367             :         // Only upload keys if they are less than half of the max or we have no unused fallback key
     368         100 :         if (keyCount < (_olmAccount!.max_number_of_one_time_keys() / 2) ||
     369             :             !unusedFallbackKey) {
     370           1 :           await uploadKeys(
     371             :             oldKeyCount:
     372           4 :                 keyCount < (_olmAccount!.max_number_of_one_time_keys() / 2)
     373             :                     ? keyCount
     374             :                     : null,
     375             :             unusedFallbackKey: haveFallbackKeys ? unusedFallbackKey : null,
     376             :           );
     377             :         }
     378             :       }),
     379             :     );
     380             :   }
     381             : 
     382          24 :   Future<void> storeOlmSession(OlmSession session) async {
     383          48 :     if (session.sessionId == null || session.pickledSession == null) {
     384             :       return;
     385             :     }
     386             : 
     387          96 :     _olmSessions[session.identityKey] ??= <OlmSession>[];
     388          72 :     final ix = _olmSessions[session.identityKey]!
     389          56 :         .indexWhere((s) => s.sessionId == session.sessionId);
     390          48 :     if (ix == -1) {
     391             :       // add a new session
     392          96 :       _olmSessions[session.identityKey]!.add(session);
     393             :     } else {
     394             :       // update an existing session
     395          28 :       _olmSessions[session.identityKey]![ix] = session;
     396             :     }
     397          72 :     await encryption.olmDatabase?.storeOlmSession(
     398          24 :       session.identityKey,
     399          24 :       session.sessionId!,
     400          24 :       session.pickledSession!,
     401          48 :       session.lastReceived?.millisecondsSinceEpoch ??
     402           0 :           DateTime.now().millisecondsSinceEpoch,
     403             :     );
     404             :   }
     405             : 
     406          25 :   Future<ToDeviceEvent> _decryptToDeviceEvent(ToDeviceEvent event) async {
     407          50 :     if (event.type != EventTypes.Encrypted) {
     408             :       return event;
     409             :     }
     410          25 :     final content = event.parsedRoomEncryptedContent;
     411          50 :     if (content.algorithm != AlgorithmTypes.olmV1Curve25519AesSha2) {
     412           0 :       throw DecryptException(DecryptException.unknownAlgorithm);
     413             :     }
     414          25 :     if (content.ciphertextOlm == null ||
     415          75 :         !content.ciphertextOlm!.containsKey(identityKey)) {
     416           6 :       throw DecryptException(DecryptException.isntSentForThisDevice);
     417             :     }
     418             :     String? plaintext;
     419          24 :     final senderKey = content.senderKey;
     420          96 :     final body = content.ciphertextOlm![identityKey]!.body;
     421          96 :     final type = content.ciphertextOlm![identityKey]!.type;
     422          24 :     if (type != 0 && type != 1) {
     423           0 :       throw DecryptException(DecryptException.unknownMessageType);
     424             :     }
     425         100 :     final device = client.userDeviceKeys[event.sender]?.deviceKeys.values
     426           8 :         .firstWhereOrNull((d) => d.curve25519Key == senderKey);
     427          48 :     final existingSessions = olmSessions[senderKey];
     428          24 :     Future<void> updateSessionUsage([OlmSession? session]) async {
     429             :       try {
     430             :         if (session != null) {
     431           2 :           session.lastReceived = DateTime.now();
     432           1 :           await storeOlmSession(session);
     433             :         }
     434             :         if (device != null) {
     435           2 :           device.lastActive = DateTime.now();
     436           3 :           await encryption.olmDatabase?.setLastActiveUserDeviceKey(
     437           2 :             device.lastActive.millisecondsSinceEpoch,
     438           1 :             device.userId,
     439           1 :             device.deviceId!,
     440             :           );
     441             :         }
     442             :       } catch (e, s) {
     443           0 :         Logs().e('Error while updating olm session timestamp', e, s);
     444             :       }
     445             :     }
     446             : 
     447             :     if (existingSessions != null) {
     448           4 :       for (final session in existingSessions) {
     449           2 :         if (session.session == null) {
     450             :           continue;
     451             :         }
     452           6 :         if (type == 0 && session.session!.matches_inbound(body)) {
     453             :           try {
     454           4 :             plaintext = session.session!.decrypt(type, body);
     455             :           } catch (e) {
     456             :             // The message was encrypted during this session, but is unable to decrypt
     457           1 :             throw DecryptException(
     458             :               DecryptException.decryptionFailed,
     459           1 :               e.toString(),
     460             :             );
     461             :           }
     462           1 :           await updateSessionUsage(session);
     463             :           break;
     464           1 :         } else if (type == 1) {
     465             :           try {
     466           0 :             plaintext = session.session!.decrypt(type, body);
     467           0 :             await updateSessionUsage(session);
     468             :             break;
     469             :           } catch (_) {
     470             :             plaintext = null;
     471             :           }
     472             :         }
     473             :       }
     474             :     }
     475          24 :     if (plaintext == null && type != 0) {
     476           0 :       throw DecryptException(DecryptException.unableToDecryptWithAnyOlmSession);
     477             :     }
     478             : 
     479             :     if (plaintext == null) {
     480          24 :       final newSession = olm.Session();
     481             :       try {
     482          48 :         newSession.create_inbound_from(_olmAccount!, senderKey, body);
     483          48 :         _olmAccount!.remove_one_time_keys(newSession);
     484          96 :         await encryption.olmDatabase?.updateClientKeys(pickledOlmAccount!);
     485             : 
     486          24 :         plaintext = newSession.decrypt(type, body);
     487             : 
     488          24 :         await storeOlmSession(
     489          24 :           OlmSession(
     490          48 :             key: client.userID!,
     491             :             identityKey: senderKey,
     492          24 :             sessionId: newSession.session_id(),
     493             :             session: newSession,
     494          24 :             lastReceived: DateTime.now(),
     495             :           ),
     496             :         );
     497          24 :         await updateSessionUsage();
     498             :       } catch (e) {
     499           0 :         newSession.free();
     500           0 :         throw DecryptException(DecryptException.decryptionFailed, e.toString());
     501             :       }
     502             :     }
     503          24 :     final Map<String, dynamic> plainContent = json.decode(plaintext);
     504          72 :     if (plainContent['sender'] != event.sender) {
     505           0 :       throw DecryptException(DecryptException.senderDoesntMatch);
     506             :     }
     507          96 :     if (plainContent['recipient'] != client.userID) {
     508           0 :       throw DecryptException(DecryptException.recipientDoesntMatch);
     509             :     }
     510          48 :     if (plainContent['recipient_keys'] is Map &&
     511          72 :         plainContent['recipient_keys']['ed25519'] is String &&
     512          96 :         plainContent['recipient_keys']['ed25519'] != fingerprintKey) {
     513           0 :       throw DecryptException(DecryptException.ownFingerprintDoesntMatch);
     514             :     }
     515          24 :     return ToDeviceEvent(
     516          24 :       content: plainContent['content'],
     517          24 :       encryptedContent: event.content,
     518          24 :       type: plainContent['type'],
     519          24 :       sender: event.sender,
     520             :     );
     521             :   }
     522             : 
     523          25 :   Future<List<OlmSession>> getOlmSessionsFromDatabase(String senderKey) async {
     524             :     final olmSessions =
     525         122 :         await encryption.olmDatabase?.getOlmSessions(senderKey, client.userID!);
     526          54 :     return olmSessions?.where((sess) => sess.isValid).toList() ?? [];
     527             :   }
     528             : 
     529          10 :   Future<void> getOlmSessionsForDevicesFromDatabase(
     530             :     List<String> senderKeys,
     531             :   ) async {
     532          30 :     final rows = await encryption.olmDatabase?.getOlmSessionsForDevices(
     533             :       senderKeys,
     534          20 :       client.userID!,
     535             :     );
     536          10 :     final res = <String, List<OlmSession>>{};
     537          14 :     for (final sess in rows ?? []) {
     538          12 :       res[sess.identityKey] ??= <OlmSession>[];
     539           4 :       if (sess.isValid) {
     540          12 :         res[sess.identityKey]!.add(sess);
     541             :       }
     542             :     }
     543          14 :     for (final entry in res.entries) {
     544          16 :       _olmSessions[entry.key] = entry.value;
     545             :     }
     546             :   }
     547             : 
     548          25 :   Future<List<OlmSession>> getOlmSessions(
     549             :     String senderKey, {
     550             :     bool getFromDb = true,
     551             :   }) async {
     552          50 :     var sess = olmSessions[senderKey];
     553           0 :     if ((getFromDb) && (sess == null || sess.isEmpty)) {
     554          25 :       final sessions = await getOlmSessionsFromDatabase(senderKey);
     555          25 :       if (sessions.isEmpty) {
     556          25 :         return [];
     557             :       }
     558           4 :       sess = _olmSessions[senderKey] = sessions;
     559             :     }
     560             :     if (sess == null) {
     561           7 :       return [];
     562             :     }
     563           7 :     sess.sort(
     564           8 :       (a, b) => a.lastReceived == b.lastReceived
     565           0 :           ? (a.sessionId ?? '').compareTo(b.sessionId ?? '')
     566           2 :           : (b.lastReceived ?? DateTime(0))
     567           4 :               .compareTo(a.lastReceived ?? DateTime(0)),
     568             :     );
     569             :     return sess;
     570             :   }
     571             : 
     572             :   final Map<String, DateTime> _restoredOlmSessionsTime = {};
     573             : 
     574           7 :   Future<void> restoreOlmSession(String userId, String senderKey) async {
     575          21 :     if (!client.userDeviceKeys.containsKey(userId)) {
     576             :       return;
     577             :     }
     578          10 :     final device = client.userDeviceKeys[userId]!.deviceKeys.values
     579           8 :         .firstWhereOrNull((d) => d.curve25519Key == senderKey);
     580             :     if (device == null) {
     581             :       return;
     582             :     }
     583             :     // per device only one olm session per hour should be restored
     584           2 :     final mapKey = '$userId;$senderKey';
     585           4 :     if (_restoredOlmSessionsTime.containsKey(mapKey) &&
     586           0 :         DateTime.now()
     587           0 :             .subtract(Duration(hours: 1))
     588           0 :             .isBefore(_restoredOlmSessionsTime[mapKey]!)) {
     589           0 :       Logs().w(
     590             :         '[OlmManager] Skipping restore session, one was restored in the past hour',
     591             :       );
     592             :       return;
     593             :     }
     594           6 :     _restoredOlmSessionsTime[mapKey] = DateTime.now();
     595           4 :     await startOutgoingOlmSessions([device]);
     596           8 :     await client.sendToDeviceEncrypted([device], EventTypes.Dummy, {});
     597             :   }
     598             : 
     599          25 :   Future<ToDeviceEvent> decryptToDeviceEvent(ToDeviceEvent event) async {
     600          50 :     if (event.type != EventTypes.Encrypted) {
     601             :       return event;
     602             :     }
     603          50 :     final senderKey = event.parsedRoomEncryptedContent.senderKey;
     604          25 :     Future<bool> loadFromDb() async {
     605          25 :       final sessions = await getOlmSessions(senderKey);
     606          25 :       return sessions.isNotEmpty;
     607             :     }
     608             : 
     609          50 :     if (!_olmSessions.containsKey(senderKey)) {
     610          25 :       await loadFromDb();
     611             :     }
     612             :     try {
     613          25 :       event = await _decryptToDeviceEvent(event);
     614          48 :       if (event.type != EventTypes.Encrypted || !(await loadFromDb())) {
     615             :         return event;
     616             :       }
     617             :       // retry to decrypt!
     618           0 :       return _decryptToDeviceEvent(event);
     619             :     } catch (_) {
     620             :       // okay, the thing errored while decrypting. It is safe to assume that the olm session is corrupt and we should generate a new one
     621          24 :       runInRoot(() => restoreOlmSession(event.senderId, senderKey));
     622             : 
     623             :       rethrow;
     624             :     }
     625             :   }
     626             : 
     627          10 :   Future<void> startOutgoingOlmSessions(List<DeviceKeys> deviceKeys) async {
     628          20 :     Logs().v(
     629          20 :       '[OlmManager] Starting session with ${deviceKeys.length} devices...',
     630             :     );
     631          10 :     final requestingKeysFrom = <String, Map<String, String>>{};
     632          20 :     for (final device in deviceKeys) {
     633          20 :       if (requestingKeysFrom[device.userId] == null) {
     634          30 :         requestingKeysFrom[device.userId] = {};
     635             :       }
     636          40 :       requestingKeysFrom[device.userId]![device.deviceId!] =
     637             :           'signed_curve25519';
     638             :     }
     639             : 
     640          20 :     final response = await client.claimKeys(requestingKeysFrom, timeout: 10000);
     641             : 
     642          30 :     for (final userKeysEntry in response.oneTimeKeys.entries) {
     643          10 :       final userId = userKeysEntry.key;
     644          30 :       for (final deviceKeysEntry in userKeysEntry.value.entries) {
     645          10 :         final deviceId = deviceKeysEntry.key;
     646             :         final fingerprintKey =
     647          60 :             client.userDeviceKeys[userId]!.deviceKeys[deviceId]!.ed25519Key;
     648             :         final identityKey =
     649          60 :             client.userDeviceKeys[userId]!.deviceKeys[deviceId]!.curve25519Key;
     650          30 :         for (final deviceKey in deviceKeysEntry.value.values) {
     651             :           if (fingerprintKey == null ||
     652             :               identityKey == null ||
     653          10 :               deviceKey is! Map<String, Object?> ||
     654          10 :               !deviceKey.checkJsonSignature(fingerprintKey, userId, deviceId) ||
     655          20 :               deviceKey['key'] is! String) {
     656           0 :             Logs().w(
     657           0 :               'Skipping invalid device key from $userId:$deviceId',
     658             :               deviceKey,
     659             :             );
     660             :             continue;
     661             :           }
     662          30 :           Logs().v('[OlmManager] Starting session with $userId:$deviceId');
     663          10 :           final session = olm.Session();
     664             :           try {
     665          10 :             session.create_outbound(
     666          10 :               _olmAccount!,
     667             :               identityKey,
     668          10 :               deviceKey.tryGet<String>('key')!,
     669             :             );
     670          10 :             await storeOlmSession(
     671          10 :               OlmSession(
     672          20 :                 key: client.userID!,
     673             :                 identityKey: identityKey,
     674          10 :                 sessionId: session.session_id(),
     675             :                 session: session,
     676             :                 lastReceived:
     677          10 :                     DateTime.now(), // we want to use a newly created session
     678             :               ),
     679             :             );
     680             :           } catch (e, s) {
     681           0 :             session.free();
     682           0 :             Logs()
     683           0 :                 .e('[LibOlm] Could not create new outbound olm session', e, s);
     684             :           }
     685             :         }
     686             :       }
     687             :     }
     688             :   }
     689             : 
     690             :   /// Encryptes a ToDeviceMessage for the given device with an existing
     691             :   /// olm session.
     692             :   /// Throws `NoOlmSessionFoundException` if there is no olm session with this
     693             :   /// device and none could be created.
     694          10 :   Future<Map<String, dynamic>> encryptToDeviceMessagePayload(
     695             :     DeviceKeys device,
     696             :     String type,
     697             :     Map<String, dynamic> payload, {
     698             :     bool getFromDb = true,
     699             :   }) async {
     700             :     final sess =
     701          20 :         await getOlmSessions(device.curve25519Key!, getFromDb: getFromDb);
     702          10 :     if (sess.isEmpty) {
     703           7 :       throw NoOlmSessionFoundException(device);
     704             :     }
     705           7 :     final fullPayload = {
     706             :       'type': type,
     707             :       'content': payload,
     708          14 :       'sender': client.userID,
     709          14 :       'keys': {'ed25519': fingerprintKey},
     710           7 :       'recipient': device.userId,
     711          14 :       'recipient_keys': {'ed25519': device.ed25519Key},
     712             :     };
     713          28 :     final encryptResult = sess.first.session!.encrypt(json.encode(fullPayload));
     714          14 :     await storeOlmSession(sess.first);
     715          14 :     if (encryption.olmDatabase != null) {
     716             :       try {
     717          21 :         await encryption.olmDatabase?.setLastSentMessageUserDeviceKey(
     718          14 :           json.encode({
     719             :             'type': type,
     720             :             'content': payload,
     721             :           }),
     722           7 :           device.userId,
     723           7 :           device.deviceId!,
     724             :         );
     725             :       } catch (e, s) {
     726             :         // we can ignore this error, since it would just make us use a different olm session possibly
     727           0 :         Logs().w('Error while updating olm usage timestamp', e, s);
     728             :       }
     729             :     }
     730           7 :     final encryptedBody = <String, dynamic>{
     731             :       'algorithm': AlgorithmTypes.olmV1Curve25519AesSha2,
     732           7 :       'sender_key': identityKey,
     733           7 :       'ciphertext': <String, dynamic>{},
     734             :     };
     735          28 :     encryptedBody['ciphertext'][device.curve25519Key] = {
     736           7 :       'type': encryptResult.type,
     737           7 :       'body': encryptResult.body,
     738             :     };
     739             :     return encryptedBody;
     740             :   }
     741             : 
     742          10 :   Future<Map<String, Map<String, Map<String, dynamic>>>> encryptToDeviceMessage(
     743             :     List<DeviceKeys> deviceKeys,
     744             :     String type,
     745             :     Map<String, dynamic> payload,
     746             :   ) async {
     747          10 :     final data = <String, Map<String, Map<String, dynamic>>>{};
     748             :     // first check if any of our sessions we want to encrypt for are in the database
     749          20 :     if (encryption.olmDatabase != null) {
     750          10 :       await getOlmSessionsForDevicesFromDatabase(
     751          40 :         deviceKeys.map((d) => d.curve25519Key!).toList(),
     752             :       );
     753             :     }
     754          10 :     final deviceKeysWithoutSession = List<DeviceKeys>.from(deviceKeys);
     755          10 :     deviceKeysWithoutSession.removeWhere(
     756          10 :       (DeviceKeys deviceKeys) =>
     757          34 :           olmSessions[deviceKeys.curve25519Key]?.isNotEmpty ?? false,
     758             :     );
     759          10 :     if (deviceKeysWithoutSession.isNotEmpty) {
     760          10 :       await startOutgoingOlmSessions(deviceKeysWithoutSession);
     761             :     }
     762          20 :     for (final device in deviceKeys) {
     763          30 :       final userData = data[device.userId] ??= {};
     764             :       try {
     765          27 :         userData[device.deviceId!] = await encryptToDeviceMessagePayload(
     766             :           device,
     767             :           type,
     768             :           payload,
     769             :           getFromDb: false,
     770             :         );
     771           7 :       } on NoOlmSessionFoundException catch (e) {
     772          14 :         Logs().d('[LibOlm] Error encrypting to-device event', e);
     773             :         continue;
     774             :       } catch (e, s) {
     775           0 :         Logs().wtf('[LibOlm] Error encrypting to-device event', e, s);
     776             :         continue;
     777             :       }
     778             :     }
     779             :     return data;
     780             :   }
     781             : 
     782           1 :   Future<void> handleToDeviceEvent(ToDeviceEvent event) async {
     783           2 :     if (event.type == EventTypes.Dummy) {
     784             :       // We received an encrypted m.dummy. This means that the other end was not able to
     785             :       // decrypt our last message. So, we re-send it.
     786           1 :       final encryptedContent = event.encryptedContent;
     787           2 :       if (encryptedContent == null || encryption.olmDatabase == null) {
     788             :         return;
     789             :       }
     790           2 :       final device = client.getUserDeviceKeysByCurve25519Key(
     791           1 :         encryptedContent.tryGet<String>('sender_key') ?? '',
     792             :       );
     793             :       if (device == null) {
     794             :         return; // device not found
     795             :       }
     796           2 :       Logs().v(
     797           3 :         '[OlmManager] Device ${device.userId}:${device.deviceId} generated a new olm session, replaying last sent message...',
     798             :       );
     799           2 :       final lastSentMessageRes = await encryption.olmDatabase
     800           3 :           ?.getLastSentMessageUserDeviceKey(device.userId, device.deviceId!);
     801             :       if (lastSentMessageRes == null ||
     802           1 :           lastSentMessageRes.isEmpty ||
     803           2 :           lastSentMessageRes.first.isEmpty) {
     804             :         return;
     805             :       }
     806           2 :       final lastSentMessage = json.decode(lastSentMessageRes.first);
     807             :       // We do *not* want to re-play m.dummy events, as they hold no value except of saying
     808             :       // what olm session is the most recent one. In fact, if we *do* replay them, then
     809             :       // we can easily land in an infinite ping-pong trap!
     810           2 :       if (lastSentMessage['type'] != EventTypes.Dummy) {
     811             :         // okay, time to send the message!
     812           2 :         await client.sendToDeviceEncrypted(
     813           1 :           [device],
     814           1 :           lastSentMessage['type'],
     815           1 :           lastSentMessage['content'],
     816             :         );
     817             :       }
     818             :     }
     819             :   }
     820             : 
     821          22 :   Future<void> dispose() async {
     822          27 :     await currentUpload?.cancel();
     823          65 :     for (final sessions in olmSessions.values) {
     824          42 :       for (final sess in sessions) {
     825          21 :         sess.dispose();
     826             :       }
     827             :     }
     828          44 :     _olmAccount?.free();
     829          22 :     _olmAccount = null;
     830             :   }
     831             : }
     832             : 
     833             : class NoOlmSessionFoundException implements Exception {
     834             :   final DeviceKeys device;
     835             : 
     836           7 :   NoOlmSessionFoundException(this.device);
     837             : 
     838           7 :   @override
     839             :   String toString() =>
     840          35 :       'No olm session found for ${device.userId}:${device.deviceId}';
     841             : }

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