fix: Reuse old key exchange when the ratchet is unacked

lib/src/double_ratchet/double_ratchet.dart

@@ -69,6 +69,7 @@ class OmemoDoubleRatchet {
     this.mkSkipped, // MKSKIPPED
     this.acknowledged,
     this.kexTimestamp,
+    this.kex,
   );
   
   factory OmemoDoubleRatchet.fromJson(Map<String, dynamic> data) {
@@ -83,10 +84,11 @@ class OmemoDoubleRatchet {
       'ns': 0,
       'nr': 0,
       'pn': 0,
-      'ik_pub': 'base/64/encoded',
+      'ik_pub': null | 'base/64/encoded',
       'session_ad': 'base/64/encoded',
       'acknowledged': true | false,
       'kex_timestamp': int,
+      'kex': 'base/64/encoded',
       'mkskipped': [
         {
           'key': 'base/64/encoded',
@@ -132,6 +134,7 @@ class OmemoDoubleRatchet {
       mkSkipped,
       data['acknowledged']! as bool,
       data['kex_timestamp']! as int,
+      data['kex'] as String?,
     );
   }
   
@@ -167,6 +170,9 @@ class OmemoDoubleRatchet {
   /// Precision is milliseconds since epoch.
   int kexTimestamp;
 
+  /// The key exchange that was used for initiating the session.
+  final String? kex;
+  
   /// Indicates whether we received an empty OMEMO message after building a session with
   /// the device. 
   bool acknowledged;
@@ -194,6 +200,7 @@ class OmemoDoubleRatchet {
       {},
       false,
       timestamp,
+      '',
     );
   }
 
@@ -216,6 +223,7 @@ class OmemoDoubleRatchet {
       {},
       false,
       kexTimestamp,
+      null,
     );
   }
 
@@ -243,6 +251,7 @@ class OmemoDoubleRatchet {
       'mkskipped': mkSkippedSerialised,
       'acknowledged': acknowledged,
       'kex_timestamp': kexTimestamp,
+      'kex': kex,
     };
   }
   
@@ -359,6 +368,30 @@ class OmemoDoubleRatchet {
       Map<SkippedKey, List<int>>.from(mkSkipped),
       acknowledged,
       kexTimestamp,
+      kex,
+    );
+  }
+
+  OmemoDoubleRatchet cloneWithKex(String kex) {
+    return OmemoDoubleRatchet(
+      dhs,
+      dhr,
+      rk,
+      cks != null ?
+        List<int>.from(cks!) :
+        null,
+      ckr != null ?
+        List<int>.from(ckr!) :
+        null,
+      ns,
+      nr,
+      pn,
+      ik,
+      sessionAd,
+      Map<SkippedKey, List<int>>.from(mkSkipped),
+      acknowledged,
+      kexTimestamp,
+      kex,
     );
   }
   

lib/src/omemo/sessionmanager.dart

@@ -170,7 +170,7 @@ class OmemoSessionManager {
   /// Build a new session with the user at [jid] with the device [deviceId] using data
   /// from the key exchange [kex]. In case [kex] contains an unknown Signed Prekey
   /// identifier an UnknownSignedPrekeyException will be thrown.
-  Future<void> _addSessionFromKeyExchange(String jid, int deviceId, OmemoKeyExchange kex) async {
+  Future<OmemoDoubleRatchet> _addSessionFromKeyExchange(String jid, int deviceId, OmemoKeyExchange kex) async {
     // Pick the correct SPK
     final device = await getDevice();
     final spk = await _lock.synchronized(() async {
@@ -204,8 +204,7 @@ class OmemoSessionManager {
       getTimestamp(),
     );
 
-    await _trustManager.onNewSession(jid, deviceId);
+    return ratchet;
-    await _addSession(jid, deviceId, ratchet);
   }
 
   /// Like [encryptToJids] but only for one Jid [jid].
@@ -264,24 +263,53 @@ class OmemoSessionManager {
           }
 
           final ratchetKey = RatchetMapKey(jid, deviceId);
-          final ratchet = _ratchetMap[ratchetKey]!;
+          var ratchet = _ratchetMap[ratchetKey]!;
           final ciphertext = (await ratchet.ratchetEncrypt(keyPayload)).ciphertext;
-
+ 
-          // Commit the ratchet
-          _eventStreamController.add(RatchetModifiedEvent(jid, deviceId, ratchet));
-          
           if (kex.isNotEmpty && kex.containsKey(deviceId)) {
+            // The ratchet did not exist
             final k = kex[deviceId]!
               ..message = OmemoAuthenticatedMessage.fromBuffer(ciphertext);
+            final buffer = base64.encode(k.writeToBuffer());
             encryptedKeys.add(
               EncryptedKey(
                 jid,
                 deviceId,
-                base64.encode(k.writeToBuffer()),
+                buffer,
                 true,
               ),
             );
+
+            ratchet = ratchet.cloneWithKex(buffer);
+            _ratchetMap[ratchetKey] = ratchet;
+          } else if (!ratchet.acknowledged) {
+            // The ratchet exists but is not acked
+            if (ratchet.kex != null) {
+              final oldKex = OmemoKeyExchange.fromBuffer(base64.decode(ratchet.kex!))
+              ..message = OmemoAuthenticatedMessage.fromBuffer(ciphertext);
+              
+              encryptedKeys.add(
+                EncryptedKey(
+                  jid,
+                  deviceId,
+                  base64.encode(oldKex.writeToBuffer()),
+                  true,
+                ),
+              );
+            } else {
+              // The ratchet is not acked but we don't have the old key exchange
+              _log.warning('Ratchet for $jid:$deviceId is not acked but the kex attribute is null');
+              encryptedKeys.add(
+                EncryptedKey(
+                  jid,
+                  deviceId,
+                  base64.encode(ciphertext),
+                  false,
+                ),
+              );
+            }
           } else {
+            // The ratchet exists and is acked
             encryptedKeys.add(
               EncryptedKey(
                 jid,
@@ -291,6 +319,9 @@ class OmemoSessionManager {
               ),
             );
           }
+
+          // Commit the ratchet
+          _eventStreamController.add(RatchetModifiedEvent(jid, deviceId, ratchet));
         }
       }
     });
@@ -319,6 +350,25 @@ class OmemoSessionManager {
       );
     });
   }
+
+  Future<String?> _decryptAndVerifyHmac(List<int>? ciphertext, List<int> keyAndHmac) async {
+    // Empty OMEMO messages should just have the key decrypted and/or session set up.
+    if (ciphertext == null) {
+      return null;
+    }
+    
+    final key = keyAndHmac.sublist(0, 32);
+    final hmac = keyAndHmac.sublist(32, 48);
+    final derivedKeys = await deriveEncryptionKeys(key, omemoPayloadInfoString);
+    final computedHmac = await truncatedHmac(ciphertext, derivedKeys.authenticationKey);
+    if (!listsEqual(hmac, computedHmac)) {
+      throw InvalidMessageHMACException();
+    }
+    
+    return utf8.decode(
+      await aes256CbcDecrypt(ciphertext, derivedKeys.encryptionKey, derivedKeys.iv),
+    );
+  }
   
   /// Attempt to decrypt [ciphertext]. [keys] refers to the <key /> elements inside the
   /// <keys /> element with a "jid" attribute matching our own. [senderJid] refers to the
@@ -342,6 +392,7 @@ class OmemoSessionManager {
 
     final ratchetKey = RatchetMapKey(senderJid, senderDeviceId);
     final decodedRawKey = base64.decode(rawKey.value);
+    List<int>? keyAndHmac;
     OmemoAuthenticatedMessage authMessage;
     OmemoDoubleRatchet? oldRatchet;
     OmemoMessage? message;
@@ -359,14 +410,34 @@ class OmemoSessionManager {
         if (oldRatchet.kexTimestamp > timestamp) {
           throw InvalidKeyExchangeException();
         }
+        
+        // Try to decrypt it
+        try {
+          final decrypted = await oldRatchet.ratchetDecrypt(message, authMessage.writeToBuffer());
+
+          // Commit the ratchet
+          _eventStreamController.add(
+            RatchetModifiedEvent(
+              senderJid,
+              senderDeviceId,
+              oldRatchet,
+            ),
+          );
+          
+          final plaintext = await _decryptAndVerifyHmac(
+            ciphertext,
+            decrypted,
+          );
+          await _addSession(senderJid, senderDeviceId, oldRatchet);
+          return plaintext;
+        } catch (_) {
+          _log.finest('Failed to use old ratchet with KEX for existing ratchet');
+        }
       }
-      
+
-      // TODO(PapaTutuWawa): Only do this when we should
+      final r = await _addSessionFromKeyExchange(senderJid, senderDeviceId, kex);
-      await _addSessionFromKeyExchange(
+      await _trustManager.onNewSession(senderJid, senderDeviceId);
-        senderJid,
+      await _addSession(senderJid, senderDeviceId, r);
-        senderDeviceId,
-        kex,
-      );
 
       // Replace the OPK
       // TODO(PapaTutuWawa): Replace the OPK when we know that the KEX worked
@@ -389,7 +460,6 @@ class OmemoSessionManager {
       throw NoDecryptionKeyException();
     }
 
-    List<int>? keyAndHmac;
     // We can guarantee that the ratchet exists at this point in time
     final ratchet = (await _getRatchet(ratchetKey))!;
     oldRatchet ??= ratchet.clone();
@@ -408,24 +478,12 @@ class OmemoSessionManager {
     // Commit the ratchet
     _eventStreamController.add(RatchetModifiedEvent(senderJid, senderDeviceId, ratchet));
 
-    // Empty OMEMO messages should just have the key decrypted and/or session set up.
+    try {
-    if (ciphertext == null) {
+      return _decryptAndVerifyHmac(ciphertext, keyAndHmac);
-      return null;
+    } catch (_) { 
-    }
-    
-    final key = keyAndHmac.sublist(0, 32);
-    final hmac = keyAndHmac.sublist(32, 48);
-    final derivedKeys = await deriveEncryptionKeys(key, omemoPayloadInfoString);
-
-    final computedHmac = await truncatedHmac(ciphertext, derivedKeys.authenticationKey);
-    if (!listsEqual(hmac, computedHmac)) {
-      // TODO(PapaTutuWawa): I am unsure if we should restore the ratchet here
       await _restoreRatchet(ratchetKey, oldRatchet);
-      throw InvalidMessageHMACException();
+      rethrow;
     }
-    
-    final plaintext = await aes256CbcDecrypt(ciphertext, derivedKeys.encryptionKey, derivedKeys.iv);
-    return utf8.decode(plaintext);
   }
 
   /// Returns the list of hex-encoded fingerprints we have for sessions with [jid].

test/omemo_test.dart

@@ -80,7 +80,7 @@ void main() {
       ],
     );
     expect(aliceMessage.encryptedKeys.length, 1);
-
+    
     // Alice sends the message to Bob
     // ...
 
@@ -106,6 +106,10 @@ void main() {
       false,
     );
 
+    // Ratchets are acked
+    await aliceSession.ratchetAcknowledged(bobJid, await bobSession.getDeviceId());
+    await bobSession.ratchetAcknowledged(aliceJid, await aliceSession.getDeviceId());
+    
     // Bob responds to Alice
     const bobResponseText = 'Oh, hello Alice!';
     final bobResponseMessage = await bobSession.encryptToJid(
@@ -176,6 +180,10 @@ void main() {
     );
     expect(messagePlaintext, bobMessage);
 
+    // Ratchets are acked
+    await aliceSession.ratchetAcknowledged(bobJid, await bobSession.getDeviceId());
+    await bobSession.ratchetAcknowledged(aliceJid, await aliceSession.getDeviceId());
+    
     // Bob responds to Alice
     const bobResponseText = 'Oh, hello Alice!';
     final bobResponseMessage = await bobSession.encryptToJid(
@@ -448,6 +456,10 @@ void main() {
       0,
     );
 
+    // Ratchets are acked
+    await aliceSession.ratchetAcknowledged(bobJid, await bobSession.getDeviceId());
+    await bobSession.ratchetAcknowledged(aliceJid, await aliceSession.getDeviceId());
+    
     for (var i = 0; i < 100; i++) {
       final messageText = 'Test Message #$i';
       // Bob responds to Alice
@@ -665,6 +677,58 @@ void main() {
     expect(await bobRatchet1.equals(bobRatchet2), false);
   });
 
+  test('Test resending key exchanges', () async {
+    const aliceJid = 'alice@server.example';
+    const bobJid = 'bob@other.server.example';
+    // Alice and Bob generate their sessions
+    final aliceSession = await OmemoSessionManager.generateNewIdentity(
+      aliceJid,
+      AlwaysTrustingTrustManager(),
+      opkAmount: 1,
+    );
+    final bobSession = await OmemoSessionManager.generateNewIdentity(
+      bobJid,
+      AlwaysTrustingTrustManager(),
+      opkAmount: 2,
+    );
+
+    // Alice sends Bob a message
+    final msg1 = await aliceSession.encryptToJid(
+      bobJid,
+      'Hallo Welt',
+      newSessions: [
+        await bobSession.getDeviceBundle(),
+      ],
+    );
+    // The first message should be a kex message
+    expect(msg1.encryptedKeys.first.kex, true);
+
+    await bobSession.decryptMessage(
+      msg1.ciphertext,
+      aliceJid,
+      await aliceSession.getDeviceId(),
+      msg1.encryptedKeys,
+      0,
+    );
+
+    // Alice is impatient and immediately sends another message before the original one
+    // can be acknowledged by Bob
+    final msg2 = await aliceSession.encryptToJid(
+      bobJid,
+      "Why don't you answer?",
+    );
+    expect(msg2.encryptedKeys.first.kex, true);
+
+    await bobSession.decryptMessage(
+      msg2.ciphertext,
+      aliceJid,
+      await aliceSession.getDeviceId(),
+      msg2.encryptedKeys,
+      getTimestamp(),
+    );
+
+  });
+  
   test('Test receiving old messages including a KEX', () async {
     const aliceJid = 'alice@server.example';
     const bobJid = 'bob@other.server.example';
@@ -703,6 +767,10 @@ void main() {
       t1,
     );
 
+    // Ratchets are acked
+    await aliceSession.ratchetAcknowledged(bobJid, await bobSession.getDeviceId());
+    await bobSession.ratchetAcknowledged(aliceJid, await aliceSession.getDeviceId());
+    
     // Bob responds
     final msg2 = await bobSession.encryptToJid(
       aliceJid,
@@ -785,4 +853,94 @@ void main() {
 
     expect(result, 'Are you okay?');
   });
+
+  test("Test ignoring a new KEX when we haven't acket it yet", () async {
+    const aliceJid = 'alice@server.example';
+    const bobJid = 'bob@other.server.example';
+    // Alice and Bob generate their sessions
+    final aliceSession = await OmemoSessionManager.generateNewIdentity(
+      aliceJid,
+      AlwaysTrustingTrustManager(),
+      opkAmount: 1,
+    );
+    final bobSession = await OmemoSessionManager.generateNewIdentity(
+      bobJid,
+      AlwaysTrustingTrustManager(),
+      opkAmount: 1,
+    );
+
+    // Alice sends Bob a message
+    final msg1 = await aliceSession.encryptToJid(
+      bobJid,
+      'Hallo Welt',
+      newSessions: [
+        await bobSession.getDeviceBundle(),
+      ],
+    );
+    expect(msg1.encryptedKeys.first.kex, true);
+
+    await bobSession.decryptMessage(
+      msg1.ciphertext,
+      aliceJid,
+      await aliceSession.getDeviceId(),
+      msg1.encryptedKeys,
+      getTimestamp(),
+    );
+
+    // Alice sends another message before the ack can reach us
+    final msg2 = await aliceSession.encryptToJid(
+      bobJid,
+      'ANSWER ME!',
+    );
+    expect(msg2.encryptedKeys.first.kex, true);
+
+    await bobSession.decryptMessage(
+      msg2.ciphertext,
+      aliceJid,
+      await aliceSession.getDeviceId(),
+      msg2.encryptedKeys,
+      getTimestamp(),
+    );
+
+    // Now the acks reach us
+    await aliceSession.ratchetAcknowledged(bobJid, await bobSession.getDeviceId());
+    await bobSession.ratchetAcknowledged(aliceJid, await aliceSession.getDeviceId());
+
+    // Alice sends another message
+    final msg3 = await aliceSession.encryptToJid(
+      bobJid,
+      "You read the message, didn't you?",
+    );
+    expect(msg3.encryptedKeys.first.kex, false);
+
+    await bobSession.decryptMessage(
+      msg3.ciphertext,
+      aliceJid,
+      await aliceSession.getDeviceId(),
+      msg3.encryptedKeys,
+      getTimestamp(),
+    );
+
+    for (var i = 0; i < 100; i++) {
+      final messageText = 'Test Message #$i';
+      // Bob responds to Alice
+      final bobResponseMessage = await bobSession.encryptToJid(
+        aliceJid,
+        messageText,
+      );
+
+      // Bob sends the message to Alice
+      // ...
+
+      // Alice decrypts it
+      final aliceReceivedMessage = await aliceSession.decryptMessage(
+        bobResponseMessage.ciphertext,
+        bobJid,
+        await bobSession.getDeviceId(),
+        bobResponseMessage.encryptedKeys,
+        0,
+      );
+      expect(messageText, aliceReceivedMessage);
+    }
+  });
 }