test: add failing tests for slow signer timeout issue #398

packages/ndk/lib/domain_layer/entities/broadcast_state.dart

@@ -78,6 +78,8 @@ class BroadcastState {
 
   late final StreamSubscription _networkSubscription;
 
+  bool _timeoutStarted = false;
+
   /// creates a new [BroadcastState] instance
   BroadcastState({
     required this.timeout,
@@ -91,7 +93,12 @@ class BroadcastState {
       // check if all relays responded
       _checkBroadcastDone();
     });
+  }
 
+  /// Starts the timeout timer. Call this after signing is complete.
+  void startTimeout() {
+    if (_timeoutStarted) return;
+    _timeoutStarted = true;
     Future.delayed(timeout, () {
       if (!publishDone) {
         _stateUpdatesController.add(this);

packages/ndk/lib/domain_layer/entities/request_state.dart

@@ -35,6 +35,8 @@ class RequestState {
   Set<String> returnedIds = {};
 
   Timer? _timeout;
+  DateTime? _timeoutStartedAt;
+  Duration? _remainingTimeout;
 
   Stream<Nip01Event> get stream => controller.stream;
 
@@ -76,11 +78,7 @@ class RequestState {
     // if we have a timeout set, we start it
     if (request.timeoutDuration != null) {
       timeoutDuration = request.timeoutDuration;
-      _timeout = Timer(timeoutDuration!, () {
-        onTimeout?.call(this);
-        // call close on all controllers
-        close();
-      });
+      _startTimeout(timeoutDuration!);
     }
     _streamSubscription = controller.listen((e) {}, onDone: () {
       if (_timeout != null) {
@@ -90,6 +88,34 @@ class RequestState {
     });
   }
 
+  void _startTimeout(Duration duration) {
+    _timeoutStartedAt = DateTime.now();
+    _timeout = Timer(duration, () {
+      onTimeout?.call(this);
+      close();
+    });
+  }
+
+  /// Pauses the timeout timer. Call this before signing starts.
+  void pauseTimeout() {
+    if (_timeout == null || timeoutDuration == null) return;
+
+    final elapsed = DateTime.now().difference(_timeoutStartedAt!);
+    _remainingTimeout = timeoutDuration! - elapsed;
+    if (_remainingTimeout!.isNegative) {
+      _remainingTimeout = Duration.zero;
+    }
+    _timeout!.cancel();
+    _timeout = null;
+  }
+
+  /// Resumes the timeout timer. Call this after signing completes.
+  void resumeTimeout() {
+    if (_remainingTimeout == null) return;
+    _startTimeout(_remainingTimeout!);
+    _remainingTimeout = null;
+  }
+
   /// checks if all requests received EOSE
   bool get didAllRequestsReceivedEOSE =>
       !requests.values.any((element) => !element.receivedEOSE);

packages/ndk/lib/domain_layer/usecases/broadcast/broadcast.dart

@@ -87,8 +87,7 @@ class Broadcast {
       nostrEvent: nostrEvent,
       signer: signer,
       specificRelays: cleanedSpecificRelays,
-      doneStream: broadcastState.stateUpdates
-          .map((state) => state.broadcasts.values.toList()),
+      broadcastState: broadcastState,
     );
   }
 

packages/ndk/lib/domain_layer/usecases/engines/network_engine.dart

@@ -10,7 +10,7 @@ abstract class NetworkEngine {
   NdkBroadcastResponse handleEventBroadcast({
     required Nip01Event nostrEvent,
     required EventSigner? signer,
-    required Stream<List<RelayBroadcastResponse>> doneStream,
+    required BroadcastState broadcastState,
     Iterable<String>? specificRelays,
   });
 }

packages/ndk/lib/domain_layer/usecases/jit_engine/jit_engine.dart

@@ -162,18 +162,24 @@ class JitEngine with Logger implements NetworkEngine {
   NdkBroadcastResponse handleEventBroadcast({
     required Nip01Event nostrEvent,
     required EventSigner? signer,
-    required Stream<List<RelayBroadcastResponse>> doneStream,
+    required BroadcastState broadcastState,
     Iterable<String>? specificRelays,
   }) {
     Future<void> asyncStuff() async {
       await relayManagerLight.seedRelaysConnected;
 
       final Nip01Event workingNostrEvent;
-      if (signer != null) {
-        workingNostrEvent = await signer.sign(nostrEvent);
-      } else {
-        workingNostrEvent = nostrEvent;
+      try {
+        if (signer != null) {
+          workingNostrEvent = await signer.sign(nostrEvent);
+        } else {
+          workingNostrEvent = nostrEvent;
+        }
+      } catch (e) {
+        broadcastState.startTimeout();
+        rethrow;
       }
+      broadcastState.startTimeout();
 
       if (specificRelays != null) {
         final cleanedSpecificRelays = cleanRelayUrls(specificRelays.toList());
@@ -216,7 +222,8 @@ class JitEngine with Logger implements NetworkEngine {
     asyncStuff();
     return NdkBroadcastResponse(
       publishEvent: nostrEvent,
-      broadcastDoneStream: doneStream,
+      broadcastDoneStream: broadcastState.stateUpdates
+          .map((state) => state.broadcasts.values.toList()),
     );
   }
 

packages/ndk/lib/domain_layer/usecases/relay_manager.dart

@@ -589,6 +589,14 @@ class RelayManager<T> {
     String challenge,
     Set<Account> accounts,
   ) {
+    // Pause timeout for all requests on this relay during AUTH signing
+    final requestsOnRelay = globalState.inFlightRequests.values
+        .where((state) => state.requests.keys.contains(relayConnectivity.url))
+        .toList();
+    for (final state in requestsOnRelay) {
+      state.pauseTimeout();
+    }
+
     int authCount = 0;
     for (final account in accounts) {
       if (account.signer.canSign()) {
@@ -597,6 +605,10 @@ class RelayManager<T> {
           ["challenge", challenge]
         ]);
         account.signer.sign(auth).then((signedAuth) {
+          // Resume timeout for requests after signing completes
+          for (final state in requestsOnRelay) {
+            state.resumeTimeout();
+          }
           send(relayConnectivity, ClientMsg(ClientMsgType.kAuth, event: signedAuth));
           Logger.log.d(
               "AUTH sent for ${account.pubkey.substring(0, 8)} to ${relayConnectivity.url}");
@@ -606,6 +618,10 @@ class RelayManager<T> {
     }
 
     if (authCount == 0) {
+      // No signing will happen, resume timeouts immediately
+      for (final state in requestsOnRelay) {
+        state.resumeTimeout();
+      }
       Logger.log.w("Received an AUTH challenge but no account can sign");
     }
   }
@@ -764,8 +780,12 @@ class RelayManager<T> {
     Logger.log.d(
         "AUTH required for REQ $reqId on ${relayConnectivity.url}, authenticating ${signableAccounts.length} account(s)...");
 
+    // Pause timeout during AUTH signing
+    state.pauseTimeout();
+
     // Track how many AUTH OKs we need before re-sending REQ
     int pendingAuthCount = signableAccounts.length;
+    int pendingSignCount = signableAccounts.length;
 
     for (final account in signableAccounts) {
       final auth = AuthEvent(pubKey: account.pubkey, tags: [
@@ -774,6 +794,12 @@ class RelayManager<T> {
       ]);
 
       account.signer.sign(auth).then((signedAuth) {
+        // Resume timeout after all signings complete
+        pendingSignCount--;
+        if (pendingSignCount == 0) {
+          state.resumeTimeout();
+        }
+
         // Store callback - only re-send REQ after last AUTH OK
         _pendingAuthCallbacks[signedAuth.id] = () {
           pendingAuthCount--;

packages/ndk/lib/domain_layer/usecases/relay_sets_engine.dart

@@ -265,17 +265,23 @@ class RelaySetsEngine implements NetworkEngine {
   NdkBroadcastResponse handleEventBroadcast({
     required Nip01Event nostrEvent,
     required EventSigner? signer,
-    required Stream<List<RelayBroadcastResponse>> doneStream,
+    required BroadcastState broadcastState,
     Iterable<String>? specificRelays,
   }) {
     Future<void> asyncStuff() async {
       final Nip01Event workingEvent;
 
-      if (signer != null) {
-        workingEvent = await signer.sign(nostrEvent);
-      } else {
-        workingEvent = nostrEvent;
+      try {
+        if (signer != null) {
+          workingEvent = await signer.sign(nostrEvent);
+        } else {
+          workingEvent = nostrEvent;
+        }
+      } catch (e) {
+        broadcastState.startTimeout();
+        rethrow;
       }
+      broadcastState.startTimeout();
 
       // =====================================================================================
       // specific relays
@@ -403,7 +409,8 @@ class RelaySetsEngine implements NetworkEngine {
 
     return NdkBroadcastResponse(
       publishEvent: nostrEvent,
-      broadcastDoneStream: doneStream,
+      broadcastDoneStream: broadcastState.stateUpdates
+          .map((state) => state.broadcasts.values.toList()),
     );
   }
 }

packages/ndk/test/mocks/mock_relay.dart

@@ -93,7 +93,8 @@ class MockRelay {
     this.server = server;
     var stream = server.transform(WebSocketTransformer());
 
-    String challenge = '';
+    // Generate challenge once for the entire server lifetime (fixes race condition on reconnect)
+    final String challenge = Helpers.getRandomString(10);
     Set<String> authenticatedPubkeys = {};
 
     stream.listen((webSocket) {
@@ -104,7 +105,6 @@ class MockRelay {
         webSocket.add(customWelcomeMessage!);
       }
       if ((requireAuthForRequests || requireAuthForEvents) && sendAuthChallenge) {
-        challenge = Helpers.getRandomString(10);
         webSocket.add(jsonEncode(["AUTH", challenge]));
       }
       webSocket.listen((message) async {

packages/ndk/test/mocks/mock_slow_signer.dart

@@ -0,0 +1,78 @@
+import 'package:ndk/domain_layer/entities/nip_01_event.dart';
+import 'package:ndk/domain_layer/entities/pending_signer_request.dart';
+import 'package:ndk/domain_layer/repositories/event_signer.dart';
+
+/// A wrapper signer that adds a delay to simulate slow signing
+/// (like NIP-46, Amber, etc.) where user interaction is required.
+class MockSlowSigner implements EventSigner {
+  final EventSigner _innerSigner;
+  final Duration _delay;
+
+  MockSlowSigner({
+    required EventSigner innerSigner,
+    required Duration delay,
+  })  : _innerSigner = innerSigner,
+        _delay = delay;
+
+  @override
+  Future<Nip01Event> sign(Nip01Event event) async {
+    await Future.delayed(_delay);
+    return _innerSigner.sign(event);
+  }
+
+  @override
+  String getPublicKey() => _innerSigner.getPublicKey();
+
+  @override
+  bool canSign() => _innerSigner.canSign();
+
+  @override
+  Future<String?> decrypt(String msg, String destPubKey, {String? id}) async {
+    await Future.delayed(_delay);
+    return _innerSigner.decrypt(msg, destPubKey, id: id);
+  }
+
+  @override
+  Future<String?> encrypt(String msg, String destPubKey, {String? id}) async {
+    await Future.delayed(_delay);
+    return _innerSigner.encrypt(msg, destPubKey, id: id);
+  }
+
+  @override
+  Future<String?> encryptNip44({
+    required String plaintext,
+    required String recipientPubKey,
+  }) async {
+    await Future.delayed(_delay);
+    return _innerSigner.encryptNip44(
+      plaintext: plaintext,
+      recipientPubKey: recipientPubKey,
+    );
+  }
+
+  @override
+  Future<String?> decryptNip44({
+    required String ciphertext,
+    required String senderPubKey,
+  }) async {
+    await Future.delayed(_delay);
+    return _innerSigner.decryptNip44(
+      ciphertext: ciphertext,
+      senderPubKey: senderPubKey,
+    );
+  }
+
+  @override
+  Stream<List<PendingSignerRequest>> get pendingRequestsStream =>
+      _innerSigner.pendingRequestsStream;
+
+  @override
+  List<PendingSignerRequest> get pendingRequests =>
+      _innerSigner.pendingRequests;
+
+  @override
+  bool cancelRequest(String requestId) => _innerSigner.cancelRequest(requestId);
+
+  @override
+  Future<void> dispose() => _innerSigner.dispose();
+}

packages/ndk/test/usecases/broadcast_test.dart

@@ -16,7 +16,7 @@ void main() async {
     late Ndk ndk;
 
     setUp(() async {
-      relay0 = MockRelay(name: "relay 0", explicitPort: 5098);
+      relay0 = MockRelay(name: "relay 0", explicitPort: 5102);
       await relay0.startServer(nip65s: {
         key0: Nip65(
             pubKey: key0.publicKey,
@@ -252,7 +252,7 @@ void main() async {
           .loginPrivateKey(pubkey: key0.publicKey, privkey: key0.privateKey!);
 
       // Create a slow relay that won't respond in time
-      MockRelay slowRelay = MockRelay(name: "slow relay", explicitPort: 5099);
+      MockRelay slowRelay = MockRelay(name: "slow relay", explicitPort: 5103);
       await slowRelay.startServer(
         nip65s: {
           key0: Nip65(
@@ -316,8 +316,8 @@ void main() async {
       ndk.accounts
           .loginPrivateKey(pubkey: key0.publicKey, privkey: key0.privateKey!);
 
-      MockRelay relay1 = MockRelay(name: "relay 1", explicitPort: 5099);
-      MockRelay relay2 = MockRelay(name: "relay 2", explicitPort: 5100);
+      MockRelay relay1 = MockRelay(name: "relay 1", explicitPort: 5104);
+      MockRelay relay2 = MockRelay(name: "relay 2", explicitPort: 5106);
 
       await relay1.startServer(nip65s: {
         key0: Nip65(