Surface terminal Nostr DM failures

bitchat/Services/NostrTransport.swift

@@ -317,16 +317,40 @@ final class NostrTransport: Transport, @unchecked Sendable {
 
     func sendPrivateMessage(_ content: String, to peerID: PeerID, recipientNickname: String, messageID: String) {
         Task { @MainActor in
-            guard let recipientNpub = resolveRecipientNpub(for: peerID),
-                  let recipientHex = npubToHex(recipientNpub),
-                  let senderIdentity = try? dependencies.currentIdentity() else { return }
+            let failurePolicy = PrivateEnvelopeFailurePolicy.userMessage(
+                messageID: messageID
+            )
+            guard let recipientNpub = resolveRecipientNpub(for: peerID) else {
+                handlePrivateEnvelopeFailure(
+                    events: [],
+                    registerPending: false,
+                    policy: failurePolicy
+                )
+                return
+            }
+            guard let recipientHex = npubToHex(recipientNpub) else {
+                handlePrivateEnvelopeFailure(
+                    events: [],
+                    registerPending: false,
+                    policy: failurePolicy
+                )
+                return
+            }
+            guard let senderIdentity = try? dependencies.currentIdentity() else {
+                handlePrivateEnvelopeFailure(
+                    events: [],
+                    registerPending: false,
+                    policy: failurePolicy
+                )
+                return
+            }
             SecureLogger.debug("NostrTransport: preparing PM to \(recipientNpub.prefix(16))… id=\(messageID.prefix(8))…", category: .session)
             guard let embedded = NostrEmbeddedBitChat.encodePMForNostr(content: content, messageID: messageID, recipientPeerID: peerID, senderPeerID: senderPeerID) else {
                 SecureLogger.error("NostrTransport: failed to embed PM packet", category: .session)
                 handlePrivateEnvelopeFailure(
                     events: [],
                     registerPending: false,
-                    policy: .userMessage(messageID: messageID)
+                    policy: failurePolicy
                 )
                 return
             }
@@ -334,7 +358,7 @@ final class NostrTransport: Transport, @unchecked Sendable {
                 content: embedded,
                 recipientHex: recipientHex,
                 senderIdentity: senderIdentity,
-                failurePolicy: .userMessage(messageID: messageID)
+                failurePolicy: failurePolicy
             )
         }
     }

bitchat/ViewModels/ChatPrivateConversationCoordinator.swift

@@ -228,9 +228,16 @@ extension ChatViewModel: ChatPrivateConversationContext {
         NotificationService.shared.sendPrivateMessageNotification(from: senderName, message: message, peerID: peerID)
     }
 
-    private func makeGeohashNostrTransport() -> NostrTransport {
-        let transport = NostrTransport(keychain: keychain, idBridge: idBridge)
+    func makeGeohashNostrTransport(
+        dependencies: NostrTransport.Dependencies? = nil
+    ) -> NostrTransport {
+        let transport = NostrTransport(
+            keychain: keychain,
+            idBridge: idBridge,
+            dependencies: dependencies
+        )
         transport.senderPeerID = meshService.myPeerID
+        transport.eventDelegate = self
         return transport
     }
 }

bitchatTests/ChatViewModelExtensionsTests.swift

@@ -786,6 +786,63 @@ struct ChatViewModelGeoDMTests {
         #expect(isFailed(status: viewModel.privateChats[convKey]?.last?.deliveryStatus))
     }
 
+    @Test @MainActor
+    func geohashTerminalRelayFailure_transitionsSentMessageToFailed() async throws {
+        let (viewModel, _) = makeTestableViewModel()
+        let sender = try NostrIdentity.generate()
+        let recipient = try NostrIdentity.generate()
+        let messageID = "geo-terminal-failure"
+        let convKey = PeerID(nostr_: recipient.publicKeyHex)
+        let message = BitchatMessage(
+            id: messageID,
+            sender: viewModel.nickname,
+            content: "queued geohash message",
+            timestamp: Date(),
+            isRelay: false,
+            isPrivate: true,
+            recipientNickname: "recipient",
+            senderPeerID: viewModel.myPeerID,
+            deliveryStatus: .sent
+        )
+        viewModel.seedPrivateChat([message], for: convKey)
+
+        var terminalFailure: (@MainActor () -> Void)?
+        let dependencies = NostrTransport.Dependencies(
+            notificationCenter: NotificationCenter(),
+            loadFavorites: { [:] },
+            favoriteStatusForNoiseKey: { _ in nil },
+            favoriteStatusForPeerID: { _ in nil },
+            currentIdentity: { sender },
+            registerPendingPrivateEnvelope: { _ in },
+            sendPrivateEnvelopeBatch: { _, failure in
+                terminalFailure = failure
+                return true
+            },
+            scheduleAfter: { _, _ in },
+            relayConnectivity: {
+                Just(false).eraseToAnyPublisher()
+            }
+        )
+        let transport = viewModel.makeGeohashNostrTransport(
+            dependencies: dependencies
+        )
+
+        let accepted = transport.sendPrivateMessageGeohash(
+            content: message.content,
+            toRecipientHex: recipient.publicKeyHex,
+            from: sender,
+            messageID: messageID
+        )
+
+        #expect(accepted)
+        #expect(viewModel.privateChats[convKey]?.first?.deliveryStatus == .sent)
+        let fail = try #require(terminalFailure)
+        fail()
+        #expect(isFailed(
+            status: viewModel.privateChats[convKey]?.first?.deliveryStatus
+        ))
+    }
+
     /// The blocked notice belongs in the DM thread the person is typing in,
     /// not on the active location-channel timeline.
     @Test @MainActor

bitchatTests/Services/NostrTransportTests.swift

@@ -424,6 +424,135 @@ struct NostrTransportTests {
         #expect(publicationProbe.sentEvents.isEmpty)
     }
 
+    @Test("Direct message with an invalid npub emits a visible failure")
+    @MainActor
+    func invalidDirectRecipientNpubEmitsVisibleFailure() async throws {
+        let keychain = MockKeychain()
+        let idBridge = NostrIdentityBridge(keychain: keychain)
+        let sender = try NostrIdentity.generate()
+        let noiseKey = Data(repeating: 0xA5, count: 32)
+        let peerID = PeerID(hexData: noiseKey)
+        let relationship = makeRelationship(
+            peerNoisePublicKey: noiseKey,
+            peerNostrPublicKey: "not-a-valid-npub",
+            peerNickname: "Invalid npub peer"
+        )
+        let eventProbe = NostrTransportEventProbe()
+        let publicationProbe = NostrTransportProbe()
+        let transport = NostrTransport(
+            keychain: keychain,
+            idBridge: idBridge,
+            dependencies: makeDependencies(
+                favoriteStatusForNoiseKey: {
+                    $0 == noiseKey ? relationship : nil
+                },
+                currentIdentity: { sender },
+                sendPrivateEnvelopeBatch: { events, _ in
+                    publicationProbe.record(batch: events)
+                }
+            )
+        )
+        transport.senderPeerID = PeerID(str: "0123456789abcdef")
+        transport.eventDelegate = eventProbe
+
+        transport.sendPrivateMessage(
+            "must fail before publication",
+            to: peerID,
+            recipientNickname: "Invalid npub peer",
+            messageID: "invalid-npub"
+        )
+
+        let failed = await TestHelpers.waitUntil(
+            { eventProbe.failedMessageIDs == ["invalid-npub"] },
+            timeout: 5.0
+        )
+        #expect(failed)
+        #expect(publicationProbe.sentEvents.isEmpty)
+    }
+
+    @Test("Direct message without a resolvable recipient emits a visible failure")
+    @MainActor
+    func missingDirectRecipientEmitsVisibleFailure() async throws {
+        let keychain = MockKeychain()
+        let idBridge = NostrIdentityBridge(keychain: keychain)
+        let sender = try NostrIdentity.generate()
+        let peerID = PeerID(hexData: Data(repeating: 0xC3, count: 32))
+        let eventProbe = NostrTransportEventProbe()
+        let publicationProbe = NostrTransportProbe()
+        let transport = NostrTransport(
+            keychain: keychain,
+            idBridge: idBridge,
+            dependencies: makeDependencies(
+                currentIdentity: { sender },
+                sendPrivateEnvelopeBatch: { events, _ in
+                    publicationProbe.record(batch: events)
+                }
+            )
+        )
+        transport.senderPeerID = PeerID(str: "0123456789abcdef")
+        transport.eventDelegate = eventProbe
+
+        transport.sendPrivateMessage(
+            "must fail without recipient",
+            to: peerID,
+            recipientNickname: "Unknown peer",
+            messageID: "missing-recipient"
+        )
+
+        let failed = await TestHelpers.waitUntil(
+            { eventProbe.failedMessageIDs == ["missing-recipient"] },
+            timeout: 5.0
+        )
+        #expect(failed)
+        #expect(publicationProbe.sentEvents.isEmpty)
+    }
+
+    @Test("Direct message without a current identity emits a visible failure")
+    @MainActor
+    func missingDirectSenderIdentityEmitsVisibleFailure() async throws {
+        let keychain = MockKeychain()
+        let idBridge = NostrIdentityBridge(keychain: keychain)
+        let recipient = try NostrIdentity.generate()
+        let noiseKey = Data(repeating: 0x5A, count: 32)
+        let peerID = PeerID(hexData: noiseKey)
+        let relationship = makeRelationship(
+            peerNoisePublicKey: noiseKey,
+            peerNostrPublicKey: recipient.npub,
+            peerNickname: "Missing identity peer"
+        )
+        let eventProbe = NostrTransportEventProbe()
+        let publicationProbe = NostrTransportProbe()
+        let transport = NostrTransport(
+            keychain: keychain,
+            idBridge: idBridge,
+            dependencies: makeDependencies(
+                favoriteStatusForNoiseKey: {
+                    $0 == noiseKey ? relationship : nil
+                },
+                currentIdentity: { nil },
+                sendPrivateEnvelopeBatch: { events, _ in
+                    publicationProbe.record(batch: events)
+                }
+            )
+        )
+        transport.senderPeerID = PeerID(str: "0123456789abcdef")
+        transport.eventDelegate = eventProbe
+
+        transport.sendPrivateMessage(
+            "must fail without identity",
+            to: peerID,
+            recipientNickname: "Missing identity peer",
+            messageID: "missing-identity"
+        )
+
+        let failed = await TestHelpers.waitUntil(
+            { eventProbe.failedMessageIDs == ["missing-identity"] },
+            timeout: 5.0
+        )
+        #expect(failed)
+        #expect(publicationProbe.sentEvents.isEmpty)
+    }
+
     @Test("Rejected favorite notification retains and retries the exact pair")
     @MainActor
     func rejectedFavoriteNotificationRetriesExactPair() async throws {