Retry private messages after Noise session replacement

bitchat/Services/MessageRouter.swift

@@ -107,12 +107,20 @@ final class MessageRouter {
     private var bridgeDepositsInFlight = Set<String>()
 
     private var outbox: [PeerID: [QueuedMessage]] = [:]
+    /// IDs whose latest router-owned transmission used an already-established
+    /// secure session and still awaits an ack. This deliberately excludes
+    /// messages handed to BLE while a handshake is pending: BLE owns those
+    /// sends and drains its queue after authentication, so retrying them here
+    /// would duplicate every normal first-handshake DM.
+    private var securelyTransmittedMessageIDs = Set<String>()
 
     // Outbox limits to prevent unbounded memory growth
     private static let maxMessagesPerPeer = 100
     private static let messageTTLSeconds: TimeInterval = 24 * 60 * 60 // 24 hours
-    // Bound resends of messages sent on a weak reachability signal that never
+    // Bound actual sends that never receive an ack, whether they used weak
-    // get a delivery ack (e.g. peer on an old client that doesn't ack).
+    // reachability or an apparently secure session that keeps being replaced.
+    // Connected pre-handshake sends are transport-owned and do not burn this
+    // cap because BLE queues/drains them itself.
     private static let maxSendAttempts = 8
     // Redundant couriers improve delivery odds; receivers dedup by message ID.
     private static let maxCouriersPerMessage = 3
@@ -171,15 +179,28 @@ final class MessageRouter {
     // MARK: - Message Sending
 
     func sendPrivate(_ content: String, to peerID: PeerID, recipientNickname: String, messageID: String) {
+        let message = QueuedMessage(
+            content: content,
+            nickname: recipientNickname,
+            messageID: messageID,
+            timestamp: now(),
+            sendAttempts: 1
+        )
+
         if let transport = connectedTransport(for: peerID), transport.canDeliverSecurely(to: peerID) {
-            // A live link that can complete an encrypted delivery is a
+            // Even an established Noise session can be stale after the peer
-            // strong delivery signal; trust it outright.
+            // restarts or replaces its app. Persist before handing the packet
+            // to the transport so a fast ack cannot race ahead of retention,
+            // then keep the copy until a delivery/read ack clears it. A
+            // replacement handshake will retry this same message ID, which
+            // receivers deduplicate.
+            enqueue(message, for: peerID)
+            securelyTransmittedMessageIDs.insert(messageID)
             SecureLogger.debug("Routing PM via \(type(of: transport)) (connected) to \(peerID.id.prefix(8))… id=\(messageID.prefix(8))…", category: .session)
             transport.sendPrivateMessage(content, to: peerID, recipientNickname: recipientNickname, messageID: messageID)
             return
         }
 
-        let message = QueuedMessage(content: content, nickname: recipientNickname, messageID: messageID, timestamp: now(), sendAttempts: 1)
         if let transport = connectedTransport(for: peerID) {
             // "Connected" without an established secure session is forgeable:
             // link bindings heal on signature-verified "direct" announces, but
@@ -197,8 +218,9 @@ final class MessageRouter {
             // deposit is cleared on ack. Don't "optimize" the courier call
             // away.
             SecureLogger.debug("Routing PM via \(type(of: transport)) (connected, no secure session) to \(peerID.id.prefix(8))… id=\(messageID.prefix(8))…", category: .session)
-            transport.sendPrivateMessage(content, to: peerID, recipientNickname: recipientNickname, messageID: messageID)
             enqueue(message, for: peerID)
+            securelyTransmittedMessageIDs.remove(messageID)
+            transport.sendPrivateMessage(content, to: peerID, recipientNickname: recipientNickname, messageID: messageID)
             attemptCourierDeposit(messageID: messageID, for: peerID)
             return
         }
@@ -209,8 +231,8 @@ final class MessageRouter {
             // Send now, but retain a copy until a delivery/read ack clears it;
             // receivers dedup resends by message ID.
             SecureLogger.debug("Routing PM via \(type(of: transport)) (reachable) to \(peerID.id.prefix(8))… id=\(messageID.prefix(8))…", category: .session)
-            transport.sendPrivateMessage(content, to: peerID, recipientNickname: recipientNickname, messageID: messageID)
             enqueue(message, for: peerID)
+            transport.sendPrivateMessage(content, to: peerID, recipientNickname: recipientNickname, messageID: messageID)
             // "Reachable" without prompt delivery means the send only joined
             // a queue (Nostr with relays down): also hand a sealed copy to
             // any connected couriers rather than waiting for internet that
@@ -356,15 +378,41 @@ final class MessageRouter {
 
     // MARK: - Outbox Management
 
-    /// A delivery or read ack confirms receipt; stop retaining the message.
+    /// A locally trusted delivery transition confirms receipt; stop retaining
+    /// every copy of the message. Authenticated remote receipts must use the
+    /// peer-bound overload below instead.
     func markDelivered(_ messageID: String) {
+        clearRetainedMessage(messageID, allowedPeerIDs: nil)
+    }
+
+    /// Stops retaining a message only for the authenticated conversation
+    /// aliases that produced the accepted receipt. A peer that learns another
+    /// conversation's message ID cannot use it to clear that conversation's
+    /// retry state.
+    func markDelivered(_ messageID: String, from peerIDs: Set<PeerID>) {
+        guard !peerIDs.isEmpty else { return }
+        clearRetainedMessage(messageID, allowedPeerIDs: peerIDs)
+    }
+
+    private func clearRetainedMessage(
+        _ messageID: String,
+        allowedPeerIDs: Set<PeerID>?
+    ) {
         var cleared = false
         for (peerID, queue) in outbox {
+            if let allowedPeerIDs, !allowedPeerIDs.contains(peerID) {
+                continue
+            }
             let filtered = queue.filter { $0.messageID != messageID }
             guard filtered.count != queue.count else { continue }
             outbox[peerID] = filtered.isEmpty ? nil : filtered
             cleared = true
         }
+        if !outbox.values.contains(where: { queue in
+            queue.contains { $0.messageID == messageID }
+        }) {
+            securelyTransmittedMessageIDs.remove(messageID)
+        }
         // The durable snapshot may still be hidden by protected data. Record
         // the ack even when this cold-load view cannot find the message, then
         // persist the current view so the store retains a removal tombstone.
@@ -391,6 +439,11 @@ final class MessageRouter {
             outbox[peerID] = filtered.isEmpty ? nil : filtered
             cleared = true
         }
+        if !outbox.values.contains(where: { queue in
+            queue.contains { $0.messageID == messageID }
+        }) {
+            securelyTransmittedMessageIDs.remove(messageID)
+        }
         // Preserve the scoped ack even when protected data hides the durable
         // queue during a cold launch.
         outboxStore?.recordRemoval(messageID: messageID, for: peerIDs)
@@ -424,7 +477,34 @@ final class MessageRouter {
         persistOutbox()
     }
 
+    @discardableResult
+    private func removeQueuedMessage(_ messageID: String, for peerID: PeerID) -> Bool {
+        guard let queue = outbox[peerID],
+              let index = queue.firstIndex(where: { $0.messageID == messageID }) else {
+            return false
+        }
+        var updated = queue
+        updated.remove(at: index)
+        outbox[peerID] = updated.isEmpty ? nil : updated
+        return true
+    }
+
+    @discardableResult
+    private func incrementSendAttemptsIfQueued(_ messageID: String, for peerID: PeerID) -> Bool {
+        guard var queue = outbox[peerID],
+              let index = queue.firstIndex(where: { $0.messageID == messageID }) else {
+            // A synchronous delivery/read ack may have cleared the retained
+            // copy while `sendPrivateMessage` was on the stack. Never
+            // resurrect it from the flush snapshot.
+            return false
+        }
+        queue[index].sendAttempts += 1
+        outbox[peerID] = queue
+        return true
+    }
+
     private func dropMessage(_ messageID: String, for peerID: PeerID) {
+        securelyTransmittedMessageIDs.remove(messageID)
         metrics?.record(.outboxDropped)
         onMessageDropped?(messageID, peerID)
     }
@@ -468,6 +548,7 @@ final class MessageRouter {
     /// Panic wipe: forget queued mail on disk and in memory.
     func wipeOutbox() {
         outbox.removeAll()
+        securelyTransmittedMessageIDs.removeAll()
         outboxStore?.wipe()
     }
 
@@ -495,26 +576,156 @@ final class MessageRouter {
         }
     }
 
+    /// Retries only messages that the router previously transmitted through
+    /// an already-established secure session and that still await an ack.
+    ///
+    /// A peer restart can leave that local session looking usable until the
+    /// replacement handshake arrives; the first ciphertext is then
+    /// undecryptable remotely. Normal pre-handshake sends are intentionally
+    /// absent from `securelyTransmittedMessageIDs` because BLE already queues
+    /// and drains them when authentication completes.
+    func retrySecurePrivateMessagesAfterAuthentication(for peerIDAliases: [PeerID]) {
+        typealias Candidate = (
+            peerID: PeerID,
+            message: QueuedMessage,
+            aliasOrder: Int,
+            queueOrder: Int
+        )
+
+        var visitedPeerIDs = Set<PeerID>()
+        var retriedMessageIDs = Set<String>()
+        var outboxChanged = false
+        let currentDate = now()
+        var candidates: [Candidate] = []
+
+        for (aliasOrder, peerID) in peerIDAliases.enumerated() {
+            guard visitedPeerIDs.insert(peerID).inserted else { continue }
+            guard let queued = outbox[peerID], !queued.isEmpty,
+                  let transport = connectedTransport(for: peerID),
+                  transport.canDeliverSecurely(to: peerID) else {
+                continue
+            }
+
+            for (queueOrder, message) in queued.enumerated() {
+                guard securelyTransmittedMessageIDs.contains(message.messageID) else { continue }
+                candidates.append((
+                    peerID: peerID,
+                    message: message,
+                    aliasOrder: aliasOrder,
+                    queueOrder: queueOrder
+                ))
+            }
+        }
+
+        // Conversation migration can leave retained messages split across the
+        // ephemeral and stable outbox keys. Merge both queues into one
+        // chronological stream so callback alias order cannot send newer mail
+        // ahead of older mail.
+        candidates.sort { lhs, rhs in
+            if lhs.message.timestamp != rhs.message.timestamp {
+                return lhs.message.timestamp < rhs.message.timestamp
+            }
+            if lhs.aliasOrder != rhs.aliasOrder {
+                return lhs.aliasOrder < rhs.aliasOrder
+            }
+            if lhs.queueOrder != rhs.queueOrder {
+                return lhs.queueOrder < rhs.queueOrder
+            }
+            return lhs.message.messageID < rhs.message.messageID
+        }
+
+        for candidate in candidates {
+            let peerID = candidate.peerID
+            let message = candidate.message
+            guard retriedMessageIDs.insert(message.messageID).inserted,
+                  securelyTransmittedMessageIDs.contains(message.messageID),
+                  queuedMessage(message.messageID, for: peerID) != nil,
+                  let transport = connectedTransport(for: peerID),
+                  transport.canDeliverSecurely(to: peerID) else {
+                continue
+            }
+
+            if currentDate.timeIntervalSince(message.timestamp) > Self.messageTTLSeconds {
+                if removeQueuedMessage(message.messageID, for: peerID) {
+                    dropMessage(message.messageID, for: peerID)
+                    outboxChanged = true
+                }
+                continue
+            }
+
+            guard message.sendAttempts < Self.maxSendAttempts else {
+                SecureLogger.warning(
+                    "📤 Dropping unacked PM for \(peerID.id.prefix(8))… id=\(message.messageID.prefix(8))… after \(message.sendAttempts) secure attempts",
+                    category: .session
+                )
+                if removeQueuedMessage(message.messageID, for: peerID) {
+                    dropMessage(message.messageID, for: peerID)
+                    outboxChanged = true
+                }
+                continue
+            }
+
+            SecureLogger.debug(
+                "Auth retry -> \(type(of: transport)) for \(peerID.id.prefix(8))… id=\(message.messageID.prefix(8))…",
+                category: .session
+            )
+            transport.sendPrivateMessage(
+                message.content,
+                to: peerID,
+                recipientNickname: message.nickname,
+                messageID: message.messageID
+            )
+            metrics?.record(.outboxResent)
+            outboxChanged = incrementSendAttemptsIfQueued(message.messageID, for: peerID) || outboxChanged
+        }
+
+        if outboxChanged {
+            persistOutbox()
+        }
+    }
+
     func flushOutbox(for peerID: PeerID) {
         guard let queued = outbox[peerID], !queued.isEmpty else { return }
         SecureLogger.debug("Flushing outbox for \(peerID.id.prefix(8))… count=\(queued.count)", category: .session)
 
         let now = now()
-        var remaining: [QueuedMessage] = []
+        var outboxChanged = false
 
         for message in queued {
+            // A synchronous ack from an earlier send in this flush may have
+            // removed an entry from the live outbox. The snapshot is only an
+            // iteration order; never use it to recreate removed messages.
+            guard queuedMessage(message.messageID, for: peerID) != nil else { continue }
+
             // Skip expired messages (TTL exceeded)
             if now.timeIntervalSince(message.timestamp) > Self.messageTTLSeconds {
                 SecureLogger.debug("⏰ Expired queued message for \(peerID.id.prefix(8))… id=\(message.messageID.prefix(8))… (age: \(Int(now.timeIntervalSince(message.timestamp)))s)", category: .session)
-                dropMessage(message.messageID, for: peerID)
+                if removeQueuedMessage(message.messageID, for: peerID) {
+                    dropMessage(message.messageID, for: peerID)
+                    outboxChanged = true
+                }
                 continue
             }
 
             if let transport = connectedTransport(for: peerID), transport.canDeliverSecurely(to: peerID) {
-                // Live link with a secure session: send and stop retaining.
+                // A secure session is meaningful enough to retry, but not
+                // proof that this particular ciphertext reached the peer: the
+                // remote app may have restarted while our old session still
+                // looked established. Retain until an ack, while bounding
+                // actual secure transmissions for peers that never ack.
+                guard message.sendAttempts < Self.maxSendAttempts else {
+                    SecureLogger.warning("📤 Dropping unacked PM for \(peerID.id.prefix(8))… id=\(message.messageID.prefix(8))… after \(message.sendAttempts) attempts", category: .session)
+                    if removeQueuedMessage(message.messageID, for: peerID) {
+                        dropMessage(message.messageID, for: peerID)
+                        outboxChanged = true
+                    }
+                    continue
+                }
                 SecureLogger.debug("Outbox -> \(type(of: transport)) (connected) for \(peerID.id.prefix(8))… id=\(message.messageID.prefix(8))…", category: .session)
+                securelyTransmittedMessageIDs.insert(message.messageID)
                 transport.sendPrivateMessage(message.content, to: peerID, recipientNickname: message.nickname, messageID: message.messageID)
                 metrics?.record(.outboxResent)
+                outboxChanged = incrementSendAttemptsIfQueued(message.messageID, for: peerID) || outboxChanged
             } else if let transport = connectedTransport(for: peerID) {
                 // "Connected" without a secure session — possibly a stolen
                 // binding from a replayed announce: send (a genuine link
@@ -527,9 +738,9 @@ final class MessageRouter {
                 // preserve. Retention stays bounded by the 24h outbox TTL
                 // and the per-peer FIFO cap.
                 SecureLogger.debug("Outbox -> \(type(of: transport)) (connected, no secure session) for \(peerID.id.prefix(8))… id=\(message.messageID.prefix(8))…", category: .session)
+                securelyTransmittedMessageIDs.remove(message.messageID)
                 transport.sendPrivateMessage(message.content, to: peerID, recipientNickname: message.nickname, messageID: message.messageID)
                 metrics?.record(.outboxResent)
-                remaining.append(message)
             } else if let transport = reachableTransport(for: peerID) {
                 // Reachability without a connection is a freshness heuristic,
                 // so the send can silently go nowhere: send but keep retaining
@@ -537,26 +748,22 @@ final class MessageRouter {
                 // that never ack.
                 guard message.sendAttempts < Self.maxSendAttempts else {
                     SecureLogger.warning("📤 Dropping unacked PM for \(peerID.id.prefix(8))… id=\(message.messageID.prefix(8))… after \(message.sendAttempts) attempts", category: .session)
-                    dropMessage(message.messageID, for: peerID)
+                    if removeQueuedMessage(message.messageID, for: peerID) {
+                        dropMessage(message.messageID, for: peerID)
+                        outboxChanged = true
+                    }
                     continue
                 }
                 SecureLogger.debug("Outbox -> \(type(of: transport)) (reachable) for \(peerID.id.prefix(8))… id=\(message.messageID.prefix(8))…", category: .session)
                 transport.sendPrivateMessage(message.content, to: peerID, recipientNickname: message.nickname, messageID: message.messageID)
                 metrics?.record(.outboxResent)
-                var retained = message
+                outboxChanged = incrementSendAttemptsIfQueued(message.messageID, for: peerID) || outboxChanged
-                retained.sendAttempts += 1
-                remaining.append(retained)
-            } else {
-                remaining.append(message)
             }
         }
 
-        if remaining.isEmpty {
+        if outboxChanged {
-            outbox.removeValue(forKey: peerID)
+            persistOutbox()
-        } else {
-            outbox[peerID] = remaining
         }
-        persistOutbox()
     }
 
     func flushAllOutbox() {

bitchat/ViewModels/ChatDeliveryCoordinator.swift

@@ -33,6 +33,12 @@ protocol ChatDeliveryContext: AnyObject {
     func notifyUIChanged()
     /// Confirms receipt so the message router stops retaining the message for resend.
     func markMessageDelivered(_ messageID: String)
+    /// Peer-bound form for authenticated remote receipts. Only the supplied
+    /// conversation aliases may have retained state terminalized.
+    func markMessageDelivered(_ messageID: String, from peerIDs: Set<PeerID>)
+    /// Returns true only when `messageID` is one of our outgoing messages in
+    /// at least one of the authenticated peer's direct-conversation aliases.
+    func isOutgoingPrivateMessage(_ messageID: String, toAny peerIDs: Set<PeerID>) -> Bool
 }
 
 extension ChatViewModel: ChatDeliveryContext {
@@ -59,6 +65,18 @@ extension ChatViewModel: ChatDeliveryContext {
             messageID: messageID
         )
     }
+
+    func markMessageDelivered(_ messageID: String, from peerIDs: Set<PeerID>) {
+        messageRouter.markDelivered(messageID, from: peerIDs)
+    }
+
+    func isOutgoingPrivateMessage(_ messageID: String, toAny peerIDs: Set<PeerID>) -> Bool {
+        peerIDs.contains { peerID in
+            privateMessages(for: peerID).contains { message in
+                message.id == messageID && message.senderPeerID == myPeerID
+            }
+        }
+    }
 }
 
 /// Thin mapper from delivery events (read receipts, transport delivery
@@ -86,9 +104,10 @@ final class ChatDeliveryCoordinator {
 
     @MainActor
     func didReceiveReadReceipt(_ receipt: ReadReceipt) {
-        updateMessageDeliveryStatus(
+        updateAcknowledgedMessageDeliveryStatus(
             receipt.originalMessageID,
-            status: .read(by: receipt.readerNickname, at: receipt.timestamp)
+            status: .read(by: receipt.readerNickname, at: receipt.timestamp),
+            from: [receipt.readerID]
         )
     }
 
@@ -105,17 +124,43 @@ final class ChatDeliveryCoordinator {
     @MainActor
     @discardableResult
     func updateMessageDeliveryStatus(_ messageID: String, status: DeliveryStatus) -> Bool {
+        guard context.setDeliveryStatus(status, forMessageID: messageID) else {
+            return false
+        }
         switch status {
         case .delivered, .read:
-            // Confirmed receipt — stop retaining the message for resend.
+            // Terminalize only after the store accepted the transition.
             context.markMessageDelivered(messageID)
         default:
             break
         }
+        context.notifyUIChanged()
+        return true
+    }
 
-        guard context.setDeliveryStatus(status, forMessageID: messageID) else {
+    /// Applies an authenticated remote delivery/read receipt only when it
+    /// belongs to one of our outgoing messages in that peer's conversation.
+    /// Retry state is cleared after, never before, the status transition is
+    /// accepted by the store.
+    @MainActor
+    @discardableResult
+    func updateAcknowledgedMessageDeliveryStatus(
+        _ messageID: String,
+        status: DeliveryStatus,
+        from peerIDAliases: Set<PeerID>
+    ) -> Bool {
+        switch status {
+        case .delivered, .read:
+            break
+        default:
             return false
         }
+        guard !peerIDAliases.isEmpty,
+              context.isOutgoingPrivateMessage(messageID, toAny: peerIDAliases),
+              context.setDeliveryStatus(status, forMessageID: messageID) else {
+            return false
+        }
+        context.markMessageDelivered(messageID, from: peerIDAliases)
         context.notifyUIChanged()
         return true
     }

bitchat/ViewModels/ChatTransportEventCoordinator.swift

@@ -62,10 +62,15 @@ protocol ChatTransportEventContext: AnyObject {
     func sendMeshDeliveryAck(for messageID: String, to peerID: PeerID)
 
     // MARK: Delivery status
-    /// Applies the status to every known location of the message.
+    /// Applies an authenticated receipt to the message only when it belongs
-    /// Returns `false` when no message with that ID was updated.
+    /// to the supplied peer conversation aliases. Returns `false` for an
+    /// unknown ID, wrong peer, or rejected status transition.
     @discardableResult
-    func applyMessageDeliveryStatus(_ messageID: String, status: DeliveryStatus) -> Bool
+    func applyAcknowledgedMessageDeliveryStatus(
+        _ messageID: String,
+        status: DeliveryStatus,
+        from peerIDAliases: Set<PeerID>
+    ) -> Bool
     func deliveryStatus(for messageID: String) -> DeliveryStatus?
 
     // MARK: Verification payloads
@@ -122,8 +127,16 @@ extension ChatViewModel: ChatTransportEventContext {
     }
 
     @discardableResult
-    func applyMessageDeliveryStatus(_ messageID: String, status: DeliveryStatus) -> Bool {
+    func applyAcknowledgedMessageDeliveryStatus(
-        deliveryCoordinator.updateMessageDeliveryStatus(messageID, status: status)
+        _ messageID: String,
+        status: DeliveryStatus,
+        from peerIDAliases: Set<PeerID>
+    ) -> Bool {
+        deliveryCoordinator.updateAcknowledgedMessageDeliveryStatus(
+            messageID,
+            status: status,
+            from: peerIDAliases
+        )
     }
 
     func deliveryStatus(for messageID: String) -> DeliveryStatus? {
@@ -446,9 +459,10 @@ private extension ChatTransportEventCoordinator {
             guard let messageID = String(data: payload, encoding: .utf8) else { return }
 
             let name = deliveryStatusName(for: peerID, in: context)
-            let didUpdate = context.applyMessageDeliveryStatus(
+            let didUpdate = context.applyAcknowledgedMessageDeliveryStatus(
                 messageID,
-                status: .delivered(to: name, at: Date())
+                status: .delivered(to: name, at: Date()),
+                from: receiptPeerAliases(for: peerID, in: context)
             )
 
             if !didUpdate {
@@ -463,9 +477,10 @@ private extension ChatTransportEventCoordinator {
             guard let messageID = String(data: payload, encoding: .utf8) else { return }
 
             let name = deliveryStatusName(for: peerID, in: context)
-            let didUpdate = context.applyMessageDeliveryStatus(
+            let didUpdate = context.applyAcknowledgedMessageDeliveryStatus(
                 messageID,
-                status: .read(by: name, at: Date())
+                status: .read(by: name, at: Date()),
+                from: receiptPeerAliases(for: peerID, in: context)
             )
 
             if !didUpdate {
@@ -503,4 +518,21 @@ private extension ChatTransportEventCoordinator {
     func deliveryStatusName(for peerID: PeerID, in context: any ChatTransportEventContext) -> String {
         context.unifiedPeer(for: peerID)?.nickname ?? context.resolveNickname(for: peerID)
     }
+
+    @MainActor
+    func receiptPeerAliases(
+        for peerID: PeerID,
+        in context: any ChatTransportEventContext
+    ) -> Set<PeerID> {
+        var aliases: Set<PeerID> = [peerID]
+        // The active authenticated Noise key is authoritative. A cached
+        // ephemeral→stable mapping can predate an identity replacement, so
+        // use it only when the live session cannot provide its static key.
+        if let keyData = context.noiseSessionPublicKeyData(for: peerID) {
+            aliases.insert(PeerID(hexData: keyData))
+        } else if let stablePeerID = context.cachedStablePeerID(for: peerID) {
+            aliases.insert(stablePeerID)
+        }
+        return aliases
+    }
 }

bitchat/ViewModels/ChatVerificationCoordinator.swift

@@ -59,6 +59,10 @@ protocol ChatVerificationContext: AnyObject {
     func hasEstablishedNoiseSession(with peerID: PeerID) -> Bool
     func triggerHandshake(with peerID: PeerID)
     func privateMediaPeerDidAuthenticate(_ peerID: PeerID)
+    /// Retries only private messages previously transmitted through a secure
+    /// session and still pending an ack. Both ephemeral and stable aliases
+    /// are supplied because either can own the outbox entry.
+    func retrySecurePrivateMessagesAfterAuthentication(for peerIDAliases: [PeerID])
     func sendVerifyChallenge(to peerID: PeerID, noiseKeyHex: String, nonceA: Data)
     func sendVerifyResponse(to peerID: PeerID, noiseKeyHex: String, nonceA: Data)
 
@@ -121,6 +125,10 @@ extension ChatViewModel: ChatVerificationContext {
         mediaTransferCoordinator.peerDidAuthenticate(peerID.toShort())
     }
 
+    func retrySecurePrivateMessagesAfterAuthentication(for peerIDAliases: [PeerID]) {
+        messageRouter.retrySecurePrivateMessagesAfterAuthentication(for: peerIDAliases)
+    }
+
     func sendVerifyChallenge(to peerID: PeerID, noiseKeyHex: String, nonceA: Data) {
         meshService.sendVerifyChallenge(to: peerID, noiseKeyHex: noiseKeyHex, nonceA: nonceA)
     }
@@ -216,16 +224,37 @@ final class ChatVerificationCoordinator {
 
                     self.context.invalidateEncryptionCache(for: peerID)
 
-                    if self.context.cachedStablePeerID(for: peerID) == nil,
+                    var authenticatedStablePeerID: PeerID?
-                       let keyData = self.context.noiseSessionPublicKeyData(for: peerID) {
+                    if let keyData = self.context.noiseSessionPublicKeyData(for: peerID) {
                         let stablePeerID = PeerID(hexData: keyData)
-                        self.context.cacheStablePeerID(stablePeerID, for: peerID)
+                        authenticatedStablePeerID = stablePeerID
+                        if self.context.cachedStablePeerID(for: peerID) != stablePeerID {
+                            // The freshly authenticated Noise key outranks a
+                            // stale announce-derived alias.
+                            self.context.cacheStablePeerID(stablePeerID, for: peerID)
+                        }
                         SecureLogger.debug(
                             "🗺️ Mapped short peerID to Noise key for header continuity: \(peerID) -> \(stablePeerID.id.prefix(8))…",
                             category: .session
                         )
                     }
 
+                    // A locally established session may have belonged to the
+                    // peer's previous app process. The first ciphertext sent
+                    // into that stale session is retained by MessageRouter;
+                    // retry it now that this newly authenticated/replacement
+                    // session can actually decrypt it.
+                    var peerIDAliases = [peerID]
+                    if let stablePeerID = authenticatedStablePeerID
+                        ?? self.context.cachedStablePeerID(for: peerID),
+                       stablePeerID != peerID {
+                        // Conversations can migrate from the ephemeral BLE ID
+                        // to the authenticated Noise-key ID. Retry both aliases
+                        // because either may own the retained outbox entry.
+                        peerIDAliases.append(stablePeerID)
+                    }
+                    self.context.retrySecurePrivateMessagesAfterAuthentication(for: peerIDAliases)
+
                     if var pending = self.pendingQRVerifications[peerID], pending.sent == false {
                         self.context.sendVerifyChallenge(
                             to: peerID,

bitchatTests/ChatTransportEventCoordinatorContextTests.swift

@@ -133,11 +133,17 @@ private final class MockChatTransportEventContext: ChatTransportEventContext {
     // Delivery status
     var applyMessageDeliveryStatusResult = true
     var deliveryStatusesByMessageID: [String: DeliveryStatus] = [:]
-    private(set) var appliedDeliveryStatuses: [(messageID: String, status: DeliveryStatus)] = []
+    private(set) var appliedDeliveryStatuses: [
+        (messageID: String, status: DeliveryStatus, peerIDAliases: Set<PeerID>)
+    ] = []
 
     @discardableResult
-    func applyMessageDeliveryStatus(_ messageID: String, status: DeliveryStatus) -> Bool {
+    func applyAcknowledgedMessageDeliveryStatus(
-        appliedDeliveryStatuses.append((messageID, status))
+        _ messageID: String,
+        status: DeliveryStatus,
+        from peerIDAliases: Set<PeerID>
+    ) -> Bool {
+        appliedDeliveryStatuses.append((messageID, status, peerIDAliases))
         return applyMessageDeliveryStatusResult
     }
 
@@ -417,6 +423,10 @@ struct ChatTransportEventCoordinatorContextTests {
         let peerID = PeerID(str: "99aabbccddeeff00")
         let noiseKey = Data(repeating: 0x44, count: 32)
         context.peersByID[peerID] = BitchatPeer(peerID: peerID, noisePublicKey: noiseKey, nickname: "alice")
+        let stablePeerID = PeerID(hexData: noiseKey)
+        let staleStablePeerID = PeerID(hexData: Data(repeating: 0x55, count: 32))
+        context.cacheStablePeerID(staleStablePeerID, for: peerID)
+        context.noiseSessionKeysByPeerID[peerID] = noiseKey
 
         // Inbound private message: decoded, handled, and delivery-acked.
         let packet = PrivateMessagePacket(messageID: "pm-1", content: "hi there")
@@ -438,6 +448,8 @@ struct ChatTransportEventCoordinatorContextTests {
         await drainMainActorTasks()
         #expect(context.appliedDeliveryStatuses.count == 2)
         #expect(context.appliedDeliveryStatuses[0].messageID == "m-1")
+        #expect(context.appliedDeliveryStatuses[0].peerIDAliases == [peerID, stablePeerID])
+        #expect(!context.appliedDeliveryStatuses[0].peerIDAliases.contains(staleStablePeerID))
         if case .delivered(let to, _) = context.appliedDeliveryStatuses[0].status {
             #expect(to == "alice")
         } else {

bitchatTests/ChatVerificationCoordinatorContextTests.swift

@@ -98,6 +98,7 @@ private final class MockChatVerificationContext: ChatVerificationContext {
     private(set) var installedCallbacks: (onPeerAuthenticated: (PeerID, String) -> Void, onHandshakeRequired: (PeerID) -> Void)?
     private(set) var triggeredHandshakes: [PeerID] = []
     private(set) var privateMediaAuthenticatedPeers: [PeerID] = []
+    private(set) var securePrivateMessageRetryAliases: [[PeerID]] = []
     private(set) var sentChallenges: [(peerID: PeerID, noiseKeyHex: String, nonceA: Data)] = []
     private(set) var sentResponses: [(peerID: PeerID, noiseKeyHex: String, nonceA: Data)] = []
 
@@ -118,6 +119,10 @@ private final class MockChatVerificationContext: ChatVerificationContext {
         privateMediaAuthenticatedPeers.append(peerID)
     }
 
+    func retrySecurePrivateMessagesAfterAuthentication(for peerIDAliases: [PeerID]) {
+        securePrivateMessageRetryAliases.append(peerIDAliases)
+    }
+
     func sendVerifyChallenge(to peerID: PeerID, noiseKeyHex: String, nonceA: Data) {
         sentChallenges.append((peerID, noiseKeyHex, nonceA))
     }
@@ -269,6 +274,10 @@ struct ChatVerificationCoordinatorContextTests {
         let peerID = PeerID(str: "1122334455667788")
         let noiseKey = Data(repeating: 0x33, count: 32)
         context.noiseSessionKeysByPeerID[peerID] = noiseKey
+        context.cacheStablePeerID(
+            PeerID(hexData: Data(repeating: 0x44, count: 32)),
+            for: peerID
+        )
         context.verifiedFingerprints = ["fp-verified"]
 
         coordinator.setupNoiseCallbacks()
@@ -279,9 +288,11 @@ struct ChatVerificationCoordinatorContextTests {
         callbacks?.onPeerAuthenticated(peerID, "fp-verified")
         await waitForMainQueue()
         #expect(context.encryptionStatuses[peerID] == .noiseVerified)
-        #expect(context.stablePeerIDCache[peerID] == PeerID(hexData: noiseKey))
+        let stablePeerID = PeerID(hexData: noiseKey)
+        #expect(context.stablePeerIDCache[peerID] == stablePeerID)
         #expect(context.invalidatedEncryptionCachePeers.contains(peerID))
         #expect(context.privateMediaAuthenticatedPeers == [peerID])
+        #expect(context.securePrivateMessageRetryAliases == [[peerID, stablePeerID]])
 
         // Handshake required -> handshaking status.
         callbacks?.onHandshakeRequired(peerID)

bitchatTests/ChatViewModelDeliveryStatusTests.swift

@@ -298,6 +298,65 @@ struct ChatViewModelDeliveryStatusTests {
         }())
     }
 
+    @Test @MainActor
+    func authenticatedNoiseAckCannotClearAnotherPeersRetryState() async {
+        let (viewModel, transport) = makeTestableViewModel()
+        let intendedPeer = PeerID(str: "0102030405060708")
+        let otherPeer = PeerID(str: "1112131415161718")
+        let messageID = "noise-peer-bound-ack"
+
+        viewModel.seedPrivateChat(
+            [
+                BitchatMessage(
+                    id: messageID,
+                    sender: viewModel.nickname,
+                    content: "Keep retrying",
+                    timestamp: Date(),
+                    isRelay: false,
+                    isPrivate: true,
+                    recipientNickname: "Intended",
+                    senderPeerID: viewModel.myPeerID,
+                    deliveryStatus: .sent
+                )
+            ],
+            for: intendedPeer
+        )
+        transport.reachablePeers.insert(intendedPeer)
+        viewModel.messageRouter.sendPrivate(
+            "Keep retrying",
+            to: intendedPeer,
+            recipientNickname: "Intended",
+            messageID: messageID
+        )
+        #expect(transport.sentPrivateMessages.count == 1)
+
+        // This models a decrypted Noise receipt: the transport-authenticated
+        // peer is authoritative, not the attacker-controlled message ID.
+        viewModel.didReceiveNoisePayload(
+            from: otherPeer,
+            type: .delivered,
+            payload: Data(messageID.utf8),
+            timestamp: Date()
+        )
+        for _ in 0..<10 { await Task.yield() }
+
+        #expect(isSent(viewModel.conversations.deliveryStatus(forMessageID: messageID)))
+        viewModel.messageRouter.flushOutbox(for: intendedPeer)
+        #expect(transport.sentPrivateMessages.count == 2)
+
+        viewModel.didReceiveNoisePayload(
+            from: intendedPeer,
+            type: .delivered,
+            payload: Data(messageID.utf8),
+            timestamp: Date()
+        )
+        for _ in 0..<10 { await Task.yield() }
+
+        #expect(isDelivered(viewModel.conversations.deliveryStatus(forMessageID: messageID)))
+        viewModel.messageRouter.flushOutbox(for: intendedPeer)
+        #expect(transport.sentPrivateMessages.count == 2)
+    }
+
     @Test @MainActor
     func cleanupOldReadReceipts_removesReceiptIDsWithoutMessages() async {
         let (viewModel, transport) = makeTestableViewModel()
@@ -577,6 +636,7 @@ private final class MockChatDeliveryContext: ChatDeliveryContext {
     var isStartupPhase = false
     private(set) var notifyUIChangedCount = 0
     private(set) var markedDeliveredMessageIDs: [String] = []
+    private(set) var peerBoundDeliveredMessages: [(messageID: String, peerIDs: Set<PeerID>)] = []
 
     @discardableResult
     func setDeliveryStatus(_ status: DeliveryStatus, forMessageID messageID: String) -> Bool {
@@ -604,6 +664,24 @@ private final class MockChatDeliveryContext: ChatDeliveryContext {
     func markMessageDelivered(_ messageID: String) {
         markedDeliveredMessageIDs.append(messageID)
     }
+
+    func markMessageDelivered(_ messageID: String, from peerIDs: Set<PeerID>) {
+        peerBoundDeliveredMessages.append((messageID, peerIDs))
+    }
+
+    func isOutgoingPrivateMessage(_ messageID: String, toAny peerIDs: Set<PeerID>) -> Bool {
+        peerIDs.contains { peerID in
+            contextMessages(for: peerID).contains { message in
+                message.id == messageID && message.senderPeerID == localPeerID
+            }
+        }
+    }
+
+    private let localPeerID = PeerID(str: "aabbccddeeff0011")
+
+    private func contextMessages(for peerID: PeerID) -> [BitchatMessage] {
+        store.conversationsByID[.directPeer(peerID)]?.messages ?? []
+    }
 }
 
 @MainActor
@@ -685,7 +763,63 @@ struct ChatDeliveryCoordinatorContextTests {
 
         #expect(isRead(coordinator.deliveryStatus(for: messageID)))
         #expect(context.notifyUIChangedCount == 1)
-        #expect(context.markedDeliveredMessageIDs == [messageID])
+        #expect(context.markedDeliveredMessageIDs.isEmpty)
+        #expect(context.peerBoundDeliveredMessages.count == 1)
+        #expect(context.peerBoundDeliveredMessages[0].messageID == messageID)
+        #expect(context.peerBoundDeliveredMessages[0].peerIDs == [peerID])
+    }
+
+    @Test @MainActor
+    func receiptFromWrongPeerDoesNotUpdateOrTerminalizeOutgoingMessage() async {
+        let context = MockChatDeliveryContext()
+        let coordinator = ChatDeliveryCoordinator(context: context)
+        let intendedPeer = PeerID(str: "0102030405060708")
+        let otherPeer = PeerID(str: "1112131415161718")
+        let messageID = "wrong-peer-receipt"
+        context.store.append(
+            makePrivateMessage(id: messageID, status: .sent),
+            to: .directPeer(intendedPeer)
+        )
+
+        coordinator.didReceiveReadReceipt(
+            ReadReceipt(
+                originalMessageID: messageID,
+                readerID: otherPeer,
+                readerNickname: "Other"
+            )
+        )
+
+        #expect(isSent(coordinator.deliveryStatus(for: messageID)))
+        #expect(context.peerBoundDeliveredMessages.isEmpty)
+        #expect(context.markedDeliveredMessageIDs.isEmpty)
+        #expect(context.notifyUIChangedCount == 0)
+    }
+
+    @Test @MainActor
+    func rejectedStaleReceiptDoesNotTerminalizeRetryState() async {
+        let context = MockChatDeliveryContext()
+        let coordinator = ChatDeliveryCoordinator(context: context)
+        let peerID = PeerID(str: "0102030405060708")
+        let messageID = "stale-receipt"
+        context.store.append(
+            makePrivateMessage(
+                id: messageID,
+                status: .read(by: "Peer", at: Date())
+            ),
+            to: .directPeer(peerID)
+        )
+
+        let didUpdate = coordinator.updateAcknowledgedMessageDeliveryStatus(
+            messageID,
+            status: .delivered(to: "Peer", at: Date()),
+            from: [peerID]
+        )
+
+        #expect(!didUpdate)
+        #expect(isRead(coordinator.deliveryStatus(for: messageID)))
+        #expect(context.peerBoundDeliveredMessages.isEmpty)
+        #expect(context.markedDeliveredMessageIDs.isEmpty)
+        #expect(context.notifyUIChangedCount == 0)
     }
 
     @Test @MainActor

bitchatTests/Mocks/MockTransport.swift

@@ -70,6 +70,9 @@ final class MockTransport: Transport, PrivateMediaDeletionPersisting {
     private var pendingDeletedPrivateMediaCompletions: [
         @MainActor (Bool) -> Void
     ] = []
+    /// Optional synchronous hook for send-ordering tests (for example, an ack
+    /// arriving before the router's send call returns).
+    var onSendPrivateMessage: (@MainActor (_ messageID: String) -> Void)?
     private let mockKeychain = MockKeychain()
 
     // MARK: - Transport Protocol Implementation
@@ -174,6 +177,11 @@ final class MockTransport: Transport, PrivateMediaDeletionPersisting {
 
     func sendPrivateMessage(_ content: String, to peerID: PeerID, recipientNickname: String, messageID: String) {
         sentPrivateMessages.append((content, peerID, recipientNickname, messageID))
+        if let onSendPrivateMessage {
+            MainActor.assumeIsolated {
+                onSendPrivateMessage(messageID)
+            }
+        }
     }
 
     func sendReadReceipt(_ receipt: ReadReceipt, to peerID: PeerID) {

bitchatTests/Performance/PerformanceBaselineTests.swift

@@ -749,6 +749,10 @@ private final class PerfDeliveryContext: ChatDeliveryContext {
 
     func notifyUIChanged() {}
     func markMessageDelivered(_ messageID: String) {}
+    func markMessageDelivered(_ messageID: String, from peerIDs: Set<PeerID>) {}
+    func isOutgoingPrivateMessage(_ messageID: String, toAny peerIDs: Set<PeerID>) -> Bool {
+        true
+    }
 
     @discardableResult
     func setDeliveryStatus(_ status: DeliveryStatus, forMessageID messageID: String) -> Bool {

bitchatTests/Services/MessageRouterTests.swift

@@ -79,18 +79,179 @@ struct MessageRouterTests {
     }
 
     @Test @MainActor
-    func sendPrivate_connectedSendIsNotRetained() async {
+    func peerBoundDeliveryAckCannotClearAnotherPeersRetainedMessage() async {
+        let intendedPeer = PeerID(str: "0000000000000023")
+        let otherPeer = PeerID(str: "0000000000000024")
+        let transport = MockTransport()
+        transport.reachablePeers = [intendedPeer, otherPeer]
+
+        let router = MessageRouter(transports: [transport])
+        router.sendPrivate(
+            "Secret",
+            to: intendedPeer,
+            recipientNickname: "Intended",
+            messageID: "peer-bound-ack"
+        )
+        #expect(transport.sentPrivateMessages.count == 1)
+
+        // Even a receipt arriving over another authenticated conversation
+        // must not terminalize the intended peer's retained retry.
+        router.markDelivered("peer-bound-ack", from: [otherPeer])
+        router.flushOutbox(for: intendedPeer)
+        #expect(transport.sentPrivateMessages.count == 2)
+
+        router.markDelivered("peer-bound-ack", from: [intendedPeer])
+        router.flushOutbox(for: intendedPeer)
+        #expect(transport.sentPrivateMessages.count == 2)
+    }
+
+    @Test @MainActor
+    func sendPrivate_connectedSecureSendRetainsUntilDeliveryAck() async {
         let peerID = PeerID(str: "0000000000000007")
         let transport = MockTransport()
         transport.connectedPeers.insert(peerID)
         transport.reachablePeers.insert(peerID)
+        transport.securePeers = [peerID]
 
         let router = MessageRouter(transports: [transport])
         router.sendPrivate("Hello", to: peerID, recipientNickname: "Peer", messageID: "m7")
         #expect(transport.sentPrivateMessages.count == 1)
 
-        router.flushOutbox(for: peerID)
+        // A newly authenticated/replacement session retries the retained
+        // message instead of losing the first ciphertext to a stale session.
+        router.retrySecurePrivateMessagesAfterAuthentication(for: [peerID])
+        #expect(transport.sentPrivateMessages.count == 2)
+
+        router.markDelivered("m7")
+        router.retrySecurePrivateMessagesAfterAuthentication(for: [peerID])
+        #expect(transport.sentPrivateMessages.count == 2)
+    }
+
+    @Test @MainActor
+    func authenticationRetry_matchesStableOutboxAliasWithoutDoubleSending() async {
+        let shortPeerID = PeerID(str: "0000000000000019")
+        let stablePeerID = PeerID(hexData: Data(repeating: 0x19, count: 32))
+        let transport = MockTransport()
+        transport.connectedPeers.insert(stablePeerID)
+        transport.securePeers = [stablePeerID]
+
+        let router = MessageRouter(transports: [transport])
+        router.sendPrivate("Hello", to: stablePeerID, recipientNickname: "Peer", messageID: "alias-retry")
+
+        router.retrySecurePrivateMessagesAfterAuthentication(for: [shortPeerID, stablePeerID, stablePeerID])
+
+        #expect(transport.sentPrivateMessages.map(\.messageID) == ["alias-retry", "alias-retry"])
+        #expect(transport.sentPrivateMessages.allSatisfy { $0.peerID == stablePeerID })
+    }
+
+    @Test @MainActor
+    func authenticationRetry_preservesFIFOAcrossSplitAliases() async {
+        let shortPeerID = PeerID(str: "0000000000000022")
+        let stablePeerID = PeerID(hexData: Data(repeating: 0x22, count: 32))
+        let transport = MockTransport()
+        transport.connectedPeers = [shortPeerID, stablePeerID]
+        transport.securePeers = [shortPeerID, stablePeerID]
+        let clock = MutableTestClock()
+        let router = MessageRouter(transports: [transport], now: { clock.now })
+
+        // The older message lives under the stable key, even though the auth
+        // callback supplies the ephemeral alias first.
+        router.sendPrivate("Older", to: stablePeerID, recipientNickname: "Peer", messageID: "fifo-old")
+        clock.now = clock.now.addingTimeInterval(1)
+        router.sendPrivate("Newer", to: shortPeerID, recipientNickname: "Peer", messageID: "fifo-new")
+        transport.resetRecordings()
+
+        router.retrySecurePrivateMessagesAfterAuthentication(for: [shortPeerID, stablePeerID])
+
+        #expect(transport.sentPrivateMessages.map(\.messageID) == ["fifo-old", "fifo-new"])
+        #expect(transport.sentPrivateMessages.map(\.peerID) == [stablePeerID, shortPeerID])
+    }
+
+    @Test @MainActor
+    func authenticationRetry_doesNotDuplicateNormalPendingHandshakeSend() async {
+        let peerID = PeerID(str: "0000000000000020")
+        let transport = MockTransport()
+        transport.connectedPeers.insert(peerID)
+        transport.securePeers = []
+
+        let router = MessageRouter(transports: [transport])
+        router.sendPrivate("Hello", to: peerID, recipientNickname: "Peer", messageID: "normal-handshake")
         #expect(transport.sentPrivateMessages.count == 1)
+
+        // BLE owns this pending send and drains it after authentication. Once
+        // the session becomes secure, the router's targeted auth retry must
+        // stay silent instead of producing a second copy.
+        transport.securePeers = [peerID]
+        router.retrySecurePrivateMessagesAfterAuthentication(for: [peerID])
+        #expect(transport.sentPrivateMessages.count == 1)
+
+        router.markDelivered("normal-handshake")
+    }
+
+    @Test @MainActor
+    func authenticationRetry_doesNotDuplicateMessageRequeuedByBLEForHandshake() async {
+        let peerID = PeerID(str: "0000000000000021")
+        let transport = MockTransport()
+        transport.connectedPeers.insert(peerID)
+        transport.securePeers = [peerID]
+
+        let router = MessageRouter(transports: [transport])
+        router.sendPrivate("Hello", to: peerID, recipientNickname: "Peer", messageID: "session-lost")
+        #expect(transport.sentPrivateMessages.count == 1)
+
+        // The session disappears before a normal outbox flush. That send is
+        // now owned by BLE's pending-handshake queue, so it clears the
+        // router's secure-auth retry marker.
+        transport.securePeers = []
+        router.flushOutbox(for: peerID)
+        #expect(transport.sentPrivateMessages.count == 2)
+
+        transport.securePeers = [peerID]
+        router.retrySecurePrivateMessagesAfterAuthentication(for: [peerID])
+        #expect(transport.sentPrivateMessages.count == 2)
+
+        router.markDelivered("session-lost")
+    }
+
+    @Test @MainActor
+    func sendPrivate_fastDeliveryAckCannotRaceAheadOfRetention() async {
+        let peerID = PeerID(str: "0000000000000017")
+        let transport = MockTransport()
+        transport.connectedPeers.insert(peerID)
+        transport.securePeers = [peerID]
+
+        let router = MessageRouter(transports: [transport])
+        transport.onSendPrivateMessage = { messageID in
+            router.markDelivered(messageID)
+        }
+
+        router.sendPrivate("Hello", to: peerID, recipientNickname: "Peer", messageID: "fast-ack")
+        #expect(transport.sentPrivateMessages.map(\.messageID) == ["fast-ack"])
+
+        transport.onSendPrivateMessage = nil
+        router.flushOutbox(for: peerID)
+        #expect(transport.sentPrivateMessages.map(\.messageID) == ["fast-ack"])
+    }
+
+    @Test @MainActor
+    func flushOutbox_synchronousAckDoesNotResurrectSnapshotEntry() async {
+        let peerID = PeerID(str: "0000000000000018")
+        let transport = MockTransport()
+        transport.connectedPeers.insert(peerID)
+        transport.securePeers = [peerID]
+
+        let router = MessageRouter(transports: [transport])
+        router.sendPrivate("Hello", to: peerID, recipientNickname: "Peer", messageID: "flush-fast-ack")
+        transport.onSendPrivateMessage = { messageID in
+            router.markDelivered(messageID)
+        }
+
+        router.flushOutbox(for: peerID)
+        #expect(transport.sentPrivateMessages.count == 2)
+
+        transport.onSendPrivateMessage = nil
+        router.flushOutbox(for: peerID)
+        #expect(transport.sentPrivateMessages.count == 2)
     }
 
     @Test @MainActor
@@ -392,10 +553,31 @@ struct MessageRouterTests {
         #expect(transport.sentPrivateMessages.count == 11)
     }
 
-    /// With an established secure session the connected fast-path stays
-    /// exactly as before: trusted outright, no retained copy, no courier.
     @Test @MainActor
-    func sendPrivate_connectedWithSecureSessionIsTrustedOutright() async {
+    func authenticationRetry_capsActualSecureTransmissions() async {
+        let peerID = PeerID(str: "00000000000000ad")
+        let transport = MockTransport()
+        transport.connectedPeers.insert(peerID)
+        transport.securePeers = [peerID]
+
+        let router = MessageRouter(transports: [transport])
+        var dropped: [String] = []
+        router.onMessageDropped = { messageID, _ in dropped.append(messageID) }
+
+        router.sendPrivate("Hello", to: peerID, recipientNickname: "Peer", messageID: "secure-retry")
+        for _ in 0..<10 {
+            router.retrySecurePrivateMessagesAfterAuthentication(for: [peerID])
+        }
+
+        #expect(dropped == ["secure-retry"])
+        #expect(transport.sentPrivateMessages.count == 8)
+    }
+
+    /// With an established secure session the connected fast-path sends
+    /// immediately and never leaks to couriers, but retains a local encrypted
+    /// outbox copy until the peer confirms receipt.
+    @Test @MainActor
+    func sendPrivate_connectedWithSecureSessionRetainsLocallyWithoutCourier() async {
         let peerID = PeerID(str: "00000000000000ab")
         let peerKey = Data(repeating: 0xAB, count: 32)
         let courier = PeerID(str: "00000000000000cc")
@@ -415,7 +597,11 @@ struct MessageRouterTests {
         #expect(transport.sentPrivateMessages.map(\.messageID) == ["cs2"])
         #expect(transport.sentCourierMessages.isEmpty)
         router.flushOutbox(for: peerID)
-        #expect(transport.sentPrivateMessages.count == 1)
+        #expect(transport.sentPrivateMessages.count == 2)
+        #expect(transport.sentCourierMessages.isEmpty)
+        router.markDelivered("cs2")
+        router.flushOutbox(for: peerID)
+        #expect(transport.sentPrivateMessages.count == 2)
     }
 
     @Test @MainActor
@@ -853,12 +1039,14 @@ struct MessageRouterTests {
         protectedDataUnavailable = false
         restoredStore.retryDeferredLoad() // captures unseen durable + known wake
 
-        // Secure direct flush removes the wake message before recovery's
+        // A secure direct retry followed by its delivery ack removes the wake
-        // MainActor merge. It must remain removed, while the unseen durable
+        // message before recovery's MainActor merge. It must remain removed,
-        // message still arrives through the pending recovery claim.
+        // while the unseen durable message still arrives through the pending
+        // recovery claim.
         transport.connectedPeers.insert(peerID)
         transport.securePeers = [peerID]
         router.flushOutbox(for: peerID)
+        router.markDelivered("recovery-gap-known")
         await Task.yield()
         await Task.yield()
 
@@ -929,7 +1117,8 @@ struct MessageRouterTests {
         restoredStore.retryDeferredLoad() // persists D+W and queues recovery
         transport.connectedPeers.insert(peerID)
         transport.securePeers = [peerID]
-        router.flushOutbox(for: peerID) // removes W before queued callback
+        router.flushOutbox(for: peerID)
+        router.markDelivered("recovery-write-failure-known") // removes W before queued callback
 
         // The gap save may remove W, but it must leave unseen D durable until
         // MessageRouter receives the pending recovery callback.