Retry confirmed private media after reconnect

bitchat/Services/BLE/BLEService.swift

@@ -1119,6 +1119,29 @@ final class BLEService: NSObject {
         collectionsQueue.sync { peerRegistry.capabilities(for: peerID) }
     }
 
+    func authenticatedPrivateMediaReceiptSessionGeneration(
+        to peerID: PeerID
+    ) -> UUID? {
+        let normalizedPeerID = peerID.toShort()
+        let currentNoiseGeneration =
+            noiseService.sessionGeneration(for: normalizedPeerID)
+        return collectionsQueue.sync {
+            guard let generation =
+                    privateMediaSessionGenerations[normalizedPeerID],
+                  generation == currentNoiseGeneration,
+                  let authenticated =
+                    authenticatedPeerStates[normalizedPeerID],
+                  authenticated.sessionGeneration == generation,
+                  authenticated.capabilities.contains(.privateMedia),
+                  authenticated.capabilities.contains(
+                    .privateMediaReceipts
+                  ) else {
+                return nil
+            }
+            return generation
+        }
+    }
+
     private func privateMediaPolicyFingerprint(
         for peerID: PeerID,
         expectedSessionGeneration: UUID?
@@ -1603,6 +1626,36 @@ final class BLEService: NSObject {
         to peerID: PeerID,
         transferId: String,
         allowLegacyFallback: Bool
+    ) {
+        sendFilePrivate(
+            filePacket,
+            to: peerID,
+            transferId: transferId,
+            allowLegacyFallback: allowLegacyFallback,
+            requiresAuthenticatedPrivateMediaReceipts: false
+        )
+    }
+
+    func sendFilePrivateReceiptRetry(
+        _ filePacket: BitchatFilePacket,
+        to peerID: PeerID,
+        transferId: String
+    ) {
+        sendFilePrivate(
+            filePacket,
+            to: peerID,
+            transferId: transferId,
+            allowLegacyFallback: false,
+            requiresAuthenticatedPrivateMediaReceipts: true
+        )
+    }
+
+    private func sendFilePrivate(
+        _ filePacket: BitchatFilePacket,
+        to peerID: PeerID,
+        transferId: String,
+        allowLegacyFallback: Bool,
+        requiresAuthenticatedPrivateMediaReceipts: Bool
     ) {
         // Register before enqueueing onto messageQueue. This closes the window
         // where cancel/delete could run first, observe no scheduler state, and
@@ -1715,6 +1768,25 @@ final class BLEService: NSObject {
                 self.privateMediaTransferAdmissions.finish(transferId)
                 return
             }
+            if requiresAuthenticatedPrivateMediaReceipts,
+               self.authenticatedPrivateMediaReceiptSessionGeneration(
+                    to: targetID
+               ) == nil {
+                SecureLogger.warning(
+                    "Private media retry blocked without current authenticated receipt support for \(targetID.id.prefix(8))…",
+                    category: .security
+                )
+                TransferProgressManager.shared.rejectBeforeStart(
+                    id: transferId,
+                    reason: String(
+                        localized: "content.delivery.reason.private_media_capability_unresolved",
+                        defaultValue: "Could not confirm encrypted media support",
+                        comment: "Failure reason when private-media capability negotiation did not resolve"
+                    )
+                )
+                self.privateMediaTransferAdmissions.finish(transferId)
+                return
+            }
             guard let typedPayload = BLENoisePayloadFactory.privateFile(filePacket) else {
                 SecureLogger.error("❌ Failed to encode file packet for private send", category: .session)
                 TransferProgressManager.shared.rejectBeforeStart(
@@ -1725,6 +1797,21 @@ final class BLEService: NSObject {
                 return
             }
             guard self.noiseService.hasEstablishedSession(with: targetID) else {
+                if requiresAuthenticatedPrivateMediaReceipts {
+                    // A retry belongs to one exact authenticated generation.
+                    // Never let it enter the ordinary pending queue where a
+                    // bit-8-only replacement session could later flush it.
+                    TransferProgressManager.shared.rejectBeforeStart(
+                        id: transferId,
+                        reason: String(
+                            localized: "content.delivery.reason.private_media_capability_unresolved",
+                            defaultValue: "Could not confirm encrypted media support",
+                            comment: "Failure reason when private-media capability negotiation did not resolve"
+                        )
+                    )
+                    self.privateMediaTransferAdmissions.finish(transferId)
+                    return
+                }
                 let queued = self.collectionsQueue.sync(flags: .barrier) {
                     self.privateMediaTransferAdmissions.withActive(transferId) {
                         self.pendingNoiseSessionQueues.appendTypedPayload(
@@ -1756,7 +1843,12 @@ final class BLEService: NSObject {
                     self.privateMediaTransferAdmissions.finish(transferId)
                     return
                 }
-                let packet = try self.makeEncryptedNoisePacket(typedPayload, to: targetID)
+                let packet = try self.makeEncryptedNoisePacket(
+                    typedPayload,
+                    to: targetID,
+                    requiresAuthenticatedPrivateMediaReceipts:
+                        requiresAuthenticatedPrivateMediaReceipts
+                )
                 guard self.privateMediaTransferAdmissions.isActive(transferId) else {
                     self.privateMediaTransferAdmissions.finish(transferId)
                     return
@@ -5164,7 +5256,11 @@ extension BLEService {
         }
     }
 
-    private func makeEncryptedNoisePacket(_ typedPayload: Data, to peerID: PeerID) throws -> BitchatPacket {
+    private func makeEncryptedNoisePacket(
+        _ typedPayload: Data,
+        to peerID: PeerID,
+        requiresAuthenticatedPrivateMediaReceipts: Bool = false
+    ) throws -> BitchatPacket {
         let encrypted: Data
         let isPrivateFile = NoisePayloadType.isPrivateFile(rawValue: typedPayload.first)
         if isPrivateFile {
@@ -5174,6 +5270,13 @@ extension BLEService {
                       let authenticated = authenticatedPeerStates[peerID],
                       authenticated.sessionGeneration == generation,
                       authenticated.capabilities.contains(.privateMedia) else { return nil }
+                if requiresAuthenticatedPrivateMediaReceipts {
+                    guard authenticated.capabilities.contains(
+                        .privateMediaReceipts
+                    ) else {
+                        return nil
+                    }
+                }
                 return generation
             }
             guard let provenGeneration else {

bitchat/Services/Transport.swift

@@ -190,6 +190,14 @@ protocol Transport: AnyObject {
         transferId: String,
         allowLegacyFallback: Bool
     )
+    /// Automatic whole-file retry is admitted only while this exact Noise
+    /// generation authenticates bit 9. It must never queue across a session
+    /// replacement or enter the signed raw legacy path.
+    func sendFilePrivateReceiptRetry(
+        _ packet: BitchatFilePacket,
+        to peerID: PeerID,
+        transferId: String
+    )
     func cancelTransfer(_ transferId: String)
 
     // Live voice / push-to-talk (mesh transports only): one encoded
@@ -236,6 +244,11 @@ protocol Transport: AnyObject {
     /// empty for peers that predate the capabilities TLV.
     func peerCapabilities(_ peerID: PeerID) -> PeerCapabilities
     func privateMediaSendPolicy(to peerID: PeerID) -> PrivateMediaSendPolicy
+    /// The exact current Noise generation that authenticated both encrypted
+    /// private media (bit 8) and durable receipts/retry (bit 9).
+    func authenticatedPrivateMediaReceiptSessionGeneration(
+        to peerID: PeerID
+    ) -> UUID?
     func resolvePrivateMediaSendPolicy(
         to peerID: PeerID,
         completion: @escaping @MainActor (PrivateMediaSendPolicy) -> Void
@@ -311,6 +324,11 @@ extension Transport {
     func broadcastGroupMessage(_ envelope: Data) {}
     func peerCapabilities(_ peerID: PeerID) -> PeerCapabilities { [] }
     func privateMediaSendPolicy(to peerID: PeerID) -> PrivateMediaSendPolicy { .blockedDowngrade }
+    func authenticatedPrivateMediaReceiptSessionGeneration(
+        to peerID: PeerID
+    ) -> UUID? {
+        nil
+    }
     func resolvePrivateMediaSendPolicy(
         to peerID: PeerID,
         completion: @escaping @MainActor (PrivateMediaSendPolicy) -> Void
@@ -345,6 +363,11 @@ extension Transport {
         guard !allowLegacyFallback else { return }
         sendFilePrivate(packet, to: peerID, transferId: transferId)
     }
+    func sendFilePrivateReceiptRetry(
+        _ packet: BitchatFilePacket,
+        to peerID: PeerID,
+        transferId: String
+    ) {}
     func cancelTransfer(_ transferId: String) {}
 
     func sendMessage(_ content: String, mentions: [String], messageID: String, timestamp: Date) {

bitchat/ViewModels/ChatDeliveryCoordinator.swift

@@ -55,6 +55,9 @@ extension ChatViewModel: ChatDeliveryContext {
 
     func markMessageDelivered(_ messageID: String) {
         messageRouter.markDelivered(messageID)
+        mediaTransferCoordinator.confirmPrivateMediaDelivery(
+            messageID: messageID
+        )
     }
 }
 

bitchat/ViewModels/ChatMediaTransferCoordinator.swift

@@ -19,6 +19,46 @@ struct PendingLegacyPrivateMediaConsent {
     let completion: @MainActor (Bool) -> Void
 }
 
+struct PrivateMediaReconnectRetryLimits: Equatable {
+    var maxRetainedPackets = 8
+    var maxRetainedBytes = 4 * 1024 * 1024
+    var maxRetriesPerMessage = 2
+    var retentionSeconds: TimeInterval = 120
+    var maxRetriesPerReconnect = 2
+}
+
+private struct PrivateMediaReconnectRetryRecord {
+    let messageID: String
+    let peerID: PeerID
+    let packet: BitchatFilePacket
+    var receiptSessionGeneration: UUID
+    var createdAt: Date
+    var retryCount: Int
+    var activeTransferID: String?
+    var retryAfterCompletion: Bool
+    var idleOutcome: PrivateMediaReconnectRetryIdleOutcome
+    var deferredTerminalFailureReason: String?
+    var expiryToken: UUID?
+
+    var retainedBytes: Int {
+        packet.content.count
+    }
+}
+
+private enum PrivateMediaReconnectRetryIdleOutcome {
+    case none
+    case locallyCompleted
+    case cancelled
+    case rejected(reason: String)
+}
+
+private struct PrivateMediaReconnectRetryCandidate {
+    let messageID: String
+    /// The receipt-capable Noise generation that owned this record when the
+    /// reconnect/authentication event captured it.
+    let receiptSessionGeneration: UUID
+}
+
 /// The narrow surface `ChatMediaTransferCoordinator` needs from its owner.
 ///
 /// Follows the `ChatDeliveryContext` exemplar: the coordinator depends on the
@@ -57,6 +97,7 @@ protocol ChatMediaTransferContext: AnyObject {
 
     // MARK: Mesh file transfer
     func privateMediaSendPolicy(to peerID: PeerID) -> PrivateMediaSendPolicy
+    func authenticatedPrivateMediaReceiptSessionGeneration(to peerID: PeerID) -> UUID?
     func resolvePrivateMediaSendPolicy(
         to peerID: PeerID,
         completion: @escaping @MainActor (PrivateMediaSendPolicy) -> Void
@@ -74,6 +115,11 @@ protocol ChatMediaTransferContext: AnyObject {
         transferId: String,
         allowLegacyFallback: Bool
     )
+    func sendFilePrivateReceiptRetry(
+        _ packet: BitchatFilePacket,
+        to peerID: PeerID,
+        transferId: String
+    )
     func sendFileBroadcast(_ packet: BitchatFilePacket, transferId: String)
     func cancelTransfer(_ transferId: String)
 }
@@ -93,6 +139,14 @@ extension ChatViewModel: ChatMediaTransferContext {
         meshService.privateMediaSendPolicy(to: peerID)
     }
 
+    func authenticatedPrivateMediaReceiptSessionGeneration(
+        to peerID: PeerID
+    ) -> UUID? {
+        meshService.authenticatedPrivateMediaReceiptSessionGeneration(
+            to: peerID
+        )
+    }
+
     func resolvePrivateMediaSendPolicy(
         to peerID: PeerID,
         completion: @escaping @MainActor (PrivateMediaSendPolicy) -> Void
@@ -135,6 +189,18 @@ extension ChatViewModel: ChatMediaTransferContext {
         )
     }
 
+    func sendFilePrivateReceiptRetry(
+        _ packet: BitchatFilePacket,
+        to peerID: PeerID,
+        transferId: String
+    ) {
+        meshService.sendFilePrivateReceiptRetry(
+            packet,
+            to: peerID,
+            transferId: transferId
+        )
+    }
+
     func sendFileBroadcast(_ packet: BitchatFilePacket, transferId: String) {
         meshService.sendFileBroadcast(packet, transferId: transferId)
     }
@@ -206,9 +272,33 @@ final class ChatMediaTransferCoordinator {
     private let prepareImagePacket: @Sendable (URL) throws -> ChatPreparedImage
     private let imagePreparationBarrier = ImagePreparationBarrier()
     private let prepareVoiceNotePacket: @Sendable (URL) throws -> BitchatFilePacket
+    private let reconnectRetryLimits: PrivateMediaReconnectRetryLimits
+    private let now: () -> Date
+    private let transferIDFactory: (String) -> String
 
     private(set) var transferIdToMessageIDs: [String: [String]] = [:]
     private(set) var messageIDToTransferId: [String: String] = [:]
+    private var reconnectRetryRecords: [
+        String: PrivateMediaReconnectRetryRecord
+    ] = [:]
+    /// A newly authenticated session supersedes any raw-connect policy
+    /// resolution still in flight for that peer.
+    private var peersResolvingReconnectRetry: [
+        PeerID: (
+            id: UUID,
+            replacingActiveTransfer: Bool,
+            candidates: [PrivateMediaReconnectRetryCandidate]
+        )
+    ] = [:]
+    private var reconnectRetryExpiryTasks: [String: Task<Void, Never>] = [:]
+
+    var retainedReconnectRetryCount: Int {
+        reconnectRetryRecords.count
+    }
+
+    var retainedReconnectRetryBytes: Int {
+        reconnectRetryRecords.values.reduce(0) { $0 + $1.retainedBytes }
+    }
 
     init(
         context: any ChatMediaTransferContext,
@@ -217,11 +307,20 @@ final class ChatMediaTransferCoordinator {
         },
         prepareVoiceNotePacket: @escaping @Sendable (URL) throws -> BitchatFilePacket = {
             try ChatMediaPreparation.prepareVoiceNotePacket(at: $0)
+        },
+        reconnectRetryLimits: PrivateMediaReconnectRetryLimits =
+            PrivateMediaReconnectRetryLimits(),
+        now: @escaping () -> Date = Date.init,
+        transferIDFactory: @escaping (String) -> String = {
+            "\($0)-\(UUID().uuidString)"
         }
     ) {
         self.context = context
         self.prepareImagePacket = prepareImagePacket
         self.prepareVoiceNotePacket = prepareVoiceNotePacket
+        self.reconnectRetryLimits = reconnectRetryLimits
+        self.now = now
+        self.transferIDFactory = transferIDFactory
     }
 
     func sendVoiceNote(at url: URL) {
@@ -513,6 +612,12 @@ final class ChatMediaTransferCoordinator {
     ) {
         switch policy {
         case .encrypted:
+            retainForReconnectRetryIfEligible(
+                packet,
+                peerID: peerID,
+                messageID: messageID,
+                activeTransferID: transferId
+            )
             context.sendFilePrivate(
                 packet,
                 to: peerID,
@@ -601,16 +706,32 @@ final class ChatMediaTransferCoordinator {
     }
 
     func makeTransferID(messageID: String) -> String {
-        "\(messageID)-\(UUID().uuidString)"
+        transferIDFactory(messageID)
     }
 
     func clearTransferMapping(for messageID: String) {
-        guard let transferId = messageIDToTransferId.removeValue(forKey: messageID) else { return }
+        guard let transferId = messageIDToTransferId[messageID] else { return }
+        clearTransferMapping(
+            transferID: transferId,
+            messageID: messageID,
+            clearCurrentOwner: true
+        )
+    }
+
+    private func clearTransferMapping(
+        transferID: String,
+        messageID: String,
+        clearCurrentOwner: Bool
+    ) {
+        if clearCurrentOwner,
+           messageIDToTransferId[messageID] == transferID {
+            messageIDToTransferId.removeValue(forKey: messageID)
+        }
         context.cancelLegacyPrivateMediaConsent(
-            transferId: transferId,
+            transferId: transferID,
             messageID: messageID
         )
-        guard var queue = transferIdToMessageIDs[transferId] else { return }
+        guard var queue = transferIdToMessageIDs[transferID] else { return }
 
         if !queue.isEmpty {
             if queue.first == messageID {
@@ -620,10 +741,32 @@ final class ChatMediaTransferCoordinator {
             }
         }
 
-        transferIdToMessageIDs[transferId] = queue.isEmpty ? nil : queue
+        transferIdToMessageIDs[transferID] = queue.isEmpty ? nil : queue
+    }
+
+    /// Returns the message still owned by this exact transfer. Replacement
+    /// retries can receive late callbacks from the cancelled predecessor;
+    /// those callbacks may clear only their stale queue entry.
+    private func currentMessageID(forTransferID transferID: String) -> String? {
+        guard let messageID = transferIdToMessageIDs[transferID]?.first else {
+            return nil
+        }
+        guard messageIDToTransferId[messageID] == transferID else {
+            clearTransferMapping(
+                transferID: transferID,
+                messageID: messageID,
+                clearCurrentOwner: false
+            )
+            return nil
+        }
+        return messageID
     }
 
     func handleMediaSendFailure(messageID: String, reason: String) {
+        discardReconnectRetry(
+            messageID: messageID,
+            cancelActiveTransfer: false
+        )
         context.updateMessageDeliveryStatus(messageID, status: .failed(reason: reason))
         clearTransferMapping(for: messageID)
     }
@@ -631,21 +774,88 @@ final class ChatMediaTransferCoordinator {
     func handleTransferEvent(_ event: TransferProgressManager.Event) {
         switch event {
         case .started(let id, let total):
-            guard let messageID = transferIdToMessageIDs[id]?.first else { return }
+            guard let messageID = currentMessageID(forTransferID: id) else {
+                return
+            }
+            if isReconnectRetryTransfer(id, messageID: messageID) {
+                return
+            }
             context.updateMessageDeliveryStatus(messageID, status: .partiallyDelivered(reached: 0, total: total))
+
         case .updated(let id, let sent, let total):
-            guard let messageID = transferIdToMessageIDs[id]?.first else { return }
+            guard let messageID = currentMessageID(forTransferID: id) else {
+                return
+            }
+            if isReconnectRetryTransfer(id, messageID: messageID) {
+                return
+            }
             context.updateMessageDeliveryStatus(messageID, status: .partiallyDelivered(reached: sent, total: total))
+
         case .completed(let id, _):
-            guard let messageID = transferIdToMessageIDs[id]?.first else { return }
+            guard let messageID = currentMessageID(forTransferID: id) else {
+                return
+            }
+            let ownsRetainedRecord =
+                reconnectRetryRecords[messageID]?.activeTransferID == id
+            let retryAfterCompletion = ownsRetainedRecord
+                && reconnectRetryRecords[messageID]?.retryAfterCompletion == true
+            let deferredTerminalReason = ownsRetainedRecord
+                ? reconnectRetryRecords[messageID]?
+                    .deferredTerminalFailureReason
+                : nil
+            if ownsRetainedRecord {
+                reconnectRetryRecords[messageID]?.activeTransferID = nil
+                reconnectRetryRecords[messageID]?.retryAfterCompletion = false
+                reconnectRetryRecords[messageID]?.idleOutcome =
+                    .locallyCompleted
+                reconnectRetryRecords[messageID]?.createdAt = now()
+            }
             context.updateMessageDeliveryStatus(messageID, status: .sent)
             clearTransferMapping(for: messageID)
+            if let deferredTerminalReason {
+                terminalizeReconnectRetry(
+                    messageID: messageID,
+                    reason: deferredTerminalReason
+                )
+            } else if retryAfterCompletion {
+                startReconnectRetry(messageID: messageID)
+            } else if ownsRetainedRecord {
+                scheduleReconnectRetryExpiry(messageID: messageID)
+            }
+
         case .cancelled(let id, _, _):
-            guard let messageID = transferIdToMessageIDs[id]?.first else { return }
+            guard let messageID = currentMessageID(forTransferID: id) else {
+                return
+            }
+            if isRetainedPrivateMediaTransfer(id, messageID: messageID) {
+                finishRetainedTransfer(
+                    id,
+                    messageID: messageID,
+                    outcome: .cancelled,
+                    rejectionReason: nil
+                )
+                return
+            }
+            discardReconnectRetry(
+                messageID: messageID,
+                cancelActiveTransfer: false
+            )
             clearTransferMapping(for: messageID)
             context.removeMessage(withID: messageID, cleanupFile: true)
+
         case .rejected(let id, let reason):
-            guard let messageID = transferIdToMessageIDs[id]?.first else { return }
+            guard let messageID = currentMessageID(forTransferID: id) else {
+                return
+            }
+            if isRetainedPrivateMediaTransfer(id, messageID: messageID) {
+                finishRetainedTransfer(
+                    id,
+                    messageID: messageID,
+                    outcome: .rejected(reason: reason),
+                    rejectionReason: reason
+                )
+                return
+            }
             handleMediaSendFailure(messageID: messageID, reason: reason)
         }
     }
@@ -677,6 +887,10 @@ final class ChatMediaTransferCoordinator {
     }
 
     func cancelMediaSend(messageID: String) {
+        discardReconnectRetry(
+            messageID: messageID,
+            cancelActiveTransfer: false
+        )
         if let transferId = messageIDToTransferId[messageID],
            let active = transferIdToMessageIDs[transferId]?.first,
            active == messageID {
@@ -687,6 +901,10 @@ final class ChatMediaTransferCoordinator {
     }
 
     func deleteMediaMessage(messageID: String) {
+        discardReconnectRetry(
+            messageID: messageID,
+            cancelActiveTransfer: false
+        )
         // Delete is also a send cancellation. In particular, an approved
         // legacy-clear send may still be waiting on BLEService.messageQueue;
         // removing only the UI mapping would let that deferred work transmit.
@@ -698,12 +916,55 @@ final class ChatMediaTransferCoordinator {
         context.removeMessage(withID: messageID, cleanupFile: true)
     }
 
+    /// A raw link callback can arrive before the replacement Noise session
+    /// proves its capabilities. Resolve against the exact session before
+    /// releasing any retained bytes into a whole-file retry.
+    func peerDidReconnect(_ peerID: PeerID) {
+        resolveReconnectRetries(
+            for: peerID,
+            replacingActiveTransfer: false
+        )
+    }
+
+    /// Authentication supersedes a raw-connect resolution that may still
+    /// refer to the cached generation and replaces only stale active sends.
+    func peerDidAuthenticate(_ peerID: PeerID) {
+        resolveReconnectRetries(
+            for: peerID,
+            replacingActiveTransfer: true
+        )
+    }
+
+    /// Local fragment completion is not proof that the recipient reconstructed
+    /// the file. Only a remote delivery/read receipt releases retry ownership.
+    func confirmPrivateMediaDelivery(messageID: String) {
+        guard PrivateMediaMessageIdentity.isStableID(messageID) else {
+            return
+        }
+        discardReconnectRetry(
+            messageID: messageID,
+            cancelActiveTransfer: true
+        )
+    }
+
+    /// Deterministic clock seam for focused tests. Production records also own
+    /// wall-clock expiry tasks.
+    func _test_expireReconnectRetries() {
+        pruneExpiredReconnectRetries()
+    }
+
     /// Invalidates detached preparation work and cancels every transfer that
     /// reached the transport. Closing image-preparation admission and joining
     /// active synchronous writers ensures the following panic media deletion
     /// is the last filesystem mutation before the transaction can complete.
     func resetForPanic() {
         imagePreparationBarrier.invalidateAndWait()
+        peersResolvingReconnectRetry.removeAll(keepingCapacity: false)
+        for task in reconnectRetryExpiryTasks.values {
+            task.cancel()
+        }
+        reconnectRetryExpiryTasks.removeAll(keepingCapacity: false)
+        reconnectRetryRecords.removeAll(keepingCapacity: false)
         let transferIDs = Set(transferIdToMessageIDs.keys)
         transferIdToMessageIDs.removeAll(keepingCapacity: false)
         messageIDToTransferId.removeAll(keepingCapacity: false)
@@ -714,6 +975,571 @@ final class ChatMediaTransferCoordinator {
 }
 
 private extension ChatMediaTransferCoordinator {
+    func reconnectRetryCandidates(
+        for peerID: PeerID,
+        limit: Int?
+    ) -> [PrivateMediaReconnectRetryCandidate] {
+        let records = reconnectRetryRecords.values
+            .filter {
+                $0.peerID == peerID
+                    && $0.retryCount
+                        < reconnectRetryLimits.maxRetriesPerMessage
+            }
+            .sorted {
+                if $0.createdAt == $1.createdAt {
+                    return $0.messageID < $1.messageID
+                }
+                return $0.createdAt < $1.createdAt
+            }
+        let selected: ArraySlice<PrivateMediaReconnectRetryRecord>
+        if let limit {
+            selected = records.prefix(max(0, limit))
+        } else {
+            selected = records[...]
+        }
+        return selected.map {
+            PrivateMediaReconnectRetryCandidate(
+                messageID: $0.messageID,
+                receiptSessionGeneration: $0.receiptSessionGeneration
+            )
+        }
+    }
+
+    func resolveReconnectRetries(
+        for peerID: PeerID,
+        replacingActiveTransfer: Bool
+    ) {
+        pruneExpiredReconnectRetries()
+        let normalizedPeerID = peerID.toShort()
+        let candidates: [PrivateMediaReconnectRetryCandidate]
+        if let pending = peersResolvingReconnectRetry[normalizedPeerID] {
+            // Authentication is the only event that may supersede a raw-link
+            // resolution; duplicate callbacks add no new proof.
+            guard replacingActiveTransfer,
+                  !pending.replacingActiveTransfer else {
+                return
+            }
+            candidates = reconnectRetryCandidates(
+                for: normalizedPeerID,
+                limit: nil
+            )
+        } else {
+            candidates = reconnectRetryCandidates(
+                for: normalizedPeerID,
+                limit: replacingActiveTransfer
+                    ? nil
+                    : max(
+                        0,
+                        reconnectRetryLimits.maxRetriesPerReconnect
+                    )
+            )
+        }
+        guard !candidates.isEmpty else { return }
+
+        let resolutionID = UUID()
+        peersResolvingReconnectRetry[normalizedPeerID] = (
+            id: resolutionID,
+            replacingActiveTransfer: replacingActiveTransfer,
+            candidates: candidates
+        )
+        context.resolvePrivateMediaSendPolicy(
+            to: normalizedPeerID
+        ) { [weak self] policy in
+            guard let self,
+                  let pending =
+                    self.peersResolvingReconnectRetry[normalizedPeerID],
+                  pending.id == resolutionID else {
+                return
+            }
+            self.peersResolvingReconnectRetry.removeValue(
+                forKey: normalizedPeerID
+            )
+            guard policy == .encrypted,
+                  let provenGeneration = self.context
+                    .authenticatedPrivateMediaReceiptSessionGeneration(
+                        to: normalizedPeerID
+                    ) else {
+                self.terminalizeUnavailableCapabilityProof(
+                    pending.candidates,
+                    for: normalizedPeerID
+                )
+                return
+            }
+            self.scheduleReconnectRetries(
+                pending.candidates,
+                for: normalizedPeerID,
+                replacingActiveTransfer:
+                    pending.replacingActiveTransfer,
+                provenGeneration: provenGeneration
+            )
+        }
+    }
+
+    func retainForReconnectRetryIfEligible(
+        _ packet: BitchatFilePacket,
+        peerID: PeerID,
+        messageID: String,
+        activeTransferID: String
+    ) {
+        let normalizedPeerID = peerID.toShort()
+        guard let receiptSessionGeneration = context
+                .authenticatedPrivateMediaReceiptSessionGeneration(
+                    to: normalizedPeerID
+                ),
+              reconnectRetryLimits.maxRetainedPackets > 0,
+              reconnectRetryLimits.maxRetainedBytes > 0,
+              reconnectRetryLimits.maxRetriesPerMessage > 0,
+              packet.content.count
+                <= reconnectRetryLimits.maxRetainedBytes,
+              PrivateMediaMessageIdentity.isStableID(messageID),
+              PrivateMediaMessageIdentity.stableID(
+                for: packet,
+                senderPeerID: context.myPeerID,
+                recipientPeerID: normalizedPeerID
+              ) == messageID else {
+            return
+        }
+
+        pruneExpiredReconnectRetries()
+        if var existing = reconnectRetryRecords[messageID] {
+            cancelReconnectRetryExpiry(messageID: messageID)
+            existing.receiptSessionGeneration = receiptSessionGeneration
+            existing.createdAt = now()
+            existing.activeTransferID = activeTransferID
+            existing.retryAfterCompletion = false
+            existing.idleOutcome = .none
+            existing.deferredTerminalFailureReason = nil
+            existing.expiryToken = nil
+            reconnectRetryRecords[messageID] = existing
+            return
+        }
+
+        makeReconnectRetryCapacity(for: packet.content.count)
+        guard reconnectRetryRecords.count
+                < reconnectRetryLimits.maxRetainedPackets,
+              retainedReconnectRetryBytes + packet.content.count
+                <= reconnectRetryLimits.maxRetainedBytes else {
+            SecureLogger.debug(
+                "Private media retry retention full; sending once id=\(messageID.prefix(12))…",
+                category: .session
+            )
+            return
+        }
+
+        reconnectRetryRecords[messageID] =
+            PrivateMediaReconnectRetryRecord(
+                messageID: messageID,
+                peerID: normalizedPeerID,
+                packet: packet,
+                receiptSessionGeneration: receiptSessionGeneration,
+                createdAt: now(),
+                retryCount: 0,
+                activeTransferID: activeTransferID,
+                retryAfterCompletion: false,
+                idleOutcome: .none,
+                deferredTerminalFailureReason: nil,
+                expiryToken: nil
+            )
+    }
+
+    func terminalizeUnavailableCapabilityProof(
+        _ candidates: [PrivateMediaReconnectRetryCandidate],
+        for peerID: PeerID
+    ) {
+        let reason = privateMediaCapabilityUnresolvedReason
+        for candidate in candidates {
+            guard var record =
+                    reconnectRetryRecords[candidate.messageID],
+                  record.peerID == peerID,
+                  record.receiptSessionGeneration
+                    == candidate.receiptSessionGeneration else {
+                continue
+            }
+            if record.activeTransferID != nil {
+                // The original transport owner can still produce a valid
+                // remote receipt. Defer failure until it releases ownership.
+                record.deferredTerminalFailureReason = reason
+                reconnectRetryRecords[candidate.messageID] = record
+            } else {
+                terminalizeReconnectRetry(
+                    messageID: candidate.messageID,
+                    reason: reason
+                )
+            }
+        }
+    }
+
+    func scheduleReconnectRetries(
+        _ candidates: [PrivateMediaReconnectRetryCandidate],
+        for peerID: PeerID,
+        replacingActiveTransfer: Bool,
+        provenGeneration: UUID
+    ) {
+        pruneExpiredReconnectRetries()
+
+        var scheduledCount = 0
+        let limit = max(
+            0,
+            reconnectRetryLimits.maxRetriesPerReconnect
+        )
+        for candidate in candidates {
+            guard scheduledCount < limit else { break }
+            let messageID = candidate.messageID
+            guard var record = reconnectRetryRecords[messageID],
+                  record.peerID == peerID,
+                  record.receiptSessionGeneration
+                    == candidate.receiptSessionGeneration,
+                  record.retryCount
+                    < reconnectRetryLimits.maxRetriesPerMessage else {
+                continue
+            }
+            if record.deferredTerminalFailureReason != nil {
+                record.deferredTerminalFailureReason = nil
+                reconnectRetryRecords[messageID] = record
+            }
+            if replacingActiveTransfer,
+               candidate.receiptSessionGeneration == provenGeneration {
+                continue
+            }
+            if record.activeTransferID != nil {
+                if replacingActiveTransfer {
+                    if replaceActiveTransferAfterAuthentication(
+                        messageID: messageID
+                    ) {
+                        scheduledCount += 1
+                    }
+                    continue
+                }
+                // Arm one retry after the current transfer drains. Duplicate
+                // reconnect callbacks cannot chain more work.
+                if record.retryCount == 0 {
+                    record.retryAfterCompletion = true
+                    reconnectRetryRecords[messageID] = record
+                    scheduledCount += 1
+                }
+            } else if startReconnectRetry(messageID: messageID) {
+                scheduledCount += 1
+            }
+        }
+    }
+
+    @discardableResult
+    func replaceActiveTransferAfterAuthentication(
+        messageID: String
+    ) -> Bool {
+        guard var record = reconnectRetryRecords[messageID],
+              let staleTransferID = record.activeTransferID,
+              record.retryCount
+                < reconnectRetryLimits.maxRetriesPerMessage else {
+            return false
+        }
+        record.activeTransferID = nil
+        record.retryAfterCompletion = false
+        record.createdAt = now()
+        reconnectRetryRecords[messageID] = record
+
+        if messageIDToTransferId[messageID] == staleTransferID {
+            clearTransferMapping(for: messageID)
+        }
+        context.cancelTransfer(staleTransferID)
+        return startReconnectRetry(messageID: messageID)
+    }
+
+    @discardableResult
+    func startReconnectRetry(messageID: String) -> Bool {
+        pruneExpiredReconnectRetries()
+        guard var record = reconnectRetryRecords[messageID],
+              record.activeTransferID == nil,
+              record.retryCount
+                < reconnectRetryLimits.maxRetriesPerMessage else {
+            return false
+        }
+        guard context.privateMediaSendPolicy(to: record.peerID)
+                == .encrypted,
+              let receiptSessionGeneration = context
+                .authenticatedPrivateMediaReceiptSessionGeneration(
+                    to: record.peerID
+                ) else {
+            terminalizeReconnectRetry(
+                messageID: messageID,
+                reason: privateMediaCapabilityUnresolvedReason
+            )
+            return false
+        }
+
+        cancelReconnectRetryExpiry(messageID: messageID)
+        let transferID = makeTransferID(messageID: messageID)
+        record.retryCount += 1
+        record.receiptSessionGeneration = receiptSessionGeneration
+        record.activeTransferID = transferID
+        record.retryAfterCompletion = false
+        record.idleOutcome = .none
+        record.deferredTerminalFailureReason = nil
+        record.expiryToken = nil
+        reconnectRetryRecords[messageID] = record
+        registerTransfer(
+            transferId: transferID,
+            messageID: messageID
+        )
+
+        SecureLogger.debug(
+            "🔄 Retrying private media after reconnect id=\(messageID.prefix(12))… attempt=\(record.retryCount)",
+            category: .session
+        )
+        context.sendFilePrivateReceiptRetry(
+            record.packet,
+            to: record.peerID,
+            transferId: transferID
+        )
+        return true
+    }
+
+    func finishRetainedTransfer(
+        _ transferID: String,
+        messageID: String,
+        outcome: PrivateMediaReconnectRetryIdleOutcome,
+        rejectionReason: String?
+    ) {
+        guard var record = reconnectRetryRecords[messageID],
+              record.activeTransferID == transferID else {
+            return
+        }
+        let retryAfterCompletion = record.retryAfterCompletion
+        let deferredTerminalReason =
+            record.deferredTerminalFailureReason
+        record.activeTransferID = nil
+        record.retryAfterCompletion = false
+        record.idleOutcome = outcome
+        record.createdAt = now()
+        reconnectRetryRecords[messageID] = record
+        clearTransferMapping(for: messageID)
+
+        if let deferredTerminalReason {
+            terminalizeReconnectRetry(
+                messageID: messageID,
+                reason: deferredTerminalReason
+            )
+        } else if retryAfterCompletion {
+            startReconnectRetry(messageID: messageID)
+        } else if record.retryCount
+                    >= reconnectRetryLimits.maxRetriesPerMessage {
+            terminalizeReconnectRetry(
+                messageID: messageID,
+                reason: rejectionReason
+                    ?? privateMediaNotDeliveredReason
+            )
+        } else {
+            scheduleReconnectRetryExpiry(messageID: messageID)
+        }
+
+        if let rejectionReason {
+            SecureLogger.debug(
+                "Private media retry rejected id=\(messageID.prefix(12))…: \(rejectionReason)",
+                category: .session
+            )
+        }
+    }
+
+    func isReconnectRetryTransfer(
+        _ transferID: String,
+        messageID: String
+    ) -> Bool {
+        guard let record = reconnectRetryRecords[messageID] else {
+            return false
+        }
+        return record.retryCount > 0
+            && record.activeTransferID == transferID
+    }
+
+    func isRetainedPrivateMediaTransfer(
+        _ transferID: String,
+        messageID: String
+    ) -> Bool {
+        reconnectRetryRecords[messageID]?.activeTransferID
+            == transferID
+    }
+
+    func discardReconnectRetry(
+        messageID: String,
+        cancelActiveTransfer: Bool
+    ) {
+        cancelReconnectRetryExpiry(messageID: messageID)
+        guard let record =
+                reconnectRetryRecords.removeValue(forKey: messageID) else {
+            return
+        }
+        guard cancelActiveTransfer,
+              let transferID = record.activeTransferID,
+              messageIDToTransferId[messageID] == transferID else {
+            return
+        }
+        // Release ownership before cancellation so its late callback cannot
+        // remove a remotely confirmed row.
+        clearTransferMapping(for: messageID)
+        context.cancelTransfer(transferID)
+    }
+
+    func pruneExpiredReconnectRetries() {
+        let current = now()
+        let lifetime = max(
+            0,
+            reconnectRetryLimits.retentionSeconds
+        )
+        let expiredMessageIDs: [String] =
+            reconnectRetryRecords.values.compactMap { record in
+                guard record.activeTransferID == nil,
+                      current.timeIntervalSince(record.createdAt)
+                        >= lifetime else {
+                    return nil
+                }
+                return record.messageID
+            }
+        for messageID in expiredMessageIDs {
+            guard let record = reconnectRetryRecords[messageID],
+                  record.activeTransferID == nil else {
+                continue
+            }
+            terminalizeReconnectRetry(
+                messageID: messageID,
+                reason: expiryFailureReason(for: record)
+            )
+        }
+    }
+
+    func makeReconnectRetryCapacity(for incomingBytes: Int) {
+        while reconnectRetryRecords.count
+                >= reconnectRetryLimits.maxRetainedPackets
+            || retainedReconnectRetryBytes + incomingBytes
+                > reconnectRetryLimits.maxRetainedBytes {
+            guard let victim = reconnectRetryRecords.values
+                .filter({ $0.activeTransferID == nil })
+                .min(by: {
+                    if $0.createdAt == $1.createdAt {
+                        return $0.messageID < $1.messageID
+                    }
+                    return $0.createdAt < $1.createdAt
+                }) else {
+                return
+            }
+            terminalizeReconnectRetry(
+                messageID: victim.messageID,
+                reason: expiryFailureReason(for: victim)
+            )
+        }
+    }
+
+    var privateMediaNotDeliveredReason: String {
+        String(
+            localized: "content.delivery.reason.not_delivered",
+            defaultValue: "Not delivered",
+            comment: "Failure reason shown when a private media transfer could not finish"
+        )
+    }
+
+    var privateMediaCapabilityUnresolvedReason: String {
+        String(
+            localized:
+                "content.delivery.reason.private_media_capability_unresolved",
+            defaultValue: "Could not confirm encrypted media support",
+            comment: "Failure reason when private-media capability negotiation did not resolve"
+        )
+    }
+
+    var privateMediaDeliveryUnconfirmedReason: String {
+        String(
+            localized:
+                "content.delivery.reason.private_media_delivery_unconfirmed",
+            defaultValue: "Delivery could not be confirmed",
+            comment: "Failure reason when private media left this device but no delivery receipt arrived"
+        )
+    }
+
+    func expiryFailureReason(
+        for record: PrivateMediaReconnectRetryRecord
+    ) -> String {
+        switch record.idleOutcome {
+        case .locallyCompleted:
+            return privateMediaDeliveryUnconfirmedReason
+        case .rejected(let reason):
+            return reason
+        case .none, .cancelled:
+            return privateMediaNotDeliveredReason
+        }
+    }
+
+    func terminalizeReconnectRetry(
+        messageID: String,
+        reason: String
+    ) {
+        guard let record = reconnectRetryRecords[messageID],
+              record.activeTransferID == nil else {
+            return
+        }
+        cancelReconnectRetryExpiry(messageID: messageID)
+        guard reconnectRetryRecords.removeValue(forKey: messageID) != nil else {
+            return
+        }
+        context.updateMessageDeliveryStatus(
+            messageID,
+            status: .failed(reason: reason)
+        )
+    }
+
+    func scheduleReconnectRetryExpiry(messageID: String) {
+        guard var record = reconnectRetryRecords[messageID],
+              record.activeTransferID == nil else {
+            return
+        }
+        cancelReconnectRetryExpiry(messageID: messageID)
+
+        let lifetime = max(
+            0,
+            reconnectRetryLimits.retentionSeconds
+        )
+        let elapsed = max(
+            0,
+            now().timeIntervalSince(record.createdAt)
+        )
+        let delay = max(0, lifetime - elapsed)
+        let token = UUID()
+        record.expiryToken = token
+        reconnectRetryRecords[messageID] = record
+
+        let nanoseconds = UInt64(
+            min(
+                delay,
+                TimeInterval(UInt64.max) / 1_000_000_000
+            ) * 1_000_000_000
+        )
+        reconnectRetryExpiryTasks[messageID] = Task {
+            @MainActor [weak self] in
+            if nanoseconds > 0 {
+                try? await Task.sleep(nanoseconds: nanoseconds)
+            }
+            guard !Task.isCancelled,
+                  let self,
+                  let current =
+                    self.reconnectRetryRecords[messageID],
+                  current.activeTransferID == nil,
+                  current.expiryToken == token else {
+                return
+            }
+            self.terminalizeReconnectRetry(
+                messageID: messageID,
+                reason: self.expiryFailureReason(for: current)
+            )
+        }
+    }
+
+    func cancelReconnectRetryExpiry(messageID: String) {
+        reconnectRetryExpiryTasks.removeValue(
+            forKey: messageID
+        )?.cancel()
+        if reconnectRetryRecords[messageID]?.expiryToken != nil {
+            reconnectRetryRecords[messageID]?.expiryToken = nil
+        }
+    }
+
     func applicationFilesDirectory() throws -> URL {
         let base = try FileManager.default.url(
             for: .applicationSupportDirectory,

bitchat/ViewModels/ChatVerificationCoordinator.swift

@@ -58,6 +58,7 @@ protocol ChatVerificationContext: AnyObject {
     func noiseStaticPublicKeyData() -> Data
     func hasEstablishedNoiseSession(with peerID: PeerID) -> Bool
     func triggerHandshake(with peerID: PeerID)
+    func privateMediaPeerDidAuthenticate(_ peerID: PeerID)
     func sendVerifyChallenge(to peerID: PeerID, noiseKeyHex: String, nonceA: Data)
     func sendVerifyResponse(to peerID: PeerID, noiseKeyHex: String, nonceA: Data)
 
@@ -116,6 +117,10 @@ extension ChatViewModel: ChatVerificationContext {
         meshService.noiseStaticPublicKeyData()
     }
 
+    func privateMediaPeerDidAuthenticate(_ peerID: PeerID) {
+        mediaTransferCoordinator.peerDidAuthenticate(peerID.toShort())
+    }
+
     func sendVerifyChallenge(to peerID: PeerID, noiseKeyHex: String, nonceA: Data) {
         meshService.sendVerifyChallenge(to: peerID, noiseKeyHex: noiseKeyHex, nonceA: nonceA)
     }
@@ -129,6 +134,10 @@ extension ChatViewModel: ChatVerificationContext {
     }
 }
 
+extension ChatVerificationContext {
+    func privateMediaPeerDidAuthenticate(_ peerID: PeerID) {}
+}
+
 @MainActor
 final class ChatVerificationCoordinator {
     struct PendingVerification {
@@ -197,6 +206,7 @@ final class ChatVerificationCoordinator {
                     guard let self else { return }
 
                     SecureLogger.debug("🔐 Authenticated: \(peerID)", category: .security)
+                    self.context.privateMediaPeerDidAuthenticate(peerID)
 
                     if self.context.isVerifiedFingerprint(fingerprint) {
                         self.context.setEncryptionStatus(.noiseVerified, for: peerID)

bitchat/ViewModels/ChatViewModel.swift

@@ -1755,6 +1755,7 @@ final class ChatViewModel: ObservableObject, BitchatDelegate, SynchronousMessage
 
         case .peerConnected(let peerID):
             transportEventCoordinator.didConnectToPeerSynchronously(peerID)
+            mediaTransferCoordinator.peerDidReconnect(peerID)
 
         case .peerDisconnected(let peerID):
             transportEventCoordinator.didDisconnectFromPeerSynchronously(peerID)
@@ -1844,6 +1845,9 @@ final class ChatViewModel: ObservableObject, BitchatDelegate, SynchronousMessage
 
     func didConnectToPeer(_ peerID: PeerID) {
         transportEventCoordinator.didConnectToPeer(peerID)
+        Task { @MainActor [weak self] in
+            self?.mediaTransferCoordinator.peerDidReconnect(peerID)
+        }
     }
 
     func didDisconnectFromPeer(_ peerID: PeerID) {

bitchatTests/ChatMediaTransferCoordinatorContextTests.swift

@@ -95,10 +95,20 @@ private final class MockChatMediaTransferContext: ChatMediaTransferContext {
         transferId: String
     )] = []
     private(set) var privateFileLegacyAllowances: [Bool] = []
+    private(set) var privateFileReceiptRetryTransferIDs: [String] = []
     private(set) var broadcastFileSends: [String] = []
     private(set) var cancelledTransfers: [String] = []
+    private(set) var privateMediaPolicyResolutionRequests: [PeerID] = []
     var privateMediaPolicy: PrivateMediaSendPolicy = .encrypted
     var resolvedPrivateMediaPolicy: PrivateMediaSendPolicy?
+    var resolvesPrivateMediaPolicyImmediately = true
+    var supportsAuthenticatedPrivateMediaReceipts = false
+    var authenticatedPrivateMediaReceiptGeneration = UUID(
+        uuidString: "00000000-0000-0000-0000-000000000001"
+    )!
+    private var pendingPrivateMediaPolicyResolutions: [
+        @MainActor (PrivateMediaSendPolicy) -> Void
+    ] = []
     private(set) var legacyConsentRequests: [(
         id: UUID,
         peerID: PeerID,
@@ -113,11 +123,40 @@ private final class MockChatMediaTransferContext: ChatMediaTransferContext {
         privateMediaPolicy
     }
 
+    func authenticatedPrivateMediaReceiptSessionGeneration(
+        to peerID: PeerID
+    ) -> UUID? {
+        supportsAuthenticatedPrivateMediaReceipts
+            ? authenticatedPrivateMediaReceiptGeneration
+            : nil
+    }
+
     func resolvePrivateMediaSendPolicy(
         to peerID: PeerID,
         completion: @escaping @MainActor (PrivateMediaSendPolicy) -> Void
     ) {
-        completion(resolvedPrivateMediaPolicy ?? privateMediaPolicy)
+        privateMediaPolicyResolutionRequests.append(peerID)
+        if resolvesPrivateMediaPolicyImmediately {
+            completion(resolvedPrivateMediaPolicy ?? privateMediaPolicy)
+        } else {
+            pendingPrivateMediaPolicyResolutions.append(completion)
+        }
+    }
+
+    var pendingPrivateMediaPolicyResolutionCount: Int {
+        pendingPrivateMediaPolicyResolutions.count
+    }
+
+    func resolveNextPrivateMediaPolicy(
+        _ policy: PrivateMediaSendPolicy? = nil
+    ) {
+        guard !pendingPrivateMediaPolicyResolutions.isEmpty else { return }
+        let completion = pendingPrivateMediaPolicyResolutions.removeFirst()
+        completion(
+            policy
+                ?? resolvedPrivateMediaPolicy
+                ?? privateMediaPolicy
+        )
     }
 
     func requestLegacyPrivateMediaConsent(
@@ -162,6 +201,16 @@ private final class MockChatMediaTransferContext: ChatMediaTransferContext {
         privateFileLegacyAllowances.append(allowLegacyFallback)
     }
 
+    func sendFilePrivateReceiptRetry(
+        _ packet: BitchatFilePacket,
+        to peerID: PeerID,
+        transferId: String
+    ) {
+        privateFileSends.append((packet, peerID, transferId))
+        privateFileLegacyAllowances.append(false)
+        privateFileReceiptRetryTransferIDs.append(transferId)
+    }
+
     func sendFileBroadcast(_ packet: BitchatFilePacket, transferId: String) {
         broadcastFileSends.append(transferId)
     }
@@ -851,6 +900,548 @@ struct ChatMediaTransferCoordinatorContextTests {
         #expect(context.legacyConsentRequests.isEmpty)
         #expect(context.privateFileSends.isEmpty)
     }
+
+    @Test @MainActor
+    func receiptCapableEncryptedMediaRetriesExactPacketAfterReconnect() async throws {
+        let context = MockChatMediaTransferContext()
+        let peerID = PeerID(str: "1122334455667788")
+        context.selectedPrivateChatPeer = peerID
+        context.supportsAuthenticatedPrivateMediaReceipts = true
+        let fileName = "voice_0011223344556677.m4a"
+        let preparer = StaticVoiceNotePreparer(fileName: fileName)
+        let transferIDs = DeterministicMediaTransferIDFactory()
+        let coordinator = ChatMediaTransferCoordinator(
+            context: context,
+            prepareVoiceNotePacket: { url in
+                try preparer.prepare(url)
+            },
+            transferIDFactory: transferIDs.make
+        )
+        let url = try makeCoordinatorVoiceURL(fileName: fileName)
+        defer {
+            try? FileManager.default.removeItem(
+                at: url.deletingLastPathComponent()
+            )
+        }
+
+        coordinator.sendVoiceNote(at: url)
+        #expect(await TestHelpers.waitUntil(
+            { context.privateFileSends.count == 1 },
+            timeout: TestConstants.longTimeout
+        ))
+        let messageID = try #require(
+            context.privateChats[peerID]?.first?.id
+        )
+        let initial = try #require(
+            context.privateFileSends.first
+        )
+        #expect(PrivateMediaMessageIdentity.isStableID(messageID))
+        #expect(coordinator.retainedReconnectRetryCount == 1)
+
+        coordinator.handleTransferEvent(.completed(
+            id: initial.transferId,
+            totalFragments: 1
+        ))
+        #expect(coordinator.retainedReconnectRetryCount == 1)
+        #expect(context.deliveryStatusUpdates.last?.status == .sent)
+
+        coordinator.peerDidReconnect(peerID)
+        #expect(context.privateFileSends.count == 2)
+        let retry = try #require(context.privateFileSends.last)
+        #expect(retry.packet.encode() == initial.packet.encode())
+        #expect(retry.peerID == peerID)
+        #expect(retry.transferId != initial.transferId)
+        #expect(context.privateFileReceiptRetryTransferIDs == [
+            retry.transferId
+        ])
+        #expect(context.privateFileLegacyAllowances == [false, false])
+
+        coordinator.confirmPrivateMediaDelivery(messageID: messageID)
+        #expect(coordinator.retainedReconnectRetryCount == 0)
+        #expect(context.cancelledTransfers == [retry.transferId])
+        #expect(context.removedMessages.isEmpty)
+        #expect(!context.deliveryStatusUpdates.contains {
+            if case .failed = $0.status { return true }
+            return false
+        })
+
+        // Receipt confirmation removes retry ownership before transport
+        // cancellation, so its late callback cannot delete the delivered row
+        // or re-arm another reconnect retry.
+        coordinator.handleTransferEvent(.cancelled(
+            id: retry.transferId,
+            sentFragments: 1,
+            totalFragments: 2
+        ))
+        coordinator.peerDidReconnect(peerID)
+        #expect(context.privateFileSends.count == 2)
+        #expect(context.removedMessages.isEmpty)
+        #expect(coordinator.messageIDToTransferId[messageID] == nil)
+    }
+
+    @Test @MainActor
+    func bit8OnlyEncryptedMediaNeverRetainsOrAutomaticallyRetries() async throws {
+        let context = MockChatMediaTransferContext()
+        let peerID = PeerID(str: "1122334455667788")
+        context.selectedPrivateChatPeer = peerID
+        context.privateMediaPolicy = .encrypted
+        context.supportsAuthenticatedPrivateMediaReceipts = false
+        let fileName = "voice_1111222233334444.m4a"
+        let preparer = StaticVoiceNotePreparer(fileName: fileName)
+        let coordinator = ChatMediaTransferCoordinator(
+            context: context,
+            prepareVoiceNotePacket: { url in
+                try preparer.prepare(url)
+            }
+        )
+        let url = try makeCoordinatorVoiceURL(fileName: fileName)
+        defer {
+            try? FileManager.default.removeItem(
+                at: url.deletingLastPathComponent()
+            )
+        }
+
+        coordinator.sendVoiceNote(at: url)
+        #expect(await TestHelpers.waitUntil(
+            { context.privateFileSends.count == 1 },
+            timeout: TestConstants.longTimeout
+        ))
+        let initial = try #require(context.privateFileSends.first)
+        coordinator.handleTransferEvent(.completed(
+            id: initial.transferId,
+            totalFragments: 1
+        ))
+        coordinator.peerDidReconnect(peerID)
+        coordinator.peerDidAuthenticate(peerID)
+
+        #expect(coordinator.retainedReconnectRetryCount == 0)
+        #expect(context.privateFileSends.count == 1)
+        #expect(context.privateFileReceiptRetryTransferIDs.isEmpty)
+        #expect(context.privateMediaPolicyResolutionRequests.isEmpty)
+    }
+
+    @Test @MainActor
+    func consentedRawLegacyMediaNeverEntersAutomaticRetry() async throws {
+        let context = MockChatMediaTransferContext()
+        let peerID = PeerID(str: "1122334455667788")
+        context.selectedPrivateChatPeer = peerID
+        context.privateMediaPolicy = .legacyRequiresConsent
+        // Even a contradictory stale bit-9 observation must not retain an
+        // invocation that actually selected the explicit raw path.
+        context.supportsAuthenticatedPrivateMediaReceipts = true
+        let fileName = "voice_2222333344445555.m4a"
+        let preparer = StaticVoiceNotePreparer(fileName: fileName)
+        let coordinator = ChatMediaTransferCoordinator(
+            context: context,
+            prepareVoiceNotePacket: { url in
+                try preparer.prepare(url)
+            }
+        )
+        let url = try makeCoordinatorVoiceURL(fileName: fileName)
+        defer {
+            try? FileManager.default.removeItem(
+                at: url.deletingLastPathComponent()
+            )
+        }
+
+        coordinator.sendVoiceNote(at: url)
+        #expect(await TestHelpers.waitUntil(
+            { context.legacyConsentRequests.count == 1 },
+            timeout: TestConstants.longTimeout
+        ))
+        context.resolveNextLegacyConsent(true)
+        let initial = try #require(context.privateFileSends.first)
+        #expect(context.privateFileLegacyAllowances == [true])
+        #expect(coordinator.retainedReconnectRetryCount == 0)
+
+        coordinator.handleTransferEvent(.completed(
+            id: initial.transferId,
+            totalFragments: 1
+        ))
+        context.privateMediaPolicy = .encrypted
+        coordinator.peerDidReconnect(peerID)
+        coordinator.peerDidAuthenticate(peerID)
+
+        #expect(context.privateFileSends.count == 1)
+        #expect(context.privateFileReceiptRetryTransferIDs.isEmpty)
+        #expect(coordinator.retainedReconnectRetryCount == 0)
+    }
+
+    @Test @MainActor
+    func authenticatedGenerationSupersedesStaleReconnectResolution() async throws {
+        let context = MockChatMediaTransferContext()
+        let peerID = PeerID(str: "1122334455667788")
+        context.selectedPrivateChatPeer = peerID
+        context.supportsAuthenticatedPrivateMediaReceipts = true
+        context.resolvesPrivateMediaPolicyImmediately = false
+        let oldGeneration = context
+            .authenticatedPrivateMediaReceiptGeneration
+        let newGeneration = UUID(
+            uuidString: "00000000-0000-0000-0000-000000000002"
+        )!
+        let fileName = "voice_3333444455556666.m4a"
+        let preparer = StaticVoiceNotePreparer(fileName: fileName)
+        let transferIDs = DeterministicMediaTransferIDFactory()
+        let coordinator = ChatMediaTransferCoordinator(
+            context: context,
+            prepareVoiceNotePacket: { url in
+                try preparer.prepare(url)
+            },
+            transferIDFactory: transferIDs.make
+        )
+        let url = try makeCoordinatorVoiceURL(fileName: fileName)
+        defer {
+            try? FileManager.default.removeItem(
+                at: url.deletingLastPathComponent()
+            )
+        }
+
+        coordinator.sendVoiceNote(at: url)
+        #expect(await TestHelpers.waitUntil(
+            { context.privateFileSends.count == 1 },
+            timeout: TestConstants.longTimeout
+        ))
+        let initial = try #require(context.privateFileSends.first)
+        coordinator.peerDidReconnect(peerID)
+        #expect(context.pendingPrivateMediaPolicyResolutionCount == 1)
+
+        context.authenticatedPrivateMediaReceiptGeneration = newGeneration
+        coordinator.peerDidAuthenticate(peerID)
+        #expect(context.pendingPrivateMediaPolicyResolutionCount == 2)
+
+        // The old-generation completion lost ownership and is inert.
+        context.resolveNextPrivateMediaPolicy(.encrypted)
+        #expect(context.privateFileReceiptRetryTransferIDs.isEmpty)
+        #expect(context.cancelledTransfers.isEmpty)
+
+        context.resolveNextPrivateMediaPolicy(.encrypted)
+        #expect(context.cancelledTransfers == [initial.transferId])
+        #expect(context.privateFileReceiptRetryTransferIDs.count == 1)
+        #expect(
+            context.authenticatedPrivateMediaReceiptGeneration
+                == newGeneration
+        )
+        #expect(oldGeneration != newGeneration)
+    }
+
+    @Test @MainActor
+    func panicClearsRetainedRetryPendingResolutionAndExpiry() async throws {
+        let context = MockChatMediaTransferContext()
+        let peerID = PeerID(str: "1122334455667788")
+        context.selectedPrivateChatPeer = peerID
+        context.supportsAuthenticatedPrivateMediaReceipts = true
+        context.resolvesPrivateMediaPolicyImmediately = false
+        let fileName = "voice_3333444455556666.m4a"
+        let preparer = StaticVoiceNotePreparer(fileName: fileName)
+        let coordinator = ChatMediaTransferCoordinator(
+            context: context,
+            prepareVoiceNotePacket: { url in
+                try preparer.prepare(url)
+            },
+            reconnectRetryLimits: PrivateMediaReconnectRetryLimits(
+                maxRetainedPackets: 1,
+                maxRetainedBytes: 1_024,
+                maxRetriesPerMessage: 1,
+                retentionSeconds: 0.1,
+                maxRetriesPerReconnect: 1
+            )
+        )
+        let url = try makeCoordinatorVoiceURL(fileName: fileName)
+        defer {
+            try? FileManager.default.removeItem(
+                at: url.deletingLastPathComponent()
+            )
+        }
+
+        coordinator.sendVoiceNote(at: url)
+        #expect(await TestHelpers.waitUntil(
+            { context.privateFileSends.count == 1 },
+            timeout: TestConstants.longTimeout
+        ))
+        let initial = try #require(context.privateFileSends.first)
+        coordinator.handleTransferEvent(.completed(
+            id: initial.transferId,
+            totalFragments: 1
+        ))
+        #expect(coordinator.retainedReconnectRetryCount == 1)
+
+        coordinator.peerDidReconnect(peerID)
+        #expect(context.pendingPrivateMediaPolicyResolutionCount == 1)
+        let failedBeforePanic = context.deliveryStatusUpdates.filter {
+            if case .failed = $0.status { return true }
+            return false
+        }.count
+
+        coordinator.resetForPanic()
+        context.resolveNextPrivateMediaPolicy(.encrypted)
+        try await Task.sleep(nanoseconds: 250_000_000)
+        coordinator._test_expireReconnectRetries()
+
+        #expect(coordinator.retainedReconnectRetryCount == 0)
+        #expect(coordinator.retainedReconnectRetryBytes == 0)
+        #expect(coordinator.transferIdToMessageIDs.isEmpty)
+        #expect(coordinator.messageIDToTransferId.isEmpty)
+        #expect(context.privateFileSends.count == 1)
+        #expect(context.privateFileReceiptRetryTransferIDs.isEmpty)
+        #expect(context.deliveryStatusUpdates.filter {
+            if case .failed = $0.status { return true }
+            return false
+        }.count == failedBeforePanic)
+    }
+
+    @Test @MainActor
+    func retryCountAndRetentionTimeEndInVisibleFailure() async throws {
+        let context = MockChatMediaTransferContext()
+        let peerID = PeerID(str: "1122334455667788")
+        context.selectedPrivateChatPeer = peerID
+        context.supportsAuthenticatedPrivateMediaReceipts = true
+        let clock = MutableMediaRetryClock(
+            Date(timeIntervalSince1970: 4_000)
+        )
+        let limits = PrivateMediaReconnectRetryLimits(
+            maxRetainedPackets: 2,
+            maxRetainedBytes: 1_024,
+            maxRetriesPerMessage: 1,
+            retentionSeconds: 10,
+            maxRetriesPerReconnect: 1
+        )
+        let fileName = "voice_4444555566667777.m4a"
+        let preparer = StaticVoiceNotePreparer(fileName: fileName)
+        let transferIDs = DeterministicMediaTransferIDFactory()
+        let coordinator = ChatMediaTransferCoordinator(
+            context: context,
+            prepareVoiceNotePacket: { url in
+                try preparer.prepare(url)
+            },
+            reconnectRetryLimits: limits,
+            now: clock.now,
+            transferIDFactory: transferIDs.make
+        )
+        let url = try makeCoordinatorVoiceURL(fileName: fileName)
+        defer {
+            try? FileManager.default.removeItem(
+                at: url.deletingLastPathComponent()
+            )
+        }
+
+        coordinator.sendVoiceNote(at: url)
+        #expect(await TestHelpers.waitUntil(
+            { context.privateFileSends.count == 1 },
+            timeout: TestConstants.longTimeout
+        ))
+        let initial = try #require(context.privateFileSends.first)
+        coordinator.handleTransferEvent(.completed(
+            id: initial.transferId,
+            totalFragments: 1
+        ))
+        coordinator.peerDidReconnect(peerID)
+        let retryID = try #require(
+            context.privateFileReceiptRetryTransferIDs.first
+        )
+        coordinator.handleTransferEvent(.cancelled(
+            id: retryID,
+            sentFragments: 0,
+            totalFragments: 1
+        ))
+
+        #expect(coordinator.retainedReconnectRetryCount == 0)
+        #expect(context.removedMessages.isEmpty)
+        #expect(context.deliveryStatusUpdates.contains {
+            $0.messageID.hasPrefix("media-")
+                && $0.status == .failed(reason: String(
+                    localized: "content.delivery.reason.not_delivered",
+                    defaultValue: "Not delivered",
+                    comment: "Failure reason shown when a private media transfer could not finish"
+                ))
+        })
+
+        // A separate retained row that locally completed but never received a
+        // remote receipt expires to a distinct visible failure.
+        let ttlFileName = "voice_5555666677778888.m4a"
+        let ttlPreparer = StaticVoiceNotePreparer(
+            fileName: ttlFileName
+        )
+        let ttlCoordinator = ChatMediaTransferCoordinator(
+            context: context,
+            prepareVoiceNotePacket: { url in
+                try ttlPreparer.prepare(url)
+            },
+            reconnectRetryLimits: limits,
+            now: clock.now,
+            transferIDFactory: transferIDs.make
+        )
+        let ttlURL = try makeCoordinatorVoiceURL(
+            fileName: ttlFileName
+        )
+        defer {
+            try? FileManager.default.removeItem(
+                at: ttlURL.deletingLastPathComponent()
+            )
+        }
+        let sendsBeforeTTL = context.privateFileSends.count
+        ttlCoordinator.sendVoiceNote(at: ttlURL)
+        #expect(await TestHelpers.waitUntil(
+            {
+                context.privateFileSends.count
+                    == sendsBeforeTTL + 1
+            },
+            timeout: TestConstants.longTimeout
+        ))
+        let ttlInitial = try #require(context.privateFileSends.last)
+        ttlCoordinator.handleTransferEvent(.completed(
+            id: ttlInitial.transferId,
+            totalFragments: 1
+        ))
+        clock.advance(by: 10)
+        ttlCoordinator._test_expireReconnectRetries()
+
+        #expect(ttlCoordinator.retainedReconnectRetryCount == 0)
+        #expect(context.deliveryStatusUpdates.contains {
+            $0.status == .failed(
+                reason: String(
+                    localized:
+                        "content.delivery.reason.private_media_delivery_unconfirmed",
+                    defaultValue: "Delivery could not be confirmed"
+                )
+            )
+        })
+    }
+
+    @Test @MainActor
+    func retentionAndPerReconnectWorkAreBounded() async throws {
+        let context = MockChatMediaTransferContext()
+        let peerID = PeerID(str: "1122334455667788")
+        context.selectedPrivateChatPeer = peerID
+        context.supportsAuthenticatedPrivateMediaReceipts = true
+        let limits = PrivateMediaReconnectRetryLimits(
+            maxRetainedPackets: 2,
+            maxRetainedBytes: 10,
+            maxRetriesPerMessage: 2,
+            retentionSeconds: 120,
+            maxRetriesPerReconnect: 1
+        )
+        let transferIDs = DeterministicMediaTransferIDFactory()
+        let coordinator = ChatMediaTransferCoordinator(
+            context: context,
+            prepareVoiceNotePacket: { url in
+                let content = Data("voice".utf8)
+                return BitchatFilePacket(
+                    fileName: url.lastPathComponent,
+                    fileSize: UInt64(content.count),
+                    mimeType: "audio/mp4",
+                    content: content
+                )
+            },
+            reconnectRetryLimits: limits,
+            transferIDFactory: transferIDs.make
+        )
+        let fileNames = [
+            "voice_6666777788889999.m4a",
+            "voice_777788889999aaaa.m4a",
+            "voice_88889999aaaabbbb.m4a"
+        ]
+        var roots: [URL] = []
+        defer {
+            for root in roots {
+                try? FileManager.default.removeItem(at: root)
+            }
+        }
+
+        for fileName in fileNames {
+            let url = try makeCoordinatorVoiceURL(
+                fileName: fileName,
+                bytes: Data("voice".utf8)
+            )
+            roots.append(url.deletingLastPathComponent())
+            // The production preparer preserves this stable filename.
+            coordinator.sendVoiceNote(at: url)
+        }
+        #expect(await TestHelpers.waitUntil(
+            { context.privateFileSends.count == 3 },
+            timeout: TestConstants.longTimeout
+        ))
+        #expect(coordinator.retainedReconnectRetryCount == 2)
+        #expect(coordinator.retainedReconnectRetryBytes <= 10)
+
+        for send in context.privateFileSends {
+            coordinator.handleTransferEvent(.completed(
+                id: send.transferId,
+                totalFragments: 1
+            ))
+        }
+        coordinator.peerDidReconnect(peerID)
+        #expect(context.privateFileReceiptRetryTransferIDs.count == 1)
+    }
+
+    @Test @MainActor
+    func userCancellationReleasesRetainedBytesAndIgnoresLateEvent() async throws {
+        let context = MockChatMediaTransferContext()
+        let peerID = PeerID(str: "1122334455667788")
+        context.selectedPrivateChatPeer = peerID
+        context.supportsAuthenticatedPrivateMediaReceipts = true
+        let fileName = "voice_9999aaaabbbbcccc.m4a"
+        let preparer = StaticVoiceNotePreparer(fileName: fileName)
+        let coordinator = ChatMediaTransferCoordinator(
+            context: context,
+            prepareVoiceNotePacket: { url in
+                try preparer.prepare(url)
+            }
+        )
+        let url = try makeCoordinatorVoiceURL(fileName: fileName)
+        defer {
+            try? FileManager.default.removeItem(
+                at: url.deletingLastPathComponent()
+            )
+        }
+
+        coordinator.sendVoiceNote(at: url)
+        #expect(await TestHelpers.waitUntil(
+            { context.privateFileSends.count == 1 },
+            timeout: TestConstants.longTimeout
+        ))
+        let messageID = try #require(
+            context.privateChats[peerID]?.first?.id
+        )
+        let transferID = try #require(
+            context.privateFileSends.first?.transferId
+        )
+
+        coordinator.cancelMediaSend(messageID: messageID)
+        coordinator.handleTransferEvent(.cancelled(
+            id: transferID,
+            sentFragments: 0,
+            totalFragments: 1
+        ))
+
+        #expect(coordinator.retainedReconnectRetryCount == 0)
+        #expect(coordinator.retainedReconnectRetryBytes == 0)
+        #expect(context.cancelledTransfers == [transferID])
+        #expect(context.removedMessages.map(\.messageID) == [
+            messageID
+        ])
+        #expect(!context.deliveryStatusUpdates.contains {
+            if case .failed = $0.status { return true }
+            return false
+        })
+    }
+}
+
+private func makeCoordinatorVoiceURL(
+    fileName: String,
+    bytes: Data = Data("voice".utf8)
+) throws -> URL {
+    let directory = FileManager.default.temporaryDirectory
+        .appendingPathComponent(
+            "media-retry-\(UUID().uuidString)",
+            isDirectory: true
+        )
+    try FileManager.default.createDirectory(
+        at: directory,
+        withIntermediateDirectories: true
+    )
+    let url = directory.appendingPathComponent(fileName)
+    try bytes.write(to: url)
+    return url
 }
 
 private final class PausedImagePreparer: @unchecked Sendable {

bitchatTests/ChatVerificationCoordinatorContextTests.swift

@@ -97,6 +97,7 @@ private final class MockChatVerificationContext: ChatVerificationContext {
     var noiseSessionKeysByPeerID: [PeerID: Data] = [:]
     private(set) var installedCallbacks: (onPeerAuthenticated: (PeerID, String) -> Void, onHandshakeRequired: (PeerID) -> Void)?
     private(set) var triggeredHandshakes: [PeerID] = []
+    private(set) var privateMediaAuthenticatedPeers: [PeerID] = []
     private(set) var sentChallenges: [(peerID: PeerID, noiseKeyHex: String, nonceA: Data)] = []
     private(set) var sentResponses: [(peerID: PeerID, noiseKeyHex: String, nonceA: Data)] = []
 
@@ -113,6 +114,9 @@ private final class MockChatVerificationContext: ChatVerificationContext {
         establishedNoiseSessions.contains(peerID)
     }
     func triggerHandshake(with peerID: PeerID) { triggeredHandshakes.append(peerID) }
+    func privateMediaPeerDidAuthenticate(_ peerID: PeerID) {
+        privateMediaAuthenticatedPeers.append(peerID)
+    }
 
     func sendVerifyChallenge(to peerID: PeerID, noiseKeyHex: String, nonceA: Data) {
         sentChallenges.append((peerID, noiseKeyHex, nonceA))
@@ -277,6 +281,7 @@ struct ChatVerificationCoordinatorContextTests {
         #expect(context.encryptionStatuses[peerID] == .noiseVerified)
         #expect(context.stablePeerIDCache[peerID] == PeerID(hexData: noiseKey))
         #expect(context.invalidatedEncryptionCachePeers.contains(peerID))
+        #expect(context.privateMediaAuthenticatedPeers == [peerID])
 
         // Handshake required -> handshaking status.
         callbacks?.onHandshakeRequired(peerID)

bitchatTests/EndToEnd/PrivateMediaEndToEndTests.swift

@@ -364,6 +364,217 @@ struct PrivateMediaEndToEndTests {
         #expect(alice.privateMediaSendPolicy(to: bob.myPeerID) == .legacyRequiresConsent)
     }
 
+    @Test
+    func privateMediaRetryRequiresExactAuthenticatedBit9Proof() async throws {
+        let root = FileManager.default.temporaryDirectory
+            .appendingPathComponent(
+                "private-media-receipt-proof-\(UUID().uuidString)",
+                isDirectory: true
+            )
+        defer { try? FileManager.default.removeItem(at: root) }
+        let alice = makeService(
+            baseDirectory: root.appendingPathComponent(
+                "alice",
+                isDirectory: true
+            )
+        )
+        let bob = makeService(
+            baseDirectory: root.appendingPathComponent(
+                "bob",
+                isDirectory: true
+            )
+        )
+        let bothCapabilities: PeerCapabilities = [
+            .privateMedia,
+            .privateMediaReceipts
+        ]
+
+        // A public bit-9 announce is discovery only.
+        alice._test_seedConnectedPeer(
+            bob.myPeerID,
+            nickname: "Bob",
+            capabilities: bothCapabilities,
+            noisePublicKey: bob.noiseStaticPublicKeyData()
+        )
+        #expect(
+            alice.authenticatedPrivateMediaReceiptSessionGeneration(
+                to: bob.myPeerID
+            ) == nil
+        )
+
+        let proofs = try await establishSessionCapturingPeerState(
+            alice: alice,
+            bob: bob
+        )
+        #expect(
+            alice.authenticatedPrivateMediaReceiptSessionGeneration(
+                to: bob.myPeerID
+            ) == nil
+        )
+
+        // Bit 8 alone preserves encrypted transfer compatibility but cannot
+        // authorize automatic resend.
+        let privateMediaOnly = try authenticatedPeerStatePacket(
+            from: bob,
+            to: alice,
+            capabilities: .privateMedia
+        )
+        alice._test_handlePacket(
+            privateMediaOnly,
+            fromPeerID: bob.myPeerID
+        )
+        #expect(await TestHelpers.waitUntil(
+            {
+                alice.privateMediaSendPolicy(to: bob.myPeerID)
+                    == .encrypted
+            },
+            timeout: TestConstants.longTimeout
+        ))
+        #expect(
+            alice.authenticatedPrivateMediaReceiptSessionGeneration(
+                to: bob.myPeerID
+            ) == nil
+        )
+
+        let receiptCapable = try authenticatedPeerStatePacket(
+            from: bob,
+            to: alice,
+            capabilities: bothCapabilities
+        )
+        alice._test_handlePacket(
+            receiptCapable,
+            fromPeerID: bob.myPeerID
+        )
+        #expect(await TestHelpers.waitUntil(
+            {
+                alice.authenticatedPrivateMediaReceiptSessionGeneration(
+                    to: bob.myPeerID
+                ) != nil
+            },
+            timeout: TestConstants.longTimeout
+        ))
+
+        bob._test_handlePacket(
+            proofs.alice,
+            fromPeerID: alice.myPeerID
+        )
+        alice._test_onOutboundPacket = nil
+        bob._test_onOutboundPacket = nil
+    }
+
+    @Test
+    func receiptRetryRechecksBit9AtDeferredTransportBoundary() async throws {
+        let root = FileManager.default.temporaryDirectory
+            .appendingPathComponent(
+                "private-media-retry-proof-race-\(UUID().uuidString)",
+                isDirectory: true
+            )
+        defer { try? FileManager.default.removeItem(at: root) }
+        let alice = makeService(
+            baseDirectory: root.appendingPathComponent(
+                "alice",
+                isDirectory: true
+            )
+        )
+        let bob = makeService(
+            baseDirectory: root.appendingPathComponent(
+                "bob",
+                isDirectory: true
+            )
+        )
+        let receiptCapabilities: PeerCapabilities = [
+            .privateMedia,
+            .privateMediaReceipts
+        ]
+        alice._test_seedConnectedPeer(
+            bob.myPeerID,
+            nickname: "Bob",
+            capabilities: receiptCapabilities,
+            noisePublicKey: bob.noiseStaticPublicKeyData()
+        )
+        bob._test_seedConnectedPeer(
+            alice.myPeerID,
+            nickname: "Alice",
+            capabilities: receiptCapabilities,
+            noisePublicKey: alice.noiseStaticPublicKeyData()
+        )
+        try await establishSession(alice: alice, bob: bob)
+        #expect(
+            alice.authenticatedPrivateMediaReceiptSessionGeneration(
+                to: bob.myPeerID
+            ) != nil
+        )
+
+        let privateMediaOnly = try authenticatedPeerStatePacket(
+            from: bob,
+            to: alice,
+            capabilities: .privateMedia
+        )
+        let transferID =
+            "receipt-proof-race-\(UUID().uuidString)"
+        let tap = PacketTap()
+        let boundaryProofs = ReceiptCapabilityRecorder()
+        let rejections = TransferCancellationRecorder()
+        let cancellable = TransferProgressManager.shared.publisher.sink {
+            rejections.record($0)
+        }
+        alice._test_onOutboundPacket = tap.record
+        alice._test_beforePrivateMediaDeferredSend = { id in
+            guard id == transferID else { return }
+            boundaryProofs.record(
+                alice
+                    .authenticatedPrivateMediaReceiptSessionGeneration(
+                        to: bob.myPeerID
+                    ) != nil
+            )
+        }
+        defer {
+            alice._test_beforePrivateMediaDeferredSend = nil
+            alice._test_onOutboundPacket = nil
+        }
+
+        // Rotate authenticated state before the deferred retry reaches its
+        // admission boundary.
+        alice._test_handlePacket(
+            privateMediaOnly,
+            fromPeerID: bob.myPeerID
+        )
+        let content = Data("%PDF-1.7\nreceipt-proof-race".utf8)
+        alice.sendFilePrivateReceiptRetry(
+            BitchatFilePacket(
+                fileName: "receipt-proof-race.pdf",
+                fileSize: UInt64(content.count),
+                mimeType: "application/pdf",
+                content: content
+            ),
+            to: bob.myPeerID,
+            transferId: transferID
+        )
+        #expect(await TestHelpers.waitUntil(
+            { boundaryProofs.snapshot() == [false] },
+            timeout: TestConstants.longTimeout
+        ))
+        await alice._test_drainPrivateMediaSendPipeline()
+
+        #expect(await TestHelpers.waitUntil(
+            { rejections.contains(transferID) },
+            timeout: TestConstants.longTimeout
+        ))
+        #expect(tap.snapshot().allSatisfy {
+            $0.type != MessageType.fileTransfer.rawValue
+                && !(
+                    $0.type == MessageType.noiseEncrypted.rawValue
+                        && $0.version == 2
+                )
+        })
+        let state = alice._test_privateMediaTransferState(
+            transferId: transferID
+        )
+        #expect(!state.admissionActive)
+        #expect(!state.pendingNoise)
+        _ = cancellable
+    }
+
     @Test
     func capabilityAnnounceCannotPoisonPinWithoutMatchingNoiseAuthentication() async throws {
         let root = FileManager.default.temporaryDirectory
@@ -1397,6 +1608,23 @@ private final class PrivateMediaPolicyRecorder: @unchecked Sendable {
     }
 }
 
+private final class ReceiptCapabilityRecorder: @unchecked Sendable {
+    private let lock = NSLock()
+    private var values: [Bool] = []
+
+    func record(_ value: Bool) {
+        lock.lock()
+        values.append(value)
+        lock.unlock()
+    }
+
+    func snapshot() -> [Bool] {
+        lock.lock()
+        defer { lock.unlock() }
+        return values
+    }
+}
+
 private final class MessageCaptureDelegate: BitchatDelegate, @unchecked Sendable {
     private let lock = NSLock()
     private var messages: [BitchatMessage] = []