Make private media deletion transactional

bitchat/Services/BLE/BLEFileTransferHandler.swift

@@ -40,6 +40,9 @@ struct BLEFileTransferHandlerEnvironment {
     let commitPrivateMediaFile: (_ messageID: String, _ storedURL: URL) -> Bool
     /// Rolls back a saved payload when its durable receipt commit fails.
     let removeIncomingFile: (_ storedURL: URL) -> Void
+    /// Releases the allocator's save-to-UI ownership guard after synchronous
+    /// conversation insertion has completed.
+    let finishIncomingFileDelivery: (_ storedURL: URL) -> Void
     /// Checks the authenticated sender before any private-media disk work.
     let isPrivateMediaSenderBlocked: (PeerID) -> Bool
     /// Updates the registry last-seen timestamp for the peer (async barrier write).
@@ -49,11 +52,14 @@ struct BLEFileTransferHandlerEnvironment {
     let acknowledgePrivateMedia: (_ messageID: String, _ peerID: PeerID) -> Void
     /// Delivers `.messageReceived` as one main-actor hop while
     /// `shouldDeliver` remains true before and after the synchronous sink.
-    /// The completion authorizes the stable-media ACK.
+    /// The completion authorizes the stable-media ACK. Finalization runs after
+    /// every delivery attempt, including rejection, so allocator ownership
+    /// cannot leak indefinitely.
     let deliverMessage: (
         _ message: BitchatMessage,
         _ shouldDeliver: @escaping () -> Bool,
-        _ completion: @escaping () -> Void
+        _ completion: @escaping () -> Void,
+        _ finalization: @escaping (TransportEventDeliveryOutcome) -> Void
     ) -> Void
 }
 
@@ -357,7 +363,24 @@ final class BLEFileTransferHandler {
                 env: env
             )
         } else {
-            env.deliverMessage(message, { true }, {})
+            env.deliverMessage(
+                message,
+                { true },
+                {},
+                { outcome in
+                    if outcome == .rejected {
+                        // Raw media has no durable receipt that can redeliver
+                        // it later. Do not leave a newly saved, UI-unowned file
+                        // available for a stale fallback path to misidentify.
+                        env.removeIncomingFile(destination)
+                    } else {
+                        // Plain delegates are invoked without synchronous
+                        // insertion confirmation. Preserve the payload for
+                        // that supported delivery path.
+                        env.finishIncomingFileDelivery(destination)
+                    }
+                }
+            )
         }
         return true
     }
@@ -381,6 +404,9 @@ final class BLEFileTransferHandler {
             },
             {
                 env.acknowledgePrivateMedia(messageID, peerID)
+            },
+            { _ in
+                env.finishIncomingFileDelivery(expectedURL)
             }
         )
     }

bitchat/Services/BLE/BLEIncomingFileStore.swift

@@ -93,7 +93,7 @@ struct PanicRecoveryOperations {
     }
 }
 
-struct BLEIncomingFileStore {
+struct BLEIncomingFileStore: @unchecked Sendable {
     enum PanicRecoveryError: Error {
         case externalMarkerCommitFailed
         case markerWriteFailed(Error)
@@ -103,7 +103,17 @@ struct BLEIncomingFileStore {
         )
     }
 
-    private static let quotaBytes: Int64 = 100 * 1024 * 1024
+    struct PrivateMediaDeletionReservation: Sendable {
+        fileprivate let id: UUID
+    }
+
+    private final class PayloadCoordination: @unchecked Sendable {
+        let lock = NSLock()
+        var pendingDeliveryPaths: Set<String> = []
+        var deletionReservations: [UUID: Set<String>] = [:]
+    }
+
+    private static let defaultQuotaBytes: Int64 = 100 * 1024 * 1024
     /// Kept outside `files/` so deleting the media tree cannot erase the
     /// fail-closed startup decision before the full panic has committed.
     private static let panicRecoveryPendingMarkerFileName =
@@ -120,7 +130,6 @@ struct BLEIncomingFileStore {
         "files/incoming",
         "files/outgoing"
     ]
-
     /// Name prefix of in-flight live voice captures (progressively written by
     /// `ChatLiveVoiceCoordinator`). Quota eviction skips them by pattern —
     /// deleting one mid-stream unlinks the inode under an open `FileHandle`
@@ -134,7 +143,9 @@ struct BLEIncomingFileStore {
     private let baseDirectory: URL?
     private let dateProvider: () -> Date
     private let panicMarkerWriter: (Data, URL) throws -> Void
+    private let quotaBytes: Int64
     private let privateMediaReceipts: BLEPrivateMediaReceiptStore
+    private let payloadCoordination: PayloadCoordination
 
     init(
         fileManager: FileManager = .default,
@@ -142,17 +153,20 @@ struct BLEIncomingFileStore {
         dateProvider: @escaping () -> Date = Date.init,
         panicMarkerWriter: @escaping (Data, URL) throws -> Void = {
             try $0.write(to: $1, options: .atomic)
-        }
+        },
+        quotaBytes: Int64 = Self.defaultQuotaBytes
     ) {
         self.fileManager = fileManager
         self.baseDirectory = baseDirectory
         self.dateProvider = dateProvider
         self.panicMarkerWriter = panicMarkerWriter
+        self.quotaBytes = max(0, quotaBytes)
         self.privateMediaReceipts = BLEPrivateMediaReceiptStore(
             fileManager: fileManager,
             baseDirectory: baseDirectory,
             now: dateProvider
         )
+        self.payloadCoordination = PayloadCoordination()
     }
 
     /// Panic-wipe every managed incoming and outgoing media artifact before
@@ -251,6 +265,9 @@ struct BLEIncomingFileStore {
         fallbackExtension: String?,
         defaultPrefix: String
     ) -> URL? {
+        payloadCoordination.lock.lock()
+        defer { payloadCoordination.lock.unlock() }
+
         do {
             let base = try filesDirectory().appendingPathComponent(subdirectory, isDirectory: true)
             try fileManager.createDirectory(at: base, withIntermediateDirectories: true, attributes: nil)
@@ -259,8 +276,26 @@ struct BLEIncomingFileStore {
                 defaultName: "\(defaultPrefix)_\(Self.timestampString(from: dateProvider()))",
                 fallbackExtension: fallbackExtension
             )
-            let destination = uniqueFileURL(in: base, fileName: sanitized)
+            let reservedPaths = privateMediaReceipts.reservedPayloadPaths()
+            let deletionPaths = payloadCoordination
+                .deletionReservations.values.reduce(into: Set<String>()) {
+                    $0.formUnion($1)
+                }
+            let allocationReservations = deletionPaths.union(
+                payloadCoordination.pendingDeliveryPaths
+            )
+            let destination = uniqueFileURL(
+                in: base,
+                fileName: sanitized,
+                reservedPaths: (reservedPaths ?? []).union(
+                    allocationReservations
+                ),
+                forceRandomizedName: reservedPaths == nil
+            )
             try data.write(to: destination, options: .atomic)
+            payloadCoordination.pendingDeliveryPaths.insert(
+                destination.standardizedFileURL.path
+            )
             return destination
         } catch {
             SecureLogger.error("❌ Failed to persist incoming media: \(error)", category: .session)
@@ -284,8 +319,75 @@ struct BLEIncomingFileStore {
         )
     }
 
+    /// Reserves every receipt/UI path before the asynchronous deletion
+    /// barrier. Allocation and reservation share one lock, so either an
+    /// in-flight raw arrival is observed and deletion fails closed, or the
+    /// arrival is forced onto a different filename.
+    func reservePrivateMediaDeletion(
+        messageIDs: [String],
+        payloadRelativePaths: [String: String]
+    ) -> PrivateMediaDeletionReservation? {
+        payloadCoordination.lock.lock()
+        defer { payloadCoordination.lock.unlock() }
+
+        guard let paths = privateMediaReceipts
+            .prospectiveDeletionPayloadPaths(
+                messageIDs: messageIDs,
+                payloadRelativePaths: payloadRelativePaths
+            ),
+        paths.isDisjoint(
+            with: payloadCoordination.pendingDeliveryPaths
+        ) else {
+            return nil
+        }
+
+        let reservation = PrivateMediaDeletionReservation(id: UUID())
+        payloadCoordination.deletionReservations[reservation.id] = paths
+        return reservation
+    }
+
+    func commitPrivateMediaDeletion(
+        reservation: PrivateMediaDeletionReservation,
+        messageIDs: [String],
+        payloadRelativePaths: [String: String],
+        protectedPayloadRelativePaths: Set<String>
+    ) -> Bool {
+        payloadCoordination.lock.lock()
+        defer {
+            payloadCoordination.deletionReservations.removeValue(
+                forKey: reservation.id
+            )
+            payloadCoordination.lock.unlock()
+        }
+        guard payloadCoordination.deletionReservations[reservation.id] != nil
+        else {
+            return false
+        }
+        return privateMediaReceipts.recordDeleted(
+            messageIDs: messageIDs,
+            payloadRelativePaths: payloadRelativePaths,
+            protectedPayloadRelativePaths: protectedPayloadRelativePaths
+        )
+    }
+
+    /// Releases the short window between disk save and synchronous
+    /// conversation insertion. Before this callback, a deletion transaction
+    /// may not infer ownership from a stale bubble that names the same path.
+    func finishIncomingFileDelivery(at storedURL: URL) {
+        payloadCoordination.lock.lock()
+        defer { payloadCoordination.lock.unlock() }
+        payloadCoordination.pendingDeliveryPaths.remove(
+            storedURL.standardizedFileURL.path
+        )
+    }
+
     /// Best-effort rollback for a payload whose durable receipt commit failed.
     func removeIncomingFile(at storedURL: URL) {
+        payloadCoordination.lock.lock()
+        defer { payloadCoordination.lock.unlock() }
+        payloadCoordination.pendingDeliveryPaths.remove(
+            storedURL.standardizedFileURL.path
+        )
         guard isURLInsideFilesDirectory(storedURL) else { return }
         do {
             try fileManager.removeItem(at: storedURL)
@@ -303,6 +405,9 @@ struct BLEIncomingFileStore {
     /// a finalized transfer can arrive at quota while a burst is still
     /// streaming — but they still count toward usage.
     func enforceQuota(reservingBytes: Int) {
+        payloadCoordination.lock.lock()
+        defer { payloadCoordination.lock.unlock() }
+
         do {
             let base = try filesDirectory()
             let incomingDirs = [
@@ -328,14 +433,26 @@ struct BLEIncomingFileStore {
             }
 
             let currentUsage = allFiles.reduce(0) { $0 + $1.size }
-            let targetUsage = Self.quotaBytes - Int64(reservingBytes)
+            let targetUsage = quotaBytes - Int64(reservingBytes)
             guard currentUsage > targetUsage else { return }
 
             let needToFree = currentUsage - targetUsage
+            let activeDeletionPaths = payloadCoordination
+                .deletionReservations.values.reduce(into: Set<String>()) {
+                    $0.formUnion($1)
+                }
+            let protectedPaths = activeDeletionPaths.union(
+                payloadCoordination.pendingDeliveryPaths
+            )
             var freedSpace: Int64 = 0
             for file in allFiles.sorted(by: { $0.modified < $1.modified }) {
                 guard freedSpace < needToFree else { break }
                 guard !file.url.lastPathComponent.hasPrefix(Self.liveCapturePrefix) else { continue }
+                guard !protectedPaths.contains(
+                    file.url.standardizedFileURL.path
+                ) else {
+                    continue
+                }
                 do {
                     try fileManager.removeItem(at: file.url)
                     freedSpace += file.size
@@ -423,11 +540,20 @@ struct BLEIncomingFileStore {
         return candidate.isEmpty ? defaultName : candidate
     }
 
-    private func uniqueFileURL(in directory: URL, fileName: String) -> URL {
+    private func uniqueFileURL(
+        in directory: URL,
+        fileName: String,
+        reservedPaths: Set<String>,
+        forceRandomizedName: Bool
+    ) -> URL {
         let directoryPath = directory.standardizedFileURL.path
         func isInsideDirectory(_ url: URL) -> Bool {
             url.standardizedFileURL.path.hasPrefix(directoryPath + "/")
         }
+        func isAvailable(_ url: URL) -> Bool {
+            !reservedPaths.contains(url.standardizedFileURL.path)
+                && !fileManager.fileExists(atPath: url.path)
+        }
 
         var candidate = directory.appendingPathComponent(fileName)
         guard isInsideDirectory(candidate) else {
@@ -435,19 +561,27 @@ struct BLEIncomingFileStore {
             return directory.appendingPathComponent("blocked_\(UUID().uuidString)")
         }
 
-        if !fileManager.fileExists(atPath: candidate.path) {
+        let baseName = (fileName as NSString).deletingPathExtension
+        let ext = (fileName as NSString).pathExtension
+        if forceRandomizedName {
+            let suffix = UUID().uuidString
+            let randomizedName = ext.isEmpty
+                ? "\(baseName)_\(suffix)"
+                : "\(baseName)_\(suffix).\(ext)"
+            return directory.appendingPathComponent(randomizedName)
+        }
+
+        if isAvailable(candidate) {
             return candidate
         }
 
-        let baseName = (fileName as NSString).deletingPathExtension
-        let ext = (fileName as NSString).pathExtension
         for counter in 1..<100 {
             let newName = ext.isEmpty ? "\(baseName) (\(counter))" : "\(baseName) (\(counter)).\(ext)"
             candidate = directory.appendingPathComponent(newName)
             guard isInsideDirectory(candidate) else {
                 return directory.appendingPathComponent("blocked_\(UUID().uuidString)")
             }
-            if !fileManager.fileExists(atPath: candidate.path) {
+            if isAvailable(candidate) {
                 return candidate
             }
         }

bitchat/Services/BLE/BLEPrivateMediaReceiptStore.swift

@@ -23,7 +23,15 @@ enum BLEPrivateMediaReceiptState: Equatable {
 final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
     typealias DirectoryReader = (_ directory: URL) throws -> [URL]
     typealias DataReader = (_ url: URL) throws -> Data
+    typealias DataWriter = (
+        _ data: Data,
+        _ url: URL,
+        _ options: Data.WritingOptions
+    ) throws -> Void
+    typealias PayloadRemover = (_ url: URL) throws -> Void
     private static let receiptDirectoryName = ".private-media-receipts"
+    private static let deletionJournalFileName = ".deletion-journal.json"
+    private static let maximumDeletionPathsPerMessage = 2
 
     private struct ReceiptRecord: Codable, Equatable {
         enum Kind: String, Codable {
@@ -38,10 +46,23 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
         let recordedAt: Date
     }
 
+    /// One atomic write of this journal is the commit point for an entire
+    /// explicit-deletion batch. Per-ID records and payload unlinks are
+    /// idempotent materialization performed only after that commit.
+    private struct DeletionJournalEntry: Codable, Equatable {
+        let relativePaths: [String]
+        let recordedAt: Date
+    }
+
+    private struct DeletionJournal: Codable {
+        let version: Int
+        let entries: [String: DeletionJournalEntry]
+    }
+
     private final class Runtime: @unchecked Sendable {
         let lock = NSLock()
         var records: [String: ReceiptRecord]?
-        var volatileTombstones: [String: Date] = [:]
+        var deletionJournal: [String: DeletionJournalEntry]?
     }
 
     private let fileManager: FileManager
@@ -51,6 +72,8 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
     private let now: () -> Date
     private let directoryReader: DirectoryReader?
     private let dataReader: DataReader?
+    private let dataWriter: DataWriter
+    private let payloadRemover: PayloadRemover
     private let runtime = Runtime()
 
     init(
@@ -60,7 +83,11 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
         ttl: TimeInterval = TransportConfig.privateMediaReceivedLedgerTTLSeconds,
         now: @escaping () -> Date = Date.init,
         directoryReader: DirectoryReader? = nil,
-        dataReader: DataReader? = nil
+        dataReader: DataReader? = nil,
+        dataWriter: @escaping DataWriter = {
+            try $0.write(to: $1, options: $2)
+        },
+        payloadRemover: PayloadRemover? = nil
     ) {
         self.fileManager = fileManager
         self.baseDirectory = baseDirectory
@@ -69,6 +96,10 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
         self.now = now
         self.directoryReader = directoryReader
         self.dataReader = dataReader
+        self.dataWriter = dataWriter
+        self.payloadRemover = payloadRemover ?? {
+            try fileManager.removeItem(at: $0)
+        }
     }
 
     /// Drops process-lifetime decisions after the enclosing media directory
@@ -78,7 +109,7 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
     func resetForPanic() {
         runtime.lock.lock()
         runtime.records = nil
-        runtime.volatileTombstones.removeAll(keepingCapacity: false)
+        runtime.deletionJournal = nil
         runtime.lock.unlock()
     }
 
@@ -91,29 +122,52 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
         defer { runtime.lock.unlock() }
 
         let date = now()
-        if let tombstonedAt = runtime.volatileTombstones[messageID] {
-            if !isExpired(tombstonedAt, at: date) {
-                return .tombstoned
-            }
-            runtime.volatileTombstones.removeValue(forKey: messageID)
-        }
-
         guard let directory = resolvedReceiptDirectory(),
-              var records = loadIndexIfNeeded(from: directory, at: date) else {
+              loadDurableStateIfNeeded(from: directory, at: date) else {
             return .unavailable
         }
-        guard let record = records[messageID] else { return .absent }
+        _ = recoverDeletionJournal(in: directory)
+        if runtime.deletionJournal?[messageID] != nil {
+            return .tombstoned
+        }
+        guard var records = runtime.records else { return .unavailable }
+        guard var record = records[messageID] else { return .absent }
 
-        if isExpired(record.recordedAt, at: date) {
+        if record.kind == .tombstone, record.relativePath != nil {
+            guard scrubLegacyTombstone(
+                record,
+                messageID: messageID,
+                in: directory,
+                records: &records
+            ) else {
+                return .tombstoned
+            }
+            guard let scrubbed = records[messageID] else {
+                return .unavailable
+            }
+            record = scrubbed
+        }
+
+        let retainsAcceptedPath =
+            record.kind == .accepted
+                && record.relativePath.flatMap(existingPayload) != nil
+        if isExpired(record.recordedAt, at: date),
+           !retainsAcceptedPath {
+            guard removeRecord(
+                messageID: messageID,
+                from: directory
+            ) else {
+                return record.kind == .tombstone
+                    ? .tombstoned
+                    : .unavailable
+            }
             records.removeValue(forKey: messageID)
             runtime.records = records
-            removeRecord(messageID: messageID, from: directory)
             return .absent
         }
 
         switch record.kind {
         case .tombstone:
-            removePayloadRecordedByTombstone(record)
             return .tombstoned
 
         case .accepted:
@@ -121,9 +175,14 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
                   let existingURL = existingPayload(relativePath: relativePath) else {
                 // Quota cleanup is not explicit deletion. Remove the stale
                 // receipt so a sender retry can restore the payload and bubble.
+                guard removeRecord(
+                    messageID: messageID,
+                    from: directory
+                ) else {
+                    return .unavailable
+                }
                 records.removeValue(forKey: messageID)
                 runtime.records = records
-                removeRecord(messageID: messageID, from: directory)
                 return .absent
             }
             return .accepted(existingURL)
@@ -144,13 +203,24 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
         defer { runtime.lock.unlock() }
 
         let date = now()
-        if let tombstonedAt = runtime.volatileTombstones[messageID],
-           !isExpired(tombstonedAt, at: date) {
+        guard let directory = resolvedReceiptDirectory(),
+              loadDurableStateIfNeeded(from: directory, at: date) else {
             return false
         }
-
-        guard let directory = resolvedReceiptDirectory(),
-              var records = loadIndexIfNeeded(from: directory, at: date) else {
+        _ = recoverDeletionJournal(in: directory)
+        guard runtime.deletionJournal?[messageID] == nil,
+              var records = runtime.records else {
+            return false
+        }
+        if runtime.deletionJournal?.values.contains(where: {
+            $0.relativePaths.contains(relativePath)
+        }) == true {
+            return false
+        }
+        if records.contains(where: { existingMessageID, record in
+            existingMessageID != messageID
+                && record.relativePath == relativePath
+        }) {
             return false
         }
         if let existing = records[messageID],
@@ -188,73 +258,232 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
         return true
     }
 
-    /// Foundation for explicit media deletion. This branch does not wire the
-    /// chat-clear UI; it only makes a tombstone durable and fail closed.
-    func recordDeleted(messageID: String) -> Bool {
-        guard PrivateMediaMessageIdentity.isStableID(messageID) else {
-            return false
-        }
+    /// Atomically commits explicit deletion for every stable ID in `messageIDs`.
+    ///
+    /// The journal is the single batch commit point: a failed write changes
+    /// neither durable nor in-memory receiver state, so callers must preserve
+    /// their bubbles. Once the write succeeds, every entry is tombstoned even
+    /// if the process exits before per-ID materialization or payload unlink.
+    /// Recovery retries both operations on the next lookup or launch.
+    func recordDeleted(
+        messageIDs: [String],
+        payloadRelativePaths: [String: String] = [:],
+        protectedPayloadRelativePaths: Set<String> = []
+    ) -> Bool {
+        let stableIDs = Array(
+            Set(messageIDs.filter(PrivateMediaMessageIdentity.isStableID))
+        ).sorted()
+        guard !stableIDs.isEmpty else { return true }
+        guard stableIDs.count <= capacity else { return false }
 
         runtime.lock.lock()
         defer { runtime.lock.unlock() }
 
         let date = now()
-        addVolatileTombstone(messageID, at: date)
-
         guard let directory = resolvedReceiptDirectory(),
-              var records = loadIndexIfNeeded(from: directory, at: date) else {
-            runtime.volatileTombstones.removeValue(forKey: messageID)
+              loadDurableStateIfNeeded(from: directory, at: date) else {
             return false
         }
-        if let existing = records[messageID],
-           existing.kind == .tombstone,
-           !isExpired(existing.recordedAt, at: date) {
-            runtime.volatileTombstones.removeValue(forKey: messageID)
-            removePayloadRecordedByTombstone(existing)
+        _ = recoverDeletionJournal(in: directory)
+        guard let records = runtime.records,
+              var journal = runtime.deletionJournal else {
+            return false
+        }
+
+        let pendingIDs = Set(journal.keys)
+        let newIDs = stableIDs.filter { messageID in
+            if pendingIDs.contains(messageID) { return false }
+            if let current = records[messageID],
+               current.kind == .tombstone,
+               !isExpired(current.recordedAt, at: date) {
+                return false
+            }
             return true
         }
-
-        let victim = capacityVictim(
-            for: .tombstone,
-            replacing: messageID,
-            in: records
-        )
-        if records[messageID]?.kind != .tombstone,
-           records.values.lazy.filter({ $0.kind == .tombstone }).count >= capacity,
-           victim == nil {
-            runtime.volatileTombstones.removeValue(forKey: messageID)
+        guard !newIDs.isEmpty else {
+            return true
+        }
+        guard Set(journal.keys).union(newIDs).count <= capacity else {
             return false
         }
 
-        let tombstone = ReceiptRecord(
-            kind: .tombstone,
-            // Retain the accepted path so a crash between the atomic record
-            // write and payload unlink can finish cleanup after relaunch.
-            relativePath: records[messageID]?.relativePath,
-            recordedAt: date
-        )
-        guard persist(tombstone, messageID: messageID, to: directory) else {
-            runtime.volatileTombstones.removeValue(forKey: messageID)
+        var newEntries: [String: DeletionJournalEntry] = [:]
+        for messageID in newIDs {
+            // Accepted receipts normally supply the exact stored path. The UI
+            // fallback is required when that receipt aged or was capacity
+            // evicted while its bubble and payload remain. They may differ
+            // after a retry selected a suffixed filename, so journal both.
+            // Never commit a new pathless tombstone: it could retire
+            // successfully while leaving an untracked payload behind.
+            let relativePaths = Array(Set([
+                records[messageID]?.relativePath,
+                payloadRelativePaths[messageID]
+            ].compactMap { $0 })).sorted()
+            guard !relativePaths.isEmpty,
+                  relativePaths.count <=
+                    Self.maximumDeletionPathsPerMessage,
+                  relativePaths.allSatisfy({
+                      isSafeDeletionTarget(relativePath: $0)
+                  }),
+                  protectedPayloadRelativePaths.isDisjoint(
+                      with: relativePaths
+                  ),
+                  !records.contains(where: { otherMessageID, record in
+                      otherMessageID != messageID
+                          && !stableIDs.contains(otherMessageID)
+                          && record.relativePath.map(
+                              relativePaths.contains
+                          ) == true
+                  }),
+                  !journal.contains(where: { otherMessageID, entry in
+                      otherMessageID != messageID
+                          && !stableIDs.contains(otherMessageID)
+                          && !Set(entry.relativePaths).isDisjoint(
+                              with: relativePaths
+                          )
+                  }) else {
+                return false
+            }
+            newEntries[messageID] = DeletionJournalEntry(
+                // The journal retains every owned path so payload deletion
+                // remains recoverable across a crash or unlink failure.
+                relativePaths: relativePaths,
+                recordedAt: date
+            )
+        }
+        journal.merge(newEntries) { _, new in new }
+
+        // Do not install any process-local tombstone before this succeeds.
+        // A failed delete must continue to resolve to its prior accepted
+        // state, otherwise a retry could be falsely ACKed while UI remains.
+        guard persistDeletionJournal(journal, in: directory) else {
             return false
         }
 
-        records[messageID] = tombstone
-        if let victim, victim != messageID {
-            records.removeValue(forKey: victim)
-            removeRecord(messageID: victim, from: directory)
-        }
-        runtime.records = records
-        runtime.volatileTombstones.removeValue(forKey: messageID)
-        removePayloadRecordedByTombstone(tombstone)
+        runtime.deletionJournal = journal
+        _ = recoverDeletionJournal(in: directory)
         return true
     }
 
-    private func loadIndexIfNeeded(
+    func recordDeleted(messageID: String) -> Bool {
+        guard PrivateMediaMessageIdentity.isStableID(messageID) else {
+            return false
+        }
+        return recordDeleted(messageIDs: [messageID])
+    }
+
+    /// Resolves every path a deletion transaction may target. The incoming
+    /// allocator reserves this set at the journal barrier so a concurrent raw
+    /// arrival cannot reuse a missing UI fallback.
+    func prospectiveDeletionPayloadPaths(
+        messageIDs: [String],
+        payloadRelativePaths: [String: String]
+    ) -> Set<String>? {
+        let stableIDs = Set(
+            messageIDs.filter(PrivateMediaMessageIdentity.isStableID)
+        )
+        guard !stableIDs.isEmpty else { return [] }
+
+        runtime.lock.lock()
+        defer { runtime.lock.unlock() }
+
+        let date = now()
+        guard let directory = resolvedReceiptDirectory(),
+              loadDurableStateIfNeeded(from: directory, at: date) else {
+            return nil
+        }
+        _ = recoverDeletionJournal(in: directory)
+        guard let journal = runtime.deletionJournal,
+              let records = runtime.records else {
+            return nil
+        }
+
+        var paths: Set<String> = []
+        for messageID in stableIDs {
+            if let entry = journal[messageID] {
+                paths.formUnion(entry.relativePaths)
+                continue
+            }
+            if let relativePath = records[messageID]?.relativePath {
+                paths.insert(relativePath)
+            }
+            if let relativePath = payloadRelativePaths[messageID] {
+                paths.insert(relativePath)
+            }
+        }
+        guard paths.allSatisfy({
+            candidatePayload(relativePath: $0) != nil
+        }) else {
+            return nil
+        }
+        return Set(paths.compactMap {
+            candidatePayload(relativePath: $0)?
+                .standardizedFileURL.path
+        })
+    }
+
+    /// Paths owned by accepted receipts, legacy pathful tombstones, or the
+    /// deletion journal. Incoming allocation must not reuse any of them for a
+    /// different ID.
+    func reservedPayloadPaths() -> Set<String>? {
+        runtime.lock.lock()
+        defer { runtime.lock.unlock() }
+
+        let date = now()
+        guard let directory = resolvedReceiptDirectory(),
+              loadDurableStateIfNeeded(from: directory, at: date) else {
+            return nil
+        }
+        _ = recoverDeletionJournal(in: directory)
+        guard let journal = runtime.deletionJournal,
+              let records = runtime.records else {
+            return nil
+        }
+        let recordPaths = records.values.compactMap(\.relativePath)
+        let journalPaths = journal.values.flatMap(\.relativePaths)
+        return Set((recordPaths + journalPaths).compactMap { relativePath in
+            candidatePayload(relativePath: relativePath)?
+                .standardizedFileURL.path
+        })
+    }
+
+    private func scrubLegacyTombstone(
+        _ tombstone: ReceiptRecord,
+        messageID: String,
+        in directory: URL,
+        records: inout [String: ReceiptRecord]
+    ) -> Bool {
+        guard tombstone.kind == .tombstone,
+              tombstone.relativePath != nil else {
+            return true
+        }
+        // Pre-journal tombstones cannot prove that the current file is still
+        // the payload they originally described. Older allocators did not
+        // reserve these paths, so a raw/public arrival may have reused the
+        // basename. Shed the ambiguous path without unlinking anything.
+        let pathless = ReceiptRecord(
+            kind: .tombstone,
+            relativePath: nil,
+            recordedAt: tombstone.recordedAt
+        )
+        guard persist(
+            pathless,
+            messageID: messageID,
+            to: directory
+        ) else {
+            return false
+        }
+        records[messageID] = pathless
+        runtime.records = records
+        return true
+    }
+
+    private func loadDurableStateIfNeeded(
         from directory: URL,
         at date: Date
-    ) -> [String: ReceiptRecord]? {
-        if let records = runtime.records {
-            return records
+    ) -> Bool {
+        if runtime.records != nil, runtime.deletionJournal != nil {
+            return true
         }
 
         do {
@@ -268,7 +497,7 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
                 "❌ Failed to create private-media receipt directory: \(error)",
                 category: .session
             )
-            return nil
+            return false
         }
 
         let urls: [URL]
@@ -287,12 +516,13 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
                 "❌ Failed to enumerate private-media receipts: \(error)",
                 category: .session
             )
-            return nil
+            return false
         }
 
         var records: [String: ReceiptRecord] = [:]
+        var scannedRecords: [String: ReceiptRecord] = [:]
         var expired: [String] = []
-        var tombstones: [ReceiptRecord] = []
+        var tombstones: [(messageID: String, record: ReceiptRecord)] = []
         for url in urls {
             guard url.pathExtension == "json" else { continue }
             let messageID = url.deletingPathExtension().lastPathComponent
@@ -311,7 +541,7 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
                     "❌ Failed to read private-media receipt \(messageID.prefix(12))…: \(error)",
                     category: .session
                 )
-                return nil
+                return false
             }
 
             guard isStructurallyValid(record) else {
@@ -319,16 +549,21 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
                     "❌ Invalid private-media receipt \(messageID.prefix(12))…",
                     category: .session
                 )
-                return nil
+                return false
             }
-            if isExpired(record.recordedAt, at: date) {
+            scannedRecords[messageID] = record
+            if record.kind == .tombstone {
+                tombstones.append((messageID, record))
+            }
+            let retainsAcceptedPath =
+                record.kind == .accepted
+                    && record.relativePath.flatMap(existingPayload) != nil
+            if isExpired(record.recordedAt, at: date),
+               !retainsAcceptedPath {
                 expired.append(messageID)
                 continue
             }
             records[messageID] = record
-            if record.kind == .tombstone {
-                tombstones.append(record)
-            }
         }
 
         let overflow = overflowVictims(in: records)
@@ -336,17 +571,229 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
             records.removeValue(forKey: messageID)
         }
 
-        // Install the index only after every stable-ID record was read and
-        // validated successfully. Cleanup cannot influence a failed scan.
-        runtime.records = records
+        let journal: [String: DeletionJournalEntry]
+        let journalURL = deletionJournalURL(in: directory)
+        if fileManager.fileExists(atPath: journalURL.path) {
+            do {
+                let data = try dataReader?(journalURL)
+                    ?? Data(contentsOf: journalURL)
+                let snapshot = try JSONDecoder().decode(
+                    DeletionJournal.self,
+                    from: data
+                )
+                guard snapshot.version == 1,
+                      snapshot.entries.count <= capacity,
+                      snapshot.entries.allSatisfy({ messageID, entry in
+                          PrivateMediaMessageIdentity.isStableID(messageID)
+                              && !entry.relativePaths.isEmpty
+                              && entry.relativePaths.count <=
+                                Self.maximumDeletionPathsPerMessage
+                              && Set(entry.relativePaths).count
+                                == entry.relativePaths.count
+                              && entry.relativePaths.allSatisfy {
+                                  candidatePayload(relativePath: $0) != nil
+                              }
+                      }) else {
+                    SecureLogger.error(
+                        "❌ Invalid private-media deletion journal",
+                        category: .session
+                    )
+                    return false
+                }
+                journal = snapshot.entries
+            } catch {
+                // The journal is the all-ID commit record. It may never be
+                // skipped or treated as empty when unreadable.
+                SecureLogger.error(
+                    "❌ Failed to read private-media deletion journal: \(error)",
+                    category: .session
+                )
+                return false
+            }
+        } else {
+            journal = [:]
+        }
+
+        var protectedFromPruning: Set<String> = []
+
+        // Old per-ID tombstones may still carry a payload path from before the
+        // deletion journal existed. That path is inherently ambiguous because
+        // old allocators did not reserve it. Convert it to a pathless
+        // tombstone without unlinking any current file.
+        for (messageID, tombstone) in tombstones
+        where journal[messageID] == nil
+            && tombstone.relativePath != nil {
+            let pathless = ReceiptRecord(
+                kind: .tombstone,
+                relativePath: nil,
+                recordedAt: tombstone.recordedAt
+            )
+            guard persist(
+                pathless,
+                messageID: messageID,
+                to: directory
+            ) else {
+                records[messageID] = tombstone
+                protectedFromPruning.insert(messageID)
+                continue
+            }
+            scannedRecords[messageID] = pathless
+            if records[messageID] != nil {
+                records[messageID] = pathless
+            }
+        }
 
         for messageID in expired + overflow {
-            removeRecord(messageID: messageID, from: directory)
+            guard !protectedFromPruning.contains(messageID) else { continue }
+            if !removeRecord(messageID: messageID, from: directory),
+               let record = scannedRecords[messageID] {
+                records[messageID] = record
+            }
         }
-        for tombstone in tombstones {
-            removePayloadRecordedByTombstone(tombstone)
+
+        // Install caches only after every per-ID record and the batch journal
+        // have been read and validated. Failed legacy cleanup remains indexed
+        // and path-reserved instead of blocking unrelated media.
+        runtime.records = records
+        runtime.deletionJournal = journal
+        return true
+    }
+
+    /// Idempotently materializes the write-ahead journal. An entry leaves the
+    /// journal only after its per-ID tombstone is durable and every recorded
+    /// payload is absent. Any failure keeps the journal authoritative for a
+    /// later lookup or process restart.
+    @discardableResult
+    private func recoverDeletionJournal(in directory: URL) -> Bool {
+        guard let journal = runtime.deletionJournal,
+              !journal.isEmpty,
+              var records = runtime.records else {
+            return true
         }
-        return records
+
+        let preservedMessageIDs = Set(journal.keys)
+        var remaining = journal
+        let orderedEntries = journal.sorted { lhs, rhs in
+            if lhs.value.recordedAt == rhs.value.recordedAt {
+                return lhs.key < rhs.key
+            }
+            return lhs.value.recordedAt < rhs.value.recordedAt
+        }
+
+        for (messageID, journalEntry) in orderedEntries {
+            let pathlessTombstone = ReceiptRecord(
+                kind: .tombstone,
+                relativePath: nil,
+                recordedAt: journalEntry.recordedAt
+            )
+            if records[messageID] != pathlessTombstone {
+                let victim = capacityVictim(
+                    for: .tombstone,
+                    replacing: messageID,
+                    in: records,
+                    preserving: preservedMessageIDs
+                )
+                if records[messageID]?.kind != .tombstone,
+                   records.values.lazy.filter({
+                       $0.kind == .tombstone
+                   }).count >= capacity,
+                   victim == nil {
+                    continue
+                }
+                guard persist(
+                    pathlessTombstone,
+                    messageID: messageID,
+                    to: directory
+                ) else {
+                    continue
+                }
+                records[messageID] = pathlessTombstone
+                if let victim, victim != messageID {
+                    records.removeValue(forKey: victim)
+                    removeRecord(messageID: victim, from: directory)
+                }
+            }
+
+            // Only the journal retains the paths. Once every unlink succeeds,
+            // the durable per-ID tombstone is pathless and cannot later
+            // delete a different payload that reused the basename.
+            let removedEveryPayload = journalEntry.relativePaths.allSatisfy {
+                removePayloadRecordedByTombstone(ReceiptRecord(
+                    kind: .tombstone,
+                    relativePath: $0,
+                    recordedAt: journalEntry.recordedAt
+                ))
+            }
+            guard removedEveryPayload else {
+                continue
+            }
+            remaining.removeValue(forKey: messageID)
+        }
+
+        runtime.records = records
+        guard remaining != journal else { return false }
+
+        if remaining.isEmpty {
+            guard removeDeletionJournal(in: directory) else { return false }
+        } else {
+            guard persistDeletionJournal(remaining, in: directory) else {
+                return false
+            }
+        }
+        runtime.deletionJournal = remaining
+        return remaining.isEmpty
+    }
+
+    private func persistDeletionJournal(
+        _ entries: [String: DeletionJournalEntry],
+        in directory: URL
+    ) -> Bool {
+        do {
+            try fileManager.createDirectory(
+                at: directory,
+                withIntermediateDirectories: true,
+                attributes: nil
+            )
+            let data = try JSONEncoder().encode(
+                DeletionJournal(version: 1, entries: entries)
+            )
+            var options: Data.WritingOptions = [.atomic]
+            #if os(iOS)
+            options.insert(
+                .completeFileProtectionUntilFirstUserAuthentication
+            )
+            #endif
+            try dataWriter(data, deletionJournalURL(in: directory), options)
+            return true
+        } catch {
+            SecureLogger.error(
+                "❌ Failed to persist private-media deletion journal: \(error)",
+                category: .session
+            )
+            return false
+        }
+    }
+
+    private func removeDeletionJournal(in directory: URL) -> Bool {
+        let url = deletionJournalURL(in: directory)
+        guard fileManager.fileExists(atPath: url.path) else { return true }
+        do {
+            try fileManager.removeItem(at: url)
+            return true
+        } catch {
+            SecureLogger.warning(
+                "⚠️ Failed to retire private-media deletion journal: \(error)",
+                category: .session
+            )
+            return false
+        }
+    }
+
+    private func deletionJournalURL(in directory: URL) -> URL {
+        directory.appendingPathComponent(
+            Self.deletionJournalFileName,
+            isDirectory: false
+        )
     }
 
     private func isStructurallyValid(_ record: ReceiptRecord) -> Bool {
@@ -369,10 +816,14 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
     ) -> [String] {
         var victims: [String] = []
         for kind in [ReceiptRecord.Kind.accepted, .tombstone] {
-            let matching = records.filter { $0.value.kind == kind }
-            let overflow = matching.count - capacity
+            let allMatching = records.filter { $0.value.kind == kind }
+            let overflow = allMatching.count - capacity
             guard overflow > 0 else { continue }
-            victims.append(contentsOf: matching.sorted { lhs, rhs in
+            let eligible = allMatching.filter { _, record in
+                guard kind == .accepted else { return true }
+                return record.relativePath.flatMap(existingPayload) == nil
+            }
+            victims.append(contentsOf: eligible.sorted { lhs, rhs in
                 if lhs.value.recordedAt == rhs.value.recordedAt {
                     return lhs.key < rhs.key
                 }
@@ -389,13 +840,24 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
     private func capacityVictim(
         for incomingKind: ReceiptRecord.Kind,
         replacing messageID: String,
-        in records: [String: ReceiptRecord]
+        in records: [String: ReceiptRecord],
+        preserving preservedMessageIDs: Set<String> = []
     ) -> String? {
         guard records[messageID]?.kind != incomingKind else { return nil }
+        // During a live session an accepted receipt is the only durable owner
+        // of its filename, even after quota removes the payload. Evicting it
+        // here could let another ID reuse the path while the old bubble still
+        // exists. The large capacity therefore acts as admission control.
+        guard incomingKind != .accepted else { return nil }
         let matching = records.filter {
-            $0.key != messageID && $0.value.kind == incomingKind
+            $0.key != messageID
+                && !preservedMessageIDs.contains($0.key)
+                && $0.value.kind == incomingKind
         }
-        guard matching.count >= capacity else { return nil }
+        let currentCount = records.values.lazy.filter {
+            $0.kind == incomingKind
+        }.count
+        guard currentCount >= capacity else { return nil }
         return matching.min { lhs, rhs in
             if lhs.value.recordedAt == rhs.value.recordedAt {
                 return lhs.key < rhs.key
@@ -421,7 +883,7 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
             options.insert(.completeFileProtectionUntilFirstUserAuthentication)
             #endif
             let url = recordURL(messageID: messageID, in: directory)
-            try data.write(to: url, options: options)
+            try dataWriter(data, url, options)
             return true
         } catch {
             SecureLogger.error(
@@ -432,16 +894,22 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
         }
     }
 
-    private func removeRecord(messageID: String, from directory: URL) {
+    @discardableResult
+    private func removeRecord(
+        messageID: String,
+        from directory: URL
+    ) -> Bool {
         let url = recordURL(messageID: messageID, in: directory)
-        guard fileManager.fileExists(atPath: url.path) else { return }
+        guard fileManager.fileExists(atPath: url.path) else { return true }
         do {
             try fileManager.removeItem(at: url)
+            return true
         } catch {
             SecureLogger.warning(
                 "⚠️ Failed to prune private-media receipt \(messageID.prefix(12))…: \(error)",
                 category: .session
             )
+            return false
         }
     }
 
@@ -451,39 +919,55 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
             .appendingPathExtension("json")
     }
 
-    private func removePayloadRecordedByTombstone(_ record: ReceiptRecord) {
+    @discardableResult
+    private func removePayloadRecordedByTombstone(
+        _ record: ReceiptRecord
+    ) -> Bool {
         guard record.kind == .tombstone,
               let relativePath = record.relativePath,
               let payload = candidatePayload(relativePath: relativePath),
               fileManager.fileExists(atPath: payload.path) else {
-            return
+            return true
+        }
+        guard let values = try? payload.resourceValues(
+            forKeys: [.isRegularFileKey]
+        ),
+        values.isRegularFile == true else {
+            SecureLogger.warning(
+                "⚠️ Refusing to remove non-file private-media payload",
+                category: .session
+            )
+            return false
         }
         do {
-            try fileManager.removeItem(at: payload)
+            try payloadRemover(payload)
+            return !fileManager.fileExists(atPath: payload.path)
         } catch {
             SecureLogger.warning(
                 "⚠️ Failed to remove explicitly deleted private media: \(error)",
                 category: .session
             )
+            return false
         }
     }
 
-    private func addVolatileTombstone(_ messageID: String, at date: Date) {
-        runtime.volatileTombstones[messageID] = date
-        let overflow = runtime.volatileTombstones.count - capacity
-        guard overflow > 0 else { return }
-        let oldest = runtime.volatileTombstones.sorted {
-            if $0.value == $1.value { return $0.key < $1.key }
-            return $0.value < $1.value
+    private func isSafeDeletionTarget(relativePath: String) -> Bool {
+        guard let payload = candidatePayload(relativePath: relativePath) else {
+            return false
         }
-        for (oldMessageID, _) in oldest.prefix(overflow) {
-            runtime.volatileTombstones.removeValue(forKey: oldMessageID)
+        guard fileManager.fileExists(atPath: payload.path) else {
+            return true
         }
+        return (try? payload.resourceValues(
+            forKeys: [.isRegularFileKey]
+        ).isRegularFile) == true
     }
 
     private func validExistingPayload(_ url: URL) -> URL? {
         let standardized = url.standardizedFileURL
-        guard isInsideFilesDirectory(standardized) else { return nil }
+        guard isInsideIncomingMediaDirectory(standardized) else {
+            return nil
+        }
         var isDirectory: ObjCBool = false
         guard fileManager.fileExists(
             atPath: standardized.path,
@@ -520,15 +1004,27 @@ final class BLEPrivateMediaReceiptStore: @unchecked Sendable {
         let candidate = filesRoot
             .appendingPathComponent(relativePath, isDirectory: false)
             .standardizedFileURL
-        guard candidate.path.hasPrefix(filesRoot.path + "/") else { return nil }
+        guard isInsideIncomingMediaDirectory(candidate) else { return nil }
         return candidate
     }
 
-    private func isInsideFilesDirectory(_ url: URL) -> Bool {
+    private func isInsideIncomingMediaDirectory(_ url: URL) -> Bool {
         guard let filesRoot = try? filesDirectory().standardizedFileURL else {
             return false
         }
-        return url.standardizedFileURL.path.hasPrefix(filesRoot.path + "/")
+        let parentPath = url.standardizedFileURL
+            .deletingLastPathComponent().path
+        return [
+            "voicenotes/incoming",
+            "images/incoming",
+            "files/incoming"
+        ].contains { relativeDirectory in
+            filesRoot.appendingPathComponent(
+                relativeDirectory,
+                isDirectory: true
+            )
+            .standardizedFileURL.path == parentPath
+        }
     }
 
     private func resolvedReceiptDirectory() -> URL? {

bitchat/Services/BLE/BLEService.swift

@@ -2660,6 +2660,18 @@ final class BLEService: NSObject {
             removeIncomingFile: { [weak self] storedURL in
                 self?.incomingFileStore.removeIncomingFile(at: storedURL)
             },
+            finishIncomingFileDelivery: { [weak self] storedURL in
+                // Serialize pending-owner release behind deletion barriers.
+                // If /clear snapshots before this UI insertion, its already
+                // queued barrier must still observe the path as pending. If
+                // insertion wins first, the next MainActor snapshot sees the
+                // new bubble and protects the path explicitly.
+                self?.messageQueue.async(flags: .barrier) {
+                    self?.incomingFileStore.finishIncomingFileDelivery(
+                        at: storedURL
+                    )
+                }
+            },
             isPrivateMediaSenderBlocked: { [weak self] peerID in
                 guard let self else { return false }
                 let senderStaticKey = self.noiseService.getPeerPublicKeyData(peerID)
@@ -2684,11 +2696,12 @@ final class BLEService: NSObject {
                 }
                 self.sendDeliveryAck(for: messageID, to: peerID)
             },
-            deliverMessage: { [weak self] message, shouldDeliver, completion in
+            deliverMessage: { [weak self] message, shouldDeliver, completion, finalization in
                 self?.emitTransportEvent(
                     .messageReceived(message),
                     shouldDeliver: shouldDeliver,
-                    completion: completion
+                    completion: completion,
+                    finalization: finalization
                 )
             }
         )
@@ -4384,8 +4397,87 @@ extension BLEService {
     // No alias rotation or advertising restarts required.
 }
 
+// MARK: - Private Media Deletion
+
+extension BLEService: PrivateMediaDeletionPersisting {
+    @MainActor
+    func persistDeletedPrivateMedia(
+        messageIDs: [String],
+        payloadRelativePaths: [String: String],
+        protectedPayloadRelativePaths: Set<String>,
+        completion: @escaping @MainActor (Bool) -> Void
+    ) {
+        let fileStore = incomingFileStore
+        messageQueue.async(flags: .barrier) {
+            guard let reservation = fileStore
+                    .reservePrivateMediaDeletion(
+                        messageIDs: messageIDs,
+                        payloadRelativePaths: payloadRelativePaths
+                    ) else {
+                Task { @MainActor in
+                    completion(false)
+                }
+                return
+            }
+            let persisted = fileStore
+                .commitPrivateMediaDeletion(
+                    reservation: reservation,
+                    messageIDs: messageIDs,
+                    payloadRelativePaths: payloadRelativePaths,
+                    protectedPayloadRelativePaths:
+                        protectedPayloadRelativePaths
+                )
+            Task { @MainActor in
+                completion(persisted)
+            }
+        }
+    }
+}
+
 // MARK: - Private Helpers
 
+enum TransportEventDeliveryOutcome: Equatable {
+    /// A synchronous sink inserted the message and revalidation succeeded.
+    case accepted
+    /// A supported plain delegate was invoked, but insertion cannot be
+    /// confirmed synchronously.
+    case invokedUnconfirmed
+    /// No sink accepted the event, or receipt revalidation rejected it.
+    case rejected
+}
+
+enum TransportEventDeliveryGate {
+    /// Runs finalization exactly once for every attempted main-actor delivery,
+    /// including pre-insertion rejection, a missing/rejecting sink, and
+    /// post-insertion revalidation failure. Only a fully accepted delivery
+    /// runs `completion` (for example, a stable-media ACK).
+    @MainActor
+    static func attempt(
+        shouldDeliver: () -> Bool,
+        deliver: () -> TransportEventDeliveryOutcome,
+        completion: () -> Void,
+        finalization: (TransportEventDeliveryOutcome) -> Void
+    ) {
+        var outcome = TransportEventDeliveryOutcome.rejected
+        defer { finalization(outcome) }
+        guard shouldDeliver() else {
+            return
+        }
+        switch deliver() {
+        case .rejected:
+            return
+        case .invokedUnconfirmed:
+            outcome = .invokedUnconfirmed
+            return
+        case .accepted:
+            break
+        }
+        guard shouldDeliver() else { return }
+        outcome = .accepted
+        completion()
+    }
+}
+
 extension BLEService {
     
     /// Notify UI on the MainActor to satisfy Swift concurrency isolation
@@ -4409,52 +4501,58 @@ extension BLEService {
     private func emitTransportEvent(
         _ event: TransportEvent,
         shouldDeliver: (() -> Bool)? = nil,
-        completion: (() -> Void)? = nil
+        completion: (() -> Void)? = nil,
+        finalization: ((TransportEventDeliveryOutcome) -> Void)? = nil
     ) {
         notifyUI { [weak self] in
-            guard let self,
-                  shouldDeliver?() ?? true,
-                  self.deliverTransportEvent(event),
-                  // Quota cleanup can race the asynchronous main-actor hop or
-                  // the synchronous ConversationStore upsert. ACK only while
-                  // the exact durable mapping and file still resolve.
-                  shouldDeliver?() ?? true else {
-                return
-            }
-            completion?()
+            TransportEventDeliveryGate.attempt(
+                shouldDeliver: { shouldDeliver?() ?? true },
+                deliver: {
+                    guard let self else { return .rejected }
+                    return self.deliverTransportEvent(event)
+                },
+                completion: { completion?() },
+                finalization: { finalization?($0) }
+            )
         }
     }
 
     @MainActor
     @discardableResult
-    private func deliverTransportEvent(_ event: TransportEvent) -> Bool {
+    private func deliverTransportEvent(
+        _ event: TransportEvent
+    ) -> TransportEventDeliveryOutcome {
         if case .messageReceived(let message) = event {
             if let synchronousDelegate =
                 eventDelegate as? SynchronousMessageTransportEventDelegate {
                 return synchronousDelegate
                     .didReceiveTransportMessageSynchronously(message)
+                    ? .accepted
+                    : .rejected
             }
             if let eventDelegate {
                 eventDelegate.didReceiveTransportEvent(event)
-                return false
+                return .invokedUnconfirmed
             }
             if let synchronousDelegate =
                 delegate as? SynchronousMessageTransportEventDelegate {
                 return synchronousDelegate
                     .didReceiveTransportMessageSynchronously(message)
+                    ? .accepted
+                    : .rejected
             }
         }
 
         if let eventDelegate {
             eventDelegate.didReceiveTransportEvent(event)
-            return true
+            return .accepted
         } else {
-            guard let delegate else { return false }
+            guard let delegate else { return .rejected }
             delegate.receiveTransportEvent(event)
             if case .messageReceived = event {
-                return false
+                return .invokedUnconfirmed
             }
-            return true
+            return .accepted
         }
     }
 

bitchat/Services/Transport.swift

@@ -97,6 +97,19 @@ enum PrivateMediaSendPolicy: Equatable {
     case blockedDowngrade
 }
 
+/// Receiver-only persistence surface for explicit private-media deletion.
+/// Kept separate from `Transport` so sender retry branches can rebase without
+/// inheriting or implementing receiver storage concerns.
+protocol PrivateMediaDeletionPersisting: AnyObject {
+    @MainActor
+    func persistDeletedPrivateMedia(
+        messageIDs: [String],
+        payloadRelativePaths: [String: String],
+        protectedPayloadRelativePaths: Set<String>,
+        completion: @escaping @MainActor (Bool) -> Void
+    )
+}
+
 protocol TransportEventDelegate: AnyObject {
     @MainActor func didReceiveTransportEvent(_ event: TransportEvent)
 }

bitchat/ViewModels/ChatMediaTransferCoordinator.swift

@@ -86,6 +86,10 @@ protocol ChatMediaTransferContext: AnyObject {
     @discardableResult
     func appendPublicMessage(_ message: BitchatMessage, to conversationID: ConversationID) -> Bool
     func removeMessage(withID messageID: String, cleanupFile: Bool)
+    /// Removes a media bubble with direction-scoped cleanup instead of the
+    /// broad compatibility cleanup path.
+    func removeUntombstonedMediaMessage(withID messageID: String)
+    func removeOutgoingMediaMessage(withID messageID: String)
     func addSystemMessage(_ content: String)
     /// Signals that message state changed so observers refresh (e.g. `objectWillChange.send()`).
     func notifyUIChanged()
@@ -122,6 +126,15 @@ protocol ChatMediaTransferContext: AnyObject {
     )
     func sendFileBroadcast(_ packet: BitchatFilePacket, transferId: String)
     func cancelTransfer(_ transferId: String)
+    /// Receiver-side stable-ID deletion commit. Implementations must invoke
+    /// completion only after the entire batch is durably tombstoned.
+    func persistDeletedPrivateMedia(
+        messageIDs: [String],
+        completion: @escaping @MainActor (Bool) -> Void
+    )
+    /// Whether any current private-chat copy of this stable ID came from a
+    /// remote peer and therefore requires a receiver tombstone.
+    func requiresPrivateMediaTombstone(messageID: String) -> Bool
 }
 
 extension ChatViewModel: ChatMediaTransferContext {
@@ -208,6 +221,130 @@ extension ChatViewModel: ChatMediaTransferContext {
     func cancelTransfer(_ transferId: String) {
         meshService.cancelTransfer(transferId)
     }
+
+    func removeUntombstonedMediaMessage(withID messageID: String) {
+        let message = conversations.conversationsByID.values.lazy
+            .flatMap(\.messages)
+            .first { $0.id == messageID }
+        if let message {
+            if !isIncomingPrivateMessage(message) {
+                mediaTransferCoordinator.cleanupOutgoingLocalFile(
+                    forMessage: message
+                )
+            }
+            // Legacy/raw incoming media has no durable ID-to-file ownership.
+            // Its basename may already belong to a pending newer arrival, so
+            // leave the payload for bounded quota cleanup rather than unlink
+            // an ambiguous path.
+        }
+        removeMessage(withID: messageID, cleanupFile: false)
+    }
+
+    func removeOutgoingMediaMessage(withID messageID: String) {
+        let message = conversations.conversationsByID.values.lazy
+            .flatMap(\.messages)
+            .first { $0.id == messageID }
+        if let message {
+            mediaTransferCoordinator.cleanupOutgoingLocalFile(
+                forMessage: message
+            )
+        }
+        removeMessage(withID: messageID, cleanupFile: false)
+    }
+
+    func persistDeletedPrivateMedia(
+        messageIDs: [String],
+        completion: @escaping @MainActor (Bool) -> Void
+    ) {
+        guard !messageIDs.isEmpty else {
+            completion(true)
+            return
+        }
+        guard let persistence =
+                meshService as? any PrivateMediaDeletionPersisting else {
+            completion(false)
+            return
+        }
+        let requestedIDs = Set(messageIDs)
+        let incomingPathReferences = Array(
+            conversations.conversationsByID.values
+                .lazy
+                .flatMap(\.messages)
+                .compactMap { message -> (
+                    messageID: String,
+                    path: String
+                )? in
+                guard self.isIncomingPrivateMessage(message),
+                      let path = self.incomingMediaRelativePath(
+                          for: message
+                      ) else {
+                    return nil
+                }
+                return (message.id, path)
+            }
+        )
+        let ownerIDsByPath = Dictionary(
+            grouping: incomingPathReferences,
+            by: { $0.path }
+        ).mapValues { Set($0.map(\.messageID)) }
+        let protectedPayloadRelativePaths = Set(
+            ownerIDsByPath.compactMap { path, ownerIDs in
+                ownerIDs.isSubset(of: requestedIDs) ? nil : path
+            }
+        )
+        var payloadRelativePaths: [String: String] = [:]
+        for reference in incomingPathReferences
+        where requestedIDs.contains(reference.messageID)
+            && ownerIDsByPath[reference.path, default: []]
+                .isSubset(of: requestedIDs) {
+            payloadRelativePaths[reference.messageID] = reference.path
+        }
+        persistence.persistDeletedPrivateMedia(
+            messageIDs: messageIDs,
+            payloadRelativePaths: payloadRelativePaths,
+            protectedPayloadRelativePaths:
+                protectedPayloadRelativePaths,
+            completion: completion
+        )
+    }
+
+    func requiresPrivateMediaTombstone(messageID: String) -> Bool {
+        guard PrivateMediaMessageIdentity.isStableID(messageID) else {
+            return false
+        }
+        return privateChats.values.lazy.flatMap { $0 }.contains { message in
+            message.id == messageID && isIncomingPrivateMessage(message)
+        }
+    }
+
+    private func isIncomingPrivateMessage(
+        _ message: BitchatMessage
+    ) -> Bool {
+        if let senderPeerID = message.senderPeerID {
+            return senderPeerID.toShort() != meshService.myPeerID.toShort()
+        }
+        return message.sender != nickname
+            && !message.sender.hasPrefix(nickname + "#")
+    }
+
+    private func incomingMediaRelativePath(
+        for message: BitchatMessage
+    ) -> String? {
+        let categories: [MimeType.Category] = [.audio, .image, .file]
+        guard let category = categories.first(where: {
+            message.content.hasPrefix($0.messagePrefix)
+        }),
+        let rawFilename = String(
+            message.content.dropFirst(category.messagePrefix.count)
+        ).trimmedOrNilIfEmpty,
+        let safeFilename =
+            (rawFilename as NSString).lastPathComponent.nilIfEmpty,
+        safeFilename != ".",
+        safeFilename != ".." else {
+            return nil
+        }
+        return "\(category.mediaDir)/incoming/\(safeFilename)"
+    }
 }
 
 /// Synchronous boundary between detached image writers and panic deletion.
@@ -841,8 +978,7 @@ final class ChatMediaTransferCoordinator {
                 cancelActiveTransfer: false
             )
             clearTransferMapping(for: messageID)
-            context.removeMessage(withID: messageID, cleanupFile: true)
-
+            context.removeOutgoingMediaMessage(withID: messageID)
         case .rejected(let id, let reason):
             guard let messageID = currentMessageID(forTransferID: id) else {
                 return
@@ -861,6 +997,40 @@ final class ChatMediaTransferCoordinator {
     }
 
     func cleanupLocalFile(forMessage message: BitchatMessage) {
+        cleanupLocalFile(
+            forMessage: message,
+            directions: ["outgoing", "incoming"],
+            searchAllCategories: true
+        )
+    }
+
+    /// `/clear` may cancel an outgoing message before receiver tombstones are
+    /// committed. Restrict cleanup to that message's outgoing directory so a
+    /// same-name incoming payload cannot be removed prematurely.
+    func cleanupOutgoingLocalFile(forMessage message: BitchatMessage) {
+        cleanupLocalFile(
+            forMessage: message,
+            directions: ["outgoing"],
+            searchAllCategories: false
+        )
+    }
+
+    /// Receiver cleanup runs only after any required tombstone commit. Keep it
+    /// scoped to the parsed media category and incoming directory so unrelated
+    /// outgoing or cross-category payloads with the same basename survive.
+    func cleanupIncomingLocalFile(forMessage message: BitchatMessage) {
+        cleanupLocalFile(
+            forMessage: message,
+            directions: ["incoming"],
+            searchAllCategories: false
+        )
+    }
+
+    private func cleanupLocalFile(
+        forMessage message: BitchatMessage,
+        directions: [String],
+        searchAllCategories: Bool
+    ) {
         let categories: [MimeType.Category] = [.audio, .image, .file]
         guard let category = categories.first(where: { message.content.hasPrefix($0.messagePrefix) }),
               let rawFilename = String(message.content.dropFirst(category.messagePrefix.count)).trimmedOrNilIfEmpty,
@@ -871,11 +1041,27 @@ final class ChatMediaTransferCoordinator {
             return
         }
 
-        let subdirs = categories.flatMap { ["\($0.mediaDir)/outgoing", "\($0.mediaDir)/incoming"] }
+        let targetCategories = searchAllCategories ? categories : [category]
+        let subdirs = targetCategories.flatMap { category in
+            directions.map { "\(category.mediaDir)/\($0)" }
+        }
         for subdir in subdirs {
             let target = base.appendingPathComponent(subdir, isDirectory: true).appendingPathComponent(safeFilename)
             guard target.path.hasPrefix(base.path) else { continue }
 
+            guard FileManager.default.fileExists(atPath: target.path) else {
+                continue
+            }
+            guard let values = try? target.resourceValues(
+                forKeys: [.isRegularFileKey]
+            ),
+            values.isRegularFile == true else {
+                SecureLogger.warning(
+                    "Refusing to cleanup non-file media target \(safeFilename)",
+                    category: .session
+                )
+                continue
+            }
             do {
                 try FileManager.default.removeItem(at: target)
             } catch CocoaError.fileNoSuchFile {
@@ -887,33 +1073,79 @@ final class ChatMediaTransferCoordinator {
     }
 
     func cancelMediaSend(messageID: String) {
-        discardReconnectRetry(
-            messageID: messageID,
-            cancelActiveTransfer: false
-        )
-        if let transferId = messageIDToTransferId[messageID],
-           let active = transferIdToMessageIDs[transferId]?.first,
-           active == messageID {
-            context.cancelTransfer(transferId)
-        }
-        clearTransferMapping(for: messageID)
-        context.removeMessage(withID: messageID, cleanupFile: true)
+        cancelAllMediaSendOwners(messageID: messageID)
+        context.removeOutgoingMediaMessage(withID: messageID)
+    }
+
+    /// Lets `/clear` cancel send ownership without implicitly deciding which
+    /// bubbles/files its deletion transaction may remove.
+    func cancelMediaTransferForConversationClear(messageID: String) {
+        cancelAllMediaSendOwners(messageID: messageID)
     }
 
     func deleteMediaMessage(messageID: String) {
+        // Stop every exact sender owner before the durable receiver commit.
+        // Otherwise a retained retry or admitted legacy send could transmit
+        // after the bubble and payload have been deleted.
+        cancelAllMediaSendOwners(messageID: messageID)
+
+        guard context.requiresPrivateMediaTombstone(
+            messageID: messageID
+        ) else {
+            finishMediaDeletion(
+                messageID: messageID,
+                receiverJournalOwnsPayload: false
+            )
+            return
+        }
+
+        context.persistDeletedPrivateMedia(
+            messageIDs: [messageID]
+        ) { [weak self] persisted in
+            guard let self else { return }
+            guard persisted else {
+                SecureLogger.error(
+                    "Refusing to delete private media without a durable tombstone id=\(messageID.prefix(12))…",
+                    category: .session
+                )
+                return
+            }
+            self.finishMediaDeletion(
+                messageID: messageID,
+                receiverJournalOwnsPayload: true
+            )
+        }
+    }
+
+    private func finishMediaDeletion(
+        messageID: String,
+        receiverJournalOwnsPayload: Bool
+    ) {
+        if receiverJournalOwnsPayload {
+            // The journal already owns the exact path. A basename cleanup here
+            // could delete a different arrival that reused it after unlink.
+            context.removeMessage(withID: messageID, cleanupFile: false)
+        } else {
+            context.removeUntombstonedMediaMessage(withID: messageID)
+        }
+    }
+
+    private func cancelAllMediaSendOwners(messageID: String) {
+        // This releases the retained packet and expiry/retry owner. When its
+        // exact active transfer still owns the mapping, it cancels that owner
+        // before any deletion persistence or UI mutation can proceed.
         discardReconnectRetry(
             messageID: messageID,
-            cancelActiveTransfer: false
+            cancelActiveTransfer: true
         )
-        // 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.
+        // In particular, an approved legacy send may still be waiting on
+        // BLEService.messageQueue. Its admission must be canceled before the
+        // mapping/consent owner is released.
         if let transferId = messageIDToTransferId[messageID],
            transferIdToMessageIDs[transferId]?.first == messageID {
             context.cancelTransfer(transferId)
         }
         clearTransferMapping(for: messageID)
-        context.removeMessage(withID: messageID, cleanupFile: true)
     }
 
     /// A raw link callback can arrive before the replacement Noise session

bitchat/ViewModels/ChatViewModel.swift

@@ -109,6 +109,16 @@ struct PanicNetworkLifecycle {
     }
 }
 
+private struct PendingPrivateChatClear {
+    let peerID: PeerID
+    let sourceConversationID: ConversationID
+    let messages: [BitchatMessage]
+    let otherMessageIDs: Set<String>
+    let localPeerID: PeerID
+    let nickname: String
+    let outgoingMedia: [BitchatMessage]
+}
+
 /// Manages the application state and business logic for BitChat.
 /// Acts as the primary coordinator between UI components and backend services,
 /// implementing the BitchatDelegate protocol to handle network events.
@@ -376,6 +386,10 @@ final class ChatViewModel: ObservableObject, BitchatDelegate, SynchronousMessage
     @Published var bluetoothAlertMessage = ""
     @Published var bluetoothState: CBManagerState = .unknown
     @Published private(set) var legacyPrivateMediaConsentRequest: LegacyPrivateMediaConsentRequest?
+    @MainActor private var queuedPrivateChatClears: [
+        PendingPrivateChatClear
+    ] = []
+    @MainActor private var privateChatClearInFlight = false
     private var pendingLegacyPrivateMediaConsents: [PendingLegacyPrivateMediaConsent] = []
 
     private func performDeliveryUpdate(_ update: @escaping @MainActor (ChatDeliveryCoordinator) -> Void) {
@@ -643,7 +657,255 @@ final class ChatViewModel: ObservableObject, BitchatDelegate, SynchronousMessage
     /// Empties the peer's chat but keeps the conversation alive (`/clear`).
     @MainActor
     func clearPrivateChat(_ peerID: PeerID) {
-        conversations.clear(.directPeer(peerID))
+        let sourceConversationID = ConversationID.directPeer(peerID)
+        // An active live-voice row owns an open FileHandle and may be
+        // republished as frames/final media arrive. Treat it like an in-flight
+        // arrival rather than unlinking its capture or removing its bubble.
+        let messages = privateMessages(for: peerID).filter {
+            !liveVoiceCoordinator.isLiveVoiceMessage($0)
+        }
+        let localPeerID = meshService.myPeerID.toShort()
+        let currentNickname = nickname
+        let mediaPrefixes = [
+            MimeType.Category.audio.messagePrefix,
+            MimeType.Category.image.messagePrefix,
+            MimeType.Category.file.messagePrefix
+        ]
+        let outgoingMedia = messages.filter { message in
+            guard mediaPrefixes.contains(where: {
+                message.content.hasPrefix($0)
+            }) else {
+                return false
+            }
+            if let senderPeerID = message.senderPeerID {
+                return senderPeerID.toShort() == localPeerID
+            }
+            return message.sender == currentNickname
+                || message.sender.hasPrefix(currentNickname + "#")
+        }
+
+        // Send ownership is canceled at command time even when another clear
+        // transaction is ahead in the queue. UI and files remain untouched
+        // until this request's receiver journal commit succeeds.
+        for message in outgoingMedia {
+            mediaTransferCoordinator
+                .cancelMediaTransferForConversationClear(
+                    messageID: message.id
+                )
+        }
+
+        queuedPrivateChatClears.append(PendingPrivateChatClear(
+            peerID: peerID,
+            sourceConversationID: sourceConversationID,
+            messages: messages,
+            otherMessageIDs: Set(
+                privateChats
+                    .filter { $0.key != peerID }
+                    .flatMap { $0.value.map(\.id) }
+            ),
+            localPeerID: localPeerID,
+            nickname: currentNickname,
+            outgoingMedia: outgoingMedia
+        ))
+        startNextPrivateChatClearIfNeeded()
+    }
+
+    @MainActor
+    private func startNextPrivateChatClearIfNeeded() {
+        guard !privateChatClearInFlight,
+              !queuedPrivateChatClears.isEmpty else {
+            return
+        }
+        privateChatClearInFlight = true
+        let request = queuedPrivateChatClears.removeFirst()
+        performPrivateChatClear(request) { [weak self] in
+            guard let self else { return }
+            self.privateChatClearInFlight = false
+            self.startNextPrivateChatClearIfNeeded()
+        }
+    }
+
+    @MainActor
+    private func performPrivateChatClear(
+        _ request: PendingPrivateChatClear,
+        completion: @escaping @MainActor () -> Void
+    ) {
+        let peerID = request.peerID
+        let selectedConversationID = request.sourceConversationID
+        let messagesToClear = request.messages
+        guard !messagesToClear.isEmpty else {
+            completion()
+            return
+        }
+
+        // Capture the transaction's exact UI set before any off-main receipt
+        // I/O. Messages arriving while the journal is written are not part of
+        // this command and must remain visible.
+        let capturedMessageIDs = Set(messagesToClear.map(\.id))
+        let survivingMessageIDs = request.otherMessageIDs
+        let mediaPrefixes = [
+            MimeType.Category.audio.messagePrefix,
+            MimeType.Category.image.messagePrefix,
+            MimeType.Category.file.messagePrefix
+        ]
+        let localPeerID = request.localPeerID
+        let isMedia: (BitchatMessage) -> Bool = { message in
+            mediaPrefixes.contains(where: message.content.hasPrefix)
+        }
+        let isFromMe: (BitchatMessage) -> Bool = { [nickname = request.nickname] message in
+            if let senderPeerID = message.senderPeerID {
+                return senderPeerID.toShort() == localPeerID
+            }
+            return message.sender == nickname
+                || message.sender.hasPrefix(nickname + "#")
+        }
+
+        let outgoingMedia = request.outgoingMedia
+        let outgoingMediaIDs = Set(outgoingMedia.map(\.id))
+
+        let capturedExclusiveIDs =
+            capturedMessageIDs.subtracting(survivingMessageIDs)
+        let capturedIncomingMedia = messagesToClear.filter {
+            isMedia($0) && !isFromMe($0)
+        }
+        let capturedStableMediaIDs = Set(
+            capturedIncomingMedia.compactMap { message in
+                PrivateMediaMessageIdentity.isStableID(message.id)
+                    ? message.id
+                    : nil
+            }
+        )
+
+        func currentRemovalPlan() -> [ConversationID: Set<String>] {
+            // Identity handoff removes the source conversation and inserts its
+            // rows elsewhere. The old source may then be recreated by a new
+            // arrival before journal I/O finishes, so always scan all direct
+            // conversations. Only IDs exclusive at command time may follow a
+            // migration; shared aliases remain outside the source.
+            var plan: [ConversationID: Set<String>] = [:]
+            for (conversationID, conversation) in
+                conversations.conversationsByID {
+                guard case .direct = conversationID else { continue }
+                let eligibleIDs = conversationID == selectedConversationID
+                    ? capturedMessageIDs
+                    : capturedExclusiveIDs
+                let matchingIDs = Set(conversation.messages.map(\.id))
+                    .intersection(eligibleIDs)
+                if !matchingIDs.isEmpty {
+                    plan[conversationID] = matchingIDs
+                }
+            }
+            return plan
+        }
+
+        func hasRemainingCopy(
+            of messageID: String,
+            after plan: [ConversationID: Set<String>]
+        ) -> Bool {
+            conversations.conversationsByID.contains { conversationID, conversation in
+                guard case .direct = conversationID else { return false }
+                return conversation.messages.contains { message in
+                    message.id == messageID
+                        && plan[conversationID]?.contains(messageID) != true
+                }
+            }
+        }
+
+        @MainActor
+        func continueClear(
+            persisted: Bool,
+            durableStableIDs: Set<String>
+        ) {
+            guard persisted else {
+                SecureLogger.error(
+                    "Refusing to clear private chat without durable media tombstones peer=\(peerID.id.prefix(8))…",
+                    category: .session
+                )
+                completion()
+                return
+            }
+
+            let plan = currentRemovalPlan()
+            let newlyLastStableIDs = Set(
+                capturedStableMediaIDs.filter {
+                    !durableStableIDs.contains($0)
+                        && !hasRemainingCopy(of: $0, after: plan)
+                }
+            )
+            if !newlyLastStableIDs.isEmpty {
+                persistDeletedPrivateMedia(
+                    messageIDs: Array(newlyLastStableIDs).sorted()
+                ) { persisted in
+                    continueClear(
+                        persisted: persisted,
+                        durableStableIDs:
+                            durableStableIDs.union(newlyLastStableIDs)
+                    )
+                }
+                return
+            }
+
+            // A stable receiver tombstone is global for that message ID.
+            // Remove any alias that arrived while journal I/O was in flight.
+            if !durableStableIDs.isEmpty {
+                let directConversationIDs = conversations
+                    .conversationsByID.keys.filter {
+                        if case .direct = $0 { return true }
+                        return false
+                    }
+                for conversationID in directConversationIDs {
+                    conversations.removeMessages(from: conversationID) {
+                        durableStableIDs.contains($0.id)
+                    }
+                }
+            }
+
+            for message in outgoingMedia {
+                mediaTransferCoordinator.cleanupOutgoingLocalFile(
+                    forMessage: message
+                )
+            }
+            if !outgoingMediaIDs.isEmpty {
+                let directConversationIDs = conversations
+                    .conversationsByID.keys.filter {
+                        if case .direct = $0 { return true }
+                        return false
+                    }
+                for conversationID in directConversationIDs {
+                    conversations.removeMessages(from: conversationID) {
+                        outgoingMediaIDs.contains($0.id)
+                    }
+                }
+            }
+
+            // Stable payload cleanup belongs entirely to the durable receiver
+            // journal. Legacy/raw incoming payloads have no durable identity,
+            // so their basenames may already belong to a pending new arrival;
+            // leave those files for bounded quota cleanup.
+            let finalPlan = currentRemovalPlan()
+
+            for (conversationID, messageIDs) in finalPlan {
+                conversations.removeMessages(from: conversationID) {
+                    messageIDs.contains($0.id)
+                }
+            }
+            completion()
+        }
+
+        let initialPlan = currentRemovalPlan()
+        let initialStableIDs = Set(
+            capturedStableMediaIDs.filter {
+                !hasRemainingCopy(of: $0, after: initialPlan)
+            }
+        )
+        persistDeletedPrivateMedia(
+            messageIDs: Array(initialStableIDs).sorted()
+        ) { persisted in
+            continueClear(
+                persisted: persisted,
+                durableStableIDs: initialStableIDs
+            )
+        }
     }
 
     /// Removes the peer's chat entirely, including unread state.

bitchatTests/ChatMediaTransferCoordinatorContextTests.swift

@@ -58,6 +58,8 @@ private final class MockChatMediaTransferContext: ChatMediaTransferContext {
 
     private(set) var appendedPublicMessages: [(message: BitchatMessage, conversationID: ConversationID)] = []
     private(set) var removedMessages: [(messageID: String, cleanupFile: Bool)] = []
+    private(set) var untombstonedMediaRemovals: [String] = []
+    private(set) var outgoingMediaRemovals: [String] = []
     private(set) var systemMessages: [String] = []
     private(set) var notifyUIChangedCount = 0
 
@@ -71,6 +73,16 @@ private final class MockChatMediaTransferContext: ChatMediaTransferContext {
         removedMessages.append((messageID, cleanupFile))
     }
 
+    func removeUntombstonedMediaMessage(withID messageID: String) {
+        untombstonedMediaRemovals.append(messageID)
+        removedMessages.append((messageID, false))
+    }
+
+    func removeOutgoingMediaMessage(withID messageID: String) {
+        outgoingMediaRemovals.append(messageID)
+        removedMessages.append((messageID, false))
+    }
+
     func addSystemMessage(_ content: String) { systemMessages.append(content) }
     func notifyUIChanged() { notifyUIChangedCount += 1 }
 
@@ -99,6 +111,13 @@ private final class MockChatMediaTransferContext: ChatMediaTransferContext {
     private(set) var broadcastFileSends: [String] = []
     private(set) var cancelledTransfers: [String] = []
     private(set) var privateMediaPolicyResolutionRequests: [PeerID] = []
+    private(set) var persistedDeletionBatches: [[String]] = []
+    var requiredTombstoneIDs: Set<String> = []
+    var deletedMediaPersistenceResult = true
+    var deferDeletedMediaPersistence = false
+    private var pendingDeletionCompletions: [
+        @MainActor (Bool) -> Void
+    ] = []
     var privateMediaPolicy: PrivateMediaSendPolicy = .encrypted
     var resolvedPrivateMediaPolicy: PrivateMediaSendPolicy?
     var resolvesPrivateMediaPolicyImmediately = true
@@ -218,6 +237,28 @@ private final class MockChatMediaTransferContext: ChatMediaTransferContext {
     func cancelTransfer(_ transferId: String) {
         cancelledTransfers.append(transferId)
     }
+
+    func persistDeletedPrivateMedia(
+        messageIDs: [String],
+        completion: @escaping @MainActor (Bool) -> Void
+    ) {
+        persistedDeletionBatches.append(messageIDs)
+        if deferDeletedMediaPersistence {
+            pendingDeletionCompletions.append(completion)
+        } else {
+            completion(deletedMediaPersistenceResult)
+        }
+    }
+
+    func requiresPrivateMediaTombstone(messageID: String) -> Bool {
+        requiredTombstoneIDs.contains(messageID)
+    }
+
+    func resolveNextDeletionPersistence(_ result: Bool? = nil) {
+        guard !pendingDeletionCompletions.isEmpty else { return }
+        let completion = pendingDeletionCompletions.removeFirst()
+        completion(result ?? deletedMediaPersistenceResult)
+    }
 }
 
 private final class PausedVoiceNotePreparer: @unchecked Sendable {
@@ -381,7 +422,8 @@ struct ChatMediaTransferCoordinatorContextTests {
         coordinator.handleTransferEvent(.cancelled(id: "t2", sentFragments: 1, totalFragments: 5))
         #expect(context.removedMessages.count == 1)
         #expect(context.removedMessages.first?.messageID == "m2")
-        #expect(context.removedMessages.first?.cleanupFile == true)
+        #expect(context.removedMessages.first?.cleanupFile == false)
+        #expect(context.outgoingMediaRemovals == ["m2"])
 
         // A pre-start rejection keeps the placeholder visible and failed,
         // including queued post-handshake encryption failures.
@@ -531,7 +573,154 @@ struct ChatMediaTransferCoordinatorContextTests {
         #expect(context.cancelledTransfers == ["approved-delete"])
         #expect(coordinator.messageIDToTransferId["message-delete"] == nil)
         #expect(context.removedMessages.map(\.messageID) == ["message-delete"])
-        #expect(context.removedMessages.first?.cleanupFile == true)
+        #expect(context.removedMessages.first?.cleanupFile == false)
+        #expect(
+            context.untombstonedMediaRemovals == ["message-delete"]
+        )
+    }
+
+    @Test @MainActor
+    func deleteIncomingStableMediaWaitsForDurableTombstone() {
+        let context = MockChatMediaTransferContext()
+        let coordinator = ChatMediaTransferCoordinator(context: context)
+        let messageID = "media-00112233445566778899aabbccddeeff"
+        context.requiredTombstoneIDs = [messageID]
+        context.deferDeletedMediaPersistence = true
+        coordinator.registerTransfer(
+            transferId: "incoming-delete",
+            messageID: messageID
+        )
+
+        coordinator.deleteMediaMessage(messageID: messageID)
+
+        #expect(context.persistedDeletionBatches == [[messageID]])
+        #expect(context.removedMessages.isEmpty)
+        #expect(context.cancelledTransfers == ["incoming-delete"])
+        #expect(coordinator.messageIDToTransferId[messageID] == nil)
+
+        context.resolveNextDeletionPersistence(true)
+
+        #expect(context.cancelledTransfers == ["incoming-delete"])
+        #expect(context.removedMessages.map(\.messageID) == [messageID])
+        #expect(context.removedMessages.first?.cleanupFile == false)
+        #expect(context.untombstonedMediaRemovals.isEmpty)
+        #expect(coordinator.messageIDToTransferId[messageID] == nil)
+    }
+
+    @Test @MainActor
+    func deleteIncomingStableMediaPreservesStateWhenTombstoneFails() {
+        let context = MockChatMediaTransferContext()
+        let coordinator = ChatMediaTransferCoordinator(context: context)
+        let messageID = "media-ffeeddccbbaa99887766554433221100"
+        context.requiredTombstoneIDs = [messageID]
+        context.deletedMediaPersistenceResult = false
+        coordinator.registerTransfer(
+            transferId: "failed-delete",
+            messageID: messageID
+        )
+
+        coordinator.deleteMediaMessage(messageID: messageID)
+
+        #expect(context.persistedDeletionBatches == [[messageID]])
+        #expect(context.removedMessages.isEmpty)
+        #expect(context.cancelledTransfers == ["failed-delete"])
+        #expect(coordinator.messageIDToTransferId[messageID] == nil)
+    }
+
+    @Test @MainActor
+    func deleteStableMediaReleasesRetainedRetryBeforeTombstoneCommit()
+        async throws
+    {
+        let context = MockChatMediaTransferContext()
+        let peerID = PeerID(str: "1122334455667788")
+        context.selectedPrivateChatPeer = peerID
+        context.supportsAuthenticatedPrivateMediaReceipts = true
+        context.deferDeletedMediaPersistence = true
+        let fileName = "voice_deadbeefdeadbeef.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
+        )
+        context.requiredTombstoneIDs = [messageID]
+        #expect(coordinator.retainedReconnectRetryCount == 1)
+
+        coordinator.deleteMediaMessage(messageID: messageID)
+
+        #expect(context.persistedDeletionBatches == [[messageID]])
+        #expect(coordinator.retainedReconnectRetryCount == 0)
+        #expect(coordinator.retainedReconnectRetryBytes == 0)
+        #expect(context.cancelledTransfers == [transferID])
+        #expect(context.removedMessages.isEmpty)
+
+        coordinator.peerDidReconnect(peerID)
+        #expect(context.privateFileSends.count == 1)
+
+        context.resolveNextDeletionPersistence(true)
+        #expect(context.removedMessages.map(\.messageID) == [messageID])
+    }
+
+    @Test @MainActor
+    func legacyCleanupNeverRecursivelyDeletesDirectoryTarget() throws {
+        let context = MockChatMediaTransferContext()
+        let coordinator = ChatMediaTransferCoordinator(context: context)
+        let incoming = try FileManager.default.url(
+            for: .applicationSupportDirectory,
+            in: .userDomainMask,
+            appropriateFor: nil,
+            create: true
+        )
+        .appendingPathComponent(
+            "files/images/incoming",
+            isDirectory: true
+        )
+        let directoryName = "cleanup-dir-\(UUID().uuidString)"
+        let directory = incoming.appendingPathComponent(
+            directoryName,
+            isDirectory: true
+        )
+        try FileManager.default.createDirectory(
+            at: directory,
+            withIntermediateDirectories: true
+        )
+        let child = directory.appendingPathComponent("child.jpg")
+        try Data([0x01]).write(to: child)
+        defer { try? FileManager.default.removeItem(at: directory) }
+        let message = BitchatMessage(
+            id: UUID().uuidString,
+            sender: "Peer",
+            content:
+                "\(MimeType.Category.image.messagePrefix)\(directoryName)",
+            timestamp: Date(),
+            isRelay: false,
+            isPrivate: true,
+            recipientNickname: "Me"
+        )
+
+        coordinator.cleanupIncomingLocalFile(forMessage: message)
+
+        #expect(FileManager.default.fileExists(atPath: directory.path))
+        #expect(FileManager.default.fileExists(atPath: child.path))
     }
 
     @Test @MainActor

bitchatTests/ChatViewModelTests.swift

@@ -1194,6 +1194,697 @@ struct ChatViewModelBluetoothTests {
     }
 }
 
+// MARK: - Private Media Deletion Tests
+
+struct ChatViewModelPrivateMediaDeletionTests {
+
+    @Test @MainActor
+    func deleteMediaMessageTombstonesIncomingButNotOutgoingStableMedia() {
+        let (viewModel, transport) = makeTestableViewModel()
+        let peerID = PeerID(str: String(repeating: "8", count: 64))
+        let incomingID = "media-\(String(repeating: "e", count: 32))"
+        let outgoingID = "media-\(String(repeating: "f", count: 32))"
+        viewModel.seedPrivateChat([
+            privateMediaMessage(
+                id: incomingID,
+                sender: "Peer",
+                senderPeerID: peerID,
+                recipient: viewModel.nickname,
+                filename: "incoming.jpg"
+            ),
+            privateMediaMessage(
+                id: outgoingID,
+                sender: viewModel.nickname,
+                senderPeerID: transport.myPeerID,
+                recipient: "Peer",
+                filename: "outgoing.jpg"
+            )
+        ], for: peerID)
+
+        viewModel.deleteMediaMessage(messageID: outgoingID)
+        #expect(transport.deletedPrivateMediaMessageIDBatches.isEmpty)
+        #expect(viewModel.privateChats[peerID]?.map(\.id) == [incomingID])
+
+        viewModel.deleteMediaMessage(messageID: incomingID)
+        #expect(
+            transport.deletedPrivateMediaMessageIDBatches == [[incomingID]]
+        )
+        #expect(
+            transport.deletedPrivateMediaRelativePaths
+                == [[incomingID: "images/incoming/incoming.jpg"]]
+        )
+        #expect((viewModel.privateChats[peerID] ?? []).isEmpty)
+    }
+
+    @Test @MainActor
+    func stableDeleteProtectsPathSharedWithLegacyBubble() {
+        let (viewModel, transport) = makeTestableViewModel()
+        transport.persistDeletedPrivateMediaResult = false
+        let peerID = PeerID(str: String(repeating: "6", count: 64))
+        let stableID = "media-\(String(repeating: "5", count: 32))"
+        let legacyID = UUID().uuidString
+        let filename = "shared-migration.jpg"
+        viewModel.seedPrivateChat([
+            privateMediaMessage(
+                id: stableID,
+                sender: "Peer",
+                senderPeerID: peerID,
+                recipient: viewModel.nickname,
+                filename: filename
+            ),
+            privateMediaMessage(
+                id: legacyID,
+                sender: "Old client",
+                senderPeerID: peerID,
+                recipient: viewModel.nickname,
+                filename: filename
+            )
+        ], for: peerID)
+
+        viewModel.deleteMediaMessage(messageID: stableID)
+
+        #expect(
+            transport.deletedPrivateMediaMessageIDBatches == [[stableID]]
+        )
+        #expect(transport.deletedPrivateMediaRelativePaths == [[:]])
+        #expect(
+            transport.protectedPrivateMediaRelativePaths == [[
+                "images/incoming/\(filename)"
+            ]]
+        )
+        #expect(
+            viewModel.privateChats[peerID]?.map(\.id)
+                == [stableID, legacyID]
+        )
+    }
+
+    @Test @MainActor
+    func legacyIncomingDeleteLeavesAmbiguousPayloadForQuota() throws {
+        let (viewModel, transport) = makeTestableViewModel()
+        let peerID = PeerID(str: String(repeating: "3", count: 64))
+        let incoming = try FileManager.default.url(
+            for: .applicationSupportDirectory,
+            in: .userDomainMask,
+            appropriateFor: nil,
+            create: true
+        )
+        .appendingPathComponent(
+            "files/images/incoming",
+            isDirectory: true
+        )
+        try FileManager.default.createDirectory(
+            at: incoming,
+            withIntermediateDirectories: true
+        )
+        let payload = incoming.appendingPathComponent(
+            "legacy-delete-\(UUID().uuidString).jpg"
+        )
+        try Data([0x01]).write(to: payload)
+        defer { try? FileManager.default.removeItem(at: payload) }
+        let legacyID = UUID().uuidString
+        viewModel.seedPrivateChat([
+            privateMediaMessage(
+                id: legacyID,
+                sender: "Old client",
+                senderPeerID: peerID,
+                recipient: viewModel.nickname,
+                filename: payload.lastPathComponent
+            )
+        ], for: peerID)
+
+        viewModel.deleteMediaMessage(messageID: legacyID)
+
+        #expect(transport.deletedPrivateMediaMessageIDBatches.isEmpty)
+        #expect((viewModel.privateChats[peerID] ?? []).isEmpty)
+        #expect(FileManager.default.fileExists(atPath: payload.path))
+    }
+
+    @Test @MainActor
+    func clearPrivateChatTombstonesIncomingAndCancelsOutgoingBeforeClear() {
+        let (viewModel, transport) = makeTestableViewModel()
+        let peerID = PeerID(str: String(repeating: "1", count: 64))
+        let incomingID = "media-\(String(repeating: "a", count: 32))"
+        let outgoingID = "media-\(String(repeating: "b", count: 32))"
+        viewModel.seedPrivateChat([
+            privateMediaMessage(
+                id: incomingID,
+                sender: "Peer",
+                senderPeerID: peerID,
+                recipient: viewModel.nickname,
+                filename: "incoming.jpg"
+            ),
+            privateMediaMessage(
+                id: outgoingID,
+                sender: viewModel.nickname,
+                senderPeerID: transport.myPeerID,
+                recipient: "Peer",
+                filename: "outgoing.jpg"
+            ),
+            BitchatMessage(
+                id: "ordinary-message",
+                sender: "Peer",
+                content: "hello",
+                timestamp: Date(),
+                isRelay: false,
+                isPrivate: true,
+                recipientNickname: viewModel.nickname,
+                senderPeerID: peerID
+            )
+        ], for: peerID)
+        viewModel.registerTransfer(
+            transferId: "outgoing-clear-transfer",
+            messageID: outgoingID
+        )
+
+        viewModel.clearPrivateChat(peerID)
+
+        #expect(
+            transport.deletedPrivateMediaMessageIDBatches == [[incomingID]]
+        )
+        #expect(
+            transport.deletedPrivateMediaRelativePaths
+                == [[incomingID: "images/incoming/incoming.jpg"]]
+        )
+        #expect(
+            transport.cancelledTransfers == ["outgoing-clear-transfer"]
+        )
+        #expect(viewModel.messageIDToTransferId[outgoingID] == nil)
+        #expect(viewModel.privateChats[peerID]?.isEmpty == true)
+    }
+
+    @Test @MainActor
+    func clearPrivateChatPreservesCapturedMessagesWhenTombstoneFails() {
+        let (viewModel, transport) = makeTestableViewModel()
+        transport.persistDeletedPrivateMediaResult = false
+        let peerID = PeerID(str: String(repeating: "2", count: 64))
+        let incomingID = "media-\(String(repeating: "c", count: 32))"
+        let outgoingID = "media-\(String(repeating: "7", count: 32))"
+        viewModel.seedPrivateChat([
+            privateMediaMessage(
+                id: incomingID,
+                sender: "Peer",
+                senderPeerID: peerID,
+                recipient: viewModel.nickname,
+                filename: "incoming.jpg"
+            ),
+            privateMediaMessage(
+                id: outgoingID,
+                sender: viewModel.nickname,
+                senderPeerID: transport.myPeerID,
+                recipient: "Peer",
+                filename: "outgoing.jpg"
+            ),
+            BitchatMessage(
+                id: "ordinary-message",
+                sender: "Peer",
+                content: "keep me on failure",
+                timestamp: Date(),
+                isRelay: false,
+                isPrivate: true,
+                recipientNickname: viewModel.nickname,
+                senderPeerID: peerID
+            )
+        ], for: peerID)
+        viewModel.registerTransfer(
+            transferId: "failed-clear-outgoing",
+            messageID: outgoingID
+        )
+
+        viewModel.clearPrivateChat(peerID)
+
+        #expect(
+            transport.deletedPrivateMediaMessageIDBatches == [[incomingID]]
+        )
+        #expect(
+            viewModel.privateChats[peerID]?.map(\.id)
+                == [incomingID, outgoingID, "ordinary-message"]
+        )
+        #expect(transport.cancelledTransfers == ["failed-clear-outgoing"])
+        #expect(viewModel.messageIDToTransferId[outgoingID] == nil)
+    }
+
+    @Test @MainActor
+    func clearFailurePreservesSameNameIncomingPayload() throws {
+        let (viewModel, transport) = makeTestableViewModel()
+        transport.persistDeletedPrivateMediaResult = false
+        let peerID = PeerID(str: String(repeating: "7", count: 64))
+        let incomingID = "media-\(String(repeating: "8", count: 32))"
+        let outgoingID = "media-\(String(repeating: "9", count: 32))"
+        let filename = "clear-collision-\(UUID().uuidString).jpg"
+        let filesDirectory = try FileManager.default.url(
+            for: .applicationSupportDirectory,
+            in: .userDomainMask,
+            appropriateFor: nil,
+            create: true
+        )
+        .appendingPathComponent("files/images", isDirectory: true)
+        let incomingDirectory = filesDirectory.appendingPathComponent(
+            "incoming",
+            isDirectory: true
+        )
+        let outgoingDirectory = filesDirectory.appendingPathComponent(
+            "outgoing",
+            isDirectory: true
+        )
+        try FileManager.default.createDirectory(
+            at: incomingDirectory,
+            withIntermediateDirectories: true
+        )
+        try FileManager.default.createDirectory(
+            at: outgoingDirectory,
+            withIntermediateDirectories: true
+        )
+        let incomingURL = incomingDirectory.appendingPathComponent(filename)
+        let outgoingURL = outgoingDirectory.appendingPathComponent(filename)
+        try Data("incoming".utf8).write(to: incomingURL, options: .atomic)
+        try Data("outgoing".utf8).write(to: outgoingURL, options: .atomic)
+        defer {
+            try? FileManager.default.removeItem(at: incomingURL)
+            try? FileManager.default.removeItem(at: outgoingURL)
+        }
+        viewModel.seedPrivateChat([
+            privateMediaMessage(
+                id: incomingID,
+                sender: "Peer",
+                senderPeerID: peerID,
+                recipient: viewModel.nickname,
+                filename: filename
+            ),
+            privateMediaMessage(
+                id: outgoingID,
+                sender: viewModel.nickname,
+                senderPeerID: transport.myPeerID,
+                recipient: "Peer",
+                filename: filename
+            )
+        ], for: peerID)
+
+        viewModel.clearPrivateChat(peerID)
+
+        #expect(FileManager.default.fileExists(atPath: incomingURL.path))
+        #expect(FileManager.default.fileExists(atPath: outgoingURL.path))
+        #expect(
+            transport.deletedPrivateMediaRelativePaths
+                == [[incomingID: "images/incoming/\(filename)"]]
+        )
+        #expect(
+            viewModel.privateChats[peerID]?.map(\.id)
+                == [incomingID, outgoingID]
+        )
+    }
+
+    @Test @MainActor
+    func clearPrivateChatPreservesArrivalDuringTombstoneIO() {
+        let (viewModel, transport) = makeTestableViewModel()
+        transport.deferDeletedPrivateMediaPersistence = true
+        let peerID = PeerID(str: String(repeating: "3", count: 64))
+        let incomingID = "media-\(String(repeating: "d", count: 32))"
+        viewModel.seedPrivateChat([
+            privateMediaMessage(
+                id: incomingID,
+                sender: "Peer",
+                senderPeerID: peerID,
+                recipient: viewModel.nickname,
+                filename: "incoming.jpg"
+            ),
+            BitchatMessage(
+                id: "captured-text",
+                sender: "Peer",
+                content: "old",
+                timestamp: Date(),
+                isRelay: false,
+                isPrivate: true,
+                recipientNickname: viewModel.nickname,
+                senderPeerID: peerID
+            )
+        ], for: peerID)
+
+        viewModel.clearPrivateChat(peerID)
+        let arrival = BitchatMessage(
+            id: "concurrent-arrival",
+            sender: "Peer",
+            content: "new",
+            timestamp: Date(),
+            isRelay: false,
+            isPrivate: true,
+            recipientNickname: viewModel.nickname,
+            senderPeerID: peerID
+        )
+        #expect(viewModel.appendPrivateMessage(arrival, to: peerID))
+
+        transport.resolveNextDeletedPrivateMediaPersistence(true)
+
+        #expect(
+            viewModel.privateChats[peerID]?.map(\.id)
+                == ["concurrent-arrival"]
+        )
+    }
+
+    @Test @MainActor
+    func clearPrivateChatPreservesActiveLiveVoiceAssembly() throws {
+        let (viewModel, transport) = makeTestableViewModel()
+        let peerID = PeerID(str: String(repeating: "7", count: 64))
+        viewModel.selectedPrivateChatPeer = peerID
+        let burstID = Data(
+            repeating: 0xE1,
+            count: VoiceBurstPacket.burstIDSize
+        )
+        let start = try #require(VoiceBurstPacket(
+            burstID: burstID,
+            seq: 0,
+            kind: .start(codec: .aacLC16kMono)
+        ))
+        let cancel = try #require(VoiceBurstPacket(
+            burstID: burstID,
+            seq: 1,
+            kind: .canceled
+        ))
+        let coordinator = viewModel.liveVoiceCoordinator
+        defer {
+            coordinator.handleVoiceFramePayload(
+                from: peerID,
+                payload: cancel.encode(),
+                timestamp: Date()
+            )
+        }
+        coordinator.handleVoiceFramePayload(
+            from: peerID,
+            payload: start.encode(),
+            timestamp: Date()
+        )
+        let liveMessage = try #require(
+            viewModel.privateChats[peerID]?.first
+        )
+        #expect(coordinator.isLiveVoiceMessage(liveMessage))
+        let ordinary = BitchatMessage(
+            id: "clear-around-live-voice",
+            sender: "Peer",
+            content: "old text",
+            timestamp: Date(),
+            isRelay: false,
+            isPrivate: true,
+            recipientNickname: viewModel.nickname,
+            senderPeerID: peerID
+        )
+        #expect(viewModel.appendPrivateMessage(ordinary, to: peerID))
+
+        viewModel.clearPrivateChat(peerID)
+
+        #expect(transport.deletedPrivateMediaMessageIDBatches.isEmpty)
+        #expect(
+            viewModel.privateChats[peerID]?.map(\.id)
+                == [liveMessage.id]
+        )
+        #expect(coordinator.isLiveVoiceMessage(liveMessage))
+    }
+
+    @Test @MainActor
+    func overlappingClearsTombstoneTheLastMirroredStableAlias() {
+        let (viewModel, transport) = makeTestableViewModel()
+        transport.deferDeletedPrivateMediaPersistence = true
+        let firstPeerID = PeerID(str: String(repeating: "b", count: 64))
+        let secondPeerID = PeerID(str: String(repeating: "c", count: 64))
+        let sharedID = "media-\(String(repeating: "1", count: 32))"
+        let firstUniqueID = "media-\(String(repeating: "2", count: 32))"
+        let secondUniqueID = "media-\(String(repeating: "3", count: 32))"
+        viewModel.seedPrivateChat([
+            privateMediaMessage(
+                id: sharedID,
+                sender: "Peer",
+                senderPeerID: firstPeerID,
+                recipient: viewModel.nickname,
+                filename: "shared.jpg"
+            ),
+            privateMediaMessage(
+                id: firstUniqueID,
+                sender: "Peer",
+                senderPeerID: firstPeerID,
+                recipient: viewModel.nickname,
+                filename: "first.jpg"
+            )
+        ], for: firstPeerID)
+        viewModel.seedPrivateChat([
+            privateMediaMessage(
+                id: sharedID,
+                sender: "Peer",
+                senderPeerID: secondPeerID,
+                recipient: viewModel.nickname,
+                filename: "shared.jpg"
+            ),
+            privateMediaMessage(
+                id: secondUniqueID,
+                sender: "Peer",
+                senderPeerID: secondPeerID,
+                recipient: viewModel.nickname,
+                filename: "second.jpg"
+            )
+        ], for: secondPeerID)
+
+        viewModel.clearPrivateChat(firstPeerID)
+        viewModel.clearPrivateChat(secondPeerID)
+        let queuedArrival = BitchatMessage(
+            id: "arrival-after-queued-clear",
+            sender: "Peer",
+            content: "new",
+            timestamp: Date(),
+            isRelay: false,
+            isPrivate: true,
+            recipientNickname: viewModel.nickname,
+            senderPeerID: secondPeerID
+        )
+        #expect(viewModel.appendPrivateMessage(
+            queuedArrival,
+            to: secondPeerID
+        ))
+
+        #expect(
+            transport.deletedPrivateMediaMessageIDBatches
+                == [[firstUniqueID]]
+        )
+
+        transport.resolveNextDeletedPrivateMediaPersistence(true)
+
+        #expect(
+            transport.deletedPrivateMediaMessageIDBatches == [
+                [firstUniqueID],
+                [secondUniqueID, sharedID].sorted()
+            ]
+        )
+
+        transport.resolveNextDeletedPrivateMediaPersistence(true)
+
+        #expect((viewModel.privateChats[firstPeerID] ?? []).isEmpty)
+        #expect(
+            viewModel.privateChats[secondPeerID]?.map(\.id)
+                == ["arrival-after-queued-clear"]
+        )
+    }
+
+    @Test @MainActor
+    func clearFollowsCapturedRowsAcrossPeerIdentityMigration() {
+        let (viewModel, transport) = makeTestableViewModel()
+        transport.deferDeletedPrivateMediaPersistence = true
+        let sourcePeerID = PeerID(str: String(repeating: "d", count: 64))
+        let destinationPeerID = PeerID(str: String(repeating: "e", count: 64))
+        let thirdPeerID = PeerID(str: String(repeating: "f", count: 64))
+        let stableID = "media-\(String(repeating: "4", count: 32))"
+        viewModel.selectedPrivateChatPeer = sourcePeerID
+        viewModel.seedPrivateChat([
+            privateMediaMessage(
+                id: stableID,
+                sender: "Peer",
+                senderPeerID: sourcePeerID,
+                recipient: viewModel.nickname,
+                filename: "migrated.jpg"
+            ),
+            BitchatMessage(
+                id: "captured-before-migration",
+                sender: "Peer",
+                content: "old",
+                timestamp: Date(),
+                isRelay: false,
+                isPrivate: true,
+                recipientNickname: viewModel.nickname,
+                senderPeerID: sourcePeerID
+            )
+        ], for: sourcePeerID)
+
+        viewModel.clearPrivateChat(sourcePeerID)
+        viewModel.migratePrivateChat(
+            from: sourcePeerID,
+            to: destinationPeerID
+        )
+        viewModel.selectedPrivateChatPeer = thirdPeerID
+        let arrival = BitchatMessage(
+            id: "arrival-after-migration",
+            sender: "Peer",
+            content: "new",
+            timestamp: Date(),
+            isRelay: false,
+            isPrivate: true,
+            recipientNickname: viewModel.nickname,
+            senderPeerID: destinationPeerID
+        )
+        #expect(viewModel.appendPrivateMessage(
+            arrival,
+            to: destinationPeerID
+        ))
+
+        transport.resolveNextDeletedPrivateMediaPersistence(true)
+
+        #expect(
+            viewModel.privateChats[destinationPeerID]?.map(\.id)
+                == ["arrival-after-migration"]
+        )
+    }
+
+    @Test @MainActor
+    func clearFollowsMigrationWhenOldSourceIsRecreated() {
+        let (viewModel, transport) = makeTestableViewModel()
+        transport.deferDeletedPrivateMediaPersistence = true
+        let sourcePeerID = PeerID(str: String(repeating: "1", count: 64))
+        let destinationPeerID = PeerID(str: String(repeating: "2", count: 64))
+        let stableID = "media-\(String(repeating: "6", count: 32))"
+        viewModel.seedPrivateChat([
+            privateMediaMessage(
+                id: stableID,
+                sender: "Peer",
+                senderPeerID: sourcePeerID,
+                recipient: viewModel.nickname,
+                filename: "migrated-recreated.jpg"
+            ),
+            BitchatMessage(
+                id: "captured-before-recreation",
+                sender: "Peer",
+                content: "old",
+                timestamp: Date(),
+                isRelay: false,
+                isPrivate: true,
+                recipientNickname: viewModel.nickname,
+                senderPeerID: sourcePeerID
+            )
+        ], for: sourcePeerID)
+
+        viewModel.clearPrivateChat(sourcePeerID)
+        viewModel.migratePrivateChat(
+            from: sourcePeerID,
+            to: destinationPeerID
+        )
+        let recreatedArrival = BitchatMessage(
+            id: "arrival-recreating-source",
+            sender: "Peer",
+            content: "new",
+            timestamp: Date(),
+            isRelay: false,
+            isPrivate: true,
+            recipientNickname: viewModel.nickname,
+            senderPeerID: sourcePeerID
+        )
+        #expect(viewModel.appendPrivateMessage(
+            recreatedArrival,
+            to: sourcePeerID
+        ))
+
+        transport.resolveNextDeletedPrivateMediaPersistence(true)
+
+        #expect(
+            (viewModel.privateChats[destinationPeerID] ?? []).isEmpty
+        )
+        #expect(
+            viewModel.privateChats[sourcePeerID]?.map(\.id)
+                == ["arrival-recreating-source"]
+        )
+    }
+
+    @Test @MainActor
+    func clearPrivateChatKeepsMediaReferencedByAnotherConversation() {
+        let (viewModel, transport) = makeTestableViewModel()
+        let firstPeerID = PeerID(str: String(repeating: "4", count: 64))
+        let aliasPeerID = PeerID(str: String(repeating: "5", count: 64))
+        let messageID = "media-\(String(repeating: "6", count: 32))"
+        let message = privateMediaMessage(
+            id: messageID,
+            sender: "Peer",
+            senderPeerID: firstPeerID,
+            recipient: viewModel.nickname,
+            filename: "mirrored.jpg"
+        )
+        viewModel.seedPrivateChat([message], for: firstPeerID)
+        viewModel.seedPrivateChat([message], for: aliasPeerID)
+
+        viewModel.clearPrivateChat(firstPeerID)
+
+        #expect(transport.deletedPrivateMediaMessageIDBatches.isEmpty)
+        #expect(viewModel.privateChats[firstPeerID]?.isEmpty == true)
+        #expect(
+            viewModel.privateChats[aliasPeerID]?.map(\.id) == [messageID]
+        )
+    }
+
+    @Test @MainActor
+    func clearPrivateChatLeavesAmbiguousLegacyFileForQuotaCleanup()
+        throws {
+        let (viewModel, transport) = makeTestableViewModel()
+        let firstPeerID = PeerID(str: String(repeating: "9", count: 64))
+        let aliasPeerID = PeerID(str: String(repeating: "a", count: 64))
+        let incomingDirectory = try FileManager.default.url(
+            for: .applicationSupportDirectory,
+            in: .userDomainMask,
+            appropriateFor: nil,
+            create: true
+        )
+        .appendingPathComponent("files/images/incoming", isDirectory: true)
+        try FileManager.default.createDirectory(
+            at: incomingDirectory,
+            withIntermediateDirectories: true
+        )
+        let fileURL = incomingDirectory.appendingPathComponent(
+            "legacy-clear-\(UUID().uuidString).jpg"
+        )
+        try Data("legacy-image".utf8).write(to: fileURL, options: .atomic)
+        defer { try? FileManager.default.removeItem(at: fileURL) }
+        let message = privateMediaMessage(
+            id: UUID().uuidString,
+            sender: "Old client",
+            senderPeerID: firstPeerID,
+            recipient: viewModel.nickname,
+            filename: fileURL.lastPathComponent
+        )
+        viewModel.seedPrivateChat([message], for: firstPeerID)
+        viewModel.seedPrivateChat([message], for: aliasPeerID)
+
+        viewModel.clearPrivateChat(firstPeerID)
+
+        #expect(transport.deletedPrivateMediaMessageIDBatches.isEmpty)
+        #expect(FileManager.default.fileExists(atPath: fileURL.path))
+        #expect(viewModel.privateChats[aliasPeerID]?.map(\.id) == [message.id])
+
+        viewModel.clearPrivateChat(aliasPeerID)
+
+        #expect(FileManager.default.fileExists(atPath: fileURL.path))
+        #expect((viewModel.privateChats[aliasPeerID] ?? []).isEmpty)
+    }
+
+    private func privateMediaMessage(
+        id: String,
+        sender: String,
+        senderPeerID: PeerID,
+        recipient: String,
+        filename: String
+    ) -> BitchatMessage {
+        BitchatMessage(
+            id: id,
+            sender: sender,
+            content: "\(MimeType.Category.image.messagePrefix)\(filename)",
+            timestamp: Date(),
+            isRelay: false,
+            isPrivate: true,
+            recipientNickname: recipient,
+            senderPeerID: senderPeerID
+        )
+    }
+}
+
 // MARK: - Panic Clear Tests
 
 struct ChatViewModelPanicTests {

bitchatTests/Mocks/MockTransport.swift

@@ -14,7 +14,7 @@ import BitFoundation
 
 /// Mock Transport implementation for testing ChatViewModel in isolation.
 /// Records all method calls and allows test code to verify interactions.
-final class MockTransport: Transport {
+final class MockTransport: Transport, PrivateMediaDeletionPersisting {
 
     // MARK: - Protocol Properties
 
@@ -38,6 +38,11 @@ final class MockTransport: Transport {
     private(set) var sentPrivateFiles: [(packet: BitchatFilePacket, peerID: PeerID, transferID: String)] = []
     private(set) var sentPrivateFileLegacyAllowances: [Bool] = []
     private(set) var cancelledTransfers: [String] = []
+    private(set) var deletedPrivateMediaMessageIDBatches: [[String]] = []
+    private(set) var deletedPrivateMediaRelativePaths: [
+        [String: String]
+    ] = []
+    private(set) var protectedPrivateMediaRelativePaths: [Set<String>] = []
     private(set) var sentVerifyChallenges: [(peerID: PeerID, noiseKeyHex: String, nonceA: Data)] = []
     private(set) var sentVerifyResponses: [(peerID: PeerID, noiseKeyHex: String, nonceA: Data)] = []
     private(set) var sentCourierMessages: [(content: String, messageID: String, recipientNoiseKey: Data, couriers: [PeerID])] = []
@@ -60,6 +65,11 @@ final class MockTransport: Transport {
     var peerFingerprints: [PeerID: String] = [:]
     var peerNoiseStates: [PeerID: LazyHandshakeState] = [:]
     var privateMediaPolicies: [PeerID: PrivateMediaSendPolicy] = [:]
+    var persistDeletedPrivateMediaResult = true
+    var deferDeletedPrivateMediaPersistence = false
+    private var pendingDeletedPrivateMediaCompletions: [
+        @MainActor (Bool) -> Void
+    ] = []
     private let mockKeychain = MockKeychain()
 
     // MARK: - Transport Protocol Implementation
@@ -217,6 +227,34 @@ final class MockTransport: Transport {
         cancelledTransfers.append(transferId)
     }
 
+    @MainActor
+    func persistDeletedPrivateMedia(
+        messageIDs: [String],
+        payloadRelativePaths: [String: String],
+        protectedPayloadRelativePaths: Set<String>,
+        completion: @escaping @MainActor (Bool) -> Void
+    ) {
+        deletedPrivateMediaMessageIDBatches.append(messageIDs)
+        deletedPrivateMediaRelativePaths.append(payloadRelativePaths)
+        protectedPrivateMediaRelativePaths.append(
+            protectedPayloadRelativePaths
+        )
+        if deferDeletedPrivateMediaPersistence {
+            pendingDeletedPrivateMediaCompletions.append(completion)
+        } else {
+            completion(persistDeletedPrivateMediaResult)
+        }
+    }
+
+    @MainActor
+    func resolveNextDeletedPrivateMediaPersistence(
+        _ result: Bool? = nil
+    ) {
+        guard !pendingDeletedPrivateMediaCompletions.isEmpty else { return }
+        let completion = pendingDeletedPrivateMediaCompletions.removeFirst()
+        completion(result ?? persistDeletedPrivateMediaResult)
+    }
+
     func sendVerifyChallenge(to peerID: PeerID, noiseKeyHex: String, nonceA: Data) {
         sentVerifyChallenges.append((peerID, noiseKeyHex, nonceA))
     }
@@ -264,6 +302,9 @@ final class MockTransport: Transport {
         sentBroadcastFiles.removeAll()
         sentPrivateFiles.removeAll()
         cancelledTransfers.removeAll()
+        deletedPrivateMediaMessageIDBatches.removeAll()
+        deletedPrivateMediaRelativePaths.removeAll()
+        protectedPrivateMediaRelativePaths.removeAll()
         sentVerifyChallenges.removeAll()
         sentVerifyResponses.removeAll()
         startServicesCallCount = 0

bitchatTests/Services/BLEFileTransferHandlerTests.swift

@@ -21,9 +21,12 @@ struct BLEFileTransferHandlerTests {
         var receiptCommits: [(messageID: String, storedURL: URL)] = []
         var receiptCommitSucceeds = true
         var removedIncomingFiles: [URL] = []
+        var finishedIncomingFileDeliveries: [URL] = []
         var lastSeenUpdates: [PeerID] = []
         var deliveryAcks: [(messageID: String, peerID: PeerID)] = []
         var deliveredMessages: [BitchatMessage] = []
+        var shouldAcceptDelivery = true
+        var deliveryOutcome = TransportEventDeliveryOutcome.accepted
         var saveOverride: ((
             _ data: Data,
             _ preferredName: String?,
@@ -34,12 +37,85 @@ struct BLEFileTransferHandlerTests {
         var receiptStateOverride: ((String) -> BLEPrivateMediaReceiptState)?
         var receiptCommitOverride: ((String, URL) -> Bool)?
         var removeIncomingFileOverride: ((URL) -> Void)?
+        var finishIncomingFileDeliveryOverride: ((URL) -> Void)?
     }
 
     private let localPeerID = PeerID(str: "0102030405060708")
     private let remotePeerID = PeerID(str: "1122334455667788")
     private let sampleSigningKey = Data(repeating: 0xAB, count: 32)
 
+    @Test @MainActor
+    func deliveryGateFinalizesInitialRejection() {
+        var completions = 0
+        var finalizations = 0
+
+        TransportEventDeliveryGate.attempt(
+            shouldDeliver: { false },
+            deliver: {
+                Issue.record("delivery sink must not run")
+                return .accepted
+            },
+            completion: { completions += 1 },
+            finalization: { _ in finalizations += 1 }
+        )
+
+        #expect(completions == 0)
+        #expect(finalizations == 1)
+    }
+
+    @Test @MainActor
+    func deliveryGateFinalizesMissingOrRejectingSink() {
+        var completions = 0
+        var finalizations = 0
+
+        TransportEventDeliveryGate.attempt(
+            shouldDeliver: { true },
+            deliver: { .rejected },
+            completion: { completions += 1 },
+            finalization: { _ in finalizations += 1 }
+        )
+
+        #expect(completions == 0)
+        #expect(finalizations == 1)
+    }
+
+    @Test @MainActor
+    func deliveryGateFinalizesPostInsertionRejection() {
+        var deliveryChecks = 0
+        var completions = 0
+        var finalizations = 0
+
+        TransportEventDeliveryGate.attempt(
+            shouldDeliver: {
+                deliveryChecks += 1
+                return deliveryChecks == 1
+            },
+            deliver: { .accepted },
+            completion: { completions += 1 },
+            finalization: { _ in finalizations += 1 }
+        )
+
+        #expect(deliveryChecks == 2)
+        #expect(completions == 0)
+        #expect(finalizations == 1)
+    }
+
+    @Test @MainActor
+    func deliveryGatePreservesInvokedUnconfirmedOutcomeWithoutAck() {
+        var completions = 0
+        var outcomes: [TransportEventDeliveryOutcome] = []
+
+        TransportEventDeliveryGate.attempt(
+            shouldDeliver: { true },
+            deliver: { .invokedUnconfirmed },
+            completion: { completions += 1 },
+            finalization: { outcomes.append($0) }
+        )
+
+        #expect(completions == 0)
+        #expect(outcomes == [.invokedUnconfirmed])
+    }
+
     private func makeHandler(recorder: Recorder) -> BLEFileTransferHandler {
         let environment = BLEFileTransferHandlerEnvironment(
             localPeerID: { [localPeerID] in localPeerID },
@@ -86,6 +162,10 @@ struct BLEFileTransferHandlerTests {
                 recorder.removedIncomingFiles.append(storedURL)
                 recorder.removeIncomingFileOverride?(storedURL)
             },
+            finishIncomingFileDelivery: { storedURL in
+                recorder.finishedIncomingFileDeliveries.append(storedURL)
+                recorder.finishIncomingFileDeliveryOverride?(storedURL)
+            },
             isPrivateMediaSenderBlocked: { peerID in
                 recorder.blockedPeers.contains(peerID)
             },
@@ -95,10 +175,18 @@ struct BLEFileTransferHandlerTests {
             acknowledgePrivateMedia: { messageID, peerID in
                 recorder.deliveryAcks.append((messageID, peerID))
             },
-            deliverMessage: { message, shouldDeliver, completion in
+            deliverMessage: { message, shouldDeliver, completion, finalization in
+                var outcome = TransportEventDeliveryOutcome.rejected
+                defer { finalization(outcome) }
+                guard recorder.shouldAcceptDelivery else { return }
                 guard shouldDeliver() else { return }
                 recorder.deliveredMessages.append(message)
                 guard shouldDeliver() else { return }
+                if recorder.deliveryOutcome == .invokedUnconfirmed {
+                    outcome = .invokedUnconfirmed
+                    return
+                }
+                outcome = .accepted
                 completion()
             }
         )
@@ -375,6 +463,73 @@ struct BLEFileTransferHandlerTests {
         #expect(recorder.deliveryAcks.first?.messageID == recorder.deliveredMessages.first?.id)
     }
 
+    @Test
+    func rejectedStableDeliveryReleasesPendingPayloadOwnership() throws {
+        let root = FileManager.default.temporaryDirectory.appendingPathComponent(
+            "private-media-handler-rejected-\(UUID().uuidString)",
+            isDirectory: true
+        )
+        defer { try? FileManager.default.removeItem(at: root) }
+        let store = BLEIncomingFileStore(baseDirectory: root)
+        let recorder = Recorder()
+        recorder.peers = [remotePeerID: makePeerInfo(
+            remotePeerID,
+            nickname: "Alice",
+            isVerified: true
+        )]
+        recorder.shouldAcceptDelivery = false
+        recorder.saveOverride = {
+            store.save(
+                data: $0,
+                preferredName: $1,
+                subdirectory: $2,
+                fallbackExtension: $3,
+                defaultPrefix: $4
+            )
+        }
+        recorder.receiptStateOverride = {
+            store.privateMediaReceiptState(messageID: $0)
+        }
+        recorder.receiptCommitOverride = {
+            store.commitPrivateMediaFile(messageID: $0, storedURL: $1)
+        }
+        recorder.removeIncomingFileOverride = {
+            store.removeIncomingFile(at: $0)
+        }
+        recorder.finishIncomingFileDeliveryOverride = {
+            store.finishIncomingFileDelivery(at: $0)
+        }
+
+        let content = Data([0xFF, 0xD8, 0xFF, 0xD9])
+        let fileName =
+            "img_20260725_105708_1CC2760D-76AA-40C3-8013-C7FAA6C2EF99.jpg"
+        let file = BitchatFilePacket(
+            fileName: fileName,
+            fileSize: UInt64(content.count),
+            mimeType: "image/jpeg",
+            content: content
+        )
+        let payload = try #require(file.encode())
+        let stableID = try #require(PrivateMediaMessageIdentity.stableID(
+            senderPeerID: remotePeerID,
+            recipientPeerID: localPeerID,
+            fileName: fileName
+        ))
+
+        #expect(makeHandler(recorder: recorder).handlePrivatePayload(
+            payload,
+            from: remotePeerID,
+            timestamp: Date(timeIntervalSince1970: 1_234)
+        ))
+        #expect(recorder.deliveredMessages.isEmpty)
+        #expect(recorder.deliveryAcks.isEmpty)
+        #expect(recorder.finishedIncomingFileDeliveries.count == 1)
+        #expect(store.reservePrivateMediaDeletion(
+            messageIDs: [stableID],
+            payloadRelativePaths: [:]
+        ) != nil)
+    }
+
     @Test
     func rawLegacyPrivateFileWithRetryShapedNameNeverUsesReceiptLedger() throws {
         let recorder = Recorder()
@@ -402,6 +557,64 @@ struct BLEFileTransferHandlerTests {
         #expect(recorder.deliveredMessages.first?.id.hasPrefix("media-") == false)
     }
 
+    @Test
+    func rejectedRawDeliveryRemovesUIUnownedPayload() throws {
+        let recorder = Recorder()
+        recorder.peers = [remotePeerID: makePeerInfo(
+            remotePeerID,
+            nickname: "Alice",
+            isVerified: true,
+            signingPublicKey: sampleSigningKey
+        )]
+        recorder.signatureVerifies = true
+        recorder.shouldAcceptDelivery = false
+        let handler = makeHandler(recorder: recorder)
+        let packet = try makeFileTransferPacket(
+            sender: remotePeerID,
+            mimeType: "image/jpeg",
+            content: Data([0xFF, 0xD8, 0xFF, 0xD9]),
+            recipientID: Data(hexString: localPeerID.id),
+            fileName: "raw-rejected.jpg"
+        )
+
+        #expect(handler.handle(packet, from: remotePeerID))
+        #expect(recorder.deliveredMessages.isEmpty)
+        #expect(recorder.removedIncomingFiles.count == 1)
+        #expect(recorder.removedIncomingFiles.first == recorder.saveResult)
+        #expect(recorder.finishedIncomingFileDeliveries.isEmpty)
+    }
+
+    @Test
+    func plainDelegateRawDeliveryPreservesPayloadWithoutSynchronousAck() throws {
+        let recorder = Recorder()
+        recorder.peers = [remotePeerID: makePeerInfo(
+            remotePeerID,
+            nickname: "Alice",
+            isVerified: true,
+            signingPublicKey: sampleSigningKey
+        )]
+        recorder.signatureVerifies = true
+        recorder.deliveryOutcome = .invokedUnconfirmed
+        let handler = makeHandler(recorder: recorder)
+        let packet = try makeFileTransferPacket(
+            sender: remotePeerID,
+            mimeType: "image/jpeg",
+            content: Data([0xFF, 0xD8, 0xFF, 0xD9]),
+            recipientID: Data(hexString: localPeerID.id),
+            fileName: "plain-delegate.jpg"
+        )
+
+        #expect(handler.handle(packet, from: remotePeerID))
+        #expect(recorder.deliveredMessages.count == 1)
+        #expect(recorder.deliveryAcks.isEmpty)
+        #expect(recorder.removedIncomingFiles.isEmpty)
+        #expect(recorder.finishedIncomingFileDeliveries.count == 1)
+        #expect(
+            recorder.finishedIncomingFileDeliveries.first
+                == recorder.saveResult
+        )
+    }
+
     @Test
     func repeatedLegacyPrivateImageNamesKeepDistinctRandomMessageIDs() throws {
         let recorder = Recorder()
@@ -502,12 +715,7 @@ struct BLEFileTransferHandlerTests {
                 nickname: "Alice",
                 isVerified: true
             )]
-            recorder.saveOverride = {
-                data,
-                preferredName,
-                subdirectory,
-                fallbackExtension,
-                defaultPrefix in
+            recorder.saveOverride = { data, preferredName, subdirectory, fallbackExtension, defaultPrefix in
                 store.save(
                     data: data,
                     preferredName: preferredName,
@@ -525,6 +733,9 @@ struct BLEFileTransferHandlerTests {
             recorder.removeIncomingFileOverride = {
                 store.removeIncomingFile(at: $0)
             }
+            recorder.finishIncomingFileDeliveryOverride = {
+                store.finishIncomingFileDelivery(at: $0)
+            }
         }
 
         let first = Recorder()
@@ -880,6 +1091,21 @@ struct BLEFileTransferHandlerTests {
         let messageID = "media-00112233445566778899aabbccddeeff"
 
         let seed = BLEPrivateMediaReceiptStore(baseDirectory: base)
+        let payload = base
+            .appendingPathComponent(
+                "files/images/incoming",
+                isDirectory: true
+            )
+            .appendingPathComponent("panic-receipt.jpg")
+        try FileManager.default.createDirectory(
+            at: payload.deletingLastPathComponent(),
+            withIntermediateDirectories: true
+        )
+        try Data("secret".utf8).write(to: payload, options: .atomic)
+        #expect(seed.commitAccepted(
+            messageID: messageID,
+            storedURL: payload
+        ))
         #expect(seed.recordDeleted(messageID: messageID))
 
         let store = BLEIncomingFileStore(baseDirectory: base)

bitchatTests/Services/BLEPrivateMediaReceiptStoreTests.swift

@@ -4,8 +4,22 @@ import Testing
 
 struct BLEPrivateMediaReceiptStoreTests {
     private struct TestError: Error {}
+    private struct ReceiptFixture: Codable {
+        let kind: String
+        let relativePath: String?
+        let recordedAt: Date
+    }
+    private struct JournalEntryFixture: Codable {
+        let relativePaths: [String]
+        let recordedAt: Date
+    }
+    private struct JournalFixture: Codable {
+        let version: Int
+        let entries: [String: JournalEntryFixture]
+    }
 
     private let messageID = "media-00112233445566778899aabbccddeeff"
+    private let secondMessageID = "media-ffeeddccbbaa99887766554433221100"
 
     @Test
     func acceptedReceiptPersistsAcrossStoreInstances() throws {
@@ -21,6 +35,215 @@ struct BLEPrivateMediaReceiptStoreTests {
         #expect(relaunched.state(for: messageID) == .accepted(payload))
     }
 
+    @Test
+    func acceptedReceiptRejectsOutgoingPayloadAndCrossIDPathReuse() throws {
+        let root = makeRoot("accepted-ownership")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let incoming = try makePayload(in: root)
+        let outgoingDirectory = root.appendingPathComponent(
+            "files/images/outgoing",
+            isDirectory: true
+        )
+        try FileManager.default.createDirectory(
+            at: outgoingDirectory,
+            withIntermediateDirectories: true
+        )
+        let outgoing = outgoingDirectory.appendingPathComponent("image.jpg")
+        try Data([0x01]).write(to: outgoing)
+        let store = BLEPrivateMediaReceiptStore(baseDirectory: root)
+
+        #expect(!store.commitAccepted(
+            messageID: messageID,
+            storedURL: outgoing
+        ))
+        #expect(store.commitAccepted(
+            messageID: messageID,
+            storedURL: incoming
+        ))
+        #expect(!store.commitAccepted(
+            messageID: secondMessageID,
+            storedURL: incoming
+        ))
+        #expect(FileManager.default.fileExists(atPath: incoming.path))
+        #expect(FileManager.default.fileExists(atPath: outgoing.path))
+    }
+
+    @Test
+    func liveAcceptedPathSurvivesTTLAndCapacityPressure() throws {
+        let root = makeRoot("accepted-retention")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let firstPayload = try makePayload(in: root, name: "first.jpg")
+        let secondPayload = try makePayload(in: root, name: "second.jpg")
+        let recordedAt = Date(timeIntervalSince1970: 2_000)
+        let seed = BLEPrivateMediaReceiptStore(
+            baseDirectory: root,
+            capacity: 1,
+            ttl: 1,
+            now: { recordedAt }
+        )
+        #expect(seed.commitAccepted(
+            messageID: messageID,
+            storedURL: firstPayload
+        ))
+
+        let relaunched = BLEPrivateMediaReceiptStore(
+            baseDirectory: root,
+            capacity: 1,
+            ttl: 1,
+            now: { recordedAt.addingTimeInterval(2) }
+        )
+        #expect(relaunched.state(for: messageID) == .accepted(firstPayload))
+        #expect(!relaunched.commitAccepted(
+            messageID: secondMessageID,
+            storedURL: secondPayload
+        ))
+        #expect(relaunched.state(for: messageID) == .accepted(firstPayload))
+    }
+
+    @Test
+    func incomingAllocationDoesNotReuseReceiptOwnedMissingPath() throws {
+        let root = makeRoot("accepted-reservation")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let original = try makePayload(in: root)
+        #expect(BLEPrivateMediaReceiptStore(
+            baseDirectory: root
+        ).commitAccepted(
+            messageID: messageID,
+            storedURL: original
+        ))
+        try FileManager.default.removeItem(at: original)
+
+        let stored = BLEIncomingFileStore(baseDirectory: root).save(
+            data: Data([0x03]),
+            preferredName: "image.jpg",
+            subdirectory: "images/incoming",
+            fallbackExtension: "jpg",
+            defaultPrefix: "image"
+        )
+
+        #expect(stored?.lastPathComponent != "image.jpg")
+        #expect(stored.map {
+            FileManager.default.fileExists(atPath: $0.path)
+        } == true)
+    }
+
+    @Test
+    func pendingRawArrivalBlocksDeletionFallbackPathReuse() throws {
+        let root = makeRoot("pending-raw-arrival")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let incoming = BLEIncomingFileStore(baseDirectory: root)
+
+        // The old stable bubble names image.jpg, but its receipt and payload
+        // have already been pruned. A raw arrival saves that basename before
+        // its main-actor bubble is inserted.
+        let rawArrival = incoming.save(
+            data: Data([0x03]),
+            preferredName: "image.jpg",
+            subdirectory: "images/incoming",
+            fallbackExtension: "jpg",
+            defaultPrefix: "image"
+        )
+        #expect(rawArrival?.lastPathComponent == "image.jpg")
+
+        let reservation = incoming.reservePrivateMediaDeletion(
+            messageIDs: [messageID],
+            payloadRelativePaths: [
+                messageID: "images/incoming/image.jpg"
+            ]
+        )
+        #expect(reservation == nil)
+        #expect(rawArrival.map {
+            FileManager.default.fileExists(atPath: $0.path)
+        } == true)
+    }
+
+    @Test
+    func quotaDoesNotEvictOrReusePendingDeliveryPath() throws {
+        let root = makeRoot("pending-quota")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let incoming = BLEIncomingFileStore(
+            baseDirectory: root,
+            quotaBytes: 1
+        )
+        let first = try #require(incoming.save(
+            data: Data([0x01, 0x02]),
+            preferredName: "image.jpg",
+            subdirectory: "images/incoming",
+            fallbackExtension: "jpg",
+            defaultPrefix: "image"
+        ))
+
+        incoming.enforceQuota(reservingBytes: 1)
+        #expect(FileManager.default.fileExists(atPath: first.path))
+
+        let second = try #require(incoming.save(
+            data: Data([0x03]),
+            preferredName: "image.jpg",
+            subdirectory: "images/incoming",
+            fallbackExtension: "jpg",
+            defaultPrefix: "image"
+        ))
+        #expect(second != first)
+        #expect(second.lastPathComponent == "image (1).jpg")
+        #expect(FileManager.default.fileExists(atPath: first.path))
+        #expect(FileManager.default.fileExists(atPath: second.path))
+    }
+
+    @Test
+    func invalidReceiptAndJournalCannotTargetOutgoingPayload() throws {
+        let root = makeRoot("invalid-owned-path")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let outgoingDirectory = root.appendingPathComponent(
+            "files/images/outgoing",
+            isDirectory: true
+        )
+        try FileManager.default.createDirectory(
+            at: outgoingDirectory,
+            withIntermediateDirectories: true
+        )
+        let victim = outgoingDirectory.appendingPathComponent("victim.jpg")
+        try Data([0x02]).write(to: victim)
+        let receiptURL = receiptRecord(in: root)
+        try FileManager.default.createDirectory(
+            at: receiptURL.deletingLastPathComponent(),
+            withIntermediateDirectories: true
+        )
+        let fixture = ReceiptFixture(
+            kind: "tombstone",
+            relativePath: "images/outgoing/victim.jpg",
+            recordedAt: Date()
+        )
+        try JSONEncoder().encode(fixture).write(
+            to: receiptURL,
+            options: .atomic
+        )
+
+        #expect(
+            BLEPrivateMediaReceiptStore(baseDirectory: root)
+                .state(for: messageID) == .unavailable
+        )
+        #expect(FileManager.default.fileExists(atPath: victim.path))
+
+        try FileManager.default.removeItem(at: receiptURL)
+        let journal = JournalFixture(
+            version: 1,
+            entries: [messageID: JournalEntryFixture(
+                relativePaths: ["images/outgoing/victim.jpg"],
+                recordedAt: fixture.recordedAt
+            )]
+        )
+        try JSONEncoder().encode(journal).write(
+            to: deletionJournal(in: root),
+            options: .atomic
+        )
+
+        #expect(
+            BLEPrivateMediaReceiptStore(baseDirectory: root)
+                .state(for: messageID) == .unavailable
+        )
+        #expect(FileManager.default.fileExists(atPath: victim.path))
+    }
+
     @Test
     func directoryEnumerationFailureIsUnavailableAndRetriesWithoutCachingEmpty() throws {
         let root = makeRoot("list-failure")
@@ -128,25 +351,447 @@ struct BLEPrivateMediaReceiptStoreTests {
     }
 
     @Test
-    func failedTombstonePersistenceDoesNotPoisonVolatileState() throws {
-        let root = makeRoot("failed-tombstone-write")
+    func deletionBatchCommitsEveryIDBeforeRemovingPayloads() throws {
+        let root = makeRoot("batch")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let firstPayload = try makePayload(in: root, name: "first.jpg")
+        let secondPayload = try makePayload(in: root, name: "second.jpg")
+        let store = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(store.commitAccepted(
+            messageID: messageID,
+            storedURL: firstPayload
+        ))
+        #expect(store.commitAccepted(
+            messageID: secondMessageID,
+            storedURL: secondPayload
+        ))
+
+        #expect(store.recordDeleted(
+            messageIDs: [secondMessageID, messageID]
+        ))
+
+        #expect(store.state(for: messageID) == .tombstoned)
+        #expect(store.state(for: secondMessageID) == .tombstoned)
+        #expect(!FileManager.default.fileExists(atPath: firstPayload.path))
+        #expect(!FileManager.default.fileExists(atPath: secondPayload.path))
+        #expect(!FileManager.default.fileExists(
+            atPath: deletionJournal(in: root).path
+        ))
+    }
+
+    @Test
+    func failedJournalCommitPreservesAcceptedStateAndPayloads() throws {
+        let root = makeRoot("journal-failure")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let firstPayload = try makePayload(in: root, name: "first.jpg")
+        let secondPayload = try makePayload(in: root, name: "second.jpg")
+        let seed = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(seed.commitAccepted(
+            messageID: messageID,
+            storedURL: firstPayload
+        ))
+        #expect(seed.commitAccepted(
+            messageID: secondMessageID,
+            storedURL: secondPayload
+        ))
+
+        let failing = BLEPrivateMediaReceiptStore(
+            baseDirectory: root,
+            dataWriter: { _, _, _ in throw TestError() }
+        )
+        #expect(!failing.recordDeleted(
+            messageIDs: [messageID, secondMessageID]
+        ))
+
+        // A failed commit must not install a volatile tombstone. Otherwise a
+        // sender retry could be ACKed although the caller kept both bubbles.
+        #expect(failing.state(for: messageID) == .accepted(firstPayload))
+        #expect(
+            failing.state(for: secondMessageID) == .accepted(secondPayload)
+        )
+        #expect(FileManager.default.fileExists(atPath: firstPayload.path))
+        #expect(FileManager.default.fileExists(atPath: secondPayload.path))
+        #expect(!FileManager.default.fileExists(
+            atPath: deletionJournal(in: root).path
+        ))
+    }
+
+    @Test
+    func journalRecoversBatchAfterCrashDuringMaterialization() throws {
+        let root = makeRoot("crash-recovery")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let firstPayload = try makePayload(in: root, name: "first.jpg")
+        let secondPayload = try makePayload(in: root, name: "second.jpg")
+        let seed = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(seed.commitAccepted(
+            messageID: messageID,
+            storedURL: firstPayload
+        ))
+        #expect(seed.commitAccepted(
+            messageID: secondMessageID,
+            storedURL: secondPayload
+        ))
+
+        let interrupted = BLEPrivateMediaReceiptStore(
+            baseDirectory: root,
+            dataWriter: { data, url, options in
+                let isJournal =
+                    url.lastPathComponent == ".deletion-journal.json"
+                let isFirstRecord =
+                    url.deletingPathExtension().lastPathComponent == messageID
+                guard isJournal || isFirstRecord else {
+                    throw TestError()
+                }
+                try data.write(to: url, options: options)
+            }
+        )
+        #expect(interrupted.recordDeleted(
+            messageIDs: [messageID, secondMessageID]
+        ))
+        #expect(FileManager.default.fileExists(
+            atPath: deletionJournal(in: root).path
+        ))
+        #expect(!FileManager.default.fileExists(atPath: firstPayload.path))
+        #expect(FileManager.default.fileExists(atPath: secondPayload.path))
+        #expect(interrupted.state(for: messageID) == .tombstoned)
+        #expect(interrupted.state(for: secondMessageID) == .tombstoned)
+
+        let relaunched = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(relaunched.state(for: messageID) == .tombstoned)
+        #expect(relaunched.state(for: secondMessageID) == .tombstoned)
+        #expect(!FileManager.default.fileExists(atPath: firstPayload.path))
+        #expect(!FileManager.default.fileExists(atPath: secondPayload.path))
+        #expect(!FileManager.default.fileExists(
+            atPath: deletionJournal(in: root).path
+        ))
+    }
+
+    @Test
+    func journalRetriesPayloadUnlinkAfterRelaunch() throws {
+        let root = makeRoot("unlink-recovery")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let payload = try makePayload(in: root)
+        let seed = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(seed.commitAccepted(
+            messageID: messageID,
+            storedURL: payload
+        ))
+
+        let unlinkFailure = BLEPrivateMediaReceiptStore(
+            baseDirectory: root,
+            payloadRemover: { _ in throw TestError() }
+        )
+        #expect(unlinkFailure.recordDeleted(messageID: messageID))
+        #expect(unlinkFailure.state(for: messageID) == .tombstoned)
+        #expect(FileManager.default.fileExists(atPath: payload.path))
+        #expect(FileManager.default.fileExists(
+            atPath: deletionJournal(in: root).path
+        ))
+
+        let relaunched = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(relaunched.state(for: messageID) == .tombstoned)
+        #expect(!FileManager.default.fileExists(atPath: payload.path))
+        #expect(!FileManager.default.fileExists(
+            atPath: deletionJournal(in: root).path
+        ))
+    }
+
+    @Test
+    func expiredReceiptUsesFallbackPathForCrashSafeCleanup() throws {
+        let root = makeRoot("expired-fallback")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let payload = try makePayload(in: root)
+        let recordedAt = Date(timeIntervalSince1970: 1_000)
+        let seed = BLEPrivateMediaReceiptStore(
+            baseDirectory: root,
+            ttl: 10,
+            now: { recordedAt }
+        )
+        #expect(seed.commitAccepted(
+            messageID: messageID,
+            storedURL: payload
+        ))
+        // Simulate a receipt pruned by an older app version while its bubble
+        // and payload remain. Current code retains live accepted-path owners.
+        try FileManager.default.removeItem(at: receiptRecord(in: root))
+
+        let afterExpiry = recordedAt.addingTimeInterval(11)
+        let interrupted = BLEPrivateMediaReceiptStore(
+            baseDirectory: root,
+            ttl: 10,
+            now: { afterExpiry },
+            payloadRemover: { _ in throw TestError() }
+        )
+        #expect(interrupted.recordDeleted(
+            messageIDs: [messageID],
+            payloadRelativePaths: [
+                messageID: "images/incoming/image.jpg"
+            ]
+        ))
+        #expect(interrupted.state(for: messageID) == .tombstoned)
+        #expect(FileManager.default.fileExists(atPath: payload.path))
+        #expect(FileManager.default.fileExists(
+            atPath: deletionJournal(in: root).path
+        ))
+
+        let relaunched = BLEPrivateMediaReceiptStore(
+            baseDirectory: root,
+            ttl: 10,
+            now: { afterExpiry }
+        )
+        #expect(relaunched.state(for: messageID) == .tombstoned)
+        #expect(!FileManager.default.fileExists(atPath: payload.path))
+        #expect(!FileManager.default.fileExists(
+            atPath: deletionJournal(in: root).path
+        ))
+    }
+
+    @Test
+    func retryAtSuffixedPathDeletesReceiptAndBubblePayloads() throws {
+        let root = makeRoot("retry-suffix")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let original = try makePayload(in: root)
+        let seed = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(seed.commitAccepted(
+            messageID: messageID,
+            storedURL: original
+        ))
+
+        // Simulate an older build pruning only the receipt. A retry must use a
+        // suffixed filename while the old bubble still references image.jpg.
+        try FileManager.default.removeItem(at: receiptRecord(in: root))
+        let retry = try makePayload(in: root, name: "image (1).jpg")
+        let retried = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(retried.commitAccepted(
+            messageID: messageID,
+            storedURL: retry
+        ))
+
+        #expect(retried.recordDeleted(
+            messageIDs: [messageID],
+            payloadRelativePaths: [
+                messageID: "images/incoming/image.jpg"
+            ]
+        ))
+        #expect(retried.state(for: messageID) == .tombstoned)
+        #expect(!FileManager.default.fileExists(atPath: original.path))
+        #expect(!FileManager.default.fileExists(atPath: retry.path))
+        #expect(!FileManager.default.fileExists(
+            atPath: deletionJournal(in: root).path
+        ))
+
+        let relaunched = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(relaunched.state(for: messageID) == .tombstoned)
+        #expect(!FileManager.default.fileExists(atPath: original.path))
+        #expect(!FileManager.default.fileExists(atPath: retry.path))
+    }
+
+    @Test
+    func protectedUIPathRejectsAcceptedReceiptDeletion() throws {
+        let root = makeRoot("protected-ui-owner")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let payload = try makePayload(in: root)
+        let store = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(store.commitAccepted(
+            messageID: messageID,
+            storedURL: payload
+        ))
+
+        #expect(!store.recordDeleted(
+            messageIDs: [messageID],
+            protectedPayloadRelativePaths: [
+                "images/incoming/image.jpg"
+            ]
+        ))
+        #expect(store.state(for: messageID) == .accepted(payload))
+        #expect(FileManager.default.fileExists(atPath: payload.path))
+    }
+
+    @Test
+    func pathlessNewDeletionFailsWithoutChangingReceiverState() {
+        let root = makeRoot("pathless-delete")
         defer { try? FileManager.default.removeItem(at: root) }
         let store = BLEPrivateMediaReceiptStore(baseDirectory: root)
-        #expect(store.state(for: messageID) == .absent)
 
-        // Force the atomic record write itself to fail after the store has
-        // successfully loaded its empty index.
-        let record = receiptRecord(in: root)
+        #expect(!store.recordDeleted(messageID: messageID))
+        #expect(store.state(for: messageID) == .absent)
+        #expect(!FileManager.default.fileExists(
+            atPath: deletionJournal(in: root).path
+        ))
+    }
+
+    @Test
+    func completedTombstoneNeverDeletesReusedPayloadPath() throws {
+        let root = makeRoot("path-reuse")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let original = try makePayload(in: root)
+        let store = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(store.commitAccepted(
+            messageID: messageID,
+            storedURL: original
+        ))
+        #expect(store.recordDeleted(messageID: messageID))
+        #expect(!FileManager.default.fileExists(atPath: original.path))
+
+        let reused = try makePayload(in: root)
+        #expect(store.commitAccepted(
+            messageID: secondMessageID,
+            storedURL: reused
+        ))
+        #expect(store.state(for: messageID) == .tombstoned)
+        #expect(FileManager.default.fileExists(atPath: reused.path))
+
+        let relaunched = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(relaunched.state(for: messageID) == .tombstoned)
+        #expect(FileManager.default.fileExists(atPath: reused.path))
+        #expect(
+            relaunched.state(for: secondMessageID) == .accepted(reused)
+        )
+    }
+
+    @Test
+    func expiredLegacyPathfulTombstoneDoesNotDeleteAcceptedOwner() throws {
+        let root = makeRoot("legacy-path-conflict")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let payload = try makePayload(in: root)
+        let receiptDirectory = receiptRecord(in: root)
+            .deletingLastPathComponent()
         try FileManager.default.createDirectory(
-            at: record,
+            at: receiptDirectory,
             withIntermediateDirectories: true
         )
-        #expect(!store.recordDeleted(messageID: messageID))
-        try FileManager.default.removeItem(at: record)
+        let recordedAt = Date(timeIntervalSince1970: 3_000)
+        try JSONEncoder().encode(ReceiptFixture(
+            kind: "tombstone",
+            relativePath: "images/incoming/image.jpg",
+            recordedAt: recordedAt
+        )).write(
+            to: receiptRecord(in: root),
+            options: .atomic
+        )
+        try JSONEncoder().encode(ReceiptFixture(
+            kind: "accepted",
+            relativePath: "images/incoming/image.jpg",
+            recordedAt: recordedAt
+        )).write(
+            to: receiptRecord(
+                in: root,
+                messageID: secondMessageID
+            ),
+            options: .atomic
+        )
 
-        // The UI must be able to report the deletion failure without a
-        // process-lifetime tombstone silently hiding a later retry.
+        let store = BLEPrivateMediaReceiptStore(
+            baseDirectory: root,
+            ttl: 1,
+            now: { recordedAt.addingTimeInterval(2) }
+        )
         #expect(store.state(for: messageID) == .absent)
+        #expect(FileManager.default.fileExists(atPath: payload.path))
+        #expect(
+            store.state(for: secondMessageID) == .accepted(payload)
+        )
+        #expect(FileManager.default.fileExists(atPath: payload.path))
+    }
+
+    @Test
+    func expiredLegacyPathfulTombstonePreservesAmbiguousPayload() throws {
+        let root = makeRoot("legacy-expired-cleanup")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let payload = try makePayload(in: root)
+        let receiptURL = receiptRecord(in: root)
+        try FileManager.default.createDirectory(
+            at: receiptURL.deletingLastPathComponent(),
+            withIntermediateDirectories: true
+        )
+        let recordedAt = Date(timeIntervalSince1970: 3_000)
+        try JSONEncoder().encode(ReceiptFixture(
+            kind: "tombstone",
+            relativePath: "images/incoming/image.jpg",
+            recordedAt: recordedAt
+        )).write(to: receiptURL, options: .atomic)
+
+        let store = BLEPrivateMediaReceiptStore(
+            baseDirectory: root,
+            ttl: 1,
+            now: { recordedAt.addingTimeInterval(2) }
+        )
+
+        #expect(store.state(for: messageID) == .absent)
+        #expect(FileManager.default.fileExists(atPath: payload.path))
+        #expect(!FileManager.default.fileExists(atPath: receiptURL.path))
+    }
+
+    @Test
+    func deletionJournalNeverRecursivelyRemovesDirectoryTarget() throws {
+        let root = makeRoot("journal-directory")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let directory = root.appendingPathComponent(
+            "files/images/incoming/archive",
+            isDirectory: true
+        )
+        try FileManager.default.createDirectory(
+            at: directory,
+            withIntermediateDirectories: true
+        )
+        let child = directory.appendingPathComponent("child.jpg")
+        try Data([0x01]).write(to: child)
+        let receiptDirectory = receiptRecord(in: root)
+            .deletingLastPathComponent()
+        try FileManager.default.createDirectory(
+            at: receiptDirectory,
+            withIntermediateDirectories: true
+        )
+        #expect(!BLEPrivateMediaReceiptStore(
+            baseDirectory: root
+        ).recordDeleted(
+            messageIDs: [messageID],
+            payloadRelativePaths: [
+                messageID: "images/incoming/archive"
+            ]
+        ))
+        #expect(!FileManager.default.fileExists(
+            atPath: deletionJournal(in: root).path
+        ))
+        try JSONEncoder().encode(JournalFixture(
+            version: 1,
+            entries: [messageID: JournalEntryFixture(
+                relativePaths: ["images/incoming/archive"],
+                recordedAt: Date()
+            )]
+        )).write(to: deletionJournal(in: root), options: .atomic)
+
+        let store = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(store.state(for: messageID) == .tombstoned)
+        #expect(FileManager.default.fileExists(atPath: directory.path))
+        #expect(FileManager.default.fileExists(atPath: child.path))
+        #expect(FileManager.default.fileExists(
+            atPath: deletionJournal(in: root).path
+        ))
+    }
+
+    @Test
+    func corruptDeletionJournalFailsClosedWithoutRemovingPayload() throws {
+        let root = makeRoot("corrupt-journal")
+        defer { try? FileManager.default.removeItem(at: root) }
+        let payload = try makePayload(in: root)
+        #expect(BLEPrivateMediaReceiptStore(
+            baseDirectory: root
+        ).commitAccepted(
+            messageID: messageID,
+            storedURL: payload
+        ))
+        let journal = deletionJournal(in: root)
+        try Data("{not-json".utf8).write(to: journal, options: .atomic)
+
+        let relaunched = BLEPrivateMediaReceiptStore(baseDirectory: root)
+        #expect(relaunched.state(for: messageID) == .unavailable)
+        #expect(!relaunched.commitAccepted(
+            messageID: messageID,
+            storedURL: payload
+        ))
+        #expect(FileManager.default.fileExists(atPath: payload.path))
+        #expect(try Data(contentsOf: journal) == Data("{not-json".utf8))
     }
 
     @Test
@@ -180,7 +825,10 @@ struct BLEPrivateMediaReceiptStoreTests {
         )
     }
 
-    private func makePayload(in root: URL) throws -> URL {
+    private func makePayload(
+        in root: URL,
+        name: String = "image.jpg"
+    ) throws -> URL {
         let directory = root.appendingPathComponent(
             "files/images/incoming",
             isDirectory: true
@@ -189,18 +837,30 @@ struct BLEPrivateMediaReceiptStoreTests {
             at: directory,
             withIntermediateDirectories: true
         )
-        let payload = directory.appendingPathComponent("image.jpg")
+        let payload = directory.appendingPathComponent(name)
         try Data([0xFF, 0xD8, 0xFF, 0xD9]).write(to: payload)
         return payload
     }
 
-    private func receiptRecord(in root: URL) -> URL {
+    private func receiptRecord(
+        in root: URL,
+        messageID requestedMessageID: String? = nil
+    ) -> URL {
         root
             .appendingPathComponent(
                 "files/.private-media-receipts",
                 isDirectory: true
             )
-            .appendingPathComponent(messageID)
+            .appendingPathComponent(requestedMessageID ?? messageID)
             .appendingPathExtension("json")
     }
+
+    private func deletionJournal(in root: URL) -> URL {
+        root
+            .appendingPathComponent(
+                "files/.private-media-receipts",
+                isDirectory: true
+            )
+            .appendingPathComponent(".deletion-journal.json")
+    }
 }