Harden panic keychain and media cleanup

bitchat/Services/KeychainManager.swift

@@ -18,6 +18,47 @@ enum KeychainInstallLifecycleAction: Equatable {
     case retryLater
 }
 
+/// Process-local fail-closed gate for an unresolved install lifecycle.
+///
+/// A blocked caller may perform one synchronous reconciliation attempt.
+/// Concurrent callers fail closed instead of reading while that cleanup is
+/// in flight. Once reconciliation succeeds, access remains open.
+final class KeychainInstallAccessGate: @unchecked Sendable {
+    private let lock = NSLock()
+    private var blocked = false
+    private var reconciliationInProgress = false
+
+    func block() {
+        lock.lock()
+        blocked = true
+        lock.unlock()
+    }
+
+    func allowsAccess(reconcile: () -> Bool) -> Bool {
+        lock.lock()
+        if !blocked {
+            lock.unlock()
+            return true
+        }
+        guard !reconciliationInProgress else {
+            lock.unlock()
+            return false
+        }
+        reconciliationInProgress = true
+        lock.unlock()
+
+        let completed = reconcile()
+
+        lock.lock()
+        if completed {
+            blocked = false
+        }
+        reconciliationInProgress = false
+        lock.unlock()
+        return completed
+    }
+}
+
 final class KeychainManager: KeychainManagerProtocol {
     /// Default keychain for components that construct their own rather than
     /// having one injected. Under test this is an in-memory keychain: the
@@ -48,6 +89,24 @@ final class KeychainManager: KeychainManagerProtocol {
     // Use consistent service name for all keychain items
     private let service = BitchatApp.bundleID
     private let appGroup = "group.\(BitchatApp.bundleID)"
+    #if os(iOS)
+    private let installAccessGate = KeychainInstallAccessGate()
+    #endif
+    /// Every generic-password service owned by this app, including names used
+    /// by older releases. Keep custom services here so one-time security
+    /// migrations and panic deletion cannot silently miss them.
+    private static let additionalApplicationOwnedServices = [
+        "chat.bitchat.nostr",
+        "chat.bitchat.favorites",
+        "chat.bitchat.outbox",
+        "com.bitchat.passwords",
+        "com.bitchat.deviceidentity",
+        "com.bitchat.noise.identity",
+        "chat.bitchat.passwords",
+        "bitchat.keychain",
+        "bitchat",
+        "com.bitchat"
+    ]
     // AfterFirstUnlock, not WhenUnlocked: the mesh keeps running with the
     // device locked (identity-cache saves failed with -25308 throughout
     // locked-phone testing), and a wake-on-proximity relaunch via BLE state
@@ -58,15 +117,27 @@ final class KeychainManager: KeychainManagerProtocol {
 
     init() {
         #if os(iOS)
-        reconcileInstallLifecycle()
+        if reconcileInstallLifecycle() {
             migrateAccessibilityIfNeeded()
+        } else {
+            installAccessGate.block()
+        }
         #endif
     }
 
     static func installLifecycleAction(
         containerKnowsMarker: Bool,
+        cleanupPending: Bool = false,
         markerRead: KeychainReadResult
     ) -> KeychainInstallLifecycleAction {
+        // Once a reinstall cleanup has started, its container-local latch
+        // must win even if the keychain marker was deleted before a later
+        // keychain operation failed. Otherwise the next launch could mistake
+        // a partial cleanup for a fresh bootstrap and preserve stale secrets.
+        if cleanupPending {
+            return .clearStaleKeys
+        }
+
         switch markerRead {
         case .success:
             return containerKnowsMarker ? .markerPresent : .clearStaleKeys
@@ -77,42 +148,158 @@ final class KeychainManager: KeychainManagerProtocol {
         }
     }
 
+    static func applicationOwnedKeychainServices(primaryService: String) -> [String] {
+        var seen = Set<String>()
+        return ([primaryService] + additionalApplicationOwnedServices).filter {
+            seen.insert($0).inserted
+        }
+    }
+
+    /// Runs every service update even after one failure. Successful updates
+    /// are idempotent, while returning false keeps the one-time flag unset so
+    /// a later unlocked launch retries the incomplete migration.
+    static func migrateAccessibilityForApplicationOwnedServices(
+        primaryService: String,
+        updateService: (String) -> OSStatus
+    ) -> Bool {
+        var completed = true
+        for serviceName in applicationOwnedKeychainServices(
+            primaryService: primaryService
+        ) {
+            let status = updateService(serviceName)
+            if status != errSecSuccess && status != errSecItemNotFound {
+                completed = false
+            }
+        }
+        return completed
+    }
+
+    /// Deletes every declared service even after one failure. An empty scope
+    /// is already clean, while any other status leaves the cleanup
+    /// incomplete so its durable retry marker remains set.
+    static func deleteApplicationOwnedKeychainServices(
+        primaryService: String,
+        deleteService: (String) -> OSStatus
+    ) -> Bool {
+        var completed = true
+        for serviceName in applicationOwnedKeychainServices(
+            primaryService: primaryService
+        ) {
+            let status = deleteService(serviceName)
+            if status != errSecSuccess && status != errSecItemNotFound {
+                completed = false
+            }
+        }
+        return completed
+    }
+
+    /// The app currently has an application-group entitlement, not a
+    /// keychain-access-group entitlement. Keep the historical group cleanup
+    /// probe as best effort without making its expected -34018 response block
+    /// panic recovery forever.
+    static func completedApplicationGroupDelete(status: OSStatus) -> Bool {
+        status == errSecSuccess
+            || status == errSecItemNotFound
+            || status == -34018
+    }
+
     #if os(iOS)
 
     private static let installMarkerAccount = "install_lifecycle_marker"
     private static let installMarkerDefaultsKey = "keychain.installLifecycleMarker.present"
+    private static let installCleanupPendingDefaultsKey =
+        "keychain.installLifecycleCleanup.pending"
 
     /// Keychain items can survive app removal while the app container and its
     /// UserDefaults do not. The first version carrying this marker bootstraps
     /// without deleting existing users' identities. On a later reinstall, a
     /// surviving keychain marker plus a missing defaults marker proves the app
     /// container was replaced, so stale secrets are removed before use.
-    private func reconcileInstallLifecycle() {
+    @discardableResult
+    private func reconcileInstallLifecycle() -> Bool {
         let defaults = UserDefaults.standard
         let containerKnowsMarker = defaults.bool(forKey: Self.installMarkerDefaultsKey)
+        let cleanupPending = defaults.bool(
+            forKey: Self.installCleanupPendingDefaultsKey
+        )
 
         let markerRead = retrieveDataWithResult(forKey: Self.installMarkerAccount)
         switch Self.installLifecycleAction(
             containerKnowsMarker: containerKnowsMarker,
+            cleanupPending: cleanupPending,
             markerRead: markerRead
         ) {
         case .markerPresent:
             defaults.set(true, forKey: Self.installMarkerDefaultsKey)
+            return true
 
         case .bootstrapMarker:
             if case .success = saveDataWithResult(Data([1]), forKey: Self.installMarkerAccount) {
                 defaults.set(true, forKey: Self.installMarkerDefaultsKey)
             }
+            // A missing marker is the intentional bootstrap path for both a
+            // fresh install and the first marker-carrying upgrade. Preserve
+            // existing users' identities even if marker creation must retry
+            // on a later construction.
+            return true
 
         case .clearStaleKeys:
-            _ = deleteAllKeychainData()
+            // Establish a container-local retry latch before deleting the
+            // surviving keychain marker. If the process exits or any keychain
+            // operation fails, the next launch retries even when that marker
+            // can no longer be read.
+            defaults.set(true, forKey: Self.installCleanupPendingDefaultsKey)
+            guard defaults.synchronize(),
+                  defaults.bool(forKey: Self.installCleanupPendingDefaultsKey)
+            else {
+                SecureLogger.error(
+                    "Could not persist reinstall keychain-cleanup intent",
+                    category: .security
+                )
+                return false
+            }
+
+            guard deleteAllKeychainData() else {
+                SecureLogger.error(
+                    "Reinstall keychain cleanup incomplete; retry remains pending",
+                    category: .security
+                )
+                return false
+            }
+
             defaults.set(true, forKey: Self.installMarkerDefaultsKey)
+            defaults.removeObject(
+                forKey: Self.installCleanupPendingDefaultsKey
+            )
+            guard defaults.synchronize(),
+                  defaults.bool(forKey: Self.installMarkerDefaultsKey),
+                  !defaults.bool(
+                    forKey: Self.installCleanupPendingDefaultsKey
+                  )
+            else {
+                // Preserve the fail-closed state in memory and make one more
+                // best-effort persistence attempt before startup continues.
+                defaults.set(
+                    true,
+                    forKey: Self.installCleanupPendingDefaultsKey
+                )
+                _ = defaults.synchronize()
+                SecureLogger.error(
+                    "Could not commit reinstall keychain-cleanup state; retry remains pending",
+                    category: .security
+                )
+                return false
+            }
+            return true
 
         case .retryLater:
             // Do not guess that a temporarily unreadable marker is absent.
-            // Leaving the defaults flag unchanged lets a later construction
+            // An established container may keep using ordinary protected-data
-            // retry once protected keychain data is available.
+            // semantics: reads fail while locked and recover after unlock. A
-            break
+            // container that has not committed the marker must stay blocked
+            // until the marker becomes readable and this state machine can
+            // distinguish bootstrap from reinstall.
+            return containerKnowsMarker
         }
     }
 
@@ -124,30 +311,59 @@ final class KeychainManager: KeychainManagerProtocol {
         let flag = "keychain.accessibility.afterFirstUnlockThisDeviceOnly.migrated"
         guard !UserDefaults.standard.bool(forKey: flag) else { return }
 
-        let query: [String: Any] = [
-            kSecClass as String: kSecClassGenericPassword,
-            kSecAttrService as String: service
-        ]
         let update: [String: Any] = [
             kSecAttrAccessible as String: Self.itemAccessibility
         ]
-        let status = SecItemUpdate(query as CFDictionary, update as CFDictionary)
+        let completed = Self.migrateAccessibilityForApplicationOwnedServices(
-        switch status {
+            primaryService: service
-        case errSecSuccess, errSecItemNotFound:
+        ) { serviceName in
-            // Nothing to migrate on a fresh install; both are terminal.
+            let query: [String: Any] = [
+                kSecClass as String: kSecClassGenericPassword,
+                kSecAttrService as String: serviceName
+            ]
+            return SecItemUpdate(
+                query as CFDictionary,
+                update as CFDictionary
+            )
+        }
+        if completed {
+            // Missing services on a fresh install are terminal, but the flag is
+            // set only after every application-owned service was considered.
             UserDefaults.standard.set(true, forKey: flag)
-            SecureLogger.info("Keychain accessibility migrated to AfterFirstUnlockThisDeviceOnly (status \(status))", category: .keychain)
+            SecureLogger.info(
-        default:
+                "Keychain accessibility migrated to AfterFirstUnlockThisDeviceOnly",
+                category: .keychain
+            )
+        } else {
             // Likely errSecInteractionNotAllowed (relaunched while locked) —
             // leave the flag unset so the next launch retries.
-            SecureLogger.warning("Keychain accessibility migration deferred (status \(status))", category: .keychain)
+            SecureLogger.warning(
+                "Keychain accessibility migration deferred for at least one application-owned service",
+                category: .keychain
+            )
         }
     }
     #endif
 
+    private func installAccessAllowed() -> Bool {
+        #if os(iOS)
+        return installAccessGate.allowsAccess { [self] in
+            guard reconcileInstallLifecycle() else { return false }
+            migrateAccessibilityIfNeeded()
+            return true
+        }
+        #else
+        return true
+        #endif
+    }
+
     // MARK: - Identity Keys
     
     func saveIdentityKey(_ keyData: Data, forKey key: String) -> Bool {
+        guard installAccessAllowed() else {
+            SecureLogger.logKeyOperation(.save, keyType: key, success: false)
+            return false
+        }
         let fullKey = "identity_\(key)"
         let result = saveData(keyData, forKey: fullKey)
         SecureLogger.logKeyOperation(.save, keyType: key, success: result)
@@ -155,11 +371,16 @@ final class KeychainManager: KeychainManagerProtocol {
     }
     
     func getIdentityKey(forKey key: String) -> Data? {
+        guard installAccessAllowed() else { return nil }
         let fullKey = "identity_\(key)"
         return retrieveData(forKey: fullKey)
     }
     
     func deleteIdentityKey(forKey key: String) -> Bool {
+        guard installAccessAllowed() else {
+            SecureLogger.logKeyOperation(.delete, keyType: key, success: false)
+            return false
+        }
         let result = delete(forKey: "identity_\(key)")
         SecureLogger.logKeyOperation(.delete, keyType: key, success: result)
         return result
@@ -170,12 +391,14 @@ final class KeychainManager: KeychainManagerProtocol {
     /// Get identity key with detailed result for proper error handling
     /// Distinguishes between missing keys (expected) and critical failures
     func getIdentityKeyWithResult(forKey key: String) -> KeychainReadResult {
+        guard installAccessAllowed() else { return .accessDenied }
         let fullKey = "identity_\(key)"
         return retrieveDataWithResult(forKey: fullKey)
     }
 
     /// Save identity key with detailed result and retry logic for transient errors
     func saveIdentityKeyWithResult(_ keyData: Data, forKey key: String) -> KeychainSaveResult {
+        guard installAccessAllowed() else { return .accessDenied }
         let fullKey = "identity_\(key)"
         return saveDataWithResult(keyData, forKey: fullKey)
     }
@@ -446,122 +669,164 @@ final class KeychainManager: KeychainManagerProtocol {
     func deleteAllKeychainData() -> Bool {
         SecureLogger.warning("Panic mode - deleting all keychain data", category: .security)
 
-        var totalDeleted = 0
+        let ownedServices = Set(
-        
+            Self.applicationOwnedKeychainServices(
-        // Search without service restriction to catch all items
+                primaryService: service
+            )
+        )
+        var enumerationCompleted = true
         let searchQuery: [String: Any] = [
             kSecClass as String: kSecClassGenericPassword,
             kSecMatchLimit as String: kSecMatchLimitAll,
             kSecReturnAttributes as String: true
         ]
-        
         var result: AnyObject?
-        let searchStatus = SecItemCopyMatching(searchQuery as CFDictionary, &result)
+        let searchStatus = SecItemCopyMatching(
+            searchQuery as CFDictionary,
+            &result
+        )
+        switch searchStatus {
+        case errSecSuccess:
+            guard let items = result as? [[String: Any]] else {
+                enumerationCompleted = false
+                SecureLogger.error(
+                    "Unable to decode application-owned keychain inventory",
+                    category: .security
+                )
+                break
+            }
 
-        if searchStatus == errSecSuccess, let items = result as? [[String: Any]] {
+            // Preserve the access-group sweep for custom services that are
+            // not yet in the declared legacy-service list.
             for item in items {
-                var shouldDelete = false
+                let account =
-                let account = item[kSecAttrAccount as String] as? String ?? ""
+                    item[kSecAttrAccount as String] as? String ?? ""
-                let service = item[kSecAttrService as String] as? String ?? ""
+                let itemService =
-                let accessGroup = item[kSecAttrAccessGroup as String] as? String
+                    item[kSecAttrService as String] as? String ?? ""
-                
+                let accessGroup =
-                // More precise deletion criteria:
+                    item[kSecAttrAccessGroup as String] as? String
-                // 1. Check for our specific app group
+                guard accessGroup == appGroup
-                // 2. OR check for our exact service name
+                        || ownedServices.contains(itemService)
-                // 3. OR check for known legacy service names
+                else {
-                if accessGroup == appGroup {
+                    continue
-                    shouldDelete = true
-                } else if service == self.service {
-                    shouldDelete = true
-                } else if [
-                    "com.bitchat.passwords",
-                    "com.bitchat.deviceidentity",
-                    "com.bitchat.noise.identity",
-                    "chat.bitchat.passwords",
-                    "bitchat.keychain",
-                    "bitchat",
-                    "com.bitchat"
-                ].contains(service) {
-                    shouldDelete = true
                 }
 
-                if shouldDelete {
-                    // Build delete query with all available attributes for precise deletion
                 var deleteQuery: [String: Any] = [
                     kSecClass as String: kSecClassGenericPassword
                 ]
-                    
                 if !account.isEmpty {
                     deleteQuery[kSecAttrAccount as String] = account
                 }
-                    if !service.isEmpty {
+                if !itemService.isEmpty {
-                        deleteQuery[kSecAttrService as String] = service
+                    deleteQuery[kSecAttrService as String] = itemService
                 }
-                    
+                if let accessGroup,
-                    // Add access group if present
+                   !accessGroup.isEmpty,
-                    if let accessGroup = item[kSecAttrAccessGroup as String] as? String,
+                   accessGroup != "test" {
-                       !accessGroup.isEmpty && accessGroup != "test" {
                     deleteQuery[kSecAttrAccessGroup as String] = accessGroup
                 }
 
-                    let deleteStatus = SecItemDelete(deleteQuery as CFDictionary)
+                let status = SecItemDelete(deleteQuery as CFDictionary)
-                    if deleteStatus == errSecSuccess {
+                if status != errSecSuccess && status != errSecItemNotFound {
-                        totalDeleted += 1
+                    enumerationCompleted = false
-                        SecureLogger.info("Deleted keychain item: \(account) from \(service)", category: .keychain)
+                    SecureLogger.error(
-                    }
+                        NSError(domain: "Keychain", code: Int(status)),
-                }
+                        context: "Unable to delete enumerated application-owned keychain item",
+                        category: .keychain
+                    )
                 }
             }
 
-        // Also try to delete by known service names and app group
+        case errSecItemNotFound:
-        // This catches any items that might have been missed above
+            break
-        let knownServices = [
-            self.service,  // Current service name
-            "com.bitchat.passwords",
-            "com.bitchat.deviceidentity", 
-            "com.bitchat.noise.identity",
-            "chat.bitchat.passwords",
-            "chat.bitchat.nostr",
-            "bitchat.keychain",
-            "bitchat",
-            "com.bitchat"
-        ]
 
-        for serviceName in knownServices {
+        default:
+            enumerationCompleted = false
+            SecureLogger.error(
+                NSError(domain: "Keychain", code: Int(searchStatus)),
+                context: "Unable to enumerate application-owned keychain items",
+                category: .keychain
+            )
+        }
+
+        // Bulk deletion by every application-owned service is authoritative
+        // and idempotent. It also verifies that every known service scope is
+        // empty even when the inventory pass found no items.
+        let servicesCompleted =
+            Self.deleteApplicationOwnedKeychainServices(
+                primaryService: service
+            ) { serviceName in
                 let query: [String: Any] = [
                     kSecClass as String: kSecClassGenericPassword,
                     kSecAttrService as String: serviceName
                 ]
-            
                 let status = SecItemDelete(query as CFDictionary)
-            if status == errSecSuccess {
+                if status != errSecSuccess && status != errSecItemNotFound {
-                totalDeleted += 1
+                    SecureLogger.error(
+                        NSError(domain: "Keychain", code: Int(status)),
+                        context: "Unable to delete application-owned keychain service \(serviceName)",
+                        category: .keychain
+                    )
                 }
+                return status
             }
 
-        // Also delete by app group to ensure complete cleanup
+        // Historical builds attempted this application-group identifier as a
+        // keychain access group. It is not currently entitled, so -34018
+        // means the scope is inapplicable rather than partially deleted.
         let groupQuery: [String: Any] = [
             kSecClass as String: kSecClassGenericPassword,
             kSecAttrAccessGroup as String: appGroup
         ]
-        
         let groupStatus = SecItemDelete(groupQuery as CFDictionary)
-        if groupStatus == errSecSuccess {
+        let groupCompleted = Self.completedApplicationGroupDelete(
-            totalDeleted += 1
+            status: groupStatus
+        )
+        if !groupCompleted {
+            SecureLogger.error(
+                NSError(domain: "Keychain", code: Int(groupStatus)),
+                context: "Unable to delete historical application-group keychain items",
+                category: .keychain
+            )
         }
 
-        SecureLogger.warning("Panic mode cleanup completed. Total items deleted: \(totalDeleted)", category: .keychain)
+        var markerCompleted = true
-
         #if os(iOS)
         // The non-secret marker is intentionally recreated after a panic so a
         // later uninstall/reinstall can still be distinguished from an in-place
-        // upgrade. It never restores any wiped identity or relationship data.
+        // upgrade. Do not commit the container-side marker here: reinstall
-        if case .success = saveDataWithResult(Data([1]), forKey: Self.installMarkerAccount) {
+        // reconciliation may still need to retry an incomplete cleanup.
-            UserDefaults.standard.set(true, forKey: Self.installMarkerDefaultsKey)
+        if case .success = saveDataWithResult(
+            Data([1]),
+            forKey: Self.installMarkerAccount
+        ) {
+            markerCompleted = true
+        } else {
+            markerCompleted = false
+            SecureLogger.error(
+                "Unable to restore install-lifecycle keychain marker",
+                category: .security
+            )
         }
         #endif
 
-        return totalDeleted > 0
+        let completed =
+            enumerationCompleted
+            && servicesCompleted
+            && groupCompleted
+            && markerCompleted
+        if completed {
+            SecureLogger.warning(
+                "Panic mode keychain cleanup completed",
+                category: .keychain
+            )
+        } else {
+            SecureLogger.error(
+                "Panic mode keychain cleanup incomplete",
+                category: .security
+            )
+        }
+        return completed
     }
     
     // MARK: - Security Utilities
@@ -587,6 +852,7 @@ final class KeychainManager: KeychainManagerProtocol {
     // MARK: - Debug
 
     func verifyIdentityKeyExists() -> Bool {
+        guard installAccessAllowed() else { return false }
         let key = "identity_noiseStaticKey"
         return retrieveData(forKey: key) != nil
     }
@@ -595,6 +861,7 @@ final class KeychainManager: KeychainManagerProtocol {
 
     /// Save data with a custom service name
     func save(key: String, data: Data, service customService: String, accessible: CFString?) {
+        guard installAccessAllowed() else { return }
         let primaryKeyQuery: [String: Any] = [
             kSecClass as String: kSecClassGenericPassword,
             kSecAttrService as String: customService,
@@ -641,6 +908,7 @@ final class KeychainManager: KeychainManagerProtocol {
     /// Load custom-service data without collapsing `itemNotFound` and
     /// protected-data/keychain failures into the same nil result.
     func loadWithResult(key: String, service customService: String) -> KeychainReadResult {
+        guard installAccessAllowed() else { return .accessDenied }
         let query: [String: Any] = [
             kSecClass as String: kSecClassGenericPassword,
             kSecAttrService as String: customService,
@@ -655,6 +923,7 @@ final class KeychainManager: KeychainManagerProtocol {
 
     /// Delete data from a custom service
     func delete(key: String, service customService: String) {
+        guard installAccessAllowed() else { return }
         let query: [String: Any] = [
             kSecClass as String: kSecClassGenericPassword,
             kSecAttrService as String: customService,
@@ -666,6 +935,7 @@ final class KeychainManager: KeychainManagerProtocol {
 
     /// Delete every item stored under a custom service
     func deleteAll(service customService: String) {
+        guard installAccessAllowed() else { return }
         let query: [String: Any] = [
             kSecClass as String: kSecClassGenericPassword,
             kSecAttrService as String: customService,

bitchat/ViewModels/ChatMediaTransferCoordinator.swift

@@ -72,16 +72,79 @@ extension ChatViewModel: ChatMediaTransferContext {
     }
 }
 
+/// Synchronous boundary between detached image writers and panic deletion.
+///
+/// Invalidation closes admission before waiting for writers that already
+/// entered. Those writers never need the main actor while inside the boundary,
+/// so a synchronous panic transaction can safely join them and then delete
+/// every output before reporting completion.
+private final class ImagePreparationBarrier: @unchecked Sendable {
+    private let condition = NSCondition()
+    private var generation: UInt64 = 0
+    private var activeOperations = 0
+
+    var currentGeneration: UInt64 {
+        condition.lock()
+        defer { condition.unlock() }
+        return generation
+    }
+
+    func isCurrent(_ candidate: UInt64) -> Bool {
+        condition.lock()
+        defer { condition.unlock() }
+        return generation == candidate
+    }
+
+    func performIfCurrent<T>(
+        generation candidate: UInt64,
+        operation: () throws -> T
+    ) rethrows -> T? {
+        condition.lock()
+        guard generation == candidate else {
+            condition.unlock()
+            return nil
+        }
+        activeOperations += 1
+        condition.unlock()
+
+        defer {
+            condition.lock()
+            activeOperations -= 1
+            if activeOperations == 0 {
+                condition.broadcast()
+            }
+            condition.unlock()
+        }
+        return try operation()
+    }
+
+    func invalidateAndWait() {
+        condition.lock()
+        generation &+= 1
+        while activeOperations > 0 {
+            condition.wait()
+        }
+        condition.unlock()
+    }
+}
+
 @MainActor
 final class ChatMediaTransferCoordinator {
     private unowned let context: any ChatMediaTransferContext
+    private let prepareImagePacket: @Sendable (URL) throws -> ChatPreparedImage
+    private let imagePreparationBarrier = ImagePreparationBarrier()
 
     private(set) var transferIdToMessageIDs: [String: [String]] = [:]
     private(set) var messageIDToTransferId: [String: String] = [:]
-    private var preparationGeneration: UInt64 = 0
 
-    init(context: any ChatMediaTransferContext) {
+    init(
+        context: any ChatMediaTransferContext,
+        prepareImagePacket: @escaping @Sendable (URL) throws -> ChatPreparedImage = {
+            try ChatMediaPreparation.prepareImagePacket(from: $0)
+        }
+    ) {
         self.context = context
+        self.prepareImagePacket = prepareImagePacket
     }
 
     func sendVoiceNote(at url: URL) {
@@ -99,14 +162,17 @@ final class ChatMediaTransferCoordinator {
         )
         let messageID = message.id
         let transferId = makeTransferID(messageID: messageID)
-        let generation = preparationGeneration
+        let generation = imagePreparationBarrier.currentGeneration
 
         Task.detached(priority: .userInitiated) { [weak self] in
             do {
                 let packet = try ChatMediaPreparation.prepareVoiceNotePacket(at: url)
 
                 await MainActor.run { [weak self] in
-                    guard let self, self.preparationGeneration == generation else { return }
+                    guard let self,
+                          self.imagePreparationBarrier.isCurrent(generation) else {
+                        return
+                    }
                     self.registerTransfer(transferId: transferId, messageID: messageID)
                     if let peerID = targetPeer {
                         self.context.sendFilePrivate(packet, to: peerID, transferId: transferId)
@@ -118,13 +184,19 @@ final class ChatMediaTransferCoordinator {
                 SecureLogger.warning("Voice note exceeds size limit (\(size) bytes)", category: .session)
                 try? FileManager.default.removeItem(at: url)
                 await MainActor.run { [weak self] in
-                    guard let self, self.preparationGeneration == generation else { return }
+                    guard let self,
+                          self.imagePreparationBarrier.isCurrent(generation) else {
+                        return
+                    }
                     self.handleMediaSendFailure(messageID: messageID, reason: String(localized: "content.delivery.reason.voice_too_large", comment: "Failure reason shown when a voice note exceeds the size limit"))
                 }
             } catch {
                 SecureLogger.error("Voice note send failed: \(error)", category: .session)
                 await MainActor.run { [weak self] in
-                    guard let self, self.preparationGeneration == generation else { return }
+                    guard let self,
+                          self.imagePreparationBarrier.isCurrent(generation) else {
+                        return
+                    }
                     self.handleMediaSendFailure(messageID: messageID, reason: String(localized: "content.delivery.reason.voice_send_failed", comment: "Failure reason shown when a voice note could not be sent"))
                 }
             }
@@ -134,12 +206,21 @@ final class ChatMediaTransferCoordinator {
     #if os(iOS)
     func processThenSendImage(_ image: UIImage?) {
         guard let image else { return }
-        let generation = preparationGeneration
+        let generation = imagePreparationBarrier.currentGeneration
-        Task.detached { [weak self] in
+        let barrier = imagePreparationBarrier
+        Task.detached(priority: .userInitiated) { [weak self, barrier] in
             do {
-                let processedURL = try ImageUtils.processImage(image)
+                guard let processedURL = try barrier.performIfCurrent(
-                await MainActor.run { [weak self] in
+                    generation: generation,
-                    guard let self, self.preparationGeneration == generation else {
+                    operation: {
+                        try ImageUtils.processImage(image)
+                    }
+                ) else {
+                    return
+                }
+                await MainActor.run { [weak self, barrier] in
+                    guard let self,
+                          barrier.isCurrent(generation) else {
                         try? FileManager.default.removeItem(at: processedURL)
                         return
                     }
@@ -153,12 +234,21 @@ final class ChatMediaTransferCoordinator {
     #elseif os(macOS)
     func processThenSendImage(from url: URL?) {
         guard let url else { return }
-        let generation = preparationGeneration
+        let generation = imagePreparationBarrier.currentGeneration
-        Task.detached { [weak self] in
+        let barrier = imagePreparationBarrier
+        Task.detached(priority: .userInitiated) { [weak self, barrier] in
             do {
-                let processedURL = try ImageUtils.processImage(at: url)
+                guard let processedURL = try barrier.performIfCurrent(
-                await MainActor.run { [weak self] in
+                    generation: generation,
-                    guard let self, self.preparationGeneration == generation else {
+                    operation: {
+                        try ImageUtils.processImage(at: url)
+                    }
+                ) else {
+                    return
+                }
+                await MainActor.run { [weak self, barrier] in
+                    guard let self,
+                          barrier.isCurrent(generation) else {
                         try? FileManager.default.removeItem(at: processedURL)
                         return
                     }
@@ -180,7 +270,7 @@ final class ChatMediaTransferCoordinator {
         }
 
         let targetPeer = context.selectedPrivateChatPeer
-        let generation = preparationGeneration
+        let generation = imagePreparationBarrier.currentGeneration
 
         do {
             try ImageUtils.validateImageSource(at: sourceURL)
@@ -190,12 +280,22 @@ final class ChatMediaTransferCoordinator {
             return
         }
 
-        Task.detached(priority: .userInitiated) { [weak self] in
+        let prepareImagePacket = self.prepareImagePacket
+        let barrier = imagePreparationBarrier
+        Task.detached(priority: .userInitiated) { [weak self, barrier] in
             do {
-                let prepared = try ChatMediaPreparation.prepareImagePacket(from: sourceURL)
+                guard let prepared = try barrier.performIfCurrent(
+                    generation: generation,
+                    operation: {
+                        try prepareImagePacket(sourceURL)
+                    }
+                ) else {
+                    return
+                }
 
-                await MainActor.run { [weak self] in
+                await MainActor.run { [weak self, barrier] in
-                    guard let self, self.preparationGeneration == generation else {
+                    guard let self,
+                          barrier.isCurrent(generation) else {
                         try? FileManager.default.removeItem(at: prepared.outputURL)
                         return
                     }
@@ -214,14 +314,20 @@ final class ChatMediaTransferCoordinator {
                 }
             } catch ChatMediaPreparationError.imageTooLarge(let size) {
                 SecureLogger.warning("Processed image exceeds size limit (\(size) bytes)", category: .session)
-                await MainActor.run { [weak self] in
+                await MainActor.run { [weak self, barrier] in
-                    guard let self, self.preparationGeneration == generation else { return }
+                    guard let self,
+                          barrier.isCurrent(generation) else {
+                        return
+                    }
                     self.context.addSystemMessage("Image is too large to send.")
                 }
             } catch {
                 SecureLogger.error("Image send preparation failed: \(error)", category: .session)
-                await MainActor.run { [weak self] in
+                await MainActor.run { [weak self, barrier] in
-                    guard let self, self.preparationGeneration == generation else { return }
+                    guard let self,
+                          barrier.isCurrent(generation) else {
+                        return
+                    }
                     self.context.addSystemMessage("Failed to prepare image for sending.")
                 }
             }
@@ -357,10 +463,11 @@ final class ChatMediaTransferCoordinator {
     }
 
     /// Invalidates detached preparation work and cancels every transfer that
-    /// reached the transport. Stale tasks check the generation before they
+    /// reached the transport. Closing image-preparation admission and joining
-    /// can recreate a message or send after a panic wipe.
+    /// active synchronous writers ensures the following panic media deletion
+    /// is the last filesystem mutation before the transaction can complete.
     func resetForPanic() {
-        preparationGeneration &+= 1
+        imagePreparationBarrier.invalidateAndWait()
         let transferIDs = Set(transferIdToMessageIDs.keys)
         transferIdToMessageIDs.removeAll(keepingCapacity: false)
         messageIDToTransferId.removeAll(keepingCapacity: false)

bitchat/_PreviewHelpers/PreviewKeychainManager.swift

@@ -14,11 +14,25 @@ final class PreviewKeychainManager: KeychainManagerProtocol {
     // every default-constructed component under test, which access it from
     // arbitrary threads.
     private let lock = NSLock()
+    private let installAccessGate: KeychainInstallAccessGate
+    private let reconcileInstallAccess: () -> Bool
     private var storage: [String: Data] = [:]
     private var serviceStorage: [String: [String: Data]] = [:]
-    init() {}
+
+    init(
+        installAccessGate: KeychainInstallAccessGate = KeychainInstallAccessGate(),
+        reconcileInstallAccess: @escaping () -> Bool = { true }
+    ) {
+        self.installAccessGate = installAccessGate
+        self.reconcileInstallAccess = reconcileInstallAccess
+    }
+
+    private func installAccessAllowed() -> Bool {
+        installAccessGate.allowsAccess(reconcile: reconcileInstallAccess)
+    }
 
     func saveIdentityKey(_ keyData: Data, forKey key: String) -> Bool {
+        guard installAccessAllowed() else { return false }
         lock.lock()
         defer { lock.unlock() }
         storage[key] = keyData
@@ -26,12 +40,14 @@ final class PreviewKeychainManager: KeychainManagerProtocol {
     }
 
     func getIdentityKey(forKey key: String) -> Data? {
+        guard installAccessAllowed() else { return nil }
         lock.lock()
         defer { lock.unlock() }
         return storage[key]
     }
 
     func deleteIdentityKey(forKey key: String) -> Bool {
+        guard installAccessAllowed() else { return false }
         lock.lock()
         defer { lock.unlock() }
         storage.removeValue(forKey: key)
@@ -51,6 +67,7 @@ final class PreviewKeychainManager: KeychainManagerProtocol {
     func secureClear(_ string: inout String) {}
 
     func verifyIdentityKeyExists() -> Bool {
+        guard installAccessAllowed() else { return false }
         lock.lock()
         defer { lock.unlock() }
         return storage["identity_noiseStaticKey"] != nil
@@ -58,6 +75,7 @@ final class PreviewKeychainManager: KeychainManagerProtocol {
 
     // BCH-01-009: New methods with proper error classification
     func getIdentityKeyWithResult(forKey key: String) -> KeychainReadResult {
+        guard installAccessAllowed() else { return .accessDenied }
         lock.lock()
         defer { lock.unlock() }
         if let data = storage[key] {
@@ -67,6 +85,7 @@ final class PreviewKeychainManager: KeychainManagerProtocol {
     }
 
     func saveIdentityKeyWithResult(_ keyData: Data, forKey key: String) -> KeychainSaveResult {
+        guard installAccessAllowed() else { return .accessDenied }
         lock.lock()
         defer { lock.unlock() }
         storage[key] = keyData
@@ -76,24 +95,38 @@ final class PreviewKeychainManager: KeychainManagerProtocol {
     // MARK: - Generic Data Storage (consolidated from KeychainHelper)
 
     func save(key: String, data: Data, service: String, accessible: CFString?) {
+        guard installAccessAllowed() else { return }
         lock.lock()
         defer { lock.unlock() }
         serviceStorage[service, default: [:]][key] = data
     }
 
     func load(key: String, service: String) -> Data? {
+        guard case .success(let data) = loadWithResult(key: key, service: service) else {
+            return nil
+        }
+        return data
+    }
+
+    func loadWithResult(key: String, service: String) -> KeychainReadResult {
+        guard installAccessAllowed() else { return .accessDenied }
         lock.lock()
         defer { lock.unlock() }
-        return serviceStorage[service]?[key]
+        guard let data = serviceStorage[service]?[key] else {
+            return .itemNotFound
+        }
+        return .success(data)
     }
 
     func delete(key: String, service: String) {
+        guard installAccessAllowed() else { return }
         lock.lock()
         defer { lock.unlock() }
         serviceStorage[service]?.removeValue(forKey: key)
     }
 
     func deleteAll(service: String) {
+        guard installAccessAllowed() else { return }
         lock.lock()
         defer { lock.unlock() }
         serviceStorage.removeValue(forKey: service)

bitchatTests/ChatMediaTransferCoordinatorContextTests.swift

@@ -16,6 +16,11 @@
 import Testing
 import Foundation
 import BitFoundation
+#if os(iOS)
+import UIKit
+#else
+import AppKit
+#endif
 @testable import bitchat
 
 // MARK: - Mock Context
@@ -203,6 +208,99 @@ struct ChatMediaTransferCoordinatorContextTests {
         #expect(coordinator.messageIDToTransferId.isEmpty)
     }
 
+    @Test @MainActor
+    func resetForPanic_waitsForActiveImageWriterBeforeReturning() async throws {
+        let context = MockChatMediaTransferContext()
+        let sourceURL = try makeCoordinatorTestImageURL()
+        let outputURL = FileManager.default.temporaryDirectory
+            .appendingPathComponent("panic-prepared-\(UUID().uuidString).jpg")
+        let preparer = PausedImagePreparer(outputURL: outputURL)
+        let coordinator = ChatMediaTransferCoordinator(
+            context: context,
+            prepareImagePacket: { sourceURL in
+                try preparer.prepare(sourceURL)
+            }
+        )
+        defer {
+            preparer.release()
+            try? FileManager.default.removeItem(at: sourceURL)
+            try? FileManager.default.removeItem(at: outputURL)
+        }
+
+        coordinator.sendImage(from: sourceURL)
+        #expect(await TestHelpers.waitUntil(
+            { preparer.hasStarted },
+            timeout: TestConstants.longTimeout
+        ))
+
+        DispatchQueue.global(qos: .userInitiated).asyncAfter(
+            deadline: .now() + .milliseconds(100)
+        ) {
+            preparer.release()
+        }
+        coordinator.resetForPanic()
+
+        // The synchronous reset boundary cannot return while a pre-panic
+        // writer can still create output. The real panic path deletes media
+        // immediately after this method returns.
+        #expect(preparer.hasFinished)
+
+        try? FileManager.default.removeItem(at: outputURL)
+        #expect(await TestHelpers.waitUntil(
+            { !FileManager.default.fileExists(atPath: outputURL.path) },
+            timeout: TestConstants.longTimeout
+        ))
+        await Task.yield()
+        #expect(context.privateFileSends.isEmpty)
+        #expect(context.broadcastFileSends.isEmpty)
+        #expect(context.systemMessages.isEmpty)
+    }
+
+    @Test @MainActor
+    func imagePreparation_doesNotRetainCoordinatorOrDeallocatedContext() async throws {
+        let sourceURL = try makeCoordinatorTestImageURL()
+        let outputURL = FileManager.default.temporaryDirectory
+            .appendingPathComponent("released-context-\(UUID().uuidString).jpg")
+        let preparer = PausedImagePreparer(outputURL: outputURL)
+        var context: MockChatMediaTransferContext? = MockChatMediaTransferContext()
+        var coordinator: ChatMediaTransferCoordinator? = ChatMediaTransferCoordinator(
+            context: context!,
+            prepareImagePacket: { sourceURL in
+                try preparer.prepare(sourceURL)
+            }
+        )
+        weak var weakContext: MockChatMediaTransferContext?
+        weak var weakCoordinator: ChatMediaTransferCoordinator?
+        weakContext = context
+        weakCoordinator = coordinator
+        defer {
+            preparer.release()
+            try? FileManager.default.removeItem(at: sourceURL)
+            try? FileManager.default.removeItem(at: outputURL)
+        }
+
+        coordinator?.sendImage(from: sourceURL)
+        #expect(await TestHelpers.waitUntil(
+            { preparer.hasStarted },
+            timeout: TestConstants.longTimeout
+        ))
+
+        coordinator = nil
+        context = nil
+        #expect(weakCoordinator == nil)
+        #expect(weakContext == nil)
+
+        preparer.release()
+        #expect(await TestHelpers.waitUntil(
+            { preparer.hasFinished },
+            timeout: TestConstants.longTimeout
+        ))
+        #expect(await TestHelpers.waitUntil(
+            { !FileManager.default.fileExists(atPath: outputURL.path) },
+            timeout: TestConstants.longTimeout
+        ))
+    }
+
     @Test @MainActor
     func sendVoiceNote_blockedContextRemovesFileAndExplains() async throws {
         let context = MockChatMediaTransferContext()
@@ -222,3 +320,91 @@ struct ChatMediaTransferCoordinatorContextTests {
         #expect(coordinator.transferIdToMessageIDs.isEmpty)
     }
 }
+
+private final class PausedImagePreparer: @unchecked Sendable {
+    private let condition = NSCondition()
+    private let outputURL: URL
+    private var started = false
+    private var released = false
+    private var finished = false
+
+    init(outputURL: URL) {
+        self.outputURL = outputURL
+    }
+
+    var hasStarted: Bool {
+        condition.lock()
+        defer { condition.unlock() }
+        return started
+    }
+
+    var hasFinished: Bool {
+        condition.lock()
+        defer { condition.unlock() }
+        return finished
+    }
+
+    func prepare(_ _: URL) throws -> ChatPreparedImage {
+        condition.lock()
+        started = true
+        condition.broadcast()
+        while !released {
+            condition.wait()
+        }
+        condition.unlock()
+
+        let data = Data("prepared image".utf8)
+        try data.write(to: outputURL, options: .atomic)
+        let packet = BitchatFilePacket(
+            fileName: outputURL.lastPathComponent,
+            fileSize: UInt64(data.count),
+            mimeType: "image/jpeg",
+            content: data
+        )
+
+        condition.lock()
+        finished = true
+        condition.broadcast()
+        condition.unlock()
+        return ChatPreparedImage(outputURL: outputURL, packet: packet)
+    }
+
+    func release() {
+        condition.lock()
+        released = true
+        condition.broadcast()
+        condition.unlock()
+    }
+}
+
+private func makeCoordinatorTestImageURL() throws -> URL {
+    let url = FileManager.default.temporaryDirectory
+        .appendingPathComponent("coordinator-image-\(UUID().uuidString).png")
+    #if os(iOS)
+    let image = UIGraphicsImageRenderer(size: CGSize(width: 16, height: 16))
+        .image { context in
+            UIColor.systemBlue.setFill()
+            context.fill(CGRect(x: 0, y: 0, width: 16, height: 16))
+        }
+    guard let data = image.pngData() else {
+        throw CoordinatorImageTestError.encodingFailed
+    }
+    #else
+    let image = NSImage(size: NSSize(width: 16, height: 16))
+    image.lockFocus()
+    NSColor.systemBlue.setFill()
+    NSRect(x: 0, y: 0, width: 16, height: 16).fill()
+    image.unlockFocus()
+    guard let tiff = image.tiffRepresentation,
+          let bitmap = NSBitmapImageRep(data: tiff),
+          let data = bitmap.representation(using: .png, properties: [:]) else {
+        throw CoordinatorImageTestError.encodingFailed
+    }
+    #endif
+    try data.write(to: url, options: .atomic)
+    return url
+}
+
+private enum CoordinatorImageTestError: Error {
+    case encodingFailed
+}

bitchatTests/PreviewKeychainManagerTests.swift

@@ -1,4 +1,5 @@
 import Foundation
+import Security
 import Testing
 import BitFoundation
 @testable import bitchat
@@ -24,6 +25,77 @@ struct PreviewKeychainManagerTests {
             containerKnowsMarker: false,
             markerRead: .deviceLocked
         ) == .retryLater)
+        #expect(KeychainManager.installLifecycleAction(
+            containerKnowsMarker: false,
+            cleanupPending: true,
+            markerRead: .itemNotFound
+        ) == .clearStaleKeys)
+    }
+
+    @Test("Accessibility migration covers custom services and retries after any incomplete update")
+    func accessibilityMigrationCoversEveryApplicationOwnedService() {
+        let primaryService = "chat.bitchat.test-primary"
+        var visitedServices: [String] = []
+
+        let completed = KeychainManager
+            .migrateAccessibilityForApplicationOwnedServices(
+                primaryService: primaryService
+            ) { service in
+                visitedServices.append(service)
+                return service == "chat.bitchat.favorites"
+                    ? errSecInteractionNotAllowed
+                    : errSecItemNotFound
+            }
+
+        #expect(!completed)
+        #expect(visitedServices.first == primaryService)
+        #expect(Set(visitedServices).isSuperset(of: [
+            "chat.bitchat.nostr",
+            "chat.bitchat.favorites",
+            "chat.bitchat.outbox"
+        ]))
+        #expect(Set(visitedServices).count == visitedServices.count)
+
+        let retryCompleted = KeychainManager
+            .migrateAccessibilityForApplicationOwnedServices(
+                primaryService: primaryService
+            ) { _ in errSecSuccess }
+        #expect(retryCompleted)
+    }
+
+    @Test("Keychain cleanup is complete only when every owned scope is clean")
+    func keychainCleanupRequiresEveryApplicationOwnedService() {
+        let primaryService = "chat.bitchat.test-primary"
+        var visitedServices: [String] = []
+
+        let partialCleanup = KeychainManager
+            .deleteApplicationOwnedKeychainServices(
+                primaryService: primaryService
+            ) { service in
+                visitedServices.append(service)
+                return service == "chat.bitchat.outbox"
+                    ? errSecInteractionNotAllowed
+                    : errSecSuccess
+            }
+
+        #expect(!partialCleanup)
+        #expect(visitedServices.first == primaryService)
+        #expect(Set(visitedServices).isSuperset(of: [
+            "chat.bitchat.nostr",
+            "chat.bitchat.favorites",
+            "chat.bitchat.outbox"
+        ]))
+        #expect(Set(visitedServices).count == visitedServices.count)
+
+        let emptyCleanup = KeychainManager
+            .deleteApplicationOwnedKeychainServices(
+                primaryService: primaryService
+            ) { _ in errSecItemNotFound }
+        #expect(emptyCleanup)
+        #expect(KeychainManager.completedApplicationGroupDelete(status: -34018))
+        #expect(!KeychainManager.completedApplicationGroupDelete(
+            status: errSecInteractionNotAllowed
+        ))
     }
 
     @Test("Preview keychain manager stores identity and service-scoped data in memory")
@@ -72,4 +144,132 @@ struct PreviewKeychainManagerTests {
             Issue.record("Expected preview keychain to be empty after deleteAllKeychainData")
         }
     }
+
+    @Test("Failed reinstall cleanup blocks stale data until a successful retry")
+    func failedReinstallCleanupBlocksEveryNamespaceUntilSuccessfulRetry() {
+        let gate = KeychainInstallAccessGate()
+        var cleanupCanComplete = false
+        var reconciliationAttempts = 0
+        var manager: PreviewKeychainManager!
+        manager = PreviewKeychainManager(
+            installAccessGate: gate
+        ) {
+            reconciliationAttempts += 1
+            guard cleanupCanComplete else { return false }
+            return manager.deleteAllKeychainData()
+        }
+
+        let staleIdentity = Data([1, 2, 3])
+        let staleFavorite = Data([4, 5, 6])
+        let staleOutbox = Data([7, 8, 9])
+        let staleCustom = Data([10, 11, 12])
+        #expect(manager.saveIdentityKey(
+            staleIdentity,
+            forKey: "noiseStaticKey"
+        ))
+        #expect(manager.saveIdentityKey(
+            staleIdentity,
+            forKey: "identity_noiseStaticKey"
+        ))
+        #expect(manager.verifyIdentityKeyExists())
+        manager.save(
+            key: "favorite",
+            data: staleFavorite,
+            service: "chat.bitchat.favorites",
+            accessible: nil
+        )
+        manager.save(
+            key: "outbox",
+            data: staleOutbox,
+            service: "chat.bitchat.outbox",
+            accessible: nil
+        )
+        manager.save(
+            key: "custom",
+            data: staleCustom,
+            service: "chat.bitchat.future-custom",
+            accessible: nil
+        )
+
+        gate.block()
+
+        #expect(manager.getIdentityKey(forKey: "noiseStaticKey") == nil)
+        #expect(!manager.verifyIdentityKeyExists())
+        if case .accessDenied = manager.getIdentityKeyWithResult(
+            forKey: "noiseStaticKey"
+        ) {
+        } else {
+            Issue.record("Expected blocked identity read to fail closed")
+        }
+
+        for (key, service) in [
+            ("favorite", "chat.bitchat.favorites"),
+            ("outbox", "chat.bitchat.outbox"),
+            ("custom", "chat.bitchat.future-custom")
+        ] {
+            #expect(manager.load(key: key, service: service) == nil)
+            if case .accessDenied = manager.loadWithResult(
+                key: key,
+                service: service
+            ) {
+            } else {
+                Issue.record(
+                    "Expected blocked \(service) read to fail closed"
+                )
+            }
+        }
+
+        #expect(!manager.saveIdentityKey(
+            Data([13]),
+            forKey: "replacement"
+        ))
+        if case .accessDenied = manager.saveIdentityKeyWithResult(
+            Data([14]),
+            forKey: "replacement"
+        ) {
+        } else {
+            Issue.record("Expected blocked identity save to fail closed")
+        }
+
+        let failedAttempts = reconciliationAttempts
+        #expect(failedAttempts > 0)
+        cleanupCanComplete = true
+
+        // The first access retries cleanup synchronously. It must not return
+        // any surviving value from before the reinstall.
+        #expect(manager.getIdentityKey(forKey: "noiseStaticKey") == nil)
+        #expect(reconciliationAttempts == failedAttempts + 1)
+        #expect(manager.load(
+            key: "favorite",
+            service: "chat.bitchat.favorites"
+        ) == nil)
+        #expect(manager.load(
+            key: "outbox",
+            service: "chat.bitchat.outbox"
+        ) == nil)
+        #expect(manager.load(
+            key: "custom",
+            service: "chat.bitchat.future-custom"
+        ) == nil)
+
+        let replacementIdentity = Data([21, 22, 23])
+        let replacementCustom = Data([24, 25, 26])
+        #expect(manager.saveIdentityKey(
+            replacementIdentity,
+            forKey: "noiseStaticKey"
+        ))
+        #expect(manager.getIdentityKey(
+            forKey: "noiseStaticKey"
+        ) == replacementIdentity)
+        manager.save(
+            key: "custom",
+            data: replacementCustom,
+            service: "chat.bitchat.future-custom",
+            accessible: nil
+        )
+        #expect(manager.load(
+            key: "custom",
+            service: "chat.bitchat.future-custom"
+        ) == replacementCustom)
+    }
 }