Signed-off-by: Matt Bruce <mbrucedogs@gmail.com>

Sources/LocalData/Helpers/SyncHelper.swift

@@ -17,6 +17,11 @@ actor SyncHelper {
     public func updateConfiguration(_ configuration: SyncConfiguration) {
         self.configuration = configuration
     }
+
+    /// Exposes the current max auto-sync size for filtering outbound payloads.
+    public func maxAutoSyncSize() -> Int {
+        configuration.maxAutoSyncSize
+    }
     
     // MARK: - Public Interface
     
@@ -68,10 +73,15 @@ actor SyncHelper {
         guard WCSession.isSupported() else { return false }
         
         let session = WCSession.default
-        guard session.activationState == .activated else { return false }
+        guard session.activationState == .activated else {
+            Logger.debug("<<< [SYNC] WCSession not activated")
+            return false
+        }
         
         #if os(iOS)
-        return session.isPaired && session.isWatchAppInstalled
+        let isAvailable = session.isPaired && session.isWatchAppInstalled
+        Logger.debug("<<< [SYNC] WCSession status paired=\(session.isPaired) installed=\(session.isWatchAppInstalled) reachable=\(session.isReachable)")
+        return isAvailable
         #else
         return true
         #endif
@@ -100,7 +110,10 @@ actor SyncHelper {
         guard session.isPaired, session.isWatchAppInstalled else { return }
         #endif
         
+        Logger.info(">>> [SYNC] Sending application context for key: \(keyName) (\(data.count) bytes)")
         try session.updateApplicationContext([keyName: data])
+        let contextKeys = session.applicationContext.keys.sorted().joined(separator: ", ")
+        Logger.info("<<< [SYNC] Application context updated for key: \(keyName). Keys now: [\(contextKeys)]")
     }
 
     private func setupSession() {

Sources/LocalData/Services/StorageRouter.swift

@@ -553,6 +553,81 @@ public actor StorageRouter: StorageProviding {
         )
     }
 
+    /// Attempts to sync any registered keys that already have stored values.
+    /// This is useful for bootstrapping watch data after app launch or reconnection.
+    public func syncRegisteredKeysIfNeeded() async {
+        let isAvailable = await sync.isSyncAvailable()
+        guard isAvailable else {
+            Logger.debug("<<< [SYNC] Skipping bootstrap sync: WatchConnectivity unavailable")
+            return
+        }
+
+        Logger.debug(">>> [SYNC] Starting bootstrap sync for registered keys")
+        for entry in registeredKeys.values {
+            let descriptor = entry.descriptor
+            guard descriptor.availability == .all || descriptor.availability == .phoneWithWatchSync else {
+                Logger.debug("<<< [SYNC] Skipping key \(descriptor.name): availability=\(descriptor.availability)")
+                continue
+            }
+            guard descriptor.syncPolicy != .never else {
+                Logger.debug("<<< [SYNC] Skipping key \(descriptor.name): syncPolicy=\(descriptor.syncPolicy)")
+                continue
+            }
+
+            do {
+                guard let storedData = try await retrieve(for: descriptor) else {
+                    Logger.debug("<<< [SYNC] No stored data for key \(descriptor.name)")
+                    continue
+                }
+                try await sync.syncIfNeeded(
+                    data: storedData,
+                    keyName: descriptor.name,
+                    availability: descriptor.availability,
+                    syncPolicy: descriptor.syncPolicy
+                )
+                Logger.debug("<<< [SYNC] Bootstrapped context for key: \(descriptor.name) (\(storedData.count) bytes)")
+            } catch {
+                Logger.error("Failed to bootstrap sync for key: \(descriptor.name)", error: error)
+            }
+        }
+    }
+
+    /// Builds a snapshot of syncable key data for immediate watch requests.
+    public func syncSnapshot() async -> [String: Data] {
+        let isAvailable = await sync.isSyncAvailable()
+        guard isAvailable else {
+            Logger.debug("<<< [SYNC] Skipping snapshot: WatchConnectivity unavailable")
+            return [:]
+        }
+
+        let maxAutoSyncSize = await sync.maxAutoSyncSize()
+        var payload: [String: Data] = [:]
+
+        for entry in registeredKeys.values {
+            let descriptor = entry.descriptor
+            guard descriptor.availability == .all || descriptor.availability == .phoneWithWatchSync else {
+                continue
+            }
+            guard descriptor.syncPolicy != .never else { continue }
+
+            do {
+                guard let storedData = try await retrieve(for: descriptor) else { continue }
+
+                if descriptor.syncPolicy == .automaticSmall, storedData.count > maxAutoSyncSize {
+                    Logger.debug("<<< [SYNC] Snapshot skip \(descriptor.name): size exceeds maxAutoSyncSize")
+                    continue
+                }
+
+                payload[descriptor.name] = storedData
+            } catch {
+                Logger.error("Failed to build sync snapshot for key: \(descriptor.name)", error: error)
+            }
+        }
+
+        Logger.debug("<<< [SYNC] Snapshot built with \(payload.count) keys")
+        return payload
+    }
+
     // MARK: - Internal Sync Handling
 
     /// Internal method to update storage from received sync data.