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

BusinessCard.xcodeproj/project.pbxproj

@@ -8,6 +8,7 @@
 
 /* Begin PBXBuildFile section */
 		EA837E672F107D6800077F87 /* Bedrock in Frameworks */ = {isa = PBXBuildFile; productRef = EA837E662F107D6800077F87 /* Bedrock */; };
+		EAAE892A2F12DE110075BC8A /* BusinessCardWatch Watch App.app in Embed Watch Content */ = {isa = PBXBuildFile; fileRef = EA837F982F11B16400077F87 /* BusinessCardWatch Watch App.app */; settings = {ATTRIBUTES = (RemoveHeadersOnCopy, ); }; };
 /* End PBXBuildFile section */
 
 /* Begin PBXContainerItemProxy section */
@@ -25,8 +26,29 @@
 			remoteGlobalIDString = EA8379222F105F2600077F87;
 			remoteInfo = BusinessCard;
 		};
+		EAAE892B2F12DE110075BC8A /* PBXContainerItemProxy */ = {
+			isa = PBXContainerItemProxy;
+			containerPortal = EA83791B2F105F2600077F87 /* Project object */;
+			proxyType = 1;
+			remoteGlobalIDString = EA837F972F11B16400077F87;
+			remoteInfo = "BusinessCardWatch Watch App";
+		};
 /* End PBXContainerItemProxy section */
 
+/* Begin PBXCopyFilesBuildPhase section */
+		EAAE892D2F12DE110075BC8A /* Embed Watch Content */ = {
+			isa = PBXCopyFilesBuildPhase;
+			buildActionMask = 2147483647;
+			dstPath = "$(CONTENTS_FOLDER_PATH)/Watch";
+			dstSubfolderSpec = 16;
+			files = (
+				EAAE892A2F12DE110075BC8A /* BusinessCardWatch Watch App.app in Embed Watch Content */,
+			);
+			name = "Embed Watch Content";
+			runOnlyForDeploymentPostprocessing = 0;
+		};
+/* End PBXCopyFilesBuildPhase section */
+
 /* Begin PBXFileReference section */
 		EA8379232F105F2600077F87 /* BusinessCard.app */ = {isa = PBXFileReference; explicitFileType = wrapper.application; includeInIndex = 0; path = BusinessCard.app; sourceTree = BUILT_PRODUCTS_DIR; };
 		EA8379302F105F2800077F87 /* BusinessCardTests.xctest */ = {isa = PBXFileReference; explicitFileType = wrapper.cfbundle; includeInIndex = 0; path = BusinessCardTests.xctest; sourceTree = BUILT_PRODUCTS_DIR; };
@@ -110,6 +132,7 @@
 				EA8379332F105F2800077F87 /* BusinessCardTests */,
 				EA83793D2F105F2800077F87 /* BusinessCardUITests */,
 				EA837F992F11B16400077F87 /* BusinessCardWatch Watch App */,
+				EAAE89292F12DE110075BC8A /* Frameworks */,
 				EA8379242F105F2600077F87 /* Products */,
 			);
 			sourceTree = "<group>";
@@ -125,6 +148,13 @@
 			name = Products;
 			sourceTree = "<group>";
 		};
+		EAAE89292F12DE110075BC8A /* Frameworks */ = {
+			isa = PBXGroup;
+			children = (
+			);
+			name = Frameworks;
+			sourceTree = "<group>";
+		};
 /* End PBXGroup section */
 
 /* Begin PBXNativeTarget section */
@@ -135,10 +165,12 @@
 				EA83791F2F105F2600077F87 /* Sources */,
 				EA8379202F105F2600077F87 /* Frameworks */,
 				EA8379212F105F2600077F87 /* Resources */,
+				EAAE892D2F12DE110075BC8A /* Embed Watch Content */,
 			);
 			buildRules = (
 			);
 			dependencies = (
+				EAAE892C2F12DE110075BC8A /* PBXTargetDependency */,
 			);
 			fileSystemSynchronizedGroups = (
 				EA8379252F105F2600077F87 /* BusinessCard */,
@@ -345,6 +377,11 @@
 			target = EA8379222F105F2600077F87 /* BusinessCard */;
 			targetProxy = EA83793B2F105F2800077F87 /* PBXContainerItemProxy */;
 		};
+		EAAE892C2F12DE110075BC8A /* PBXTargetDependency */ = {
+			isa = PBXTargetDependency;
+			target = EA837F972F11B16400077F87 /* BusinessCardWatch Watch App */;
+			targetProxy = EAAE892B2F12DE110075BC8A /* PBXContainerItemProxy */;
+		};
 /* End PBXTargetDependency section */
 
 /* Begin XCBuildConfiguration section */

BusinessCard/Services/WatchConnectivityService.swift

@@ -59,7 +59,9 @@ final class WatchConnectivityService: NSObject {
     }
     
     private func sendCardsToWatch(_ cards: [BusinessCard]) {
-        Design.debugLog("WatchConnectivity: Syncing \(cards.count) cards to Watch")
+        guard let session = session else { return }
+        
+        Design.debugLog("WatchConnectivity: Syncing \(cards.count) cards to Watch (reachable: \(session.isReachable))")
         
         let syncableCards = cards.map { card in
             createSyncableCard(from: card)
@@ -67,12 +69,26 @@ final class WatchConnectivityService: NSObject {
         
         do {
             let encoded = try JSONEncoder().encode(syncableCards)
-            let userInfo: [String: Any] = ["cards": encoded]
+            let message: [String: Any] = ["cards": encoded]
             
-            // Use transferUserInfo instead of updateApplicationContext
+            // ALWAYS update application context - this persists and will be available
-            // This queues the transfer and works even in debug mode
+            // when watch app launches, even if not currently reachable
-            session?.transferUserInfo(userInfo)
+            do {
-            Design.debugLog("WatchConnectivity: Queued \(encoded.count) bytes via transferUserInfo")
+                try session.updateApplicationContext(message)
+                Design.debugLog("WatchConnectivity: Updated application context with \(encoded.count) bytes")
+            } catch {
+                Design.debugLog("WatchConnectivity: updateApplicationContext failed: \(error)")
+            }
+            
+            // Also try immediate delivery if reachable
+            if session.isReachable {
+                session.sendMessage(message, replyHandler: nil) { error in
+                    Task { @MainActor in
+                        Design.debugLog("WatchConnectivity: sendMessage failed: \(error)")
+                    }
+                }
+                Design.debugLog("WatchConnectivity: Also sent via sendMessage (reachable)")
+            }
         } catch {
             Design.debugLog("WatchConnectivity: ERROR - Failed to encode: \(error)")
         }
@@ -81,6 +97,8 @@ final class WatchConnectivityService: NSObject {
     fileprivate func handleActivation() {
         isActivated = true
         
+        Design.debugLog("WatchConnectivity: Activation complete - paired: \(session?.isPaired ?? false), installed: \(session?.isWatchAppInstalled ?? false), reachable: \(session?.isReachable ?? false)")
+        
         // Send any pending cards that were queued before activation
         if let cards = pendingCards {
             Design.debugLog("WatchConnectivity: Sending \(cards.count) queued cards after activation")
@@ -89,6 +107,17 @@ final class WatchConnectivityService: NSObject {
         }
     }
     
+    /// Force a retry - call this after watch app is confirmed running
+    func retrySyncIfNeeded() {
+        guard let session = session else { return }
+        Design.debugLog("WatchConnectivity: Manual retry - paired: \(session.isPaired), installed: \(session.isWatchAppInstalled), reachable: \(session.isReachable)")
+        
+        if let cards = pendingCards {
+            pendingCards = nil
+            syncCards(cards)
+        }
+    }
+    
     private func createSyncableCard(from card: BusinessCard) -> SyncableCard {
         // Get first email, phone, website, location from contact fields
         let email = card.firstContactField(ofType: "email")?.value ?? ""

BusinessCardWatch Watch App/Services/WatchConnectivityService.swift

@@ -96,6 +96,13 @@ extension WatchConnectivityService: WCSessionDelegate {
             processReceivedContext(userInfo)
         }
     }
+    
+    nonisolated func session(_ session: WCSession, didReceiveMessage message: [String: Any]) {
+        Task { @MainActor in
+            WatchDesign.debugLog("WatchConnectivity: Received message")
+            processReceivedContext(message)
+        }
+    }
 }
 
 /// Syncable card structure matching iOS side (for decoding)

BusinessCardWatch Watch App/State/WatchCardStore.swift

@@ -16,8 +16,41 @@ final class WatchCardStore {
     init() {
         loadDefaultID()
         WatchDesign.debugLog("WatchCardStore: Initialized, waiting for cards from iPhone")
+        
+        // Set up callback for when cards are received from iPhone
+        WatchConnectivityService.shared.onCardsReceived = { [weak self] cards in
+            self?.updateCards(cards)
         }
         
+        #if targetEnvironment(simulator)
+        // Load sample data on simulator since WatchConnectivity often doesn't work
+        if cards.isEmpty {
+            loadSimulatorSampleData()
+        }
+        #endif
+    }
+    
+    #if targetEnvironment(simulator)
+    private func loadSimulatorSampleData() {
+        WatchDesign.debugLog("WatchCardStore: Loading simulator sample data")
+        cards = [
+            WatchCard(
+                id: UUID(),
+                displayName: "Test User",
+                role: "iOS Developer",
+                company: "Sample Corp",
+                email: "test@example.com",
+                phone: "+1 555-0123",
+                website: "example.com",
+                location: "San Francisco, CA",
+                isDefault: true,
+                qrCodeImageData: nil
+            )
+        ]
+        defaultCardID = cards.first?.id
+    }
+    #endif
+
     var defaultCard: WatchCard? {
         guard let defaultCardID else { return cards.first(where: { $0.isDefault }) ?? cards.first }
         return cards.first(where: { $0.id == defaultCardID }) ?? cards.first(where: { $0.isDefault }) ?? cards.first