diff --git a/src/hooks/useOfflineSync.ts b/src/hooks/useOfflineSync.ts
index 03dcafa6..44f99cf6 100644
--- a/src/hooks/useOfflineSync.ts
+++ b/src/hooks/useOfflineSync.ts
@@ -48,7 +48,17 @@ export function useOfflineSync({
 
     if (wasLocalOnly && isNowOnline) {
       console.log('✈️ Detected transition: Flight Mode → Online')
-      syncLocalEventsToRemote(relayPool, account)
+      console.log('📊 Relay state:', {
+        connectedRelays: connectedRelays.length,
+        remoteRelays: connectedRelays.filter(r => !isLocalRelay(r.url)).length,
+        localRelays: connectedRelays.filter(r => isLocalRelay(r.url)).length
+      })
+      
+      // Wait a moment for relays to fully establish connections
+      setTimeout(() => {
+        console.log('🚀 Starting sync after delay...')
+        syncLocalEventsToRemote(relayPool, account)
+      }, 2000)
     }
 
     previousStateRef.current.hasRemoteRelays = hasRemoteRelays
diff --git a/src/services/highlightCreationService.ts b/src/services/highlightCreationService.ts
index 663e072e..5ba69b1b 100644
--- a/src/services/highlightCreationService.ts
+++ b/src/services/highlightCreationService.ts
@@ -8,6 +8,7 @@ import { RELAYS } from '../config/relays'
 import { Highlight } from '../types/highlights'
 import { UserSettings } from './settingsService'
 import { areAllRelaysLocal } from '../utils/helpers'
+import { markEventAsOfflineCreated } from './offlineSyncService'
 
 // Boris pubkey for zap splits
 const BORIS_PUBKEY = '6e468422dfb74a5738702a8823b9b28168fc6cfb119d613e49ca0ec5a0bbd0c3'
@@ -142,6 +143,11 @@ export async function createHighlight(
     eventId: signedEvent.id
   })
   
+  // If we're in local-only mode, mark this event for later sync
+  if (isLocalOnly) {
+    markEventAsOfflineCreated(signedEvent.id)
+  }
+  
   // Convert to Highlight with relay tracking info
   const highlight = eventToHighlight(signedEvent)
   highlight.publishedRelays = actualPublishedRelays
diff --git a/src/services/offlineSyncService.ts b/src/services/offlineSyncService.ts
index 7b282efb..191b6970 100644
--- a/src/services/offlineSyncService.ts
+++ b/src/services/offlineSyncService.ts
@@ -6,6 +6,17 @@ import { isLocalRelay } from '../utils/helpers'
 
 let isSyncing = false
 
+// Track events created during offline period
+const offlineCreatedEvents = new Set<string>()
+
+/**
+ * Marks an event as created during offline period
+ */
+export function markEventAsOfflineCreated(eventId: string): void {
+  offlineCreatedEvents.add(eventId)
+  console.log(`📝 Marked event ${eventId.slice(0, 8)} as offline-created. Total: ${offlineCreatedEvents.size}`)
+}
+
 /**
  * Syncs local-only events to remote relays when coming back online
  */
@@ -19,14 +30,24 @@ export async function syncLocalEventsToRemote(
   }
 
   console.log('🔄 Coming back online - syncing local events to remote relays...')
+  console.log(`📦 Offline events tracked: ${offlineCreatedEvents.size}`)
   isSyncing = true
 
   try {
     const localRelays = RELAYS.filter(isLocalRelay)
     const remoteRelays = RELAYS.filter(url => !isLocalRelay(url))
 
-    if (localRelays.length === 0 || remoteRelays.length === 0) {
-      console.log('⚠️ No local or remote relays available for sync')
+    console.log(`📡 Local relays: ${localRelays.length}, Remote relays: ${remoteRelays.length}`)
+    
+    if (localRelays.length === 0) {
+      console.log('⚠️ No local relays available for sync')
+      isSyncing = false
+      return
+    }
+    
+    if (remoteRelays.length === 0) {
+      console.log('⚠️ No remote relays available for sync')
+      isSyncing = false
       return
     }
 
@@ -34,6 +55,8 @@ export async function syncLocalEventsToRemote(
     const since = Math.floor(Date.now() / 1000) - (24 * 60 * 60)
     const eventsToSync: NostrEvent[] = []
 
+    console.log(`🔍 Querying local relays for events since ${new Date(since * 1000).toISOString()}...`)
+
     // Query for user's events from local relays
     const filters = [
       { kinds: [9802], authors: [account.pubkey], since }, // Highlights
@@ -41,31 +64,38 @@ export async function syncLocalEventsToRemote(
     ]
 
     for (const filter of filters) {
+      console.log(`🔎 Querying with filter:`, filter)
       const events = await new Promise<NostrEvent[]>((resolve) => {
         const collected: NostrEvent[] = []
         const sub = relayPool.req(localRelays, filter, {
           onevent: (event: NostrEvent) => {
+            console.log(`📥 Received event ${event.id.slice(0, 8)} (kind ${event.kind}) from local relay`)
             collected.push(event)
           },
           oneose: () => {
+            console.log(`✅ EOSE received, collected ${collected.length} events`)
             sub.close()
             resolve(collected)
           }
         })
 
-        // Timeout after 5 seconds
+        // Timeout after 10 seconds (increased from 5)
         setTimeout(() => {
+          console.log(`⏱️ Query timeout, collected ${collected.length} events`)
           sub.close()
           resolve(collected)
-        }, 5000)
+        }, 10000)
       })
 
       eventsToSync.push(...events)
     }
 
+    console.log(`📊 Total events collected: ${eventsToSync.length}`)
+
     if (eventsToSync.length === 0) {
       console.log('✅ No local events to sync')
       isSyncing = false
+      offlineCreatedEvents.clear()
       return
     }
 
@@ -88,6 +118,9 @@ export async function syncLocalEventsToRemote(
     }
 
     console.log(`✅ Synced ${successCount}/${uniqueEvents.length} events to remote relays`)
+    
+    // Clear offline events tracking after successful sync
+    offlineCreatedEvents.clear()
   } catch (error) {
     console.error('❌ Error during offline sync:', error)
   } finally {