diff --git a/crates/db-user/src/events_ops.rs b/crates/db-user/src/events_ops.rs
index 90e52d5a59..d451e142c4 100644
--- a/crates/db-user/src/events_ops.rs
+++ b/crates/db-user/src/events_ops.rs
@@ -40,7 +40,8 @@ impl UserDatabase {
                     start_date = :start_date,
                     end_date = :end_date,
                     google_event_url = :google_event_url,
-                    participants = :participants
+                    participants = :participants,
+                    is_recurring = :is_recurring
                 WHERE id = :id
                 RETURNING *",
                 libsql::named_params! {
@@ -53,6 +54,7 @@ impl UserDatabase {
                     ":end_date": event.end_date.to_rfc3339(),
                     ":google_event_url": event.google_event_url,
                     ":participants": event.participants,
+                    ":is_recurring": event.is_recurring,
                 },
             )
             .await?;
@@ -84,7 +86,8 @@ impl UserDatabase {
                     start_date,
                     end_date,
                     google_event_url,
-                    participants
+                    participants,
+                    is_recurring
                 ) VALUES (
                     :id,
                     :user_id,
@@ -95,14 +98,16 @@ impl UserDatabase {
                     :start_date,
                     :end_date,
                     :google_event_url,
-                    :participants
+                    :participants,
+                    :is_recurring
                 ) ON CONFLICT(tracking_id) DO UPDATE SET
                     name = :name,
                     note = :note,
                     start_date = :start_date,
                     end_date = :end_date,
                     google_event_url = :google_event_url,
-                    participants = :participants
+                    participants = :participants,
+                    is_recurring = :is_recurring
                 RETURNING *",
                 libsql::named_params! {
                     ":id": event.id,
@@ -115,6 +120,7 @@ impl UserDatabase {
                     ":end_date": event.end_date.to_rfc3339(),
                     ":google_event_url": event.google_event_url,
                     ":participants": event.participants,
+                    ":is_recurring": event.is_recurring,
                 },
             )
             .await?;
@@ -241,6 +247,7 @@ mod tests {
             end_date: chrono::Utc::now(),
             google_event_url: None,
             participants: None,
+            is_recurring: false,
         };
 
         let event = db.upsert_event(event).await.unwrap();
diff --git a/plugins/apple-calendar/src/sync.rs b/plugins/apple-calendar/src/sync.rs
index 56785d5abb..679ae38c28 100644
--- a/plugins/apple-calendar/src/sync.rs
+++ b/plugins/apple-calendar/src/sync.rs
@@ -269,6 +269,48 @@ async fn _sync_events(
                     continue;
                 }
 
+                // Check for backward compatibility: recurring event replacing old non-recurring
+                if system_event.is_recurring {
+                    // Look for old format event with session
+                    if let Some((_, session)) =
+                        db_events_with_session.iter().find(|(db_event, session)| {
+                            db_event.tracking_id == system_event.id &&  // Old format used base ID only
+                        db_event.start_date == system_event.start_date &&
+                        db_event.name == system_event.name &&
+                        !db_event.is_recurring &&  // Was stored as non-recurring
+                        session.is_some() // Has a session
+                        })
+                    {
+                        // Store session ID for transfer after new event is created
+                        if let Some(session) = session {
+                            let new_event_id = uuid::Uuid::new_v4().to_string();
+                            state
+                                .session_transfers
+                                .push((session.id.clone(), new_event_id.clone()));
+
+                            let new_event = hypr_db_user::Event {
+                                id: new_event_id,
+                                tracking_id: composite_tracking_id,
+                                user_id: user_id.clone(),
+                                calendar_id: Some(db_calendar.id.clone()),
+                                name: system_event.name.clone(),
+                                note: system_event.note.clone(),
+                                start_date: system_event.start_date,
+                                end_date: system_event.end_date,
+                                google_event_url: None,
+                                participants: Some(
+                                    serde_json::to_string(&system_event.participants)
+                                        .unwrap_or_else(|_| "[]".to_string()),
+                                ),
+                                is_recurring: system_event.is_recurring,
+                            };
+
+                            state.to_upsert.push(new_event);
+                            continue;
+                        }
+                    }
+                }
+
                 // This is a genuinely new event
                 let new_event = hypr_db_user::Event {
                     id: uuid::Uuid::new_v4().to_string(),
@@ -286,6 +328,7 @@ async fn _sync_events(
                     ),
                     is_recurring: system_event.is_recurring,
                 };
+
                 state.to_upsert.push(new_event);
             }
         }
@@ -498,6 +541,7 @@ struct EventSyncState {
     to_delete: Vec<hypr_db_user::Event>,
     to_upsert: Vec<hypr_db_user::Event>,
     to_update: Vec<hypr_db_user::Event>,
+    session_transfers: Vec<(String, String)>, // (session_id, new_event_id)
 }
 
 impl CalendarSyncState {
@@ -518,21 +562,31 @@ impl CalendarSyncState {
 
 impl EventSyncState {
     async fn execute(self, db: &hypr_db_user::UserDatabase) {
-        for event in self.to_delete {
-            if let Err(e) = db.delete_event(&event.id).await {
-                tracing::error!("delete_event_error: {}", e);
+        // 1. Create new events first
+        for event in self.to_upsert {
+            if let Err(e) = db.upsert_event(event).await {
+                tracing::error!("upsert_event_error: {}", e);
             }
         }
 
+        // 2. Update existing events
         for event in self.to_update {
             if let Err(e) = db.update_event(event).await {
                 tracing::error!("update_event_error: {}", e);
             }
         }
 
-        for event in self.to_upsert {
-            if let Err(e) = db.upsert_event(event).await {
-                tracing::error!("upsert_event_error: {}", e);
+        // 3. Transfer sessions from old events to new events
+        for (session_id, new_event_id) in self.session_transfers {
+            if let Err(e) = db.session_set_event(session_id, Some(new_event_id)).await {
+                tracing::error!("session_transfer_error: {}", e);
+            }
+        }
+
+        // 4. Delete old events last (after sessions have been transferred)
+        for event in self.to_delete {
+            if let Err(e) = db.delete_event(&event.id).await {
+                tracing::error!("delete_event_error: {}", e);
             }
         }
     }