diff --git a/apps/desktop/src/services/apple-calendar/process/events/execute.ts b/apps/desktop/src/services/apple-calendar/process/events/execute.ts
index c7d62b8df3..fcbfff6278 100644
--- a/apps/desktop/src/services/apple-calendar/process/events/execute.ts
+++ b/apps/desktop/src/services/apple-calendar/process/events/execute.ts
@@ -1,4 +1,5 @@
 import type { EventStorage, SessionEvent } from "@hypr/store";
+import { format, safeParseDate, TZDate } from "@hypr/utils";
 
 import { id } from "../../../../utils";
 import {
@@ -97,8 +98,13 @@ export function syncSessionEmbeddedEvents(
   timezone?: string,
 ): void {
   const incomingByKey = new Map<string, IncomingEvent>();
+  const incomingByTrackingId = new Map<string, IncomingEvent[]>();
   for (const event of incoming) {
     incomingByKey.set(eventMatchingKey(event, timezone), event);
+    const tid = event.tracking_id_event;
+    const arr = incomingByTrackingId.get(tid) ?? [];
+    arr.push(event);
+    incomingByTrackingId.set(tid, arr);
   }
 
   ctx.store.transaction(() => {
@@ -107,7 +113,14 @@ export function syncSessionEmbeddedEvents(
       if (!sessionEvent) return;
       const key = sessionEventMatchingKey(sessionEvent, timezone);
 
-      const incomingEvent = incomingByKey.get(key);
+      let incomingEvent = incomingByKey.get(key);
+      if (!incomingEvent) {
+        incomingEvent = findIncomingByTrackingIdAndDay(
+          incomingByTrackingId,
+          sessionEvent,
+          timezone,
+        );
+      }
       if (!incomingEvent) return;
 
       const calendarId =
@@ -134,3 +147,26 @@ export function syncSessionEmbeddedEvents(
     });
   });
 }
+
+function dayFromDateLocal(
+  dateStr: string | null | undefined,
+  timezone?: string,
+): string {
+  const parsed = safeParseDate(dateStr);
+  if (!parsed) return "1970-01-01";
+  const date = timezone ? new TZDate(parsed, timezone) : parsed;
+  return format(date, "yyyy-MM-dd");
+}
+
+function findIncomingByTrackingIdAndDay(
+  incomingByTrackingId: Map<string, IncomingEvent[]>,
+  sessionEvent: SessionEvent,
+  timezone?: string,
+): IncomingEvent | undefined {
+  const candidates = incomingByTrackingId.get(sessionEvent.tracking_id);
+  if (!candidates) return undefined;
+  const sessionDay = dayFromDateLocal(sessionEvent.started_at, timezone);
+  return candidates.find(
+    (e) => dayFromDateLocal(e.started_at, timezone) === sessionDay,
+  );
+}
diff --git a/apps/desktop/src/utils/session-event.ts b/apps/desktop/src/utils/session-event.ts
index 1a3f3eb6df..55ef6949a9 100644
--- a/apps/desktop/src/utils/session-event.ts
+++ b/apps/desktop/src/utils/session-event.ts
@@ -73,11 +73,34 @@ export function findSessionByKey(
     if (!sessionEvent) return;
     if (sessionEventMatchingKey(sessionEvent, timezone) === key) {
       found = rowId;
+      return;
+    }
+    if (matchesWithFallback(sessionEvent, key, timezone)) {
+      found = rowId;
     }
   });
   return found;
 }
 
+function matchesWithFallback(
+  sessionEvent: SessionEvent,
+  targetKey: string,
+  timezone?: string,
+): boolean {
+  const colonIdx = targetKey.indexOf(":");
+  if (colonIdx === -1) {
+    return false;
+  }
+
+  const targetTrackingId = targetKey.substring(0, colonIdx);
+  const targetDay = targetKey.substring(colonIdx + 1);
+  if (sessionEvent.tracking_id !== targetTrackingId) {
+    return false;
+  }
+  const sessionDay = dayFromDate(sessionEvent.started_at, timezone);
+  return sessionDay === targetDay;
+}
+
 export function findSessionByTrackingId(
   store: Store,
   trackingId: string,