When accessing Outlook Calendar via a browser shortcut on your iPad, the system treats it like a fresh browser session. This means you’ll be prompted to sign in each time, especially if session cookies expire or aren’t retained.

🧭 Key Points

• Browser shortcuts open Outlook Calendar as if you’re accessing it directly from Safari or Chrome
• Due to security and session handling, repeated sign-ins are expected behavior
• This does not happen when using the Outlook app, which maintains your login session securely

✅ Recommended Solution

• Install the Microsoft Outlook app from the App Store
• Sign in once, and your calendar will remain accessible without repeated prompts
• The app also offers smoother integration with notifications, scheduling, and Teams meetings