Troubleshooting a Broken External Calendar Sync

An external calendar connection that was working fine can break without any obvious change on your end. Here's a structured way to find out why.

Start with the connection itself

1. Go to your profile's Calendar Connections and confirm the integration still shows as connected — a status showing disconnected, expired, or needing re-authorization is the single most common cause of broken sync.
2. If it shows connected but sync still isn't working, disconnect and reconnect the integration. This forces a fresh authorization and often resolves silent permission issues that don't show up as an obvious error.

Check permissions on the provider's side

Google, Outlook, and iCloud all let you review and revoke connected third-party apps from their own account settings. A permission that was revoked there — intentionally or by an automatic security review — will break sync while still showing as "connected" on the calendar side until you try to reconnect.

Confirm which calendar is actually linked

If you have multiple calendars under one account (personal, work, shared), verify the correct one is still set as your linked calendar. It's easy to accidentally have events landing in the wrong calendar, which looks like "sync is broken" when it's actually working — just against the wrong destination.

Check for a token expiration pattern

If sync breaks on a predictable schedule (say, every few weeks), that points to a token or permission that needs periodic re-authorization rather than a one-off glitch — reconnecting proactively on a schedule can avoid the disruption.

Good to know: Test with a simple round trip — create a test event directly in the external calendar and confirm it blocks a matching slot on your booking page within a few minutes — rather than only checking settings screens.