my outlook calendar is not communicating with my bookings calendar and it is blank

Try these checks in Microsoft Bookings first:

1. In Bookings > Staff > select the affected staff member, make sure Events on Office calendar affect availability is enabled. If it is already enabled, turn it off, Save, turn it on again, and Save again.
2. Verify the Outlook appointments are on the staff member’s primary Outlook calendar. Appointments on shared or secondary calendars do not affect Bookings availability.
3. Make sure the Outlook appointments are marked Busy. Events marked Free, Tentative, or Working elsewhere can still appear as available in Bookings.
4. Wait a few minutes after updating Outlook, then refresh the Bookings page. A short delay can occur before Outlook changes appear in Bookings.
5. If the Bookings calendar itself is blank or there is a sync warning, this can be a transient sync issue. These usually resolve after a few minutes.
6. If the issue continues, use Outlook on the web calendar troubleshooting to send calendar logs: Settings > Options > Settings > Calendar > Let us help you troubleshoot your calendar.
7. If Bookings still does not update after that, contact Microsoft support. The documented Bookings guidance states that persistent unidentified syncing errors should be escalated.

If the problem is specifically in the Outlook mobile app, also try:

1. Outlook app > Settings > select the account > Reset Account.
2. If that does not help, delete and re-add the account.

References:

• Shared Bookings Frequently Asked Questions (FAQ)
• Calendar in Microsoft Bookings is not syncing with Outlook - Microsoft Q&A I did a lot of testing on our Booking calendar, and it seems that the Booking page does not sync our availability from Outlook Calendar. I marked myself busy in outlook but in booking page it still shows as available.
• Calendar settings in Outlook Web App
• Can't sync calendar and contacts with my phone or tablet