Calendar Problems

How to Allow Double Booking in Microsoft Bookings and Outlook

Khadija Khan Oct 12, 2026 869 views

Question details

The user wants to know how to enable double booking in Microsoft Bookings when their Outlook calendar already has overlapping events.

How to Allow Double Booking in Microsoft Bookings and Outlook

Product: Microsoft Bookings
Device & OS: not provided
Scenario: Scheduling new appointments in Microsoft Bookings while maintaining overlapping personal or work events in an Outlook calendar.
Observed behavior: Microsoft Bookings blocks appointment scheduling and prevents double booking if the user's synced Outlook calendar has an existing event marked as 'Busy'.

Before you start

Verify your Microsoft 365 permissions and ensure you have access to modify events in your personal Outlook calendar as well as administrator access to the Bookings page.

Solution 1Recommended

Change Outlook Event Status to 'Free'

Since Microsoft Bookings strictly reads the 'Busy' status to block available times, you can bypass this restriction by setting overlapping Outlook events to 'Free'.

Microsoft Bookings does not natively provide a toggle to allow double booking when an Outlook calendar event marks you as busy. Modifying your event's 'Show As' status directly in Outlook is the most effective native workaround.

Open Outlook Calendar

Launch Microsoft Outlook and navigate to your Calendar view.

Select the Existing Event

Double-click the existing event that is currently blocking your Bookings availability.

Modify the 'Show As' Status

In the Event ribbon at the top, locate the 'Show As' dropdown menu.

Set to Free

Change the selection from 'Busy' to 'Free' and click 'Save & Close'. Microsoft Bookings will now read this time slot as available.

Sync Delay: It may take a few minutes for the status change in Outlook to reflect on your public Microsoft Bookings page.

Solution 2

Disable Outlook Calendar Sync for the Staff Member

If you want Bookings to completely ignore your Outlook schedule and allow infinite double bookings, you can disable calendar syncing entirely.

Solution 3

Submit a Feature Request

For specialized enterprise assistance or to advocate for a native double-booking feature, consult the official Microsoft Tech Community.

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Frequently Asked Questions

Why does Bookings say I am unavailable when my Outlook calendar looks clear?

This usually happens if your Bookings business hours are restricted, or if a hidden background event in Outlook, such as an all-day event or holiday, is set to 'Busy'.

Will marking my Outlook event as 'Tentative' allow Bookings appointments?

Yes, Microsoft Bookings generally treats 'Tentative' or 'Free' time slots as available for new bookings, while 'Busy' or 'Out of Office' slots are strictly blocked.

Can I allow double booking for specific services only in Microsoft Bookings?

Currently, Microsoft Bookings does not support service-level double booking rules based on Outlook sync. The availability is determined globally by the staff member's Outlook calendar status and defined business hours.

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