Dear @Emilie LeBrell,
Good day, and I appreciate the clear explanation of your concern.
In Microsoft 365, Outlook’s Scheduling Assistant and the “Book with me” feature rely on the same calendar availability data and your Personal Bookings settings. If this data is out of sync or booking rules are too restricted, your calendar may appear fully booked and no available times will show on your booking page.
Please see the following workarounds that will help you verify the issue:
Note: Since your post is tagged for the Classic Outlook app, the instructions above reflect that version. If you are using New Outlook instead, feel free to tell me and I will provide the exact steps.
Ensure that your Windows system and the Outlook application are fully up to date.
Step 1: Verify working hours and time settings
- In Classic Outlook for Windows: Go to File > Select Options > Choose Calendar.
- Confirm your Start time, End time and working days are correct.
Please confirm that your working hours are set correctly, as incorrect settings can cause availability to be calculated incorrectly.
Note: These settings are shared across Microsoft 365 and can affect both Outlook scheduling and Book with me availability.
Step 2: Refresh and repair calendar free/busy data
This is the most common cause when Outlook shows you as busy incorrectly.
- Close Classic Outlook completely.
- Press Windows key + R to open the Run dialog.
- Enter the following command and select OK: outlook.exe /cleanroamedprefs
- Reopen Outlook.
- Allow a few minutes for synchronization.
- Test by creating a new meeting and checking whether your own availability now shows correctly.
This action does not delete calendar data. It forces Outlook to rebuild certain hidden settings that affect scheduling behavior.
Calendar availability issues can occur when hidden mailbox settings related to free and busy information become out of sync.
Step 3: Confirm Personal Bookings and “Book with me” settings
Because Book with me uses your Outlook calendar availability, any calendar issue can also affect your booking page. In addition, your booking page only shows availability based on how meeting types are configured.
Please review these steps in your Personal Bookings page:
1/ Go to office.com > Apps > Bookings and open your Personal booking page.
If you do not have any meeting types, create one first.
2/ If meeting types already exist, select one and review its settings.
Make sure at least one meeting type is set to Public.
Confirm the available hours include the times you want to offer.
Save your changes.
3/ Restart Classic Outlook, send yourself a test email and click the booking link in your signature.
4/ If the link does not open the booking page, reset your signature.
Open Classic Outlook > File > Options > Mail > Signatures.
Delete the existing signature and save.
5/ To recreate the default “Book time to meet with me” signature, use Outlook on the web.
Go to office.com > Open Outlook > Settings > Account > Signatures.
Select Add signature, enter a name and choose Include a link to my booking pages in my signature, then save.
After creating the signature in Outlook on the web, please allow some time for it to sync. You will then be able to use the same signature in Classic Outlook.
This will restore the default booking link that opens the Booking with me page correctly.
Additional information is available in the following resource: Preview and share your personal booking page | Microsoft Learn
Step 4: Repair and reset the Outlook app
This article provides further guidance on the topic: Repair an Office application - Microsoft Support
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I hope this information is helpful. If you have any questions or need further support, please don’t hesitate to reach out at any time.
Thank you for your patience and understanding.
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