Microsoft Bookings reminder emails recently stopped being sent

Question

Microsoft Bookings reminder emails recently stopped being sent

Technical Head 0

Hi,

We are facing an issue with Microsoft Bookings where customer reminder emails are not being sent for a specific service.

The issue started only a few days ago. Reminder emails were working previously.

Service: Financial Coaching Session* Customer: External customer (Gmail)

The service has the following customer email reminders configured:

2 hours before the appointment
3 days before the appointment
2 weeks before the appointment

The affected appointment also contains all three reminders at the appointment level, including the configured reminder messages.

We have verified:

Customer email address is correct.
optOutOfCustomerEmail is false.
Reminder configurations are present on the appointment.
Confirmation emails are being received.
However, the expected reminder emails are not being received.
There is no corresponding entry for these reminder emails in Exchange Online Message Trace.
The service name was changed approximately one month ago, but the reminder configurations are still present.

Could you please advise why Microsoft Bookings would stop triggering reminder emails even though the reminders are correctly configured on both the service and appointment, and what is the recommended way to resolve or rebuild the reminder scheduling for affected appointments?

Thank you.

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1 answer

Your answer

Answer 1

Hi,

Since the reminder messages never appear in the Exchange Online Message Trace, Microsoft Bookings likely did not generate them. If Gmail were rejecting or filtering the messages, they would normally still appear in Message Trace with a delivery, failure, or filtering status. I checked the Microsoft 365 Service Health dashboard in the Microsoft 365 Admin Center, and there is currently no Microsoft Bookings-related advisory.

I recommend creating a completely new test appointment:

Do not reuse or reschedule an existing appointment for the first test.
Create the appointment after rebuilding the reminders.
Use a short reminder interval, such as 15 minutes, and test with both Gmail and an internal Microsoft 365 mailbox.
Ensure the appointment is created far enough in advance for the reminder interval to be scheduled.

If the issue persists in the new appointment, this is likely a service-side scheduling issue. In that case, for the best possible assistance, I recommend contacting your IT administrator and asking them to create a support ticket directly with Microsoft through the Microsoft 365 admin center by navigating to Support > Help & Support. This route ensures you can contact a technical support engineer who can perform a remote session to investigate the issue, verify backend configurations, and run necessary diagnostics. If needed, they can escalate the case to a specialized engineering team that is well-equipped to perform advanced troubleshooting and provide targeted solutions.

For guidance on how to request support in the admin center, please share this link with your IT admin: Get support - Microsoft 365 admin. 
If you are unsure who your IT administrator is, you can refer to this official Microsoft guide for assistance: How do I find my Microsoft 365 admin? - Microsoft Support.

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.