Using New Outlook on Windows for personal email, calendar, and contact management
Hello Ashe Goodwin,
Thank you for reaching out to us in the Microsoft community. We are happy to assist you.
I understand that you are looking for a procedure/option to set up an alert specifically for meetings that have been rescheduled more than twice.
After reviewing your scenario and considering the available options, I regret to inform you that this feature is currently not feasible.
Meanwhile, I also believe that some specific configuration or settings options should be developed under the Outlook, I do understand your concerns about how it can help you be more productive in your busy daily work schedule, but since it's related Microsoft 365 product services and features option under product design, I believe that the related product team can develop some convenient configuration based on customer requests.
Therefore, Microsoft recommend submitting feedback by going in Ideas · Community (microsoft.com)
This community team and the Microsoft product development team are separate. Therefore, for features suggestions or design queries, users need to submit feedback to the Microsoft product design team from their side. Once a user sends feedback through the above means, it will sent directly to Microsoft and routed to the relevant product team so that can review it to do specific development in different OS devices.
To see more details on how to submit feedback, see this article Learn about how to provide feedback to Microsoft - Microsoft 365 admin | Microsoft Learn
I hope I have provided you with all the required process information for this current scenario. If you need any further information from our side, please feel free to do so.
I would really appreciate your precious time. Thank you again for your kind cooperation.
Have a good day.
Sincerely
Feroz Mahmud | Microsoft Community Moderator