Outlook sent incorrect auto-reminder

Dear @Stephen Vavasis,

Based on the details provided, Outlook appears to have interpreted or displayed the flight event using a different calendar time zone. Since Chicago and Toronto are one hour apart, a 5:55 PM departure from O’Hare in Central Time may appear as 6:55 PM when shown in Eastern/Toronto time.

Outlook can automatically add flight reservations from email to the calendar, and Outlook calendar items are stored in UTC and displayed according to the selected calendar/device time zone. This can sometimes make travel events look shifted if the reminder does not clearly show the time zone.

Please open the flight event in Outlook Calendar and verify the event’s time zone. Also check Outlook’s time-zone setting under Settings > Calendar > View > Time zones. If you frequently travel, enabling the option to ask before updating time zones and adding a second time zone can help prevent confusion. Manage time zone settings in Outlook | Microsoft Support

If you prefer not to rely on automatic travel detection, you can turn off automatic events from email under Settings > Calendar > Events from email. For critical travel, I recommend creating a manual backup calendar item showing the departure airport’s local time, such as “Depart ORD 5:55 PM Central,” to avoid ambiguity. Automatically add events from your email to your calendar | Microsoft Support

I hope the information shared helps point you in the right direction. Please try the steps above and let me know if they work. If not, we can continue working together to narrow this down.

The first response may not always resolve the issue right away, but with your help and more details, we can work toward a solution.

As a moderator, I do not have the tools to investigate your specific account directly, as this is a support forum between users. Moderators and collaborators, including external Microsoft employees, may not directly intervene in the functionality of Microsoft products or access internal systems. Our role is limited to providing technical guidance on reported problems, requests, or ideas. However, I will do my best to guide you as clearly as possible.

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment". 

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.