Outlook widget on iPhone and Applewatch not working

Hello @Jared,  

Thank you for reaching out to the Q&A forum! 

After receiving your information, I tested this scenario in my own environment (iPhone 15 Pro Max, iOS 26.2.1), and at the moment the Outlook widget is still displaying the next appointment correctly. 

Therefore, to help you further, could you please provide a bit more information: 

1. Could you tell me the current iOS version on your iPhone and the watchOS version on your Apple Watch? 
2. Could you share a screenshot of what the widget is currently showing? (You mentioned that it only shows “Open Outlook,” so I’d like to verify the exact behavior.) 
3. You mentioned that you reinstalled the app on the Apple Watch. Have you already tried reinstalling Outlook on both the iPhone and the Apple Watch during the same troubleshooting cycle?  And if yes, does the issue still persist afterward? 
4. I also noticed your post is tagged as “Business.” Can you confirm whether you are using a work/school (organization) account, or a personal Microsoft account such as outlook.com / hotmail.com? 
5. If this is a work account, could you check whether any of your colleagues are experiencing the same issue with the widget? 

I will wait for the screenshot from you so that I can research the issue further.  

Please understand that our initial response may not always resolve the issue immediately. However, with your help and more detailed information, we can work together to identify the root cause and find a solution.     

Looking forward to hearing from you! 

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I was able to solve the problem on the Apple Watch by deleting the outlook app and re-installing it from the Appstore on the Apple Watch.
Now it works again.

It seems that you are experiencing issues with the Outlook widget on your iPhone and Apple Watch not displaying the next appointment as it used to. Unfortunately, the provided context does not contain specific troubleshooting steps or solutions for issues related to the Outlook widget on mobile devices or Apple Watch.

I recommend checking for any available updates for the Outlook app on your iPhone and ensuring that your device's operating system is also up to date. Additionally, you might consider removing the widget and re-adding it to see if that resolves the issue. If the problem persists, reaching out to Microsoft support or checking their official forums could provide more tailored assistance.

References:

• AutoComplete not working correctly in Outlook 2010
• Meetings incorrectly display the '(UTC) Monrovia, Reykjavik' time zone
• No meeting reminders for delegates
• The Outlook meeting tracking tab is not updated
• Widgets is missing the setting gear and the Sign in button is not working. - Microsoft Q&A