Dear Lorne Goldenberg,
Thanks for your post in Microsoft Community.
Thank you for providing a detailed description of the issue you encountered while using Outlook for Mac (version 16.92). Based on your description, it appears to be a synchronization problem. Gmail's security protocols may be set up in such a way for third-party applications that they require reconfiguration after a certain period to handle the synchronization process. This is why you need to remove and then re-add your Gmail account in Outlook to update all content and restore normal usage.
This phenomenon seems to occur approximately every six months, which might be because Gmail's security protocols require regular confirmation of the identity and permissions of third-party applications. To resolve this issue, you can follow these steps:
- Regularly check and update the configuration of your Gmail account in Outlook.
- If you find that the Sent folder in Outlook is not updating in a timely manner, you can try manually synchronizing your email.
- Keep both your Outlook for Mac and Gmail account software up to date to minimize compatibility issues.
Please note that this reconfiguration is a normal maintenance step and can help ensure that your email synchronization remains secure and stable. If you encounter similar issues in the future, you can try the aforementioned methods to resolve them. I hope this information is helpful to you, and if you have any more questions, feel free to ask. Thank you!
Best regards
Yolanda - MSFT | Microsoft Community Support Specialist