Hi Dale,
Thanks for the updates.
First, I’d like to know if you have tried to create a new identity for your Office 365 account in Outlook for Mac. If not, please try to do that with the steps in my previous post. Also, if possible, please log into your account on another Mac to see if this issue persists. This would help to narrow down this issue.
Besides, for further investigation, please provide some related screenshots about the error message. To upload the screenshots in the forum, you can click Use rich formatting in the forum and then click the icon on the Insert Image.
Regarding “I also get a continual stream of these error messages: [ALERT] Message too large. support.google.com/.../answer.py”, could you please provide some more detailed information? It seems that the link you provided is not an error message. If you want to upload some attachments, also click Use rich formatting and then click Options to add attachments.
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Best Regards,
Richard Ji
Thanks for the updates.
First, I’d like to know if you have tried to create a new identity for your Office 365 account in Outlook for Mac. If not, please try to do that with the steps in my previous post. Also, if possible, please log into your account on another Mac to see if this issue persists. This would help to narrow down this issue.
Besides, for further investigation, please provide some related screenshots about the error message. To upload the screenshots in the forum, you can click Use rich formatting in the forum and then click the icon on the Insert Image.
Regarding “I also get a continual stream of these error messages: [ALERT] Message too large. support.google.com/.../answer.py”, could you please provide some more detailed information? It seems that the link you provided is not an error message. If you want to upload some attachments, also click Use rich formatting and then click Options to add attachments.

Best Regards,
Richard Ji