Hi JonHumiston,
To narrow down the root cause of the issue, could you provide the following information for us?
1. Have you tried adding the Office 365 account in another Mac client to check if the issue persists?
2. Are there any other users in the same organization encountering the same issue?
3. Could you capture a screenshot of the status in the bottom right corner on Outlook client, so that we can know it clearly?
4. I have provided a test account for you via private message, please add the test account in your Outlook for Mac client to check if the issue persists.
Here are the steps to access the Private Message:
1. Go to Your details on the upper right corner of the forum.
2. Click Private messages.
3. Click the subject title of the response to read the message.
Best Regards,
Anna Shi