Hi @Stites Dragan
Thank you for posting your question in the Microsoft Q&A forum.
I'm sorry for the inconvenience you are facing, I know this interrupts your workflow.
To assist you better, I will need some more information.
Please go to Send/Receive tab > Show Progress, check if any issue is listed there.
If yes, would you please share a screenshot, remember to cover any personal information such as email address, ....
When the message is not updated, if you press this button, does it update the emails?
Meanwhile, we can try some basic troubleshooting steps:
- Remove and re-add your account.
- Repair an Office application - Microsoft Support (Choose Repair Online)
- Lastly, check out this article Fix your Outlook email connection by repairing your profile - Microsoft Support
I look forward for your reply.
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