Recently, I've encountered a strange issue with Outlook (M365) where new emails that appear to be recent are actually old messages from several days to a week ago. This seems to be happening to me and a few others as well. All the emails affected are internal communications. The peculiar thing is that the original emails are missing, so it seems like Outlook is somehow just reshuffling the same message. Interestingly, all the duplicated emails are questions or actionable items, almost like Outlook is trying to trigger a reminder for follow-ups without informing anyone about it. Has anyone else experienced this?
3 Answers
We noticed something similar as well, but we didn't find a solid solution other than reverting the affected users back to Classic Outlook. It seems isolated to the New Outlook version, unfortunately.
We had a case where it affected just one email because the email defender flagged a link it deemed suspicious and wanted to scan it first. There's a policy called "email messages containing malicious URLs removed after delivery" that could play a role here.
This issue can definitely cause confusion. I remember a similar scenario where iPhone users using the default mail app accidentally sent out old calendar invites after changing their password. It might be a good idea to check if something like that is happening here too.
I get that it's frustrating to suggest Classic Outlook as a workaround, especially when the root cause is still a mystery. I’ve faced some oddities with Teams as well, impacting certain users in a similar way.