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Microsoft confirms Outlook bug that could wreck your replies
https://www.windowscentral.com/author/sean-endicott · 2026-06-23 · via Latest from Windows Central

Microsoft Outlook for Mac has a peculiar bug that removes the content from a previous conversation when replying to or forwarding an email. Microsoft has confirmed the issue but a fix has not shipped yet.

A user flagged the unwanted Outlook behavior and described what's happening.

Normally, replying to or forwarding an email through Outlook includes the entire original message. That inclusion makes it easier for the sender to draft their message and the recipient to have context of the conversation. But the buggy behavior in Outlook removes the previous conversation, leaving just the new message.

The problem only occurs in the legacy version of Outlook for Mac. That older Outlook, which is a native application that's been around in some form for decades, is set to be retired in October. After the cutoff, legacy Outlook for Mac will receive security updates but will no longer work with Exchange Online mailboxes.

Outlook Client Hero

The web-based Outlook has proven controversial on Windows 11. In contrast, the new Outlook on macOS is a native app. (Image credit: Future)

Over 95% of Microsoft 365 users have transitioned to the new Outlook app for Mac, according to Microsoft. The new Outlook is focused on cloud accounts and is the main version going forward.

Over on the Windows side of things, Microsoft's shift to what is essentially a web app as the primary Outlook has been controversial. But the new Outlook for macOS is a native application, making an odd situation where Outlook is arguably better on macOS than on Windows.

Issues with Microsoft Outlook are nothing new. Problems even extended beyond planet earth when Commander Wiseman of the Artemis II couldn't check his email in space. But unwanted behavior is still frustrating.

"This is an extremely frustrating bug in this last update, and I hope a fix is on the way," said user Stephan in response to the original thread. They added, "This is frankly quite disappointing that something major like this completely evaded the software testing process before it was being rolled out."

While Microsoft is investigating the issue with legacy Outlook for Mac, you have two options. You can either migrate to the new Outlook (official recommendation from Microsoft) or roll back to version 16.109 of legacy Outlook for Mac.


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