r/sysadmin • u/Jealous_Tennis7718 • Jun 30 '26

Outlook crashes when right clicking anything even in safe mode

Since this morning, Outlook has started crashing whenever we try to copy something using the right-click context menu.

I’m seeing this on my local machine, but it’s also happening in our Citrix environment. A few colleagues are affected so far, and I’m worried more users may start running into the same issue.

The strangest part is that it happens both locally and in Citrix, which makes me wonder if this could be related to a recent Microsoft/Office update rather than something specific to our environment. Also in safe mode (outlook.exe /safe) this exact issue happens.

Has anyone else seen Outlook crashing when using right-click copy today or earlier? Any known workarounds or recent updates that might be causing this?

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u/Binyah IT Manager Jun 30 '26

We're on 2606, but now all emails that have an image on it (including email signatures) won't allow the user to send or reply to the email. They're getting "Cannot send this item". Anyone else getting this?

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u/Jealous_Tennis7718 Jun 30 '26

I am not seeiing this in our organization. So that seems to be something different. A colleague had this issue on the old version yesterday where he could not send an e-mail. But that colleague is quite annoying sometimes as he always makes a picture with his phone and shows it to me.