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Recent Items not attaching to emails in Outlook 2016

I have a user on Outlook 2016 having a problem with Recent Files.

The user sees the drop-down list of recent files, he is able to attach them normally, but they do not end up attached for the recipient.  The recipient just gets a mail with no attachment.

If I look at the user's Sent folder, I see the message, I see the paperclip, but there is no further visual indicator of an attachment.

He can attach a file if he goes through the browse menu, just not through the Recent Items menu.  This issue happens for xls, doc, pdf's...also happens both with files saved locally and on a network drive.

I'm sure it's probably some temp file that got locked or an unchecked checkbox somewhere, but I can't find it.  Any thoughts?

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Andrew Leniart

8/22/2022 - Mon
Andrew Leniart

I'm sure it's probably some temp file that got locked or an unchecked checkbox somewhere, but I can't find it.  Any thoughts?

I think you're on the right track thinking it's a temp file issue. I'd start by clearing the %temp% folder and seeing if that resolves it. I've struck similar problems with PDF's especially and clearing temp folders resolved the issues. Programs not cleaning up after themselves properly.

Windows + R
%temp% then hit enter
Clear everything out of that folder - anything in use will just give an error so click Ignore or Skip on anything that can't be removed. Take a look at what's left

Might also pay to do a Disk Cleanup at the same time. Right click C: drive in File Explorer, select Properties. Then click Disk Cleanup from the General tab.

Hope that helps.

Regards, Andrew

No dice.

Cleared out a nice amount of stuff as you would expect, but had no bearing on the issue.
Andrew Leniart

Hmm... Have you tried running an Office repair? I'll give it some more thought and research and see if I can't come up with some other suggestions. Meanwhile, someone else may have some other ideas.
Your help has saved me hundreds of hours of internet surfing.

Not sure how exactly, but issue SEEMS to have resolved after an MS update.  At least that is my assumption as nothing else was done for this and issue is seemingly resolved.

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Andrew Leniart

A classic example of MS not testing their updates properly before rolling them out perhaps? Either way, glad the issue resolved itself for you. Thanks for updating your question.

Regards, Andrew