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Recent Items not attaching to emails in Outlook 2016

J4sstrom asked
Last Modified: 2020-03-19
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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