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?
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.