Quote:
I have to fix it to work the way he wants it to.


If it's Just The Way Outlook Was Made, then there's nothing you can do to fix it, other than possibly upgrading outlook to a newer version. (my PC at work has the 2007 version of Outlook, I'll check today and see if it behaves the way he wants it to behave.)

Understand that sometimes, a file-selection field MUST BE hard coded to take only one file, because the rest of the software doesn't support multiple files from that point in the code. If that's the case here, it means he's got to go throught the file attachment dialog box more than once for multiple files.

If it's a huge group of files, he should zip them into a single file archive before attaching them anyway.

But before we make the assumption that all of the above is really what's happening, let's take a step back and double check it.

Open Windows Explorer, and browse the folders on the drive, and see if this one-file-only behavior still applies. In Explorer you should be able to select multiple files. If not, then there is truly something weird going on where his shift and control keys aren't working.
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Tony Fabris