Windows mail recipient cannot open attached files

One of my colleagues is unable to open mail attachments from me. Here are the facts that I know:
I am using Mail.app. I have sent the attachments in both windows friendly and mac formats. The files are .pdf, and MS Word 2004 .doc format.
My friend can open files from everyone else, but not me.
All my other windows friends can open my files, but he cannot.
Are there settings on his machine (either Outlook or Outlook express) that might prevent him from opening my attached files?
PowerBookG4 Mac OS X (10.4.9)

Allan...
I have noticed Windows Exchange Server 2003 "stripping" out my attachments when I select the "Windows Friendly" checkbox. Allow me to elaborate...
When sending a basic Microsoft Word document from my Mac to his PC (document was composed in Office X, sent via Mac Mail), I selected the "Windows Friendly" option as I typically do for other Windows users.
He received a .dat file of exactly the same file size and file name. When he attempted to open the .dat file using Microsoft Word the file became corrupted and unusable.
Ironically, sending the same attachment without the check box (Windows Friendly) the file went through flawlessly as a .doc!
Yet, another time (to the same user) I accidentally checked the Windows Friendly box and the file went through just fine as a .doc!
Odd... Yep! But, I'd say 1 out of ever 10-12 emails I send with the "Windows Friendly" checkbox checked to his MSE server '03 results in the .dat file corruption. It's quite odd!

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