Strange problem with Mail: Refuses to send a specific .doc file?

Hey all, I posting on behalf of a friend who I am trying to help with a very strange problem with the Mail application. I'm something of a new Mac user but something of a computer buff (longtime builder of PC gaming rigs) and my friend is a longtime Mac user who knows very little about computers outside of his work.

He is simply attempting to use the Mail application on OSX Snow Tiger to send an attachment consisting of a 6-page text-only very lightly-formatted .doc file to his editor for the newspaper for which he works. His email account is a @mac account, which he has been using without many problems prior to this for years. The Office Suite is the 2008 edition for Mac.

The issue is that Mail simply refuses to send this document, and seemingly only this document. Occasionally it will not even accept it as an attachment until the second or third attempt to attach it, prior to which it will simply not attach it after the finder window is closed or after it is dragged from the desktop to the Mail window. After it is seemingly attached, the email can be sent, but will simply never show up in the target address. We tried sending it to him, to me at multiple addresses, etc. Nothing. Furthermore, another two-sentence junk .doc file we typed up and tried went through fine.

Even stranger, we tried copying the text of the .doc file into a new Word window and saving and sending that version (even with a different completely unrelated file name!) and there was no change.

The only way we were finally able to get the document to send was by opening a secondary gmail account he no longer uses in Safari and using the webmail to send it from the Google address, which succeeded in sending it to my address after some delay.


In all my years of doing amateur tech repair and work for friends and clients, I have never seen anything like this. It is truly bizarre, and I am past the point of being embarrassed if someone would point out a glaringly stupid simple solution or something I'm missing, I just want to help him make it work at this point.

The only theories I can come up with are that either A: there is some sort of macro virus in his Word which somehow jumped to only that document? (highly unlikely) or B: there is some sort of internal spam filtering that is going on in Apple's webmail servers that doesn't even allow this document to be sent because the text looks enough like run-of-the-mill spam or something.

Any help would be greatly appreciated.