Mac Mail to Gmail truncates attachments names and removes exstenstions

I have a user that has mac Mail 2.1.1 and is on OS X 10.4.9. Sometimes when he sends mails to his colleagues, the attachments are truncated and the extensions are removed. For Example:
In Mail, he attaches a file called "Heid Survey.doc". Mail sends the file and the Sent mail looks ok. On a windows machine, using firefox and gmail.com, another person checks the email and gets an attachment named "heid". It does not recognize it as a word file. If the attachment is downloaded and the .doc added to it, it will open. If the same recipient checks the mail message in Mac Mail, the email and attachment come through fine.
I have tried this using both "Send Windows Friendly attachments" and with out it.
This does not always happen he reports, but I was able to recreate it with my gmail account and his laptop consistently. My Mac Mail shows the attachments fine as well.
I also tried to zip the file before sending it to gmail, and gmail recognized that it was a zip file, but when I tried to save it to the desktop on windows, it only saved the truncated version after gmail un-zipped it.
I do not know if this is a Mac Mail or a Gmail issue. I am not sure what is happening to these messages. Can any shed some light or give me some troubleshooting tips? Anything that I can try would be great. Thanks!

It has nothing to do with the contains. I believe it's a bug, and if you search translators lists like Systran's, you will discover this issue is spreading virically. Do not know what happens. What is known about this by embattled Mac users who now have to stop using Mail app: the phenomena begins out of the blue, one day works, one do not, it affects every file type (seems to be a problem with the name only, nothing to do with ASCII issues) and also, activating the "windows friendly" part does nothing. My case is really funny because I have one mac account with several mail accounts included, and it began with the main one (the others sent files ok) and now every account is affected. My boss is crazy with this. After a certain amount of time in the gmail account, the names appear fully sometimes, but obviously you can't tell a client, "sorry, you have to wait one day to check your mail, because I'm using Mac and it looks great, but it can't send attchments". Google says it's Apple's error, and Apple do not answer.

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