Mail not sending attachments

On behalf of a friend who I usually do phone support for when he has a problem.
This problem has stumped me!
Mail 4.5 (1084)
Mac OSX 10.6.8
He has mail set to access Gmail (IMAP) and it works fine when sending a normal email, however, when sending an attachment, the activity monitor, goes halfway and then the reate drops off and the mesage about cannot be sent from this outgoing server is displayed. - mesage goes to outbox. - Open that message back up, delete the attachment and send, it goes no problems.
Tried to work out what the problem is, by:
checking Gmail (with attachments) through browser, sent OK
trying different file types, jpg, txt, zip, and different ways of attaching them, either from menu or dragging them into the meassga pain. - No send
repair permissions for mac, incase any pref files corrupt. - No send
brand new jpg created from photoshop - No send
image emailed from me, copied to desktop and then sent back to me - No send
So wondering what it could be.
I'm thinking of suggesting he updates to Lion, however, he has some equipment and software (scanner and camera) that may not work with Lion!
You guys got any ideas? - thanks in advance!

Thanks Gerry
The files are tiny (few kb)
I thought about windows friendly files, but we are both Mac (and Mail) users. I will suggest that.

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