Can't send e-mails+attachments

I've read through past posts from people who are unable to send messages using Mail. I'm having a variation of this problem.
I'm using a .Mac account and the smtp.mac.com server. I seem to be able send simple text-only messages, but anything with an attachment, even if it's a small .txt file, gets stuck in the outbox, and I eventually receive the "unable to send mail using the SMTP server"-type message that others have reported. I've tried using Entourage and Thunderbird as well, with similar results.
Is there a reason my ISP would block only emails with attachments that come from an external SMTP? I'm brand new to OS X, so I'm probably overlooking something very obvious.
Thanks in advance
Chris
iMac Intel Core Duo   Mac OS X (10.4.4)  

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