Attachments Being Duplicated in Outgoing Messages

Friend of mine is using Mail on a Tiger (10.4.11) machine with Verizon DSL (POP). When she sends attachments, to some people they're duplicated, others they're not. She test sent me one to my Earthlink account (which I checked with Webmail) and the attachment was duplicated.
Also, some of her Word attachments get corrupted. Should she send them as .zip files instead of .doc files?
Thanks!

On the webmail, there were two attachments when she only sent one. They were both Testimonials.doc. The first one came across as garbage, the second one was fine (opened with Open Office since I don't have Word).
She mostly deals with Word and PDF documents (things that don't need editing go as PDFs) and has these problems.
I'll check about the "Windows friendly" setting.

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