Mail not sending attachments properly

Hi- I'm trying to send clients emails with attachments. They are receiving the emails, but with no attachment. I sent it to a coworker and the attachment was there. Additionally, another coworker sent the same message to the client, and the attachment was sent with it. "Always send Windows-friendly Attachments" is checked, the whole attaching process is completely normal, but some clients are not getting my attachments.
The machine I am using is a Mac Mini with OS 10.5.8, Mail version 3.6.
Any ideas of what I could do?

You aren't the only one having this problem. Maybe this will help. If you monitor the "More Like This" box, other solved threads appear. Opening them usually displays other threads.
https://discussions.apple.com/message/16146962#16146962

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