a user has a few contacts he cannot send attachments to, each on different domains (1 gmail, 1 hotmail, etc). another user in same office, using same exact setup can send same attachment to same contacts, so it doesn't seem to be the recipients error. Attachments range from tiffs to pdfs to office docs. The email is received, but the attachments are removed. Checked all settings and I can't find anything set differently. I already looked at the contact entry and set it to send emails as plain text instead of html in case it was a translation issue, but that didn't fix it. Our office is running exchange 2008.