Outlook – Forward Outlook Web Access (OWA) to GMail using POP and SMTP

My best guess would be that Outlook is using the Quoted-Printable encoding for your attachment, which would make it much larger than the original.

You may want to try and follow the directions in KB 278134 and edit the InternetMailTextEncoding key in the HKEY_CURRENT_USER\Software\Microsoft\Office\12.0\Outlook\Options\Mail registry subtree. If you assign a DWORD value of 2 (use Base64) or 3 (don't encode, send 8-bit attachments) to it, and that solves the problem, then you'd have found the culprit.

A server will respond by removing everything from owa and on, and not using https:// either.

So the server address will become: email.jwu.edu

You should be able to setup email on your iPhone if the administrators have enabled access for it.