Yea I know.. 2002.. wtf? My company doesnt like to spend money on new software.. Anyhow, I have an employee that uses pop3 on outlook 2002 and is able to send and receive files. He can send word docs and excel files but when he tries to send Images I guess from what he is saying is that it gets to like 75% on sending the files and then all of the sudden it goes in reverse and drops from 75%-66% and so on. I tried to google the issue but I am having no luck at the moment. The employee is a field employee and is rarely ever at the home office so I have not seen this issue in person.

Hi WiR3D. I assume these images are sent as attachments?
Word and Excel docs are considerably smaller then image files. His ISP may have a limit on individual e-mail size.
He can test that by sending a very small image file (under 1mb) to see if it gets through. If it does, that's the problem.
There are free alternatives such as YouSendIt Lite.

Yes, the images are being sent as attachments. The file size limit is 10mb. Ive already checked on the file size for it. He's trying to send 2mb images but is not having any luck. Yousendit wouldnt be an alternative as this is a constant thing with sending images.. not the issue just that the images are being sent all the time. I checked with an old co-worker and they suggested that it may be the virus scan program... So I will give this a shot and post back on my findings.