I'm using winrar to zip up some pictures and send in an email. This is the only program available to me at work. I don't know if I'm doing something wrong, but it doesn't actually seem to do anything as far as compression. The size of the rar or zip file is the same size as the folder I'm trying to compress!
Nope. In fact, when zipping already compressed files, the zip may end up being slightly larger, but it still gives you the convenience of being able to send one file. If the resulting file is too big to e-mail, YouSendIt is a free service I use that can send up to 100Mb file. They will temporarily store the file online and send yourself and the recipient a link to download it.
You could always kick it old school, and use winrar to create a multi-file archive (.rar, .r01, .r02, ...), with each part being under your size limit (eg 20 5mb files, etc).
