For sending, you can try free web-based sending (mentioned above) instead which won't care about the .zip Examples: http://www.sendthisfile.com/ http://www.yousendit.com/

That said, if it's the spam filter that's killing you (and not the virus filter), then this may not help. Spam filters are getting more aggressive. We've had some problems receiving recently with our existing mail service after they made the spam filtering more aggressive.

Usually attachments as long as they're from some otherwise legitimate source are skewered by rules that are designed to catch viruses and not by the spam filter. The free sending will fix that. Sends a plain email with link to the file.

Oh, in case it helps, very common virus filtering is to kill anything with two file extensions, so if you are zipping one file called abcxyz.doc and your resulting file is abcxyz.doc.zip it will be flagged as suspicious by many anti-virus schemes. If that's what you're doing, you can easily fix it by making your .zip file have only the .zip extension. (Once it is unzipped, it will have the proper extension.)