Internet · June 29, 2008 17

How to send executable (.exe) files as attachments in Gmail

Encrypted Email AttachmentGmail (and many of the major free email service providers) normally don’t allow you to attach executable (.exe) files and send them over to someone, because of security reasons – i.e. by barring this file type, they restrict the spread of various Worms and Trojans to a large extent. Even script files like .bat are blocked. This holds true even if you  rename such files, zip  them all up and try sending – because even zipped archives can be scanned.

However, there are genuine cases where you DO need to send over such files to your contact in a hurry, but due to the restrictions you’ve to opt for third-party file-hosting solutions like RapidShare or And… invariably every time you’ve wished how convenient it would have been if you were able to zip them all up and send along with your mail. Would have kept everything in one place and to the context.

Well… here’s a quick tip that’ll put you right on track. As I’ve pointed out earlier zip files can be scanned and renamed .exe files can easily be caught by examining the file header. So how do you go about it?

Have you ever utilised a feature called Encrypt in WinZip? This is meant for storing sensitive and confidential data in the archive and locking it up with a password. What WinZip essentially does is to employ a industry standard encryption algorithm (you can take your pick) and entirely encrypt the contents of the archive using your password as the key phrase. The encryption renders the contents of the zip file unreadable and such encrypted files cannot be scanned properly by Gmail – thus letting your executable files slip through normally. All you need to do is send along the password in your mail to your recipient – so that he/she can successfully unzip the archive and extract the contents.

WinZip Encrypted Email Attachment

This trick hold true for almost any zipping software (other than WinZip) – for these days 99% of them come with the option of encryption. Say bye bye to attachment hiccups. Give it a shot yourself and see 🙂

Update: Google’s grown clever and now can see through this. However, if you use 7-Zip instead of WinZip you can still pull this trick off. Thanks to ces for providing this tip.