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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 Box.net. 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.

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17 Comments

  1. Anurag Bansal

     

    Cool tip man…
    It will really help in sending small *.exe files to my brother in India.

    Thanks..

  2. miCRoSCoPiC^eaRthLinG

     

    Thanks man :) Good to see someone finding this tip useful. I was getting frustrated while trying to send over some files to a client today – when this idea struck me all of sudden!! Immediately came up with a post.

    Cheers,
    m^e

  3. Bonobo

     

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  4. Entreview.com

     

    How to send executable (.exe) files as attachments in Gmail » Chaos Laboratory…

    Shows you how to send executable (.exe,.com,.bat,.cmd) files as attachments in Gmail….

  5. bleuken

     

    nice, i’m having the same trouble about this attachments and uses 3rd party file hosting to solve this but never tried this tip. I will definitely try this advice of yours. thanks for this information.

  6. Mike

     

    This doesn’t work anymore.

  7. miCRoSCoPiC^eaRthLinG

     

    @Mike: Really? When did you try out last? I gave it a shot myself right after I read it comment and it worked for me just fine :o

  8. Sue Harris

     

    This is one of the best tips I have every found! Thank you so much. I had to download a copy of Winzip, which I used to thoroughly hate using around 5 years ago. It’s so much easier now! And the encription seems to have worked a treat. I used this to send the DVD of an angiogram of my husband’s heart to a doctor in the US. A real lifesaving tip, thank you so much.

  9. Billy Bob

     

    It’s actually even simpler. You just need to append a file extension that is not likely to cause automatic execution of your attachment. E.g., if you want to send sdk_installer.exe, just rename it as sdk_installer.exe.remove. GMail will ignore it, since the recipient must take deliberate action (removing the bogus extension) before his system will run the file.

  10. David Lenz

     

    Billy Bob, many users are not very good at doing things like renaming extensions, the encryption method still remains a more universal solution.

  11. Tahir Hassan

     

    This technique no longer works.

    What worked for me was zipping it with 7-Zip, with its own file format .7z, and this works without encryption.

    7-Zip is free (and open-source) by the way.

  12. Mukund

     

    This method is not complete. What I found when I used windows’s archiver was that each file inside the zip is encrypted with the password and not the zip archive itself. So the file name is readable without the password and only the contents are encrypted. So gmail can see the file extension as an .exe and still block it.
    So what you do when you are using windows’s archiver to do the job is to rename the exe into something else (or just remove the .exe at the end) and then zip it (looks like you cannot change the filename after encrypting it) and then add a password to it and then attach in gmail.
    Long steps to send just one small file, there must be a simpler way, like a firefox extension or something.

  13. Felipe Alvarez

     

    7-zip! 100%!

  14. ces

     

    It works with 7zip without encryption but the original suggestion doesn’t work anymore.

    Thanks for the tip!

  15. Ed Bishop

     

    If you compress the file with winrar (to a .rar file), gmail will not examine it to check the file names.

    Cheers,

    Ed

  16. miCRoSCoPiC^eaRthLinG

     

    Thanks Ed. That’s another great way of doing it.

    Cheers,
    m^e

  17. yashpal rajput

     

    well,we can also simply change the .exe extension of file to any simple file extension like “.txt” or “.pdf”.but at receiver side there is need to change the simple extension to “.exe”.(this is applicable only for some files according to my experiment)

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