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How To Email Executable Program File In Gmail Or Hotmail

Few hours ago, I wrote a post about how to send an executable program file with the office email server that enforce attachment filtering. (Although it’s a “useful” trick, but I hope the trick is applied in an ethical manner).

If you’re a student who relies on Internet email for communication, you might encounter similar problem where the attachment filtering system blocks emails that attach potentially dangerous file types from sending or receiving.

With Yahoo! Mail, you can send and receive emails that attach executable program files (max 10MB). It’s working at this moment, but I believe this won’t be forever. Anyway, I guess that’s why most of my fellow friends and colleagues keep their Yahoo! Mail active, no matter how responsive the Gmail is.

Yahoo! Mail allows users to send and receive executable program files.

However, Gmail or Windows Live Mail (previous known as Hotmail) do not allow users to send and/or receive executable program files.
Hotmail / Windows Live Mail:
Windows Live Mail has blocked some attachments in this email because they appear unsafe.

Outlook / Ms Exchange Server:
Outlook blocked access to the following potentially unsafe attachments:md5sum.exe

Gmail: failed after I sent the message.
Remote host said: 552-5.7.0 Our system detected an illegal attachment on your message.
552-5.7.0 Please visit http://mail.google.com/support/bin/answer.py?answer=6590

How to send program file in Gmail or Windows Live Mail

If you prefer Gmail or Hotmail (Windows Live Mail) than Yahoo! Mail, you can use the trick I mentioned in earlier post, i.e. embed the compressed executable program files (any blocked file types) into Microsoft Office document that support embedded object feature (e.g. Microsoft Word or Microsoft Excel) and then email the Office document as a normal attachment will do! (Again, I believe that this trick will fail eventually, if someone abuses it for non-ethical purpose!)
You can’t simply compress or zip the executable program file and email it. Most of the email attachment filtering system, e.g. those available in Gmail or Exchange server, can scan compressed or zipped attachment files and block them from sending/receiving if any executable program is detected!

How to embed a compressed program file into Microsoft Word document?

Apparently, recipient has to open this attachment with Microsoft Word (not sure can Microsoft Word Viewer open the embedded object) and uncompress program (e.g. Winzip, Power Archiver, WinRar, etc) to extract the zipped executable program file.

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  2. Joe 26-09-08@06:07

    Just so you know, you can change the extension to .bmp or .jpg or some such (anything really) and send it. Just send a note to change the extension back to it’s proper type after receipt. The bits stay the same one way or the other!

  3. Walker 27-09-08@11:45

    Simply rename the executable file extension will not pass the attachment filtering system:


    Anyway, the trick of sending program files in Gmail should only be used if you’ve a good reason to do, i.e. not with an intention to send malicious program!

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  6. bruno 21-08-09@01:59

    thanks! this worked great. I needed to send a program to a friend and his email server would keep blocking it , I tried changing extension, compressing and splitting in parts, nothing but this worked.

  7. Bill 10-11-09@23:29

    You can download a free compression utility called 7zip. You can compress using the zip format, but you can also use the 7zip format which gmail currently doesn’t scan.

  8. MM11s 27-05-11@23:19

    Or use WinZip and put your .exe in there. then put a .txt file with rnd shit until it gets around 500mb. compress it and send. file will not be blocked :)

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