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Bypass Exchange Server Attachment Filtering System

I was told to send an executable program file urgently to vendor for debugging. However, the Exchange server attachment filtering system block all emails that attached with potentially dangerous file types (e.g. exe, msi, bat, csh, wsh, vbe, etc).

To get this email relayed successfully, I’ve to inform email administrators at both end to release the email. Due to urgency, we can’t wait for the escalation processes that take some time to happen.

So, what could I do to get my email bypass the attachment filtering system? There are two choices for you to try (both methods work well at this moment, but not they work forever):

Using Microsoft Office program to embed the compressed executable file

This is the first option I’ve used this morning to email an executable program file to vendor.

By inserting the compressed executable program file as an embedded object in Microsoft Excel / Word, the Exchange server attachment filtering system automatically “allow” the email that attach Microsoft Office document, to be send and receive at both end.
This guide refer to Microsoft Word 2007. However, you may use Microsoft Excel 2007 or any other version of Microsoft Office program that support embedded object feature.
  1. Compress the executable program file (or any other file types that the email attachment filtering system blocks by default).
  2. Open Microsoft Word 2007, click Insert menu, look at the Text ribbon and click the Object icon to bring up the Object dialog box, go to Create From File tab, use the Browse button to select the compressed exe file and click OK to complete.
    Using Microsoft Word embedded object feature to bypass email server attachment filtering system.

    Use Microsoft Word embedded object feature to insert a compressed executable file.

    Embed compressed exe files into Microsoft Word to bypass email server attachment filtering system
  3. Now, send the Microsoft Word document (that embed the compressed executable file) as normal attachment.

Using Yahoo Mail! to send and receive executable file attachment

No special requirements for this method to work, except that you have to send and receive the email that attached with executable program files in Yahoo! Mail account. That’s to say, you don’t have to compress the exe file or embed it to MS Office document.

I tested it before and it still work at this time being. The testing just now proved that an email attached with md5sum.exe (28KB) can be sent from my Yahoo! Mail account and open by another Yahoo! Mail account as normal.

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  5. Yener 16-04-11@20:26

    Great article, THANK YOU VERY MUCH, you saved my life!

  6. konin 07-05-12@15:04

    if you zip the executable file with winRAR
    it does still not work, gmail will not send it.

  7. Devin T 31-10-12@11:26

    I still get this message:

    Symantec Mail Security replaced FILENAME.docx with this text message. The original file contained a filtering violation and was quarantined.

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