4 Ways To Email Attachments When The File Extension Is Blocked

Tina Sieber 25-03-2010

Have you ever tried to email an .exe file?


Most mail servers provide anti-virus protection. This means they scan file attachments of emails you send and receive. Some providers even go as far as to block a number of file extensions per default.

Gmail for example won’t let you send .exe files, even if they are archived in a .zip, .tar, .tgz, .taz, .z, or .gz file. Messages sent to you containing an .exe file will be bounced back to the sender.

So do you unblock attachments to send or receive .exe files nevertheless?

There are several simple tricks. Please note however, that some of them may violate the Terms Of Service of your email provider. Violating the TOS may result in your email account being locked or closed.

1. Upload The File to A File Hosting Service

how to unblock attachmentsA perfectly legal alternative to sending an .exe file is to upload the file to a file host and email the URL to the intended recipient.


We have previously covered several file hosting services on MakeUseOf. For some of them you don’t even have to sign up.

2. Put The Files In A Zip File

If you want to send several files and unblock individual attachments, this is the best way to go in the first place as the archive reduces the total file size. However, as I have mentioned in my introduction, if you add an .exe file to your .zip archive, it will still be blocked by Gmail and possibly other mail services.

Zip files contain archived file name listings, which are not encrypted, even if you password protect the .zip file. This is different with .rar archives, which do not easily reveal their content. You can download WinRAR here. Note that this is not a free tool. However, it offers a free trial and has been known to work even after the trial period expires.

3. Manually Change the File Extension

You can rename the .exe file extension to .jpg for example.


In order for this to work you must be able to see file extensions. In Windows, open the folder that contains the file you want to rename, go to > Tools > Folder Options… and open the > View tab. Under > Files and Folders remove the check mark for > Hide extensions for known file types. Click > OK to save your changes.

Now you can change the file extension. Windows will warn you that if you change a file name extension, the file may become unusable. Don’t worry, you can change it back later, so go ahead.

how to unblock attachments

4. Add An “Imaginary” File Extension

Changing the file extension has one major drawback: it’s not obvious, so you may forget that you changed it or someone else may not recognize it.


An alternative to unblock attachments is to rename the file, but instead of changing the file extension, simply add an additional one. For example, rename setup.exe to setup.exe.remove.

This post was inspired by a question posted on MakeUseOf Answers.


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  1. Luis
    July 12, 2016 at 8:55 pm

    Changing the exe file extension inside the zip still works to send it through Gmail

    • Tina Sieber
      July 12, 2016 at 9:25 pm

      Thank you for the update, Luis!

  2. Mike
    April 21, 2016 at 7:53 pm

    Some notes...

    1. This is a very old post, the information is slightly outdated, a lot has changed since the comments started 6 years ago.

    2. Using a zip is not enough. If you want to be sure it will send, you have to encrypt the archive with a password and encrypt filenames we well.

    The easiest way is to upload the file to Google Drive, OneDrive, Dropbox, etc and send a link. Those services do not have the same restriction and will allow any format, as long as it's not malware (they do scan files for viruses, etc).

    • Tina Sieber
      July 12, 2016 at 9:26 pm

      All true. Thank you for your feedback and ideas, Mike!

  3. David H
    March 4, 2016 at 11:55 pm

    Changing the file manually is simple and great BUT gmail, and other servers, will still add the actual file extension on at the end automatically. So, a file named zebra.exe that is manually changed to zebra.wexe will then be automatically changed to zebra.wexe.exe when attached to an email. Not as simple a solution as many think.

  4. rchard2scout
    March 31, 2010 at 10:34 pm

    you can't put it in a zip file, because of the file name listing, but what happens if you put it in a zip file, and put that file (together with some others) in another zip file? would that work?

  5. Ray
    March 28, 2010 at 9:39 am

    The article over complicates something that is very simple...change the extension of the file, notify the recipient that they need to change it back.

    A 600 word blog post was not necessary. Your site often provides fair to good article, but It's obvious when you guys are just filling up space.

    • Itz*
      November 30, 2016 at 7:35 am

      Doesn't work. You've oversimplified the solution.

      • Tina Sieber
        December 4, 2016 at 9:45 am

        Which solution worked for you?

  6. @Sreevas
    March 28, 2010 at 12:20 am

    Has really good tips....

  7. hfng
    March 26, 2010 at 5:03 am

    Changing the extension is the easiest solution I think.

    • Johnny
      March 28, 2010 at 9:42 am

      I concur, do people not already know this??

  8. Cambridge Computer Repair
    March 26, 2010 at 3:01 am

    +1 for 7zip - it's very flexable with how it creates it's archives

  9. Albert
    March 25, 2010 at 5:58 pm

    7-zip has the option to encrypt file names as well, and it's FREE!