How To Send An Executable File Via Gmail

Up until today I have never tried to send an executable file via Google's email service. When I tried that today, it looked at first as if it was not a problem. The file was uploading fine and showing up under attachments in the send message window.

When I tried to send the email however, I received an error message. It stated: Error. File.exe is an executable file. For security reasons, Google Mail does not allow you to send this type of file.

A click on OK displayed the compose message screen again, with the file still being attached to the email.

What I needed was a workaround. Sure, I could for instance upload the executable file to a file hosting website like Mediafire, and copy and paste the share file url in the email instead. That's a possibility and not a bad one.

Then again, I prefer a more straightforward approach. I first tried zipping the file to see if that was enough to bypass the file filter on Gmail. It was not. The very same message was displayed and the email failed to send.

Next thing I tried was to zip the executable file and apply a password to the file to see if that would bypass the executable file filter which it did not as well. Both options did not yield the desired result. Gmail was still blocking the email from being send. I did some experiments with different encryption formats, and found out that 7-zip files that contain executable files can be send, while more common extensions like zip or gz are blocked.

Lastly I decided to change the file extension of the executable, from exe to txt. And lo and behold, the email went through the filters. Changing the file extension of the attachment can be problematic in itself, especially so if you are not the recipient of the email. You need to provide instructions, preferably in the message, that the file extension needs to be changed before the file can be run on the target computer.

So, if you want to send an executable as an attachment from your Gmail account, you either need to rename the file extension to bypass the filter, upload the file elsewhere and link to it in the mail body, or use a compression format like 7z. The latter being the most comfortable option if the recipient uses a tool that supports the unpacking of those files.

Is there an option that I have overlooked? Let me know in the comments.

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