How do I send a .exe file if Gmail won't let me?

Let's say that I want to send a copy of procexp.exe to someone as an attachment. (Side note: This is an example only - the proper way to get procexp.exe is to download it from Microsoft.)

As you can see, it's blocked because Gmail recognizes that ".exe" is an executable file.

We're going to have to trick Gmail.

Rename the file

The first approach is to simply rename the file that you're attempting to send or make a copy with a different name, making sure to change the extension. So procexp.exe, which we see Gmail blocking above, might be renamed to "procexp.leo", as ".leo" is not an extension that indicates an executable file.

You'll need to include instructions for your recipient to save and then rename the attachment back to its original name in order to use it.

Zip the file

Another approach is to use a zipping utility like WinZip, or my favorite, 7-zip, to create a ".zip" archive that includes the file you want. An additional benefit is that you can include more than one file in the archive and the archive will typically be compressed to be smaller than the original file.

Whoops...

While this technique works with many mail systems, Gmail is smart enough to peek inside the .zip file and notice that there's a ".exe" file within. As a result, it blocks the send.

Because I use 7-zip, I'll create a ".7z" archive and send that instead:

That worked. In this case, you would then instruct your recipient to get 7-Zip if he or she didn't already have it and use it to extract files from the archive.

Rename the zip

Finally, ".zip" file format is probably easier for most, as support for it is built into Windows. So instead of using an alternate archive format, I'll just create the .zip as I did above, but rename it before I send it:

Note that I used the same non-executable file extension, ".leo" as I did before. It doesn't matter what you use as long as it's not one of the file extensions that your mailer might consider to be an executable program, like ".exe".

And once again, you'll need to instruct your recipient to rename the file from ".leo" (or whatever you choose) to ".zip" so that they can then access the contents.

What's the security issue, anyway?

What Gmail is attempting to protect against is that malware often propagates as executable attachments. The net effect is that many email systems simply block emails that contain them. Even if you had been able to attach your ".exe" file, it's extremely likely that your recipient's email program may have prevented him from being able to access it.

Forcing you to jump through a few hoops to send the file as something that is not immediately executable forces your recipient to have to take extra steps to actually run the program. They can safely adhere to the "never, ever, run executable attachments" rule, while still being able to accept executable files from you.

And they're forced to think about it before they just run whatever they recieve.

Finally, I do have to add that because of malware and the general advice to not open any attachments, even from people you do trust (due to email account theft and hijacking) - you might just want to consider an alternate approach to getting an executable file from point A to point B on the internet. Perhaps using one of the several services, like DropBox, which allows you to share files securely and privately.