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I read through this: How can I send a Windows executable via Gmail? (and similar questions here and on SO), but all of the answers I came across rely on the e-mail recipient doing something special such as

  • changing filename extensions, or
  • accessing cloud storage services.

First, linking to another cloud service is not sending via GMail. There are reasons you may not want to use an outside service.

Second...What about sending e-mails to people who are not tech-savvy??

There are many kinds of files that Google does not want attached directly (described here https://support.google.com/mail/answer/6590?hl=en), but you should still be able to send them in some way that

  • leaves them accessible to casual computer users (who may have file extensions hidden, for example), and
  • does not require the use of other cloud services.

Actually, I finally did find an answer to this, but instead of just posting my answer right away I am going to delay that for a while in the spirit of giving other people a chance at answer rep. :)

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Why wouldn't you add it as an answer to the question you linked? –  Al E. Jul 16 '13 at 21:17
That's not a terrible idea, and maybe people should do that, but answers here are likely to involve some extra inconvenience to the sender as a trade-off for convenience for the receiver, so the focus of the questions is different. Answers people post here will also apply to that question, but may not be any better than the answers already there. –  A.M. Jul 16 '13 at 21:29

4 Answers 4

Create a self-extracting archive with 7-Zip, make sure it is password protected and the file names are encrypted:

enter image description here

Google will not detect the exe inside and let it through. The recipient has just to know the password (don’t send that with Gmail :)).

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What is the extension on that? Will the file look clickable to the user? Can the user open it without having 7-Zip installed? (I'm pretty sure that last one must be true, but I just want to check.) –  A.M. Jul 16 '13 at 21:07
The user doesn’t have to install 7-Zip for that; the extraction routine is part of the archive. The filename extension must be changed to something the recipient’s computer can handle, unfortunately. –  toscho Jul 16 '13 at 21:11
When I do this, it creates a file with an extension of .exe, which brings us back to square one, unfortunately. I had never read "SFX" as "self-extracting", though, so I am going to give your answer +1 for that random helpful fact alone (in a while, so that people don't think this completely solves the problem)! –  A.M. Jul 16 '13 at 21:17
up vote 4 down vote accepted

Here is what worked for me:

  1. "Add" your .exe file to a (new) encrypted .zip file (the "inner file".)

  2. Change the file extension from .zip to .zipx. (Of course, other extensions probably work. You could even make the extension .thepasswordisHuckleberry!)

  3. "Add" the .zipx file to a (new) unencrypted .zip file (the "outer file".)

  4. E-mail the outer (.zip) file along with the password for the inner file.

That's it.

When you open the outer (.zip) file in Windows File Explorer, which is what a non-technical user is likely to use, it automatically detects the inner (.zipx) file as a valid .zip file. That means it can be opened just by double-clicking on it and entering the password when prompted.

You can change the extension if you want, but it is not required!

Here is what it looks like for the receiver after opening the .zip file and then double-clicking on the .zipx file

enter image description here

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The trick is to just zip the already zipped file and Gmail won’t detect the .exe file. But to zip the already zipped file, just add an extra file, like a text file with it, then zip it.

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All the answers above (July 25 '13 through July 16 '13) appear not to work. It looks as if Google has refined its filters, so that it detects .exe (and other) executable files within zip or other compressed files, even if they are renamed to some other file extension. Encrypting the file makes it immediately rejected, so that doesn't work. I even tried 7-Zip (.7z file extension) because that extension was not listed at the link mentioned in the top post on Google's Support page (https://support.google.com/mail/answer/6590?hl=en ). But it, too, was detected! (Also, double zipping the file, as suggested in the October 30 '13 post, does not work, either!)*

The following procedure worked for me: Take the exe file and zip it; rename the zip file from .zip to .txt; attach the "text" (.txt) file to an email and send it. (Of course, in the email, describe what you've done so the steps can be reversed by the recipient!) I tested this by sending an email to myself from my Yahoo! Mail account to my Gmail address, and it worked!

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