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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 email 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.
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  • Why wouldn't you add it as an answer to the question you linked? – ale 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
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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. – fuxia Jul 16 '13 at 21:11
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    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
  • As A.M. noted this just turns an exe into a different exe. You still have to change the file extension, and as of now (2015) changing the file extension of an ordinary unencrypted zip appears to still work. – Timmmm Jun 15 '15 at 19:50
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    This method works no longer as any archive with encrypted file names gets blocked by Gmail. But there is a workaround with google drive attachment: webapps.stackexchange.com/questions/67396/… – Vadzim Jan 3 '18 at 21:27
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Gmail actually allows sending .exe files. And you don't need to do anything outside of Gmail.

Instead of clicking on the clipper icon(attachment) you click on triangle icon next to it (Google Drive icon). That's it - from there its more or less the same procedure.

Gmail does not allow .exe attachments but at the same time offers an option to add/attach Google Drive file(s) to your email.

Additional info:
After clicking on Google Drive icon you just select an already uploaded file or pick from your local files to upload. If the recipient is not Google/Gmail user it will send a private "share link". If the recipient is Google/Gmail user it will further secure the file by assigning stricter access rights.

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  • This answer assumes that the sender uses Gmail, but the problem (Gmail blocks exes) also arises when the recipient uses Gmail but the sender does not. What then? – Louis Strous Jan 27 at 10:56
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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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  • This no longer works. Gmail disallows any encrypted zips. – Timmmm Jun 15 '15 at 19:45
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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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  • As of 2015, this appears to be the only thing that works. Encrypted zips or zips within zips do not work. I'm not sure what the point of creating a self extracting archive is since that itself is an exe and is blocked. – Timmmm Jun 15 '15 at 19:49
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    This no longer works. Zipping an exe and renaming the zip to [anything] does not work as Gmail inspects the binary information of the file, its algo does not care for file names or extensions. – leoinlios Dec 25 '18 at 15:25
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I've just now (November 2015) sent a zipped folder (over 8MB when zipped) via Gmail by changing its file extension to .txt. Looks like it worked because I've just opened the email from my Sent folder, dowloaded the attachment, selected "Show in folder", changed the extension back to .zip and launched WinZip, which didn't seem to object. Too easy to be true?

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    This solution was already presented in this answer. – SightSpirit Nov 3 '15 at 18:15
  • I realize that. I just thought it would be worth confirming that the method still works after a year has elapsed. After all, Gmail might have spotted the ruse and done something about it in that time. Nice to know they haven't. – John of York Nov 3 '15 at 20:06
  • A comment would have sufficed, then. Answer posts are reserved for different answers/solutions to questions. (This Help Center article details what doesn't quite fit as an entire answer post.) All that being said, confirmation that an answer remains valid/current is still great information for readers to have, so that kind of comment in particular is pretty valuable all around. :) – SightSpirit Nov 3 '15 at 20:35
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    Got it, SightSpirit. Will adhere to protocol from now on, now I know what to do. Cheers. – John of York Nov 3 '15 at 23:52
  • As noted in @aboutblank's answer, this no longer works (since at least the end of 2018). AFAICS, Gmail is forcing you to use 3rd party hosting services like DropBox. Attaching directly to an email, and assuming its benign, is a little old-fashioned anyway...the email gets deleted, copied, archived, lost, etc. – AlainD Apr 14 '20 at 16:46
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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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    Does not work as of now. – Timmmm Jun 15 '15 at 19:45

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