Problem sending executable files through Gmail

Hey, I’ve recently realized I can’t send executable files as an attachment through gmail. I can’t even do this if they are in a password protected zip file.

As I need to do this in order to report suspicious files this is a problem. Also, the samples need to be in a zip file, so other formats are not possible, and also they need to be able to be read by the automated processes put in place by many antivirus vendors.

Does anyone have any suggestions for how I can recommend people to do this while still using Gmail?


Hi Chiron ,

Why just recently? That is very well known old ■■■■■■ problem

It was discussed & investigated by me loooong(!) time ago :slight_smile:

Since I stopped using ZIP with Google, I’m not aware that the issue was not fixed yet … ha! - the ■■■■■■ is still there Wow!

Read the following - it’s an old quote from my post in a different forum

...You can use [b]winRAR [/b](see note below)

Here is the secret about Gmail and passworded ZIP (stressing – ZIP)

As you noticed when you open the passworded ZIP the GUI of your archiver will show the content
You can see the list of files inside.
Only when you try to extract particular file (or all of the content) you will be asked about password

What Gmail dumb ■■■■■ are doing - is checking just file names!!! at that point , which is “not very clever”, softly speaking

It does not check the format of the files as others (clients) do.

So it is enough for them to find EXE extension just because the list of file names is available.

Try this trick:

  • rename .exe to .TXT;
  • use the same zipping Utility with password;
  • send the archive to yourself;

You will be pleased. That will be sent and received :wink:

Google promised to fix that long ago! …

note about RAR:
Described above will not happen with RAR compressed archives in conjunction with Gmail even if you are not encrypting internal content.

Here we go! use the latter

Sure you can always use 7z (the best! archiver) … there could be some specifics, but please ask after testing if any issues

Hope that helps


Renaming is faster. But if you want, another option is by splitting the file. I prefer this over renaming because it allows me to speed up uploads.b ;D

Gmail Help: Some file types are blocked

Hi JoWa ,

Unfortunately that was (is) not an answer by Gmail re: the problem raised by Chiron (please read my post above).

Many clients are not accepting certain types of files & that is fine, but sending passworded archive must be allowed.
It is just a coincidental “fault” by (native) ZIP as described … they cannot & do not check file type … just an extension of an item in the list(!!!) before the password was supplied, which is pretty much stupid :wink:

Please use passworded (win)RAR or 7z with native 7z / zip or rar encryption (+internal content)

I retested right now with passworded rar & 7z - working fine,
therefore the second paragraph of the linked statement is at least partially wrong
… well as I said, I’ve tested that long ago … just was surprised they did not fix the bug yet, when read the post by Chiron


Can you guys help me out. It appears that Google may actually be causing problems that don’t allow me to send files to Returnil. (Yes, even the password protected samples they ask for :o)

Can you guys please try sending password protected samples to and let me know if they are bounced back for you. At least for me the file is bounced back within about 15 seconds.

I’m currently talking with their tech support so I hope if I give them more information they may be able to figure out something.


Actually nevermind. It is a problem on their end.

Also, SiberLynx, you are correct. Using 7zip extension gets past Gmail. Thus I am advising that my readers use that.

Gmail is getting really annoying.