How can I send an executable file?

March 23, 2010 6:45 AM

How can I send an executable file, namely, the Skydur VPN software, to a friend in China (I am also in China)? Gmail does not allow this, and her options for alternatives are rather limited. As is my knowledge about these things...

I have tired everything I know, and because of circumstances cannot try again for 12 hours or so, but I want to help my girlfriend install and set up a VPN...
how can I do this, using her existing programs?
I could easily do it if I were at her PC, but I am not, and won't be for a month at the least...

posted by dawson to Computers & Internet (15 answers total)

You could use a service like RapidShare or YouSendIt.
posted by proj at 6:48 AM on March 23, 2010

Best answer: Can you rename it with a *.doc (or similarly innocuous) extension, and separately instruct her to save it and rename it back to *.exe (or whatever it was originally) extension before opening?
posted by aqsakal at 6:48 AM on March 23, 2010 [1 favorite]

Best answer: I havent' used the trick in a while, but if you rename an executable file to anything BUT .exe, gmail will generally let you send it.

so instead of filename.exe, change it to filename.bck or filename.nothingtoseeheregoogle and it'll go through, then just change it again on the other side.
posted by TomMelee at 6:49 AM on March 23, 2010

Best answer: What's the problem, exactly? That you can't email the .exe file as an attachment in Gmail? Can you use Dropbox to transfer the file? (i.e. you both download & install Dropbox, sign in using the same logon, and then you copy the .exe into your Dropbox folder and it's uploaded to her Dropbox folder).
posted by EndsOfInvention at 6:49 AM on March 23, 2010

We rename executables to *.jpg, works like a charm.
posted by Billegible at 7:00 AM on March 23, 2010

You used to not be able to zip files and send them over Gmail, but I've used that solution recently (to send something to myself).
posted by MCMikeNamara at 7:02 AM on March 23, 2010

Response by poster: sounds like changing the name would work, but the file name is cm_skydur-setup and only when i attach and try to send to I get "skydur-setup.exe is an executable file. For security reasons, Gmail does not allow you to send this type of file"...pardon the stupid
posted by dawson at 7:03 AM on March 23, 2010

Best answer: You say the name of the file is "cm_skydur-setup". It should have a file extension on the end (e.g. cm_skydur-setup.exe), but if that is not showing up in Windows Explorer, you need to unhide file extensions for known file types. This will display the .exe on the end and allow you to change it to .jpg or whatever.
posted by EndsOfInvention at 7:11 AM on March 23, 2010

I just zipped skydur_setup.exe and then renamed the zip to .jpg and gmail allowed me to send it.
posted by sharkfu at 7:26 AM on March 23, 2010

If for some reason the rename of the file does not work, another well worn trick is to use a non standard compression program to hide the exe.

The idea with this is that most scanners might do zip, but perhaps they dont do 7z,
which you can create with 7zip.

Looking deeper into the problem you could adopt a steganograhpic appraoch.
This will hide hide the content you wish to transfer inside a different file.
You could embed your vpn client inside a video file for instance.
You can use Invisible Secrets for instance


If you want, you could also look into installing Dropbox and give your girlfirend your account information and she installs the client. That way you can easily exchange files.
(Combined with the approaches above you can hide what you are sending)
posted by digividal at 7:29 AM on March 23, 2010

Response by poster: thanks...I will work my way through all this info and report back later...surely the answer is above. pardon my slowness, I have suck internet at the moment, but that should improve in a bit... thanks again, I now know this can be done...
posted by dawson at 7:37 AM on March 23, 2010

With Dropbox, you would just have to save the file in a public folder, and send your gf a link to the file...
posted by KokuRyu at 7:50 AM on March 23, 2010

FWIW, last time I was in China, most of the US-based file sharing services were blocked. (Remember the whole "great firewall" thing? Yeah, that's not made up.)

The way I used the Internet in China was through my US-based virtual host. Perhaps you can buy some time on Amazon's EC2, upload the file to your server, and let your friend download it from there. Then shut the EC2 instance down, for a total cost of like 8 cents.

Dunno if Amazon is blocked or not; I use slicehost and that was not bocked.
posted by jrockway at 8:55 AM on March 23, 2010

nthing the rename the file extension. Using the instructions from EndsofInventionto show extensions. Rename file to .bak (or .jpg. or whatever, doesnt matter). Email through gmail. Then friend opens file, it's better if you've used a non-standard extension (.bak), it won't have a file association, and your friend will simply see the extension without having to do the show extensions trick. She renames to .exe, and blam! you're done!
posted by defcom1 at 5:45 PM on March 23, 2010

Response by poster: Thanks, sincerely, to all who replied, every response was most helpful...for whatever reason, dropbox would not work for her, so changing the extension name worked like a freakin charm...she now has unlimited internet access, for the first time in her life, thanks to those of you who provide tips, suggestions and seconds...
thanks again....
posted by dawson at 7:00 AM on March 24, 2010