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up vote 23 down vote favorite

Gmail seems to prevent the sending of Windows .exe files as attachments. What's the easiest and most reliable way around this?

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6 Answers

up vote 22 down vote accepted

Rename your file to something like example.exe_ and try again.

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4  
Thanks. Just tried this and it works - for some reason, I thought that google scanner was smarter than that... – Roddy Jul 18 '10 at 22:14
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This didn't work for me. I expect the content detection is done by file header inspection instead. – William Jul 18 '10 at 22:15
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@Roddy, It just checks for the extension, or for common renames of the extension. If you zip the file it opens that and checks the extensions of the files it contains. – ChrisF♦ Jul 18 '10 at 22:16
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@William are you sure you changed the file extension? – Lipis Jul 18 '10 at 22:19
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We usually use filename.exe.renamed that way you just tell them to remove the .renamed and it will start working again. Haven't had any problems with attachments being blocked using this scheme. – Greg Bray Jul 20 '10 at 21:23
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up vote 8 down vote

Most if not all of the methods for sending large files work for this as well, especially if the recipient is not too tech-savy, as it doesn't require renaming a file extension or downloading an alternate archive application.

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I was about to add that as an alternative, but it has it's own question/answer so this is more specific for executables via gmail. – Lipis Jul 18 '10 at 22:15
up vote 4 down vote

Zip it up using Winrar or 7zip. Gmail understands .zip format but not .rar and .7z.

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up vote 2 down vote

Changing file extension is OK as long as it is like *.zip1 or *.cnvrt. But, we should never change it to *.png or *.doc because the recipient might have known extension hidden (under Folder Options) and downloaded file will be associated with default application. If s/he is not tech-savvy, you might have to put extra effort to tell the person to turn that setting off so that the file could be made viewable by intended application.

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up vote 1 down vote

Zip it up with a password (using, say, WinZip or 7Zip).

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If I remember right it won't work if it's a .zip file.. maybe with a .7z extension, but the other party should have 7-zip installed. – Lipis Jul 18 '10 at 22:10
You may find that it needs to be a password-protected zip file, so that the content scanning engine can't unpack it during processing. – William Jul 18 '10 at 22:12
Just tried it - it doesn't work. – Gelatin Jul 18 '10 at 22:14
@William: You don't need a ZIP's password to see the file names, only their contents. Edit: It works though. – Gelatin Jul 18 '10 at 22:15
and on the other hand.. it's kinda annoying in 2010 unzipping, entering the passwords, etc... – Lipis Jul 18 '10 at 22:17
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up vote 0 down vote

As others have mentioned if an executable is in a zip archive the Gmail scanner will still find it and stop you sending it. However if you bzip2 the zip it goes through OK. This could also slightly reduce the zip size.

This obviously requires platforms that support bzip2 on both ends. I took this route on a linux machine where there was no .exe extension to rename.

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