GMail - too smart for my good

Yesterday, I had a small 40KB program I needed to move to a couple different machines. I figured it would be simplest to just mail it to the various people who needed it. One of the recipients has Gmail. So I sent the file and a couple of helper “BAT” files along with a TXT of the user guide.

GMail AntiVirus Scanner Blocks EXE filesThe Gmail user calls me and asks when am I going to send the email. I already had. About half an hour later I get an “undelivered” message. Turns out the BAT files were removed by my corporate mail system as “unsafe” and Gmail didn’t like the EXE and threw the whole email out. So I try a different tact. I ZIP all the files and mail that. GMail didn’t like that either.

By this point everyone else had the email, had installed the necessary software and was running. The GMail user was stuck behind an unwielding a giant. Personally, GMail has some of the best SPAM detection out there but I always thought it always put SPAM in the SPAM folder. I never thought it would summarily throw away the email.

The final solution was to rename the file, changing the file extension to ZIPTXT, tell the recipient to rename the file once it arrived, and that worked. <PITA>

However, the odds are good that renaming the file extension is in violation of the GMail terms of service and could result in the loss of the Gmail account.

As a security measure to prevent potential viruses, Gmail doesn’t allow you to send or receive executable files (such as files ending in .exe) that could contain damaging executable code.
Gmail won’t accept these types of files even if they are sent in a zipped (.zip, .tar, .tgz, .taz, .z, .gz) format. If this type of message is sent to your Gmail account, it is bounced back to the sender automatically. 

Source: Google Help > Gmail Help > Attachments

There should be a solution that allows you to mail attachments to GMail users but at the moment there is not for some types of files.

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