Gmail wont send my files

Posted by james on March 19, 2008

Gmail is awesome, and I've been using it for quite a while. There simply is no going back once you've gotten used to quick web email with instant searching, labeling, etc. However, I recently ran into a problem sending attachments. I zipped up a folder and tried to send it to someone, and got:
"contains an executable file. For security reasons, Gmail does not allow you to send this type of file."

Which is incredibly annoying. The problem is, there are no executables in the file I was sending. There wasn't anything the could even be mistaken as an executable. Narrowing down the test cases, I was able to replicate the problem with a zip file containing a single JPG or HTML file in a subfolder. The same JPG/HTML file worked fine if zipped without a subfolder. This means gmail's unzipping mechanism has problems and blocks certain zip files depending on the zip structure, regardless of the actual content.

Not to mention that blocking executables in the first place is incredibly awful. I understand the reasoning behind it, and yes if we stopped stupid/ignorant computer users from making these kinds of mistakes then we'd have a much safer computing environment for everyone. But what do we do if we need to send executables? The old standbys of using an external file sending service or renaming the file is just awful and a horrible hurdle to have to use. Google has managed to do so many things right, with just the right amount of compromise. But this one just stinks of other, more restrictive service providers. It truly is the only thing about GMail that I absolutely hate.