Google Mail attachment guidelines: tell it like it is!

I sent a friend an email with an attached Zip file. It bounced, with a message from “System Administrator” that read

Your message did not reach some or all of the intended recipients.

Subject: xxxxxxxxxxxxxxxx
The following recipient(s) could not be reached: xxxxxxxxxxxxxxx …

552 5.7.0 review our attachment guidelines. u14sm9443132gvf.20

I figured maybe the note is from my friend’s system – maybe the file was too large? So I resent it to him to another mail address, with the same outcome. Then it occurred to me to mail the file to myself… long story short, eventually I went to the source of all wisdom – ironically, Google – and discovered that Google Mail, through which I was sending, has a policy forbidding any zip file that contains an executable (which my attachment, quite lawfully, did).

So I sent the file via yousendit, and that was that. But it did occur to me that I would’ve saved a lot of time had Google Mail elected to phrase their bounce message in human-friendly informative terms, such as:

Your message did not reach some or all of the intended recipients.
– – –

It was blocked by GMail’l outgoing mail server, because it has a zip attachment containing an executable file. GMail does not allow this. For more info, see http://…..

Not as succinct as u14sm9443132gvf.20, but rather more useful, don’t you think?

12 Responses to “Google Mail attachment guidelines: tell it like it is!”

  1. 1 Stephen S.

    I had the exact same problem. I wish they could say it like that, it would have saved me a half hour of confusion and it would have reached my recipient a few hours ago!

  2. 2 flavius

    happened to me too but with some php files inside the zipped archive. so we now know it’s not limited to *.exe 🙂

  3. 3 Sergey

    I had the same problem. My zip archive contain sources of web-site – some .js, .vb, .dll

  4. 4 bill

    I get around this by just renaming files to exclude the extension, and tell the recipient to re-add the extension after saving the file. Good enough for occasional use.

  5. 5 Pissed User

    Absolutely ridiculous. I find this after I’ve moved all my email accounts to Google’s service because it’s so nice in other ways.

    I would say that a great majority of zip files contain exe, com vb, dll etc files. This is the reason ZIP was originally invented. To archive source files. Another frigging byproduct of the WIntel Virus machinery.

    Use RAR archive files. They can’t scan them (yet). If they do some day, you can password protect them, including the filenames. I just checked, and even password protected ZIP files get bounced, as ZIP only encrypts the file contents, not the filenames.

  6. 6 Ross Presser

    A quick workaround is to rename the file with a .txt extension. I.e., foo.exe to foo.exe.txt, to, etc. This gets the file through, and no mail client on earth will actually try to execute it, so it’s safe for your recipient too.

  7. 7 Kapitano

    Yes, a truly stupid policy move by google. They create a mail system that’s great for secondary use as a cloud storage backup…and forbid you to use it for storage.

    I pack my files into an self extracting RAR, then add .txt to the filename – making Blahblah.sfx.exe.txt – and send. Then I can download, take off the .txt and run.

    It looks like google have gone to a lot of trouble to put their users through a little trouble.

  8. 8 Gopinath

    Happened to me. I figured out the problem from the line attachment guidelines. I really think they should specifically state the reason as someone not very familiar with computers will never be able to find out the reason!

  9. 9 Andy

    Agreed – it is disgusting. I am sending a program from my work to my home through a service I pay for. I DON’T NEED TO BE PROTECTED FROM MY SELF!!!

    This is Bull$hit

  10. 10 Andy W

    I tried to email my wife a pdf and received the “552 5.7.0 message content and attachment content guidelines.” So it is not just exe files. Make no sense to me either.

  11. 11 Bold-Erdene

    It happened to me today. I sent some zip attachment to my collegues and immediately get mail from System Administrator ” Your message did not reach some or all of the intended recipients.
    552 5.7.0 message content and attachment content guidelines. as1sm693469pbc.39 – gsmtp”. Same with rar attachments. Is this problem still happeneing?

  12. 12 HenkS

    It does not like helpfiles either.
    I rewrote a helpfile (.chm) and got bounced back.
    I just send it with another server, and that worked.

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