I'm emailing some psd files with Gmail / Google Apps. They are above the 25mb send limit, so I'm zipping them. I sent a few successfully, but one file now won't send—I'm getting the error message:

filename.psd.zip contains an executable file. For security reasons, Wordfruit Mail does not allow you to send this type of file.

The other files were the same type and they sent ok.

I also tried sending the same file with a Gmail account that's not Google Apps and it sent ok.

Is there a different setting related to sending attachments from my Google Apps account? Can I change this setting or otherwise send the file with my Google Apps Gmail? How?

  • Have you tried zipping the zip. I don't know if it will read through multiple compression layers Feb 20, 2012 at 13:35

6 Answers 6


Upload the PSD file to Google Docs & share it over email. The advantage with this approach is that Google Docs Viewer will even let recipients view the file online with Google Docs Viewer instead of opening it with PhotoShop.


To get around the security check, you can change the extension of your file so that it won't be scanned by GMail. For example, just rename your 'psdfile.zip' to 'psdfile.zi'

That's just a workaround since the recipient has to rename the file back, losing some usability... But that's ok in most of the case.


I was having this exact issue and it was due to me having a directory within the zip file containing the string ".com". Once I removed this offending string the file sent fine and had nothing to do with the PSD files within. For me at least.

Also, the ".com" was originally at the end of the directory name. I tried appending an extra string to the end but that made no difference and still wouldn't send.


Did you make self-extracting archive? If so, then first file would be EXE. Gmail blocks sending executables to avoid spread of viruses.

Google also scans ZIP files and blocks them, if there is executable inside. But I noticed, that it doesn't scan RAR files, so you may try to compress it using this method. And avoid self-extracting archives.

EDIT: Actually, that also didn't work well. The e-mail was sent, but then it was bounced by google mail.

Our system detected an illegal attachment on your message. Please visit http://support.google.com/mail/bin/answer.py?answer=6590 to review our attachment guidelines


Also, it seems, if you have a .ZIP file within the .ZIP file, Gmail believes it is executable as well. So make sure there is nothing already compressed within the group of files you are planning to compress.


Delete the zip file and zip again. it worked for me.

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