[Doc HM]

This started mid last week. Up until now have been able to send zipped attachments just fine (always just jpegs or tiff files) but now suddenly gmail is saying that the files contravene its guidelines on types of files that can be sent.

I guess it's mis interpreting the zipped file content as an exe or similar.

Any ideas on how to stop it. Sometimes it allows them through, then stops sending them again.

Using MS Office entourage 2008 and IMAP. Switching to mail.app is not an option.

[Big Mac]

I guess they're getting too many spammers sending zip files.

[Cold Warrior]

That's really frustrating, I hope it's not permanent. You could try Thunderbird or their web interface to see if it's an application (Entourage) issue.

Otherwise Dropbox is a nice workaround.