I have Outlook configured to automatically sign and encrypt (when possible) outgoing messages. When I send mail to my Gmail (for testing, to see how this appears to addressees) I see that Gmail doesn't identify the signature as such, and simply shows it as an attachment.
Is there any way to tell Gmail to check the signatures and even (gasp!) sign outgoing messages?
Best Answer
Check Penango, it's "the successor to Gmail S/MIME". (Edit - Dead link to old index page replaced by download page for version for free Gmail. Support for Google Apps and paid-for Gmail is a pay-for product.)