Besides feeling a bit of kinship to a blog that seems to really get PKI and security, they had an interesting post a couple of days ago about S/MIME support in Gmail.   It is a Firefox plug-in called Gmail S/MIME.  From reading the blog entry and the plug-in home page, it sounds like it essentually wraps your message in an attachment (which is basically what an S/MIME message is anyhow) and uploads to Gmail.

I gave it a test run by sending a message from Gmail to Outlook 2007 (only after an hour and a half of trying to fix Outlook…thx Gist plugin).  I get an underlying security message error in Outlook…odd.  That is usually related to trust or odd formatting of a message.  If I had some more time, I’d dig into the attachment.  Still a cool idea, and it has lots of promise.  One of the challenges of webmail (and mail on mobile devices) is signing and encrypting email.

But it is 4/16 after all…time to watch the boys finish OGBC!