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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?

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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.)

Penango makes secure e-mail easy to use, simple to manage, and accessible everywhere. We make a suite of web browser extensions that let you send and receive authenticated and encrypted messages directly in your webmail environment.

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@AlEverett Thanks Al! I'll +1 Penango now that I've used it for a few days: in the world of S/MIME not much is easy. Penango is easy. – jeffreypriebe Feb 21 '13 at 1:08

I've been using the GMail S/MIME for Firefox plugin for a while…

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This plug-in appears to be old and no longer functional. See armb's link for a plug-in that works as of this writing on FF 18 – jeffreypriebe Feb 20 '13 at 2:32

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