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10.3: S/MIME encryption and Mail.app
Authored by: Schwie on Jan 01, '07 09:32:59PM

I had this same problem and I managed to figure it out.

I had my certificates working in Mail for over a year when today I got cute and tried to update my certificate to include my GMail account. When I deleted my old Thawte personal email certificate from Keychain Access, I screwed up and deleted the personal certificate ALONG with the X509Anchors entries for Thawte. This was crucial, because when I created the new/updated certificate at Thawte and went to import it back into Keychain Access, it imported fine, but Thawte didn't replace my X509Anchors entries. Hence, when I fired up Mail, the padlock S/MIME icons weren't appearing for signing individual messages. After pulling my hair out for too much time, I finally got smart and hopped on another Mac I have and I exported the Thawte certificates from Keychain Access and imported them back on to the machine that I impaired.

After doing this, my new/updated certificate now works flawlessly (and I switched to CACert now, so we'll see how this goes).



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