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I do a lot of work with S/MIME and am very familiar with the standard and the software.

Since upgrading to 10.11 (El Captain), S/MIME-signed and encrypted messages have not been appearing as such in my Apple Mail App on my laptop. The same messages do show signed and/or encrypted on my iPhone.

I have never seen a problem like this. Any suggestions, other than reinstalling the OS or wiping out the Mail preferences?

  • Is this in Inbox or Sent? In 10.10.5 I see all signed msgs as signed in Inbox, but in my Sent folder, where virtually all my outgoing emails are signed, there are occasionally emails not marked in the GUI as signed (although if you look at the source of the emails, they are indeed signed). – Conrad Feb 4 '16 at 14:22
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I use S/MIME extensively also, and have not seen this behavior in ElCap. I would try the following:

  1. Rebuild your mailboxes. This will update the index metadata to point to the right messages, and is relatively painless to do (though if on a platter drive, possibly time consuming.)
  2. As you suggested, delete your plists.
  • Hm. it seems that some messages I receive are marked as SIGNED and others (like the ones I send) are not... – vy32 Dec 15 '15 at 16:30

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