Two SMIME certificates for a contact. Only working

I have contact (call her Kim). She has two email addresses:

Kim (at) gmail.com

Kim (at) yahoo.com

I created two SMIME certificates for it - and got her to send me the cert appropriate using each email address. I used these emails to load the certificates on my Mac and iPad. However, Mac Mail, I can only send using SMIME when I use kim (at) gmail.com. If I choose another e-mail address - kim (at) yahoo.com, turns it off lock icon and the e-mail is sent "in the clear".

If I look at the details in the Contacts, I can see his two addresses, and each has a star/checkmark beside it to indicate that the cert SMIME is available. I click on the star, and I see that each certificate is self-signed and "marked as approved for the < email address >." Looking in Keychain Access, I can see the two certificates, and do a get info on the two I can see that they are absolutely identical, with the exception of the email (and, of course, the key data).

I know SMIME working - I use it a lot for work and it works if I send an e-mail to kim (at) gmail.com.

Notes:

  1. I don't think this is a limitation of the capable SMIME email by contact address. I tried to make a double contact with an e-mail address by contact. It still does not work.
  2. I checked the email addresses - they both correspond exactly to what is in the cert.
  3. On my iPad, it works perfectly. I can send e-mail to kim (at) gmail.com and kim (at) yahoo.com and they get properly encrypted. It seems that there is a problem with the Mac only. I loaded the CERT of the enamel, exactly as I did for the Mac.

BTW - I'm on the latest version of everything - OS, applications etc. I'm a compulsive updater :-).

Ping! No one sees it?

It is true that its probably rare - SMIME and two email addresses.

I'm crossing my fingers :-)

Tags: Mac OS & System Software

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