Apple Mail 5.2 with SMIME Always asking for Password

This has now been bugging me for some time.  I have setup Mail on my Mac with my smime private key and I have a few public keys of my friends.  The issue was that every time that I opened mail, went to another mail folder with an encrypted message, or woke my computer from sleep it would ask me for the admin account, and password for every single encrypted message in the folder that I was viewing.  The worst part is that the Mail app got stuck in a loop and I could not use/close/quit the application until I entered the account name and password about 20 times!  If all I had to do was enter the password that many times I would be fine, but the username was also blank so I had to enter my name and password each time.

Well I finally got right pissed off with this today and decided that I just needed to get it fixed.  So what do you do when you want to fix something on your computer quick?  Yep go to Google.  However as I found out not many people use smime on their Mac (don’t ask me why not).  So the searches, advanced searches, and google hacking turned up nothing but forum strings of people that have issues setting up SSL, IMAP, or POP3 accounts, barely anything about smile and the issues I was having.

So if anyone googled and got here these are the symptoms

*  Mail is always asking for your username and password for the SYSTEM keychain
*  Started happening after you installed an smile private key
*  You are probably going bald with frustration because of Mail pissing you off.  Maybe this is why people don’t use smime with mail?

The fix?  Well as it worked for me … 
*  Go into Applications -> Utilities -> and open Keychain Access

*  On the left hand side click on “system” under keychains

*  Click on “Keys” under Category

*  Look at all the keys that you have in the main part of the window.  You will have public and private keys.  At this time just worry about the private keys.  Look for the key that doesn’t belong.  Come on now you did this when you were a kid watching sesame street.  For me it was easy, every private key was named com.apple.blah.blah but one was totally different.

*  Open that different key

*  Click on Access Control

*  Enter your username and password … if you are here you have done this enough and should be a pro at it

 

*  See the app kcproxy in the window?  Click the + and add Mail.app to this list (mine disappeared after????)

*  Click save changes

*  What’s this!?  Yep enter your username and password … AGAIN

*  Click allow

*  Your done … mail shouldn’t ask you for your password again, just don’t ask me why. (If this does not work for you, I had my mail application open while I was doing this)

 

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