Leopard Keychain Problems, Fix
November 2nd, 2007
I mentioned earlier that one of my Leopard problems was the keychain not remembering passwords (and therefore making receiving and sending email from multiple accounts a pain) on the Mac mini. I finally set aside a few minutes to get to the root of the problem (no pun intended) and fix it.
Here’s the handy document I used to troubleshoot my problem, over at MacFixit.
Keychains are still kind of confusing to me. Basically there’s a keychain management utility called Keychain Access located in Applications/Utilities.
First try: I fired up that program and tried repairing the “System Keychain” which found some issues but didn’t fix anything.
Second try: After seeing how the keychains are set up in Leopard on my MacBook, It seems there should be a keychain called “login” that holds all your info when you login to your account. I located one named login.keychain in the ~/Library/Keychains/ folder and opened it. My passwords appeared briefly in the Keychain Access program – but didn’t stick. The next time I opened Keychain Access that login information had vanished, and Mail was still bugging me for passwords.

Solution: At this point I decided to just create a new keychain named “login” and enter all my passwords from scratch (Apple Expert JC suggested this as a solution). I deleted login.keychain located in ~/Library/Keychains and created a new keychain called “login” via the Keychain Access (File -> New Keychain). I then fired up Mail and entered my passwords (for like the 324th time). I then tested the passwords by logging in and out, and restarting – and the problem now looks to be solved – no more password frustration!
Update: Luke mentions an additional step you may need to take on your keychain – with the keychain selected, click the info button, go to Access Control, and make sure “Allow all applications to access this item” is checked.
After all is said and done, I think something got munged a few months ago, when I used the Migration Assistant to migrate an account from an iMac that we had for several years and therefore several past versions of OS X.