Leopard Keychain Problems, Fix

November 2nd, 2007

AppleI 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.

Keychain

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.

Disclosure: I own a tiny amount of Apple stock.

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11 comments!

  1. comment Gravatar Apple OS X Leopard: Still Thumbs Up » Webomatica - Technology and Entertainment Digest - November 8th, 2007

    [...] two cents to toss in is personally: I’ve only had a few minor issues - my keychain problem (which has been resolved) and Front Row not working ideally on the MacBook when viewing the Mac Mini [...]

  2. comment Gravatar Shawn Blanc » How to Repair the Empty Keychain Passwords in Leopard - November 10th, 2007

    [...] discovered Jason was having the same problem, and his solution was pretty basic: delete the login keychain and start [...]

  3. comment Gravatar luke - November 12th, 2007

    The above did not work!
    Instead it created even more annoying problems. now everytime mail opens it ask for a keychain password. once that password is typed I still have to type my password for each account.
    I strongly do not recommend doing the above.
    I have searched high and low and tried everything to fix leopard mail password issues.

    One very disgruntled mac user.

  4. comment Gravatar luke - November 12th, 2007

    re: my last comment. I found the way around this was on the new login file that was created was to right click (get info) click the button (allow all applications to access the item) then save changes.
    All working fine.
    Although I wonder if this action could have been done from the start without deleting the original keychain login file.

    Best

    L

  5. comment Gravatar webomatica - November 12th, 2007

    Luke, adding access to all your applications is a necessary step if you want the keychain to remember your passwords. In my case, I definitely had to recreate the keychain because I checked that setting on the keychain I deleted and it was active. Part of the problem was the broken keychain might remember my passwords during one session but the next time I booted up the computer I’d have to re-enter all the information again.

  6. comment Gravatar Ed - November 20th, 2007

    I have the same problem using Leopard on a MacBook Pro. I’ve been using Leopard for a week now and once in a while the keychain access password would not work. It seemed hit and miss until today. I had opened up the keychain but it wouldn’t accept my keychain password to unlock access. While I was reading these comments, I ran Disk Utility to correct permissions. Although it said it had a minute remaining, it STAYED a minute remaining for close to 5 minutes and I didn’t hear any disk accesses. Forcing quit and trying it again didn’t get any better. Forced quit the second time just to give up. BUT the kicker is now my passwords work!! I have not done anymore research on this yet, but it may be worth a try for anyone else having a password problem.

  7. comment Gravatar STEVE - December 6th, 2007

    LUKE…

    re: my last comment. I found the way around this was on the new login file that was created was to right click (get info) click the button (allow all applications to access the item) then save changes.
    All working fine.
    Although I wonder if this action could have been done from the start without deleting the original keychain login file.

    Please help Luke….when you say to right click on the login file do you mean from keychain application as I can’t seem to locate it !!!! HELP PLEASE OB1 THIS IS DOING MY NUT IN…..

  8. comment Gravatar Terri - December 31st, 2007

    I am having the exact same problems you guys are, only to complicate the matter further, it doesn’t except my password, and so i cannot even unlock them to delete.
    And since it demands the keychain password in entourage, i cannot send email…
    Help!

  9. comment Gravatar Mark - January 16th, 2008

    This had been bugging me to no end — strangely not enough to get me to do anything about it until now though. Anyway, thanks for doing the more difficult work for us who waited it out.

  10. comment Gravatar Pit - March 26th, 2008

    Hi

    I had similar problems as you have decibed here. In may case the permission of the file ~/Library/Keychains/login.keychain wasn’t correct. Make sure that you have read/write access rights to the file.

    Pit

  11. comment Gravatar Leon Ho » Blog Archive » Leopard Upgrade Problem - Keys do not stick on Keychain - May 8th, 2008

    [...] Webomatica and MacFixit have mentioned other ways to fix common problems on Keychain. [...]

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