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Keychain won't save password to mail when computer sleeps. GRRRRRRR

Why does Mail ask for my login keychain password whenever the computer wakes from sleep? I have been on the phone with apple support on this issue for 2 months!
I am not joking. I bought a brand new MBP 2 weeks ago and the stinkin problem transferred to the NEW computer!
I believe this is a mobile me issue of some sort.
I am on hold again. This problem is very sporadic.

He can't figure it out either.
Does anyone have any idea's how to fix this???????

MacBook Pro, Mac OS X (10.6.2)

Posted on Jan 7, 2010 6:00 AM

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1 reply

Jan 7, 2010 6:51 AM in response to Kaiser.roll

Disable keychain syncing in MobileMe while trying to debug this. Having it enabled will just add more complexity and you'll want to make sure your keychain is working correctly locally before you throw MobileMe syncing into the mix (you can leave other MobileMe syncing services on -- just switch off the keychain sync.)

Open your Keychain Preferences. In the upper left corner of the window (under "Keychains") how many keychains do you have and which one is in bold font?

You should have a "System Roots", "System" and then at least one additional keychain which will either be named "login" or will have a name which matches the shortname of your login account (e.g. for me it's named "tim") Which of these is listed in bold and is the padlock shackled opened or closed?

The user keychains (not the System or System Roots) themselves live in +<your home folder>+/Library/Keychains. *Make backups of these files.*

With your user keychain(s) backed up:

1) Select "Keychain Access" -> "Preferences" -> "First Aid"
2) Make sure "Syncrhonize login keychain password with account" is enabled (checked)
3) Make sure "Set login keychain as default" is enabled.
4) Make sure "Keep login keychain unlocked" is enabled (technically this would be your choice but if you don't want the system to prompt you for keychain password to unlock it each time then you need to check this box.)

Close Keychain Access & log out, then back in. Sleep & wake your computer to test. Were you prompted for your keychain password? If not then your problem is hopefully fixed and you can skip the rest of the steps.

If so, continue with the following.

5) Highlight the keychain listed in bold (probably this will be the keychain named "login").
6) Select "Keychain Access" -> "Keychain First Aid"
7) Type in your password, select "Repair" and click "Start"

When it's completed, log out, then log back in. Test sleep/wake again. Fixed?

If not, change your login password to something else, then change it back again. This should force the system to re-sync your login password with your keychain password. Go into "System Preferences" -> "Accounts", select your own user account, then click "Change Password...". There are other ways to change the password but the Mac uses your password and keys based on your password in many locations other than just performing a login (in other words changing the password does a lot more than you might think.) Using this panel to change password will ensure that all the changes that need to happen will be performed correctly.

This hopefully should have fixed your keychain issues. If not, take a look at "Keychain Access" -> "Preferences" -> "General". There's an option to "Reset My Default Keychain" (hopefully you don't need to use that.)

I've seen some odd issues occur when syncing the Keychain to other Macs via MobileMe -- but I think mostly these are issues when not all Macs use the same user password for your login account.

Message was edited by: Tim Campbell1

Keychain won't save password to mail when computer sleeps. GRRRRRRR

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