On the day Leopard was released it immediately found its place on my hard disk. At first it seemed like there haven't been any problems with it, but within the next few days I stumbled across keychain problems again and again. Sometimes I had to enter my MobileMe password again, or my Mail.app passwords couldn't be saved and things like that.
I tried to fix it using a method I found on the web, which was deleting the default keychain (called "Login") and creating a new one manually followed by making the new one the default keychain again. And it seemed to work quite good... well, but it worked only in the first place. When I synced my MacBook with the same MobileMe account again, the keychain got totally borked. My iMac's Snow Leopard couldn't even use the trash any more. Instead of moving files to the trash every file had to be removed immediatly - and permanently.
When this problem came up, I searched for permission problems of any kind, using Finder, Disk Utility and even the Terminal. Permissions seemed to be correctly set, but I still could not use the trash any more and the keychain didn't work only temporarily, too.
I tried everything that came to my mind, primarily resetting my MobileMe sync data with fresh keychains and such, but it all didn't help. Either the iMac or the MacBook didn't use the keychain I created and if one actually did, it threw errors or didn't save the passwords I typed. Even without syncing the keychains at all I wasn't able to use the keychain I created correctly.
I already thought about installing Snow Leopard again, but luckily I tend to find the problems when it comes to the hard steps ;-)
I played around with the first aid option of the Keychain Access application and found out, that the newly emerged problems seemed to have something to do with me following the guide of resetting the default keychain. I deleted my new default keychain again and ran the first aid on my keychains again. And well, how shall I put it? It fixed everything. The first aid with no (!) default keychain recreated it for me and after this one was created, everything worked fine again. Of course I had to make sure that MobileMe wasn't syncing the bad data again, so I reset the keychain data on the MobileMe side again, disabled syncing for the time I ran the first aid and then manually synced the working keychain back again.
But now everything works again. I just had a small "problem" again, which turned out to be just a setting in the keychain itself. Every five minutes my Mail.app and the MobileMe sync client asked for a password to use the keychain again, but this could be fixed by disabling both security options the keychain offers. These two options are usually disabled by default to avoid this "Windows Vista madness" of too many security checks bugging the user, but were enabled when the first aid wizard created it for me.
I don't really know what went wrong here, I can just guess that it's got something to do with my user profiles not being the same that I used on Leopard before. When I installed Snow Leopard I created the same users again, but I didn't restore them from my backup but created them using the installation wizard. Maybe the data that got synced from MobileMe had different ownerships or something like that. Two users with the same username don't have to be the same user from the UNIX point of view, so maybe that was the problem, I don't know. But what I know is that I've got a smoothly running system back!
So if you run into keychain problems after migrating to a new Mac OS X version I suggest to clean up your default keychain like I did. Luckily all my really important passwords reside in 1password and if it's not the same for you, you may want to manually migrate some of your keychain items. But it can be essential to remove the keychain and let it be recreated by the first aid wizard. Don't create one manually, just use the wizard and I hope you'll be fine :-)
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