Mail keeps asking for password and icloud setting do not load in system preferences

Hector;

I have the same problem. The solution is to log into your client, open Keychain, run Keychain First Aid under file menu. If it fails to find your keychain, note the path, mount the disk that it is looking for, and rerun.

In short, you need to have the disk that your keychain is sitting on mounted. While your user account is mounted, Maveriks cannot match the reference path. Looking like a bug.

Example:

my folder sits on a second disk on server. It is properly setup in the mavericks server.

On the server, it is locally referred to as: /Volumes/my_disk/Users/my_user. I can log in to mail on the server when I log in with my user name.

In the workgroup manager, the same location is referred to as:

afp://my_server.local/Users/my_user (or smb)

/Network/Servers/my_server.local/Volumes/my_disk/Users/my_user

So this is the network path. So the client should be looking for that. But instead, it looks for the local disk, which is not mounted as such. In other words, it looks for:

/Volumes/my_disk/Users/my_user/Library/Keychains

instead of

/Network/Servers/my_server.local/Volumes/my_disk/Users/my_user/Library/Keychains

To eliminate this problem, you mount the volume on the client, so it can find. I will keep the editorial to myself, but this is not quality software.

Ali

Hector;

I permanently solved it using these instructions, in particular the ones under repair access control. In summary this is what you need to do:

1. Open your keychain on client.
2. Select login and Passwords respectively on the left panel boxes.
3. For each and every email account, get info (command I) and under Access Control, add the Mail.app.
4. I noticed I had more than one entry for each of my mail accounts, one having mail.app, and the other not. All of them need to have Mail.app added, if not already present.
5. Launch Mail, and if it does not readily connect, hit the '~' sign next to the one of the inbox'es. Enter password(s) for one last time, then it sticks.

Yes this is a bug. Unfortunately, my respect for Apple has taken a serious hit in the last two years. It no longer 'just works'.

If it's not Keychain, then verify the DNS and the network connections from the client to the server.

Mail.app has the habit and the history of tossing up password dialogs for a variety of connectivity errors. On the client, start with a DNS test and confirm the client is referencing the DNS server on your Mac Mini Server via Network Preferences, and make sure your server is running local DNS services and the following Terminal.app command (Applications > Utilities) reports no changes required:

sudo changeip -checkhostname

That'll require an administrative password. It's a diagnostic, and no changes will be made. It'll report either no changes needed, or it'll report on some of the common DNS or network configuration problems.

Also confirm you're not using .local as your local DNS domain within your OS X Server configuration, as that tends to cause weird errors.

Hector;

I had exactly the symptoms that you described, and mine is now fixed, per the instructions I posted. Since you already said none of the accounts had 'mail', that has to be it.

My suggestions to you:

1. make sure you added /Applications/Mail.app to all of the right entries in the keychain. That'd be smtp/pop/imap etc.
2. make sure it sticks by doing it while logged in only one machine. I noticed keychain gets locked otherwise.
3. relaunch mail, and when it asks, make sure you enter the right mail password(s). (It will ask one last time.)

PS. make sure you are able write to your keychain by reopening and verifying that 'Mail.app' is now in there.

10.9.1 broke this again. Following this solves the problem. But it does not stick. If you log into to your server with the same user, and launch mail, you're back to square one. Mail <-> Keychain interaction in server-client set-up remains badly broken.

Nope. I keep it going as I described in my previous post. This problem has not been fixed, and clearly not a priority for Apple.

Hector and Ali,

Just getting a Mavericks server going. Have bumped up against the same problems you are having here. Terribly inconvenient for our users. Will post if I make any headway.

-Erich

Hector, generally speaking, when users log out, in my case, I do not show users logged in. So this has not been a problem with me. But the problem is still here with 10.9.1 and server 3.0.2. The only solution I have at the moment is to delete in user's machine:

~/Library/Keychains/3CA665E5-E8E5-6BED-885D-77C88A4252A9

the numbers will be different, obviously, and there can me more than one folder of this kind. Delete all, restart client, reenter mail passwords, and it works. Annoying. And if you have hundreds of users, you are toast.

Ali