.Mac failures (#3): E-mail: Repeated password request, sending mail fixes; Sync failure fixes; more

E-mail: Repeated password requests -- fix for non-server related issues, sending e-mail fixes We continue to cover an issue where access to .Mac e-mail services fails because the user password is repeatedly requested and never accepted. Many of the cases we've covered in the past few days have been caused by inexplicable issues with Apple's servers. However, some variations of this problem are caused by keychain and/or .Mac settings issues.

As such, if you're having problems with repeated password requests, try the following workarounds to rule out client-side issues:

Perform a Keychain repair This is accomplished by using the "Keychain Access" application, located in the Applications/Utilities folder on a standard Mac OS X installation. Once you have opened this application, go to the "Keychain Access" menu and select "Keychain First Aid."

Upon entering your keychain password, you will be able to start either a verification or repair process. First verify, and if a problem appears, attempt repair.

Delete Keychain .Mac entry Open the "Keychain Access" application located in /Applications/Utilities. Type ".mac" in the search field located in the upper-right corner. Delete any .Mac-related entries in the listing below.

Delete Keychain folder Try deleting the following folder:

• ~/Library/Keychain

then restarting. You will then have to re-enter your password.

MacFixIt reader J Dalton writes:

"(In my case) the problem was a corrupted ~/library/keychain folder. The solution was to throw the entire folder in the trash and then re-boot, start mail and re-enter the password (once). Also the box 'remember password in keychain' needed to be checked."

If you are having issues sending mail through .Mac servers, try modifying your account settings via the following instructions for Mail.app:

1. Go to Mail.app's preferences (under the "Edit" menu)
2. Click on the Accounts pane
3. Select your .Mac account from the list at left
4. Click on the "Account Information" tab
5. Next to  "Outgoing Mail Server" click "Server settings"
6. Next to "Authentication" pick "Password)
7. Make sure that your .Mac username (just the username, not the @mac.com portion) and password are correctly entered
8. For "Server port" enter 587

For other e-mail clients, including Entourage, look for similar settings in Account preferences.

Also, note that some of the aforementioned Keychain-based workarounds may also be applicable for problems receiving or sending mail.

Synchronization failures Many users continue to report issues with .Mac synchronization from Address Book and other enabled applications.

MacFixIt reader Philip Howe writes:

"I have had repeated failures to sync my G5 - running 10.4.6 and now 10.4.7 - with .Mac for nearly all of this year. [...] I was lead to believe that updating from 10.4.6 to 10.4.7 would fix this problem but it has not turned out to be the case. I am still told repeatedly '.Mac Error - .Mac is not available at this time. Please try again later.'  It is distressing that such an important feature of .Mac membership fails in one iteration of the OS after another. I used to rely on this synchronization feature, it was so handy. Now it is clearly useless."

Like the e-mail issues mentioned above, some instances of synchronization failures are caused be Apple server-side issues, and others are caused by client-side problems.

Fixes for client-side issues

Turn off, then back on, .Mac synching Use the following steps to disable then re-enable .Mac synch

1. Open System Preferences and access the .Mac pane
2. Click the "Sync" tab
3. Uncheck the "Synchronize with .Mac" checkbox
4. Close System Preferences
5. Re-open System Preferences and repeat steps 1 and 2
6. Re-check the "Synchronize with .Mac" checkbox

Disable keychain synchronization If the above process does not re-allow synchronization, you may need to leave Keychain synchronization turned off in the "Sync" tab of the .Mac System Preferences pane.

General failure to send/receive mail Larry Herzberg writes: "I've been experiencing this, at unpredictable times and for durations as long as several hours.  I have two IMAP accounts from which I retrieve messages using Mail; the one works fine consistently, while .Mac has failed at least three times in the last few months.  The first time it happened, I experiences the repeated inquiry for my .Mac password first (or maybe Keychain password, I don't remember), rejections of it, followed by a server timeout.  Since then, there has simply been a failure to connect with the .Mac server, followed by a timeout.  I'm using 10.4.8."

Bob Walder writes: "I use Entourage to retrieve mail from .Mac and it is failing up to 30-60 times a day at present with "invalid password" type messages. The client is correctly configured (i.e. It has worked fine before!) and nothing has changed this end. I have tried re-entering user/password data in case something on the client got messed up, but to no avail. E-mail between two .Mac accounts is taking up to four days to arrive on occasion. Other times it simply does not arrive at all.

Previous coverage:

• .Mac problems (#2): Failure to retrieve/send e-mail; synchronization issues; Backup will not copy files; more
• .Mac outages: Inability to retrieve mail, problems synchronizing, more

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