Mavericks Mail not sync'ing IMAP act. (Not GMail)

Hab1 -- Indeed. It's been working now for almost 24 hours, but I will keep you updated. I think Csound1 is right that it has something to do with the iCloud Keychain and its interaction with Apple Mail. My point is simply that true forced rebuild of Apple Mail is no longer accomplished simply by deleting the Mail folder from ~/Library. You have to turn off iCloud (maybe just the Keycain, but that's now I did it) so new Mail folder from ~/Library is truly new and not just repopulated by Mavericks with the old information from iCloud (Keychain). Because that's what's been happening, and, it seems, makes Apple Mail different in Mavericks than it was in previous versions.

REVISED HOW I FIXED APPLE MAIL SYNCING ISSUES WITH GMAIL (AND, I PRESUME ALL IMAPS)

**Revised to add a Step 8 on repeating the process for your other Macs after you do the first one**

**Revised for additional clarity (hopefully)**

----

In our long discussion on this, and my own tinkering, I suspected this issue had something to do with Mavericks now keeping all our internet accounts information in the cloud (through the Keychain?). If you go to settings, Internet Accounts, you can see the list of your various internet accounts. It is no longer possible to completely remove an email account in the Mail app. You can only disable it or enable it. To remove the account, you have to delete it from the Internet Accounts menu in settings.

Many users in these forums have suggested deleting the Mail folder in ~/Library then restarting Mail to have it rebuild all your internet accounts. In this scenario, when you restart Apple Mail you're asked to type in the information for an email account. However, I noticed each time I did this within seconds the new Mail folder created in ~/Library upon restart of the Mail app would be populated with information from all of my email accounts and not just the single one I had entered when the Apple Mail was started.

I have suspected that this was part of the problem. Perhaps my settings and such were messed up and that caused a glitch when I initially upgraded to Mavericks, and the glitch was forever saved in the Internet Accounts menu (through Keychain), or in all of my messing around before the so-called fix was issued I had messed something up, which, again, was set in stone in Internet Accounts because of iCloud not saves the information for all your internet accounts.

I know the Internet Accounts in the settings menu is now stored in iCloud (Keychain) because I use a MacBook Air, and two different iMacs. As soon as you sign in to iCloud on any Mac, and turn on Keychain, that Internet Accounts screen your system settings is populated with all your internet accounts.

So here's what I did to get a complete fresh start and it has worked for me.

Step 1: Quit Apple Mail

Step 2: Go to Settings --> Internet Accounts. Delete the Gmail (or the offending IMAP account) account (you'll be asked to remove it across all your OS X computers--say yes). I mean DELETE, not just disable. Hit the minus sign at the bottom left of the list with Gmail highlighted.

Step 3: Then delete the iCloud account as you did the Gmail account.

Step 4: Then delete the rest of the internet accounts on the computer.

(I think this sequence is important. You are deleting the offending email account from the iCloud Keychain, which should remove it from all your computers. Then you're deleting the iCloud account, which leaves the other internet accounts you have intact on your computer and in the information intact in iCloud Keychain. But you also need to delete the other internet accounts from your settings to get the true clean start for Apple Mail.)

Step 5: Go to the Library folder in your users file. (Which you can do by going to the Finder, selecting Go from the top menu, then selecting Go to Folder... typing in this: ~/Library.) Find the Mail folder and drag it to the trash. Empty the trash. If you get a message that a file is in use and so the process can't be completed, restart the computer then empty trash immediately.

Step 6: Open Mail App. It will ask you to put in information for an email account. Put your GMAIL account in (or your IMAP) account FIRST!! (A MUST!) Give it some time to get everything in there. At this point, you will notice that the problem is gone. Your mail will sync properly, archived/deleted messages will move properly, and read/unread counters will function properly.

Step 7: Add the iCloud account from the Internet Accounts screen. Once you turn on Keychain and get it approved through another device (which should then add your other email accounts). I did this reluctantly, but it has worked. My other email accounts were added to Mail (the ones I didn't delete BEFORE I deleted the iCloud account back in Step 2).

Step 8: When repeating this on your next Mac running for Mavericks, delete iCloud FIRST from Internet Accounts in System Settings, then proceed with Step 4.

Also, one other interesting thing that suggests the issue may be with the iCloud Keychain is that after I fixed the first Mac computer and everything went fine. I followed the above process for my second Mac. Once it started working, I kept receiving notices on both of my iOS devices (iPhone 5s and iPad Mini with Retina) that the username and password for my Gmail was not correct.

I went to iOS settings, typed in the correct password several times, and the device could not connect.

I deleted the account from the iOS device, then tried to add it again. Again, wrong password. (In the meantime, I'm checking by logging into the website and, no, my password was not mysteriously changed.) After performing a hard reset, I was able to successfully add the Gmail account back. This happened for both iOS devices after the second and then the third Macs were fixed.

Am I wrong or did Apple not release Keychain with Mavericks initially as planned, and only added it after an update?

This is a pure guess: but perhaps there's been an issue with Keychain screwing up the login information for some of our email accounts. (If I were brave, I'd change my Gmail password, then change it in Apple Mail to see if that goes across the board.)

good to know FriarOP

i'll be trying this when home, have some time to read it properly and carry this out with a clear head and no children running around.

interesting you say about passwords and keychains. i did the part re-install where i deleted the mail account from Mail. I'm trying to remember if i did it in just mail or icloud also. I thought it was just Mail but if I'm right you cant actually do just mail any more... doesn't it point you automatically to iCloud to delete an Internet account?

anyway, when i did it, reentered passwords it kept saying passwords were wrong, when they weren't, and when mail was sending, and being received, from those accounts it was saying were wrong. Something in the keychain across devices seemed to be slightly wonky.

i also started receiving Mail Certificate Errors from a long gone Mail account also... could be connected.

2 macs down - all appears fine. Could this be the second coming of Mavericks? I like many others was at wits end and ready to punt mail. Fingers are crossed.

why use a forum if you are not prepared to 'try things out'?

I don't think there is anything "Convoluted" about FriarOP ‘s possible solution to this issue. It's pretty darn straightforward and I'll simplify if for you.

0: Close the Mail app and probably all other apps that are running.

1: Delete the offending IMAP Account in SysPref’s Internet Accounts

2: Delete the iCloud Account

3: Delete the other Internet Accounts

4: Goto the ~/Library folder, find Mail Folder & Trash it and empty trash

5: Open Mail and when asked, add the offending IMAP Account back in and let it sync

6: Add the iCloud account from the Internet Accounts screen in Sys Pref and turn on Keychain

7: Other internet accounts will be added automatically.

So what is so "Convoluted" about that? Yes he offers a lot of other details that probably could be left out but offers value of what's happening as the above process is carried out.

Sounds to me that you’re just not patient enough to read through the entire process of what FriarOP wrote and figure out the simple steps as I have done above.

Hope this helps.

G.

RazorV,

Awesome explanation. Two questions: if all my imap accounts are misbehaving, do I add them all one at a time before adding the icloud account back?

And: I don't fully understand Keychain. Is there somewhere to turn this off and then turn it back on?

Thanks...

bob,

To answer your first q - Delete all offending IMAP accounts prior to deleting the iCloud Account. Then when readding your accounts through the Mail App, add all offending IMAP accounts (that you deleted prior to deleting the iCloud account) prior to adding the iCloud account.

Turning iCloud Keychain on/off - it's a simple as going to SysPref, then iCloud, unchecking Keychain. Checking it re-enables it.

There is a good white paper on what the iClould Keychain is from apple in the below link. I suggest you may want to read it as it explains (easily) what keychain is and how it works - in a fairly simplistic way.

http://support.apple.com/kb/HT5813

Correct me if I'm wrong anyone.

G.

UPDATE

Thanks for that excellent simplification RazorV. I'm not used to writing out workarounds.

If I could modify it slightly, which also modifies my own earlier post. I did some further testing,as the Apple Mail program on one of my Macs started again to show the same issue of not syncing. In an earlier post, I mentioned the strange effect this process on OS X had on my iOS devices, and I'm hypothesizing it has to do with Keychain.

I really wonder if the bug is in Keychain and how Keychain is interacting across different OS X machines running Mavericks and with the iOS-version Keychain, and how all this interacts with Apple Mail.

I recommend this modfiication below. It works similarly to the other but without trusting Keychain, which is the major change in how Mavericks Mail works compared to its earlier version.

0: Close the Mail app and probably all other apps that are running.

1: Turn off Keychain under iCloud Account in SysPref’s Internet Accounts. Ok to keep passwords on your computer.

2: Delete the iCloud Account

3: Delete all other Internet Accounts

4: Goto the ~/Library folder, find Mail Folder & Trash it and empty trash (may require a restart to complete).

5: Open Mail and when asked, add the first IMAP Account back in and let it sync.

6: Manually add all other mail accounts through Apple Mail Preferences. Let them sync before adding the next one.

7: Add iCloud account last but do NOT turn Keychain on. Leave it off.

Turning Keychain off means Apple Mail is running more similarly to its pre-Mavericks version when it comes to settings on internet accounts. I did this for all of my computers and so far none of them have gone awry.

FriarOP,

Thanks for updating it. Humm, so now we leave the keychain off? Is that not going to cause sync issues across my other Mac's and iOS Devices with Calendar, Notes, Contacts, Messages, passwords and credit card info, favorites, etc.? Just asking, cause I'm not sure but I think I may be.

I have a MBP and everything is fine. However, I have a friend that has a new iMac (2 of them - one for his wife) and his iMac is experiencing the issue with IMAP. Why his wife's is not, I have no clue because she has the same mail accounts, but different apple ID.

Go figure. I'm going to try your procedure tonight on his iMac but leave the keychain on and see what happens.

Any other suggestion just let me know.

Also I want to thank you for taking the time in writing that procedure and giving the detail. I'm an IT Director for a large company and I'd say 70% of my time I spend reading stuff like this or learning. I don't think I ever left college, I just stopped taking the tests.

G.

Didn't mean to ruffle your feathers, but I was replying to the word you used to describe his procedure. And that word was "Convoluted".

G