Help: Apple Mail people

Now, i know that i hate email and i know that it hates me, but our standoff has reached new levels, creating absolute chaos. I know that many of you are Mac people so i could really use your help since Apple’s site is oh so not helpful.

I use Apple Mail. It’s connected to an IMAP server at school. There’s a procmail process remotely that moves various messages into various folders. That procmail process also forwards certain emails off to my Sidekick.

Apple Mail has never automatically updated those folders so, instead of “check mail,” i’ve always right clicked and selected “synchronize folders.” I read email, i move it to other folders. It stops being “new” and when i reply, it gets a little arrow next to it. This is normal.

Well, something has gone terribly wrong and normal no longer exists. Now, when i “synchronize” a random assortment of “old” messages reappear in each box. Most are marked as “new” and some are not. Some of the moved ones are in the folders i moved them to; some are not. Some of the ones i reply to have the arrow; most do not. Messages that i swore i sent are not in my sent directory (nor in my drafts or out directory).

I’m completely baffled. Help?

[Or perhaps this should be a sign that i’m never going to catch up on email and i should quit now.]

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8 thoughts on “Help: Apple Mail people

  1. Harald Wagener

    Apple is known to screw up all sorts of caching stuff. First thing I’d do is check if is set up to ‘Automatically synchronize changed mailboxes’ in Preferences->Accounts->Advanced.

    If that is the case, it might help moving some cache files out of the way. In ~/Library/Mail/IMAP-, Your mail is synchronized.

    You could get away with moving this directory out of the way, and redoing the caching from start.

    If You don’t want to do that, You could move the files .OfflineCache and .mboxCache.plist contained in that directory out of the way and see if it helps.

    Apple Mail is especially slow and buggy when it comes to large amounts of mail (especially if the mails themselves are big, too).


  2. Matt

    I’ve experienced similar problems in the past when Mail was doing a poor job (for whatever reason) of deleting the mail that was on the server. On prefs->accounts->advanced there’s that “remove copy from server after one week” business… and a couple times it’s just decided to stop doing that.

    I’ve started getting “old” messages delivered as new, so I go and talk to my sysadmin – he reports I’ve got a billion email messages on the server. So I hit that “remove now” a few times on the Mail advanced prefs tab, make sure my junk mail and trash are in order… and it has cleared up the probs. I think. It’s been a while.

  3. Patrick Gavin

    I’ve noticed that stuff like this happens when you have more than one Apple Mail client running on different machines (like if I forget to logout at work or at home)

    Woah! deja vu!

  4. geeked.

    5-star Gmail suggestion

    It’s news to no one that i hate email (and lord knows i’m not the only one). Gmail is a light when all others have gone out, but it made me realize last night that it still retains one of the critical flaws of email systems, which is that i can…

  5. paul

    1. Make sure to check the box Harold referred to.

    2. Make sure that Apple Mail is using the same “sent messages” folder as your other programs/devices.

    When using multiple Mail clients, you end up with two, i.e. “Sent Messages,” “Sent Items.” If you see you have two, move all the messages to one (whatever your other device uses), and then control-click on the mailbox and choose “Use this mailbox for sent messages” (or some similar wording).

    If you’re still having problems, bug me via email/IM and I’ll help you chase it down.

  6. zephoria

    So, i tried all of this and it hasn’t fixed anything. I’ve only been working on one laptop all week – not checking my email from any other machine. Yesterday, after trying to recover lost emails, i cleaned out my INBOX. Came back today, most of the messages are back. Also, i still have to synchronize manually to get any of my messages, even with Harold’s suggestion. Thank you so much for your advice. Any other thoughts?

  7. Chris McLay

    This happened to Jacquie recently and it turned out some of her Account settings had slipped. In the advanced tab make sure “Automatically Synchronise Changed Mailboxes” is on, check the Path Prefix is also right, and make sure all the Special Mailboxes are set to be stored on the server.

    The other option is to disable the account and set up a new one. If this works well then you should be able to delete the old one safely…

  8. paul

    If you deleted the messages and they came back, it sounds like your ISP is having issues.

    Any messages from Mail in the console log?

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