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Mail Improvements in OS X 10.9.2

It seems to happen like clockwork: I release a book about some Apple product or service, and within a week, Apple updates its offerings in such a way as to invalidate what I wrote. But this time I had a tiny bit of luck: Apple’s 10.9.2 update (see “10.9.2 Fixes Critical SSL Security Bug, Adds FaceTime Audio,” 25 February 2014) was released hours before we planned to publish my new book, “Take Control of Apple Mail,” and that gave me just enough time to revisit problems in previous versions of Mail and edit the manuscript to reflect the changes.

I’m pleased to report that the new version of Mail in 10.9.2 (version 7.2, build 1874) is far better than its predecessors, about which I complained mightily in “Mail in Mavericks Changes the Gmail Equation” (22 October 2013) and (to a slightly lesser extent) “Mail in Mavericks: Is It Safe Yet?” (11 November 2013). That meant I was able to delete quite a few paragraphs from my book detailing bugs and other infelicitous changes. But, to keep this in perspective: Mail is now at the point where it should have been when Mavericks was released.

Since those paragraphs will no longer be in the book, I wanted to report what I’ve found. I’ll begin with the usual disclaimers: not every problem has disappeared, and what works for one person doesn’t necessarily work for everyone. As evidenced by the long list of comments on this article, plenty of people are still experiencing significant problems. Even so, this is the first version of Mail in Mavericks that feels reasonably reliable, and it’s about time!

As always, Apple’s own claims about what has changed are vague and incomplete. The relevant lines from the release notes are as follows:

  • Includes general improvements to the stability and compatibility of Mail
  • Improves the accuracy of unread counts in Mail
  • Resolves an issue that prevented Mail from receiving new messages from certain providers
  • Improves VoiceOver navigation in Mail and Finder
  • Improves compatibility with Gmail Archive mailboxes
  • Includes improvements to Gmail labels

That all sounds encouraging, if not terribly clear. So, take Apple’s list with a grain of salt. Here’s what my tests have shown:

  • Unified mailbox behavior: In 10.8 Mountain Lion and before, you could drag a message from any mailbox to the unified Inbox icon (which contains the Inboxes for all your accounts), and Mail would move it to the Inbox of the account where the message was stored — unless it was stored locally and thus not in any account, in which case it would be moved to the account shown first under the unified mailbox. The same went for other unified mailboxes — Drafts, Sent, Junk, Trash, and Archive. However, in 10.9.0 and 10.9.1, this convenience feature was gone; when dragging a message to any unified mailbox, you had to expand it and select a specific account underneath. Now, in 10.9.2, we’re back to the more convenient Mountain Lion behavior.

  • Gmail special mailboxes: In the first two releases of Mavericks, although you could uncheck the Store Draft Messages on the Server, Store Sent Messages on the Server, Store Junk Messages on the Server, or Move Deleted Messages to the Trash Mailbox checkboxes on the Mailbox Behaviors view of your Gmail account preferences, as soon as you reopened the Preferences window, you’d see that they were checked again. In other words, you were obligated to store Gmail drafts, sent, junk, and trash email on the server whether you wanted to or not. Furthermore, Mail forced you to use the default locations for Gmail’s Drafts, Sent, Junk, and Trash mailboxes. (That is, if you selected another mailbox and chose Mailbox > Use This Mailbox For, the submenu was dimmed.) Both of those annoyances are now gone; you can store special Gmail mailboxes on the server or not, and if you do, you can choose nonstandard mailboxes if you prefer.

  • Gmail mailbox order: Previously, you could not rearrange Gmail mailboxes in Mail’s sidebar; those at the top level of your Gmail account were always in alphabetical order (although, strangely, mailboxes nested within another mailbox could still be reordered). Now you can reorder Gmail mailboxes, but not the special-purpose mailboxes Gmail creates automatically, such as Important and Chats.

  • Gmail AppleScript problems: If you had an AppleScript that targeted a Gmail mailbox other than Inbox or Archive/All Mail, it would fail, because AppleScript saw all the other Gmail mailboxes as being empty. Now AppleScripts can again see into Gmail mailboxes properly.

  • Exchange reliability: Users with Exchange accounts had found that Mail checked for new messages on launch, but not afterwards; you had to either quit and reopen Mail or take your accounts offline and then check for new messages manually (as described in this Apple support article). That has now been fixed, at least for most users.

  • Addressing to Smart Groups: The Contacts app lets you create groups of addresses — for example, a Family group that contains the contact records of your family members. You can type a portion of a group’s name and Mail autocompletes it just as it would for an individual name. Autocomplete does not work for Smart Groups (so, that much hasn’t changed since 10.9.1), but now, if you type the entire, exact name of the Smart Group and type a comma or press Tab or Return, Mail at least displays the group name in a nice blue bubble, and the Smart Group does in fact work — Mail sends the message to the correct addresses.

That’s as much as my testing has revealed so far. I wouldn’t be surprised to find more improvements (or new bugs, for that matter). I can’t yet say whether other issues with Gmail or Exchange have been dealt with. And although Apple may have improved the accuracy of unread counts (perhaps for Smart Mailbox badges), I’ve read multiple reports that the badge on Mail’s Dock icon still isn’t accurate. Numerous other issues remain, as well, but on the whole the bugs seem to be fewer and less severe than before.

If you’ve noticed additional improvements, things that are still broken, or new bugs, please share them with us in the comments. And if you ever feel as though your email is out of control, my brand new 175-page book “Take Control of Apple Mail” will help you become more productive with Apple Mail in 10.9 Mavericks and iOS 7, providing essential advice for Gmail, iCloud, IMAP, and Exchange accounts. It reveals hidden interface elements, shows how to customize Mail, explains my strategy for avoiding email overload, demystifies encrypted email, and provides solutions to common problems, among many other things.

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