Take Control of Apple Mail (1.0) (2014)

Learn What's New in Mavericks and iOS 7 Mail

The Mavericks and iOS 7 versions of Mail contain useful new features, as well as controversial design decisions (particularly in Mavericks). Skim over this chapter to see which of these changes may be important to you.

Mail Changes in Mavericks

The Mavericks version of Mail looks almost identical to its predecessor at first glance, but it’s much different underneath. Here are the changes in Mavericks I think you should be aware of:

· Address completion always on: Automatic address completion is now always on; the preference to turn it off, formerly on the Composing pane of Mail’s Preferences window, is gone. Also gone from the same location is the Configure LDAP button, although you can still set up LDAP servers in System Preferences > Internet Preferences (by clicking the plus button followed by Add Other Account and Add an LDAP Account).

· More-useful notifications: If you have Mail configured to use Alerts or Banners in System Preferences > Notifications, the alert now includes Delete and Reply buttons; click Delete to delete the message immediately or Reply to switch to Mail with a reply window for that message already open. (With Banner notifications, these buttons appear only when you move your pointer over the banner.)

· Passbook changes: If you receive a Passbook pass as an email attachment, Mail adds a special bar to the top of the message window alerting you to the pass’s presence, including a View Pass button that lets you display it, add it to Passbook on your iPhone (via iCloud), share it, or get more information about it. If you want to search for messages containing these attachments, you can type pass in the search field and choose one of the selected options from the results list; or type coupon to limit the search to coupon passes.

· Other search changes: You can now search for flagged messages, and search for attachments by name or type.

· Smarter mailboxes: Selecting a smart mailbox folder (a group of smart mailboxes) now causes Mail to display all the messages across the grouped smart mailboxes. When setting up a smart mailbox, your criteria can now specify which account the matching messages must be in; however, there’s no direct way to exclude a certain account from your search.

· iCloud account syncing: If you have an iCloud account set up on your Mac, with Documents & Data enabled in System Preferences > iCloud, the settings for all your email accounts (not just your iCloud account) will sync automatically with all your other Macs—as long as those other Macs are also signed in to the same iCloud account, with that preference enabled. This means, for example, that when you set up a new account on one Mac, you won’t have to repeat the procedure on your other Macs.

Although rules sync as part of this process, their enabled status doesn’t sync, because you might not want the same rules enabled on each Mac. And, sorry, but synced account settings don’t sync with iOS devices.

· Where you configure accounts: You can add, edit, and (sometimes) delete accounts on the Accounts pane of Mail’s Preferences window, as before. But some settings can be changed only on the Internet Accounts pane of System Preferences (called Mail, Contacts & Calendars prior to Mavericks). For example, if you want to change your iCloud password (which affects more than just Mail), you must do so either on the Internet Accounts preference pane or on the iCloud pane. And deleting a Mail account that’s being synced via iCloud (per the previous bullet point), again, that requires a trip to Internet Accounts.

· Automatic new message checking: On the General pane of Mail’s preferences window, the Check for New Messages pop-up menu has a new option: Automatically. According to Mail’s Help, this setting means: “Mail varies how often it gets messages, based on whether your Mac is plugged into an electrical outlet.” This setting applies only to the frequency with which Mail fetches messages; it does not, as you might suppose, have anything to do with push or IMAP IDLE (see Fetch, Push, and IMAP IDLE, later). In fact, IMAP IDLE applies regardless of the frequency with which Mail checks for new messages. (And, because Mail doesn’t support push message delivery for Exchange accounts, using the Automatic setting will likely make it take longer for you to get messages from an Exchange server.)

· Automatically download all attachments: This new checkbox, in Mail > Preferences > Accounts > Advanced and enabled by default, ensures that Mail downloads all attachments when retrieving messages rather than waiting until you request them.

· No more forcing plain-text incoming messages: In previous versions of Mail, a secret “defaults write” command in Terminal forced all incoming or saved messages to display in plain text, if available; you could toggle between different formats using commands on the View > Message submenu. Unfortunately for lovers of plain text (like me), that Terminal command no longer works, and the options to switch among message formats are gone.

· No more buddy status: Before Mavericks, Mail could optionally display a colored dot indicating whether people in your Messages instant messaging accounts (such as AIM) were online. That feature is gone, along with its associated preference and menu command. I presume this is due to the fact that Apple expects most users to favor iMessage over older instant messaging protocols—and iMessage doesn’t care about “online” status.

· IMAP caching: In previous versions of Mail, you could choose, for IMAP accounts, whether to download and cache full messages including attachments, only message text, only read messages, or none of the above. Unfortunately, in Mavericks, downloading the full text of every message is mandatory for IMAP accounts. You can opt to skip attachments, but that’s it.

· Gmail differences: Mail now handles Gmail accounts much differently than before. As I detailed in my TidBITS article Mail in Mavericks Changes the Gmail Equation and followed up on in Mail in Mavericks: Is It Safe Yet?, Apple was undoubtedly well-intentioned—and indeed, some of the changes are quite positive—but the devil is in the details.

Here are a few of them:

§ No more duplicates: In earlier versions of Mail, if you left all your Gmail settings at their defaults, Mail would download at least two copies of each message—one in the All Mail mailbox and one for each label you’d applied in Gmail (since labels in Gmail are translated into mailboxes in Mail when you use IMAP). That made for lots of duplicate messages, wasting bandwidth and disk space. Now, Mail downloads just one copy of each message (the one in All Mail), and invisibly “tags” each message to indicate which other mailbox(es), if any, it should also appear in. That’s a better approach, and it means there’s no longer any need, using settings on the Gmail Web site, to hide the All Mail label from IMAP clients (unless that’s essential for another IMAP client you also use)—and in fact, Mail in Mavericks appears to work better if All Mail is enabled.

§ Gmail-like archiving: Speaking of All Mail, the Archive mailbox in Mail’s sidebar for Gmail accounts now shows All Mail—that is, what you’d see if you clicked All Mail on the Gmail Web site. And now, when you move a Gmail message to the Archive mailbox (whether by dragging or by clicking the optional Archive button on the toolbar), Mail removes the Inbox label so that the message appears only in Archive/All Mail—which, again, is just what happens on the Gmail site. However, pressing Delete when you’re viewing a Gmail message actually deletes it (that is, sends it to the Trash mailbox); it does not archive the message as some Gmail users might expect. Although I recommend against equating “delete” with “archive,” you can use a plug-in calledDelete2Archive to make Mail’s Delete key simply remove the Inbox label from Gmail messages.

Numerous other problems with Gmail in Mavericks Mail have been reported, but in my brief testing just before this book was published, the OS X 10.9.2 update fixed a great many of them. Be that as it may, anecdotal evidence suggests that the more messages you have stored in your Gmail account, the greater your chances of encountering problems in Mavericks Mail.

· Exchange issues: Anecdotal reports indicate that the 10.9.2 update fixes some Exchange-related issues, such as a failure to retrieve new messages automatically. I wouldn’t go so far as to say Exchange is now trouble-free in Mail, but the signs are encouraging. The discussion thread Exchange servers and Mavericks Mail on the Apple Support Communities site has over 500 posts discussing numerous problems, and although most of those were written before 10.9.2, you may find it useful to look over that discussion—particularly pages 35 and beyond—to learn about what is and isn’t working for other users.

Tip: If you haven’t yet updated to OS X 10.9.2, do so now! This list would be significantly longer (as in, detailing several appalling bugs) for versions 10.9.0 and 10.9.1.

Mail Changes in iOS 7

The iOS 7 version of Mail is also much different—but, I’m pleased to say, the changes in this version have been almost entirely positive. For an in-depth look at what’s changed, read Dan Frakes’s Macworld article Get to know iOS 7: Mail. Here are the changes I think are most noteworthy:

· New look and feel: Like other Apple apps, Mail adopts the “flat” iOS 7 user interface, with fewer borders, less shading, and more-modern-looking icons and controls.

· Customizable top-level mailbox view: The topmost Mailboxes view in iOS 6 showed only All Inboxes, the VIP Inbox, the Inbox for each account, and a list of each account (so you can navigate to any individual mailbox). In iOS 7, you can customize this top-level view—for example, you can remove VIP if you don’t use it, or you can add Flagged, Unread, Attachments, or numerous other dynamic mailboxes (which are somewhat like smart mailboxes in OS X). You can also add any conventional mailbox from your existing accounts. To add, remove, or rearrange these mailboxes, navigate to the top-level Mailboxes view and tap Edit.

Note: Once you add a conventional mailbox to this list, there appears to be no way to delete it. You can hide it, but it remains in the Edit list permanently.

· Global search: You’re no longer restricted to searching only the current mailbox from within Mail; search terms typed in Mail’s search box now apply across all mailboxes and accounts. However, if you want to restrict a search to the current mailbox, you can tap Current Mailbox at the top of the results list.

· Shake to undo: The familiar iOS “shake to undo/redo” gesture now applies to moving and deleting messages in Mail, too. If you mistakenly filed or trashed a message, shake your iOS device and tap Undo Action.

· New gestures: If you swipe from the very left edge of the screen toward the right, you can view the next-higher mailbox or list, which produces the same effect as tapping whatever textual “button” is in the top-left corner of the screen (such as Mailboxes, All Inboxes, or the current mailbox).

And, if you swipe from right to left on a message preview in any message list, you’ll see two buttons—Trash (or Delete, for items already in the Trash), which used to appear when you swiped rightward as well; and More, which displays several additional operations: Reply (or Reply All), Forward, Flag (or Unflag), Mark as Unread (or Read), Move to Junk, and Move Message.

· Multiple From addresses: Some email providers let you send mail from multiple addresses (even in different domains). Although it was possible in iOS 6 to set up Mail to use multiple From addresses, it was a complex, awkward process. Now it’s easy: go to Settings > Mail, Contacts, Calendars > Account Name > Account > Email (where Account Name is the name of the account you want to modify), tap Add Another Email, and follow the prompts. Whichever address is checked on the Email screen will be the default; to change the From address for the message you’re composing, tap the Cc/Bcc, From line; tap From; and then tap the address you want to use.

Unfortunately, as cool as this feature is, many services don’t support it. You can’t do this with iCloud (although iCloud accounts can use aliases, which I discuss generally in Use iCloud Aliases, and more specifically for iOS 7 in Use iCloud Aliases in iOS 7), nor with Exchange, AOL, or Yahoo accounts. It doesn’t work with Gmail accounts either, unless you have the account set up as a standard IMAP account, which is possible in iOS 7 but not Mavericks (see Set Up Gmail as a Regular IMAP Account). Even then, you’ll want to be sure you’ve already set up the alternative address(es) on Gmail’s Web site in Settings > Accounts > Send Mail As.

· Automatic sending account choice: Mail notices which account you usually use for sending email to each person, automatically defaulting to that account for that recipient—unless you’re in an account-specific mailbox. (As before, when creating a new message from within an account-specific mailbox, Mail always sends from that account.)

· Flag style: In Settings > Mail, Contacts, Calendars, under the Mail heading, a Flag Style option lets you choose whether message flags appear as colored circles or as actual flag icons.

· Short names: In Settings > Mail, Contacts, Calendars, under the Contacts heading, a new Short Name option, when enabled, lets you select the way you prefer names to appear—both in Mail and in Contacts. For example, you can choose First Name Only or First Initial & Last Name; you can also turn on Prefer Nicknames to display a person’s nickname instead, if one is entered in Contacts.

· Removed features: A few minor capabilities available in the iOS 6 version of Mail are now gone. For example, you can no longer specify how many messages to download at one time. However, it’s difficult to determine how many messages Mail does download at once, since the count of downloaded messages in each mailbox has also disappeared!