Customize Mail - Take Control of Apple Mail (1.0) (2014)

Take Control of Apple Mail (1.0) (2014)

Customize Mail

Mail isn’t the fanciest or most powerful email client for the Mac, and many people have dismissed it as being too unsophisticated for email power users. I agree with that sentiment to a point—in its default configuration, Mail isn’t a fantastic email program. However, you can customize Mail in many ways, including by adding plug-ins that both dramatically increase its capabilities and modify standard behaviors to become much more useful. The result is that with a bit of effort, you can turn a so-so email client into a deluxe and highly optimized tool.

In this chapter, I acquaint you with some of the most important ways to customize Mail. I don’t list every single option, nor do I go into tremendous detail about each one, but I do want to make sure you’re aware of what so many Mail users aren’t—you don’t have to live with the stock version of Mail, and you can improve your enjoyment of the app a great deal with a bit of grooming.


The sidebar is the area on the left of Mail’s main window that contains all your mailboxes. Don’t see it? Choose View > Show Mailbox List. Prefer to keep it hidden? Choose View > Hide Mailbox List. (Apple seems to think Mail is easier to use when the sidebar is hidden, but for most people with multiple accounts or more than a few mailboxes, the sidebar is indispensable.)

You can also rearrange items in the sidebar by dragging them to new locations, with certain limitations:

· Top-level categories with titles in all caps (such as MAILBOXES, which contains your Special Mailboxes; individual accounts; and SMART MAILBOXES) can be reordered—for example, you might want to show your smart mailboxes at the top of the list and your special mailboxes at the bottom.

· Within the MAILBOXES category, the order of (unified) special mailboxes is fixed; for example, Drafts always appears above Sent. However, you can reorder accounts within a unified special mailbox. For example, if your Gmail account is listed before iCloud under Sent, you can drag iCloud above Gmail—and that modified order will be reflected under all your unified special mailboxes.

· You can reorder the mailboxes within any given account, except certain special mailboxes (such as Important and Chats—see Gmail on the Web vs. Gmail in Mail) that appear in Gmail accounts.

· You can click Show or Hide next to a sidebar category to expand or collapse its contents (see Hidden Interface Elements), but you can’t manually hide the categories themselves. On the other hand, Mail automatically hides the names of accounts that have no sub-mailboxes beneath them.

At the bottom of the sidebar is an optional Mail Activity pane, which you can show or hide by clicking the appropriate icon beneath it. But I’ve found this pane to be so inaccurate and limited as to be essentially useless. A far better way to see what Mail is up to is to choose Window > Activity.


The toolbar is the area at the top of a window, just below its title, that contains a series of buttons and other controls. Mail has three different toolbars, one for each type of window:

· Viewer window: Mail’s main window, which Apple calls the Viewer window, lists your messages and shows their contents. It has a toolbar that includes buttons such as Get New Messages and Compose New Message , which apply across accounts, as well as things like Trash and Reply , which apply to the currently selected message(s).

· Incoming message window: If you double-click a message in the Viewer window, that message opens in its own message window. The message window’s toolbar contains some of the same buttons as the Viewer window (such as Trash and Reply ) but also a Print button.

· Compose new message window: When you’re writing a new message (including replying and forwarding), the window’s toolbar contains only relevant buttons, such as Send and Attachments .

You can customize each of these toolbars individually. Open a window of the appropriate sort, choose View > Customize Toolbar, and drag buttons on or off the toolbar, or to new locations, to suit your needs. By doing so, you can add frequently used controls (such as Archive, for the Viewer window and incoming message window) and remove any controls you seldom use.

Message Header

The term “message header” is a bit ambiguous in Mail, because what it normally means in the context of email is the information at the top of a message that includes sender, recipient, subject, date sent, and lots of other (normally hidden) data such as the addresses of the mail servers the message passed through to get from the sender to you, and the name of the app used to send it. But Mail also uses “message header” to refer to the top portion of the new message window, which contains the address fields and a row of controls underneath it (Figure 4). That’s what we’re concerned with here.

**Figure 4:** The message header portion of the outgoing message window. Yours may look different, because you can customize it!

Figure 4: The message header portion of the outgoing message window. Yours may look different, because you can customize it!

What you may not realize is that you can change many things about this portion of the window to suit your needs. To do so, click the unlabeled pop-up menu and choose Customize. The window changes to look something like Figure 5.

**Figure 5:** Customize the message header to include or omit other controls.

Figure 5: Customize the message header to include or omit other controls.

In this view, you can select or deselect checkboxes to turn various interface features on or off:

· CC, Bcc, and Reply To fields: Enabling these here has the same effect as choosing the corresponding commands from the View menu.

· From pop-up menu: This menu lets you choose which account the message is sent from; and, for accounts with more than one address, the specific address.

· Server pop-up menu: This unlabeled menu, which appears to the right of the From menu, lets you choose an alternative SMTP server for sending the current message—assuming you have more than one such server configured, and that you don’t have Use Only This Server selected in Mail > Preferences > Accounts > Account Name > Account Information. (If only one server is available, the menu doesn’t appear regardless of whether its checkbox is selected.)

· Signature pop-up menu: Use this menu to choose from among any signatures you’ve set up for the selected account.

· Priority pop-up menu: Choose !! (high priority), ! (normal priority), or – (low priority) for outgoing messages; these flags normally show up in the recipient’s client to indicate how important you, the sender, think the message is.

· Encryption and digital signature buttons: The final checkbox enables buttons to encrypt and/or digitally sign a message with S/MIME—but it’s present only if you’ve configured a digital certificate for yourself (see Use S/MIME Encryption).

Click OK to accept changes, which then apply for all future outgoing messages (until you customize the controls again).


By default, Mail’s main Viewer window displays an optional sidebar, a vertical list of messages including brief excerpts, and a preview pane on the right showing the contents of the selected message.

If you prefer, you can switch to what Mail calls the “classic” layout (Figure 6), which puts the preview pane at the bottom instead of on the right, and presents the message list as a sortable table, but without excerpts. To use the classic layout, go to Mail > Preferences > Viewing and select Use Classic Layout.

**Figure 6:** The Viewer window in the “classic” layout.

Figure 6: The Viewer window in the “classic” layout.

Tip: Sorting in classic layout is simply a matter of clicking column heads. To sort in the default layout, use the commands on the View > Sort By submenu, or on the tiny Sort By pop-up menu above the message list.

The layout of the Viewing pane in Mail preferences may suggest otherwise, but the three options beneath the Classic Layout checkbox apply only when you are not using the classic layout:

· Show To/Cc Label in the Message List: Indicates whether you were a To/Cc addressee, as opposed to a Bcc or mailing list addressee

· Show Contact Photos in the Message List: Pulls contacts’ photos, if any, from the Contacts app and displays them alongside the message excerpt

· List Preview: How many lines of text (if any) to show as an excerpt in the main message list

In addition to the overall window layout, you can also enable or disable Organize by Conversation (choose View > Organize by Conversation), which applies only to the currently selected mailbox and groups together all the sent and received messages in a given thread, even if only one of them actually resides in the current mailbox. (Usually, but not always, Mail is smart enough to group messages into a conversation even if someone changes the subject line along the way.) Thanks to this feature, there’s no need to move sent and received messages to the same mailbox in order to view them as a thread.

Tip: Did you know you can have more than one Viewer window open at once? You can—although they’ll all use the same (default or classic) view. To open a new one, choose File > New Viewer Window.

Favorites Bar

A thin strip below the toolbar in the Viewer window (Figure 7) shows your Favorite mailboxes—those to which you’d like one-click access, even if the sidebar is hidden. If you drag a special mailbox (or any mailbox with sub-mailboxes) to this bar, you see a tiny arrow to the right of the mailbox name; click and hold on the arrow to display a pop-up menu of the individual accounts or sub-mailboxes. A number in parentheses indicates the number of unread messages in that mailbox.

**Figure 7:** The Favorite Mailboxes bar, slightly customized.

Figure 7: The Favorite Mailboxes bar, slightly customized.

To add a mailbox to the Favorites bar, drag it from Mail’s sidebar. To remove a mailbox, drag it off the bar. You can also drag mailboxes left or right in the bar to reorder them.

Each of the first ten favorites, starting from the left, gets an automatic keyboard shortcut with a corresponding number—Command-1 for the first, Command-2 for the second, and so on up to Command-0. So in the figure above, Junk, which is the sixth favorite from the left, would be Command-6. Pressing a shortcut displays the contents of the corresponding mailbox in the Viewer window.


In Mail, a VIP is any sender you designate as being especially important. Mail can use your list of VIPs in a variety of ways to call special attention to messages from those people. VIPs you set up in the Mavericks version of Mail sync to the iOS version and vice-versa, as long as both devices are configured to use the same iCloud account (with Mail enabled in System Preferences > iCloud).

To put someone on your VIP list, open any message from that person. Move your pointer to the area next to the sender’s name in the header of the message (Figure 8) and click the star ☆ icon that appears there. Repeat as often as you like for other senders; or, to remove someone from the VIP list, click that person’s star ☆ again.

**Figure 8:** When you move your pointer here, a star appears; click it to designate this sender as a VIP.

Figure 8: When you move your pointer here, a star appears; click it to designate this sender as a VIP.

Tip: VIPs work best when you have relatively few people on your VIP list. Once it gets beyond, say, a dozen or so, the list becomes unwieldy—and it begins to dilute the meaning of “VIP.”

Once you have at least one VIP, Mail creates a new VIPs entry in your mailbox list along with the other Special Mailboxes. You can select that mailbox to see messages from all your VIPs, regardless of where their messages are filed; or, expand the list and select any particular VIP’s name to see messages from just that person.

Similarly, a VIPs category appears in your Favorites bar (Figure 9). Click that favorite to show mail from all VIPs, or choose a person from the pop-up menu that appears when you click the arrow beside the favorite.

**Figure 9:** The VIPs favorite lists all your designated VIPs.

Figure 9: The VIPs favorite lists all your designated VIPs.

Besides being able to jump right to messages from any or all of your VIPs, you can do the following using the VIPs feature:

· Use VIPs in notifications: Set Mail’s Notifications preferences to notify you only when email arrives from VIPs. See Notifications for more information.

· Use VIPs in rules: Perform any sort of automated action (play a sound, run an AppleScript, send a special reply, etc.) when a message from a VIP arrives. See the sidebar VIPs and Notifications in Rules, later in this book.


A signature is boilerplate content that is appended to the end of your email messages, typically containing your contact information or perhaps a pithy quote.

You can define as many signatures as you need, mix and match them with accounts as you deem appropriate, set which signature (if any) each account uses by default, and even rotate or randomize signatures within an account.

Configure Signatures

To set up signatures, go to Mail > Preferences > Signatures. The left column lists your email accounts, the center column lists your signatures, and the right column displays the contents of each signature (Figure 10).

**Figure 10:** Enter signatures, and assign them to accounts, in the Signatures preference pane.

Figure 10: Enter signatures, and assign them to accounts, in the Signatures preference pane.

First follow these steps to create your signatures:

1. In the left column, select All Signatures if it isn’t already selected.

2. Click the plus button to create a new signature, and give it a name that will help you distinguish it from other signatures.

3. In the right-hand column, add your signature. Here are some tips:

§ To make your signature use the default font you set for outgoing messages, select Always Match My Default Message Font. (This setting uses the font selected in the Fonts & Colors preference pane, along with the default message format—plain text or rich text—set in the Composing pane.)

§ You are not restricted to plain text—you can apply fonts, sizes, colors, and styles using commands on the Format menu—but I advise sticking with plain text to avoid forcing the entire outgoing message to be rich text. (For more on this, see Choose Formatting Wisely, later.)

§ You can drag in (or paste in) a graphic, but I do not recommend it, since it may annoy recipients. (For one thing, an image in a signature counts as an attachment, so every message from you will appear, to the recipient, as a message with an attachment.)

§ Keep your signature short—two or three lines is plenty. Nobody likes receiving email with signatures that go on and on, or that are longer than the message itself (especially those with line after line of pointless and unenforceable legalese)!

§ If your signature is too wide for Mail’s preferences window, you can actually—unlike with most Preferences windows—resize the window for a better view.

4. Repeat the above steps for as many signatures as you want to create.

You now have signatures defined, but before you can use them, you must assign them to particular accounts and configure their 'margin-bottom:8.4pt;margin-left:18.0pt;text-indent: -18.0pt;line-height:16.2pt'>1. Assign each new signature to one account, or to multiple accounts. To do so, drag a signature’s name from the middle column onto an account name at the left.

The number under the account name indicates how many signatures are associated with that account. To see just the signatures in one account, select the account name on the left.

2. Set how Mail will add signatures to messages sent from each account. Select an account in the left column, and then choose an option from the Choose Signature pop-up menu:

§ Automatically: Choose a single signature or choose At Random or In Sequential Order.

§ Manually: Choose None.

Repeat this step for each account listed in the left column.

3. By default, signatures appear at the bottom of messages, below any quoted text. If you prefer to put your signature above the quoted text, if any, select Place Signature above Quoted Text. Note that this setting affects all signatures, in all accounts.

4. Close the Preferences window.

Your new signatures are now available for use in outgoing messages.

To apply a signature to an outgoing message (or to change the one Mail has applied automatically), choose it from the Signature pop-up menu when composing a message. Unlike some email applications, which append signatures after you click Send, Mail displays the signature as editable text, so that you can change or delete it manually if you like.

Keyboard Shortcuts

You can assign keyboard shortcuts to nearly any command in Mail. To do this, go to System Preferences > Keyboard > Shortcuts > App Shortcuts. Click the plus button, choose Mail from the Application pop-up menu, type the name of the menu command in the Menu Title field, click in the Keyboard Shortcut field, and press the keystroke combination you want to use. Then click Add.

There’s just one problem, which occurs if you try to do this for any of the mailboxes on the Move To or Copy To submenus. Both the Move To and Copy To submenus contain exactly the same commands, and by default, OS X keyboard shortcuts are tied only to the name of the command, not to the submenu name. That means you’ll have a hard time predicting whether a given keyboard shortcut will copy or move messages (and indeed, the behavior changes, depending on which action—copy or move—you performed most recently). To solve this problem, type the full path of the menu command, with -> to represent submenus, as in: Message->Move to->Travel (with no spaces before or after ->).

If you want even more flexibility in assigning keyboard shortcuts, opt for a third-party keyboard shortcut tool such as Keyboard Maestro or Mail Act-On (described just ahead).


Dozens of third-party Mail plug-ins exist. These enable you to change unwanted behaviors, add new features, and enable significant new customization options. For example, plug-ins can stop spam, encrypt email messages, offer advanced message filing options, change the way attachments are handled, modify Mail’s method of quoting text in replies, and much more.

I won’t attempt to catalog all the available Mail plug-ins here, but allow me to refer you to lists that other people have compiled and maintain: Maximizing Mail: Add-ons for Mac OS X’s Mail app at Macworld, and Apple Mail Plugins and Tools. I mention a few of my personal favorites in notes and tips throughout this book.

However, I do want to put in a plug (so to speak) for the one plug-in that I positively can’t live without: Indev’s Mail Act-On. It’s a multipurpose tool that adds numerous new features, but the one I like best is its clever approach to filing messages. Mail’s built-in rules run automatically when messages are received, but Mail Act-On adds another layer of rules that run on demand, via keyboard shortcuts—or when a message is sent. You can even combine multiple rules into a single keyboard shortcut.

For example, I can select a message and press my user-defined keyboard shortcut that means “do the right thing with this message,” and it will move the message into Mailbox A if it’s from person A, B, or C, but put it into Mailbox B if it’s from person X, Y, or Z. It’s extremely clever, and that’s only one tiny example of what Mail Act-On can do.

Note: As I write this, a Mavericks-compatible version of Mail Act-On is in beta testing, with a public release expected within the month.

Plug-ins and OS X Updates

Although I love my Mail plug-ins, one thing I do not love is that every time Mail (or OS X) is updated—no matter how tiny or insignificant the update—every plug-in is disabled and must be updated. Mail moves all plug-ins it deems “incompatible” it to ~/Library/Mail/Bundles (Disabled), and moving them back won’t reenable them. What makes Mail think a plug-in is incompatible? Every version of Mail has a special UUID (universally unique identifier), and unless that’s included in a plug-in, the plug-in won’t work.

Most of the time, plug-in developers release updates in a day or two that add the new UUID, but if you can’t wait for an official fix, try the free MailPluginFix, which adds the newest UUID to any disabled Mail plug-ins. It doesn’t always work (sometimes developers need to fix bugs or address deeper compatibility problems), but it often does, and it sure beats waiting.