Mail, like Outlook Express, lists your various email folders in a column on the left-hand side of the window. In this Mailboxes column, you’ll find the usual suspects, sometimes hidden by flippy triangles: Inbox, Outbox, Sent, Drafts, and so on. Only a few of these mailboxes may be new to you:

Figure 11-1. If you’ve ever used iTunes, you’ll notice a lot of similarities with the Mail window. All your information sources—mailboxes, notes, To Do items, and RSS Feeds—are grouped tidily in the far left column where you can always see them. Buttons along the top of the Mail window let you create new messages, notes, and tasks with a click. To see what’s in one of these folders, click it once. The list of its messages appears in the top half of the right side of the window (the Messages list). When you click a message name, the message itself appears in the bottom half of the main window (the Preview pane).

To see what’s in one of these folders, click it once. The list of its messages appears in the top half of the main window. Now, when you click a message name, the message itself appears in the Preview pane.

Figure 11-1 shows the idea.

Sending little text messages is fine, but it’s not much help when you want to send somebody a photograph, a sound, or a Word document. To attach a file to a message you’ve written, use one of these methods:

To remove an attachment, drag across its icon to highlight it, and then press the Delete key. (You can also drag an attachment icon clear out of the window into your Dock’s Trash, or choose Message→Remove Attachments.)

If you have a high-speed connection like a cable modem, by the way, have pity on your recipient. A big picture or movie file might take you only seconds to send, but tie up your correspondent’s modem for hours.

Signatures are bits of text that get stamped at the bottom of your outgoing email messages. A signature might contain a name, a postal address, a pithy quote, or even a scan of your real signature.

You can customize your signatures by choosing Mail→Preferences, and then clicking the Signatures icon. Here’s what you should know:

Threading is one of the most useful mail-sorting methods to come along in a long time—and it’s available in Mail. When threading is turned on, Mail groups emails with the same subject (like “Raccoons” and “Re: Raccoons”) as a single item in the main mail list.

To turn on threading, choose View→Organize by Thread. If several messages have the same subject, they all turn light blue to indicate their membership in a thread (Figure 11-5).

Here are some powerful ways to use threading:

Figure 11-5. Threads have two parts: a heading (the subject of the thread, listed in dark blue when it’s not selected) and members (the individual messages in the thread, listed in light blue and indented). Often, the main list shows only a thread’s heading; click the flippy triangle to reveal its members.

When you choose the Message→Add Sender To Address Book command, Mail memorizes the email address of the person whose message is on the screen. In fact, you can highlight a huge number of messages and add all the senders simultaneously using this technique.

Thereafter, you’ll be able to write new messages to somebody just by typing the first few letters of the name or email address.

Mail recognizes commonly used bits of information that may appear in a message: a physical address, a phone number, a date and time, and so on. With one quick click, you can send that information into the appropriate Mac OS X program, like iCal, Address Book, or your Web browser (for looking an address up on a map).

Here’s how it works. When you spot a name, address, date, or time, point to it without clicking. Mail draws a dotted rectangle around it. right-click inside the rectangle, or right-click, or click the pop-up ▾ at the right side.

As shown in Figure 11-6, a shortcut menu appears. Its contents vary depending on what you’re pointing to:

Figure 11-6. Mail can detect street addresses, phone numbers, dates, and times. When it spots something you may want to add to another program like Address Book or iCal, it draws a dotted line around the info when you point to it without clicking. Click the little ▾ to get a shortcut menu for further options—like automatically adding the address to your Address Book program or seeing the address pinpointed on a Google map.

Just as you can attach files to a message, so people often send files to you.

Like Outlook Express for Windows, Mail doesn’t store downloaded files as normal file icons on your hard drive. They’re actually encoded right into Mail’s internal .mbox mailbox database files. To extract an attached file from this mass of software, you must proceed in one of these ways:

To answer a message, click the Reply button on the message toolbar (or choose Message→Reply, or press -R). If the message was originally addressed to multiple recipients, you can send your reply to everyone simultaneously by clicking Reply All instead.

A new message window opens, already addressed. As a courtesy to your correspondent, Mail places the original message at the bottom of the window, set off by a vertical bar, as shown in Figure 11-7.

Figure 11-7. In Rich Text-formatted Mail messages (not to be confused with RTF [Rich Text Format] word processing format, which is very different), a reply includes the original message, marked in a special color (which you can change in Mail→Preferences) and with a vertical bar to differentiate it from the text of your reply. (In plain-text messages, each line of the reply is >denoted >with >brackets, although only your recipient will see them.) The original sender’s name is automatically placed in the “To:” field. The subject is the same as the original subject with the addition of Re: (shorthand for Regarding). You’re now ready to type your response.

At this point, you can add or delete recipients, edit the Subject line or the original message, attach a file, and so on.

When you’re finished, click Send. (If you click Reply All in the message window now, your message goes to everyone who received the original note, even if you began the reply process by clicking Reply. Mac OS X, in other words, gives you a second chance to address your reply to everyone.)

Instead of replying to the person who sent you a message, you may sometimes want to pass the note on to a third person.

To do so, click the Forward toolbar button (or choose Message→Forward, or press Shift--F). A new message opens, looking a lot like the one that appears when you reply. You may wish to precede the original message with a comment of your own, along the lines of: “Frank: I thought you’d be interested in this joke about your mom.”

Finally, address it as you would any outgoing piece of mail.

A redirected message is similar to a forwarded message, with one useful difference: When you forward a message, your recipient sees that it came from you. When you redirect it, your recipient sees the original writer’s name as the sender. In other words, a redirected message uses you as a low-profile relay station between two other people.

Treasure this feature. Plenty of email programs, including Outlook and Outlook Express for Windows, don’t offer a Redirect command at all. You can use it to transfer messages from one of your own accounts to another, or to pass along a message that came to you by mistake.

To redirect a message, choose Message→Redirect, or press Shift--E. You get an outgoing copy of the message—this time without any quoting marks. (You can edit redirected messages before you send them, too, which is perfect for April Fools’ Day pranks.)

Sometimes there’s no substitute for a printout. Choose File→Print, or press -P to summon the Print dialog box.

Mail lets you create new mailboxes in the Mailboxes pane. You might create one for important messages, another for order confirmations from Web shopping, still another for friends and family, and so on. You can even create mailboxes inside these mailboxes, a feature beloved by the hopelessly organized.

Mail in Leopard even offers smart mailboxes—self-updating folders that show you all your mail from your boss, for example, or every message with “mortgage” in its subject. It’s the same idea as smart folders in the Finder or smart playlists in iTunes: folders whose contents are based around criteria that you specify (Figure 11-8).

Figure 11-8. Mail lets you create self-populating folders. In this example, the “New Mail from Steve” smart mailbox will automatically display all messages from Steve Jobs at Apple that you’ve received in the past week.

The commands you need are all in the Mailbox menu. For example, to create a new mailbox folder, choose Mailbox→New Mailbox, or click the + button at the bottom of the Mailboxes column. To create a smart mailbox, choose Mailbox→New Smart Mailbox.

Mail asks you to name the new mailbox. If you have more than one email account, you can specify which one will contain the new folder. (Smart mailboxes, however, always sit outside your other mailboxes.) When you click OK, a new icon appears in the mailbox column, ready for use.

You can move a message (or group of messages) into a mailbox folder in any of three ways:

Of course, the only way to change the contents of a smart mailbox is to change the criteria that it uses to populate itself. To do so, double-click the smart mailbox icon and use the dialog box that appears.

Sometimes you’ll receive email that prompts you to some sort of action, but you may not have the time (or the fortitude) to face the task at the moment. (“Hi there... it’s me, your accountant. Would you mind rounding up your expenses for 1997 through 2007 and sending me a list by email?”)

That’s why Mail lets you flag a message, summoning a little flag icon in a new column next to a message’s name. These indicators can mean anything you like—they simply call attention to certain messages. You can sort your mail list so that all your flagged messages are listed first; click the flag at the top of the column heading.

To flag a message in this way, select the message (or several messages) and then choose Message→Mark→As Flagged, or press Option--L, or right-click the message’s name in the list and, from the shortcut menu, choose Mark→As Flagged. (To clear the flags, repeat the procedure, but use the Mark→As Unflagged command instead.)

When you deal with masses of email, you may come to rely on Mail’s dedicated searching tools. They’re fast and convenient, and when you’re done with them, you can go right back to browsing your Message list as it was.

Finding messages within a mailbox

The box in the upper-right corner of the main mail window is Mail’s own private Spotlight. You can use it to hide all but certain messages, as shown in Figure 11-9.

Tip

You can also set up Mail to show you only certain messages that you’ve manually selected, hiding all others in the list. To do so, highlight the messages you want, using the usual selection techniques (Shift-clicking, for example). Then choose View→Display Selected Messages Only. (To see all of them again, choose View→Display All Messages.)

Figure 11-9. You can jump to the search box by clicking or by pressing Option--F. As you type, Mail shrinks the list of messages. You can fine-tune your results using the buttons just above the list. To return to the full message list, click the tiny at the right side of the search box.

In Leopard, this search field is more powerful than ever. For example:

• You have the power of Spotlight charging up your search rankings; the most relevant messages for your search appear high on the list. And Notes and To Do items show up in the search results now, too.

• When you’re searching, a thin row of buttons appears underneath the toolbar. You can use these buttons to narrow your results to only messages with your search term in their subject, for example, or to only those messages in the currently selected mailbox.

• When you select a message in the search view, the Preview pane pops up from the bottom of the window. If you click Show in Mailbox, on the other hand, you exit the search view and jump straight to the message in whatever mailbox it came from. That’s perfect if the message is part of a thread, since jumping to the message also displays all the other messages from its thread.

• If you think you’ll want to perform the current search again sometime, click Save in the upper-right corner of the window. Mail displays a dialog box with your search term and criteria filled in; all you have to do is give it a name and click OK to transform your search into a smart mailbox that you can open any time.

Sometimes it’s junk mail. Sometimes you’re just done with it. Either way, it’s a snap to delete a selected message, several selected messages, or a message that’s currently before you on the screen. You can press the Delete key, click the Delete button on the toolbar, choose Edit→Delete, or drag messages out of the list window and into your Trash mailbox—or even onto the Dock’s Trash icon.

All of these commands move the messages to the Trash folder. If you like, you can then click its icon to view a list of the messages you’ve deleted. You can even rescue messages by dragging them back into another mailbox (back to the Inbox, for example).

Method 2: Deleted mail turns invisible

Mail offers a second—and very unusual—method of deleting messages that doesn’t involve the Trash folder at all. Using this method, pressing the Delete key (or clicking the Delete toolbar button) simply hides the selected message in the list. Hidden messages remain hidden, but don’t go away for good until you use the Rebuild Mailbox command described in the box in TROUBLESHOOTING MOMENT: Rebuilding Your Mail Databases.

If this arrangement sounds useful, choose Mail→Preferences; click Accounts and select the account from the list on the left; click Mailbox Behaviors; and then turn off the checkbox called “Move deleted messages to a separate folder” or “Move deleted messages to the Trash mailbox.” (The checkbox’s wording depends on what kind of account you have.) From now on, messages you delete vanish from the list.

They’re not really gone, however. You can bring them back, at least in ghostly form, by choosing View→Show Deleted Messages (or pressing -L). Figure 11-10 shows the idea.

Figure 11-10. To resurrect a deleted message (indicated in light gray type), right-click it and choose Undelete from the shortcut menu.

Using this system, in other words, you never truly delete messages; you just hide them.

At first, you might be concerned about the disk space and database size involved in keeping your old messages around forever like this. Truth is that Mac OS X is perfectly capable of maintaining many thousands of messages in its mailbox databases—and with the sizes of hard drives nowadays, a few thousand messages aren’t likely to make much of a dent.

Meanwhile, there’s a huge benefit to this arrangement. At some point, almost everyone wishes they could resurrect a deleted message—maybe months later, maybe years later. Using the hidden-deleted-message system, your old messages are always around for reference. (The downside to this system, of course, is that SEC investigators can use it to find incriminating mail that you thought you’d deleted.)

When you do want to purge these messages for good, you can always return to the Special Mailboxes dialog box and turn the “Move deleted mail to a separate folder” checkbox back on.

Once you know how to create folders, the next step in managing your email is to set up a series of message rules (filters) that file, answer, or delete incoming messages automatically based on their contents (such as their subject, address, and/or size). Message rules require you to think like the distant relative of a programmer, but the mental effort can reward you many times over. Message rules turn Mail into a surprisingly smart and efficient secretary.

You’ll see the effects of Mail’s spam filter the first time you check your mail: A certain swath of message titles appears in color. These are the messages that Mail considers junk.

During your first couple of weeks with Mail, your job is to supervise Mail’s coloring job. That is, if you get spam that Mail misses, click the message, and then click the Junk button at the top of its window, or the Junk icon on the toolbar. On the other hand, if Mail flags legitimate mail as spam, slap it gently on the wrist by clicking the Not Junk button. Over time, Mail gets better and better at filtering your mail; it even does surprisingly well against the new breed of image-only spam.

The trouble with this so-called Training mode is that you’re still left with the task of trashing the spam yourself, saving you no time whatsoever.

Once Mail has perfected its filtering skills to your satisfaction, though, open Mail’s preferences, click Junk Mail, and click “Move it to the Junk mailbox.” From now on, Mail automatically files what it deems junk into a Junk mailbox, where it’s much easier to scan and delete the messages en masse.

The Junk filter goes a long way toward cleaning out the spam from your mail collection—but it doesn’t catch everything. If you’re overrun by spam, here are some other steps you can take:

Here are some suggestions for avoiding landing on spammers’ lists in the first place:

And for goodness’ sake, don’t order anything sold by the spammers. If only one person in 500,000 does so, the spammer makes money.

With just a few clicks, you can bring the news of the world right in with the rest of your mail. Choose File→Add RSS Feeds, and then proceed as shown in Figure 11-12.

Figure 11-12. In the Add RSS Feeds box, you can click to add sites you’ve already subscribed to in Safari. If you don’t already have the feed bookmarked in Safari, click “Specify a custom feed URL” and paste the feed’s address into the resulting box. If you’ve got a ton of feeds and don’t want to wade through them all, use the search box to seek out the specific feed you need.

If you want the RSS headlines to appear in your Inbox like regular email messages, turn on “Show in Inbox.” Finally, once you’ve chosen the feeds you want to see, click Add. Your feeds now appear wherever you told them to go: either the Inbox or the Mailboxes column.

Now, in the RSS category of your Mailboxes list, the names of your RSS feeds show up; the number in the small gray circle tells you how many unread headlines are in the list. If a feed headline intrigues you enough to want more information, click “Read More...” to do just that. Safari pops up and whisks you away to the Web site that sent out the feed in the first place.

After you’ve read a news item and are done with it, click the Delete button at the top of the window. You can tell Mail to dump all the old articles after a certain amount of time (a day, a week, a month...) in Mail→Preferences→RSS→Remove Articles.

Or, to get rid of an RSS feed altogether, select it and then choose Maibox→Delete Feed. (Right-clicking the name gives you the same option.)

You can use To Dos in several different ways. For example, when you get an email message that requires further action (“I need the photos for the condo association newsletter by Friday”), highlight the important part of the text. Then do any of these things:

In each case, Mail pops a copy of the selected text into a yellow strip of note-style paper at the top of the message, as shown in Figure 11-14.

That task is also listed in the Reminders area of the Mailboxes list. If you need to see all the tasks that await you from all your mail accounts, click the flippy triangle to have it spin open and reveal your chores. The number in the gray circle indicates how many To Do items you still need to do.

When you click the To Do area of the Mailboxes list, all your tasks are listed in the center of the Mail window. Click the gray arrow after each To Do subject line to jump back to the original message it came from.

When you complete a task, click the small checkbox in front of the To Do subject line—either in the message itself or in the Reminders list. Once you’ve marked a task as Done this way, the number of total tasks in the Reminders list goes down by one, and that’s one less thing you have to deal with.

To delete a big yellow To Do banner from a message, point to the left side of the banner until a red handwritten-looking X appears. Click the X to zap the To Do banner from the message.

You can delete a To Do item from the Reminders list by selecting it and then pressing Delete, among other methods.

Seeing your To Do items in Mail is great—when you’re working in Mail. Getting them into iCal is even better, though, because you can see the big picture of an entire day, week, or month. As it turns out, Mail and iCal share the exact same To Do list. Create a To Do in one program, and it shows up instantly in the other one.

Each entry in Address Book is called a card—like a paper Rolodex card, with predefined spaces to hold all the standard contact information.

To add a new person, choose File→New Card, press -N, or click the + button beneath the Name column. Then type in the contact information, pressing the Tab key to move from field to field, as shown in Figure 11-16.

Figure 11-16. If one of your contacts happens to have three office phone extensions, a pager number, two home phone lines, a cellphone, and a couple of fax machines, no problem—you can add as many fields as you need. Click the little green + buttons when editing a card to add more phone, email, chat name, and address fields. (The buttons appear only when the existing fields are filled.) Click a field’s name to change its label; you can select one of the standard labels from the pop-up menu (Home, Work, and so on) or make up your own labels by choosing Custom, as seen in the lower portion of this figure.

Each card also contains a free-form Notes field at the bottom, where you can type any other random crumbs of information you’d like to store about the person (pet’s name, embarrassing nicknames, favorite Chinese restaurant, and so on).

A group is a collection of related address cards, saved under a single descriptive name (as shown in Figure 11-16).

Organizing your contacts into groups can make them much easier to find and use—especially when your database of addresses climbs into the hundreds. For example, if you regularly send out a family newsletter to 35 relatives, you might gather the address cards of all your assorted siblings, cousins, nieces, nephews, uncles, and aunts into a single group called Family. When addressing an outgoing message using Mail, you can type this group name to reach all of your kin at once. A person can be a member of as many different groups as you want.

To create a group, click the + button at the bottom of the Group column in the Address Book window, or choose File→New Group (Shift--N.) Type a name for the newly spawned group icon in the Group column, and then populate it with address cards by dragging entries from the Name list into the group. Clicking a group name automatically locates and displays (in the Names column) all the names that are a part of that group—and hides any that aren’t.

You can dress up each Address Book entry with a photo. Whenever you’re editing somebody’s address book card, drag a digital photo—preferably 64 pixels square, or a multiple of it—onto the empty headshot square; the image shows up as shown in Figure 11-17. Or double-click the picture well; now you can either browse to a picture on your hard drive by clicking Choose, or, if this person is with you, take a new photo by clicking the camera icon. (Don’t miss the swirly button next to it, which lets you apply nutty Photo Boothish effects.) At that point, you can enlarge, reposition, and crop the new photo.)

You don’t necessarily have to use a photo, of course. You could add any graphic that you want to represent someone, even if it’s a Bart Simpson face or a skull and crossbones. You can use any standard image file in an address card—a JPEG, GIF, PNG, TIFF, or even a PDF.

From now on, if you receive an email from that person, the photo shows up right in the email message.

You can search for an Address Book entry inside the currently selected group by typing a few letters of a name (or address, or any other snippet of contact information) in the Search box (Figure 11-17). To search all your contacts instead of just the current group, click All in the Group list.

If Address Book finds more than one matching card, use the and keys, or Return and Shift-Return, to navigate through them.

Once you’ve found the card you’re looking for, you can perform some interesting stunts. If you click the label of a phone number (“home” or “office”, for example), you see the Large Type option: Address Book displays the number in an absurdly gigantic font that fills the entire width of your screen, making it possible to read the number as you dial from across the room. You can also click the label of an email address to create a preaddressed email message, or click a home page to launch your Web browser and go to somebody’s site.

Figure 11-17. With each letter you type, Address Book filters your social circle and displays the number of matches at the bottom. The matching records themselves appear in the Name column, the first of the matching card entries appears in the far-right pane, and the matching text itself appears highlighted in the matching card.

Figure 11-18. The options that become available when you click the field labels on an address card vary according to field type. Pop-up menus let you send email, open a Web page, or view a map, depending on the type of field you’ve clicked.

You can also copy and paste (or drag) address card info into another program.

You can’t do much to customize Address Book’s appearance, but the Preferences pane (Address Book→Preferences) gives you at least a couple of options in the General pane that are worth checking out:

When you choose File→Print and click the ▾ to expand the Print box, the Style pop-up menu offers four ways to print whatever addresses are selected at the moment:

As you fiddle with the options presented here, you get to see a miniature preview, right in the dialog box, that shows what you’re going to get.

No matter which mode you choose, the only cards that print are the ones that were selected when you chose File→Print. If you want to print all your cards, therefore, click All in the Group column before you print.

When you think about it, the contents of your Address Book may represent years of typing and compiling effort. Losing all that information to a corrupted database or a hard drive crash could be devastating. Here are four ways to protect your Address Book data: