Chapter  10

Working with Mail

Mail is Apple's e-mail application, and has been part of OS X from its start. With each new release of OS X, Apple refines the Mail application a bit. With Lion, Mail not only picks up a few features, but gets a facelift in the process. This chapter will walk you through this latest version of Mail, showing you the following:

  • How to get around the new Mail interface
  • How to add and configure e-mail accounts
  • How to compose new messages
  • How to set up mail signatures
  • How to deal with junk mail
  • How to manage mail and mailboxes
  • How to use other Mail features like Notes and RSS

Introducing Apple's Mail Application

Up until Lion, most of the changes to Mail, at least as far as the interface, have been evolutionary. In Lion, not only has Apple added new features, but it has given Mail's interface a rather significant upgrade (Figure 10–1).

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Figure 10–1. Mail's main Message Viewer window has a new look in Mac OS X 10.7.

One of the first new things users who have used Apple's Mail application before will notice is that the layout has changed. The new layout presents three columns side by side: the mailbox list is in the first column; the messages in the selected mailbox are displayed in the second column; and finally the message view, which displays the selected message (or message thread), is prominently displayed in the third column.

Besides the new layout, elements within the layout have changed as well. The toolbar has been streamlined with new icons (Figure 10–2), and offers the new ability to flag messages with different flags (similar to labels in the Finder). Also, the message view can now display entire threads in one single view, and provides additional options in the message header, including a small toolbar that appears when you hover your cursor over the header separator (Figure 10–3). Finally, beneath the toolbar, there is a new Favorites bar. Mailboxes from the mailbox list can be dragged up to the Favorites bar for easy access. Then you can click the Hide button on the Favorites bar to hide the mailbox list for a cleaner two-column view.

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Figure 10–2. The new default toolbar in Mail. Like most toolbars this can be customized to your needs or desires.

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Figure 10–3. A small toolbar is available from the message view in the separator between the header and the message.

Besides the options provided by the interface, Mail provides a number of additional commands and options on the menu bar. Interesting commands that may not be obvious are covered in Table 10–1.

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Of course, before you start digging into Mail, the first thing you need to do is add an e-mail account (or accounts).

Adding E-mail Accounts

The easiest way to add a new e-mail account to Mail is to select File > Add Account… from the menu. This will open up a dialog that will guide you through the steps needed to add your new account. You can also access this account setup walkthrough when you add an account from the Accounts tab in Mail's System Preferences. The information you'll need to know varies with the type of account and the mail service you use.

NOTE: There are a number of ways to add an e-mail account for Mail in Mac OS X. When you first set up Mac OS X, you are prompted for your MobileMe account information if you have a MobileMe account, so that account may already be present when you launch Mail the first time. Also, the System Preferences contains a new Mail, Contacts & Calendars preference pane where you can set up accounts that may be recognized by Mail. We are only covering how to add accounts from Mail here; other methods will be covered elsewhere in the book.

The first bits of information you will need to know for all e-mail accounts are your e-mail address and your password (Figure 10–4). Once you enter this information, Mail contacts the server and attempts to autoconfigure the e-mail account. This is effective for a large number of e-mail services, including Gmail, Yahoo, and MobileMe, and even many Exchange 2007 servers that have their autoconfigure options set. If you get the option to set up an account automatically, select that option, and let Mail do the rest.

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Figure 10–4. The first step in setting up a new e-mail account in Mail is to enter your name, e-mail address, and password.

If your account isn't set up automatically, then you'll need some more information to set up both your incoming and outgoing mail servers. To configure your incoming server (the one you receive your e-mail from), you'll need to know the following information (Figure 10–5):

  • The type of server or protocol you are using: POP, IMAP, Exchange 2007, or Exchange IMAP.
  • The address of your incoming mail server.

If you are configuring an Exchange IMAP server, you'll also be asked for the address of the Outlook Web Access (OWA) server. You'll also be asked for a description, which will be the name by which Mail refers to this account.

NOTE: There are two options here for Microsoft Exchange support. For Exchange 2007 and newer Exchange servers, Mail offers native support and the Exchange option should work fine (and will also allow you to add contacts and calendar support). For older Exchange servers, however, you must use the Exchange IMAP option, and the Exchange server in question has to be set up to support IMAP. If you are setting your access for a company exchange server, the specific information you need should be available from your IT department or person.

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Figure 10–5. If Mail cannot automatically fill in your mail settings based on your e-mail address, it will first prompt you for information about your incoming mail server.

NOTE: Figure 10–5 shows the configuring of an IMAP account. This dialog box will look the same when you configure a POP account, but for an Exchange server, it will appear a bit different. For an Exchange 2007 and newer servers, it will provide a couple of check boxes asking you if you'd like set up your Exchange contacts and calendar. If you check these, you will be able to access your Exchange contacts in Address Book, and your Exchange calendar items in iCal. For an Exchange IMAP connection, you will need to know the web address of your OWA server.

Once you enter all your information and click the Continue button, Mail will try to contact the server and determine the best means of connecting to it. If this fails, then you will get a message warning you that Mail was unable to connect to the mail server. This usually means something was entered incorrectly, the mail server is down or not accepting connections, or the server is unreachable (perhaps behind a firewall that requires a VPN connection). If you get this warning you may want to double-check that all the information is correct and fix any mistakes. If you are sure everything is correct, you can click Continue again to move on.

At this point, depending on what happened when Mail contacted your incoming server, you may or may not be prompted to select your security settings (Figure 10–6). If you are, you should enter them here. We strongly encourage you to select SSL encryption.

NOTE: When Mail first attempts to contact your account, if it connects successfully and discovers that an SSL connection is available, it will automatically utilize that.

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Figure 10–6. If prompted to choose an SSL connection, you should do so.

The next step is selecting your outgoing mail server for this account (Figure 10–7). Here you can either choose an existing outgoing mail server (one from an existing account) to use when sending mail from this account or enter the details of a new one. Usually you will want to enter the outgoing account information associated with the account you are setting up.

NOTE: SSL encryption encrypts the data being passed between your computer and the server at the other end. Some services, for whatever reason, don't accept SSL encryption (or any other encryption) for e-mail. If this is the case, we strongly urge you to find another e-mail provider and not use the account lacking encryption. Checking your e-mail over an unencrypted connection and sending your username and e-mail address across the Internet in easy-to-read plain text that anyone with a little know-how can intercept is very, very bad. For Mac users, Apple provides free iCloud e-mail addresses, and you can always get a free, permanent, secure Gmail account at www.gmail.com (which may redirect you to Google—it's OK, Gmail is synonymous with Google Mail), so you have no excuses.

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Figure 10–7. Configuring your outgoing (SMTP) server

NOTE: Almost all outgoing servers will be Simple Mail Transfer Protocol (SMTP) servers. SMTP is what makes e-mail work by moving your message from SMTP server to SMTP server until your message reaches its destination. Unfortunately, as the name implies, it is very simple, but it is also very old. It was written for a day long ago when the Internet and e-mail were used mainly by educational, government, and research institutions. Spam wasn't a problem. Today, most SMTP servers have evolved to provide some checks in an attempt to limit spam, but the fundamental design of SMTP is to accept and route all e-mail as quickly and effortlessly as possible. As such, spam gets through. This presents some issues for non-spammers (well, spammers too, but the more “issues” they have, the better, right?). Certain public Internet connections routinely block SMTP traffic, so if you find yourself attempting to send an e-mail from a public place or even from work or a hotel room, you may find it doesn't work. In some cases, there is a special SMTP server you can gain access to (Mail will present you with the opportunity to change or add an SMTP server when it fails to connect to the default SMTP server tied with a particular account); other times, it's just not going to work. About the only real solution we've found in some of these situations is to send messages through a web mail interface.

TIP: Since many service providers block the standard SMTP ports, many e-mail services offer up port 587 as an alternative SMTP port. Mail by default will try both the standard port 25 and common alternates (465 and 587).

Just like when you configure your incoming account, when you enter new outgoing account information, Mail will attempt to contact the server to acquire additional information about the server and to verify the connection when you click the Continue button. If Mail can't connect to the server, you will get a warning asking whether you'd like to continue. After you click Continue, you may or may not get the Security Options screen to set up a secure connection for outgoing mail.

Upon completion of entering your outgoing mail information, you will be presented with a summary of your new account information (Figure 10–8). If everything is correct, click the Create button to create your new account.

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Figure 10–8. Preview your e-mail account information, and click Create to create your new account.

Once your accounts are set up, you can edit or delete an account in Mail's preferences under the Accounts tab (Figure 10–9). By selecting an account on the Accounts pane, you can edit that account using one of the three subtabs: Account Information, Mailbox Behaviors, or Advanced. The Account Information pane allows you to edit the server information, username, and password (essentially the same stuff you used to set up the account, unless your account was autoconfigured). The Mailbox Behaviors pane allows you to select how messages are stored and how Mail should deal with specific types of messages (including notes, trash, and suspected junk mail). The options provided here, as well as the specific behavior, will vary depending on the account type. The Advanced tab contains a number of other options for your account, including the ability to disable the account in Mail or to toggle SSL for connecting to the incoming server.

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Figure 10–9. Mail's Accounts preferences allow you to revisit the configuration of your mail accounts, plus make a few additional choices about how Mail will work with a specific account.

NOTE: If you configure an IMAP account manually (or sometimes even if it's autoconfigured), and everything connects OK, but you notice a number of strange mailboxes popping up in Mail (and possibly no mail), it's likely that you will need to set the IMAP path prefix under Mail's Advanced Accounts preferences. What specifically needs to be set here will vary with your account, but if one of those strange folders that pops up says something like “Mail,” that's a good place to start. (Of course, the most effective thing would be to contact the server's support people or administrator and ask.)

TIP: If you have more than one e-mail account in Mail, the order in which the accounts are listed in the Accounts preferences is important. Mail considers the account listed first as the default mail account. When you create a new message, it generally associates that message with this account. To reorder your accounts, you can simply select and drag them up or down in the Accounts pane.

Receiving and Managing E-mail

Receiving, reading, and managing e-mail messages are the main tasks that most people are occupied with when using their mail clients. Mail provides some nice features for this, whether you deal with a few messages from a single account every day or hundreds from multiple accounts.

Checking and Reading New E-mail

Mail is set up, by default, to automatically check for new e-mail in each of your active, online accounts every 5 minutes. This interval is adjustable on the General tab of Mail's System Preferences (Figure 10–10) from the “Check for new messages” drop-down list. Of course, you are always free to check your e-mail manually by clicking the Get Mail button in Mail's toolbar or by using one of the Get Mail options on the Mailbox menu.

By default, when Mail discovers new messages for one of your accounts, the new messages are downloaded into the inbox associated with the account, and the “new mail” sound will play, notifying you of new mail. Additionally, the number of unread messages in your inbox will appear on the Mail icon in the Dock (known as a badge), as well as next to your inbox. Unread messages in the message list area of the Message Viewer window will be flagged with a small blue dot, which will go away when you select the message to read.

NOTE: In the mailbox list in Mail's Message Viewer window, Mail provides a single inbox that expands into separate inbox folders for each account. This allows you to view your messages from different accounts either together by selecting the inbox item or separately by account by selecting one of the subitems under Inbox.

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Figure 10–10. The General tab of Mail's preferences provides many of the common options you may want to adjust.

When you select a message, its contents appear next to the message list area in the message view area of the Message Viewer window. You can scroll through it there, or if you double-click the message item in the message list area, the message will open in a separate window.

Dealing with Junk E-mail

Mail has a built-in system to help you identify and deal with junk mail, or spam. This system is actually quite good, and with proper training, should be sufficient for most users. For the best results, however, the Junk mail filter must be trained. By default, Mail's junk filter is pretty average as far as filters go, but as you mark missed messages as Junk and mislabeled good mail as Not Junk, Mail will learn over a fairly rapid period of time what you consider to be junk and what you don't.

Most of the configurable options regarding how junk mail works are contained on the Junk Mail tab of Mail's preferences (Figure 10–11).

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Figure 10–11. The Junk Mail tab provides options regarding how Mail deals with mail it considers to be spam.

The first option on the Junk Mail preferences tab is to enable junk mail filtering. Below that are options for what Mail should do with e-mail it considers junk. The “Mark as junk mail, but leave it in my Inbox” option is the best choice when you are first training Mail as to what you consider junk and what you don't. When you think Mail is identifying junk mail at a good rate, you can alter this setting. The “Move it to the Junk mailbox” option creates a new mailbox called Junk where, when this option is activated, Mail will store junk mail rather than in your inbox. The final option, “Perform custom actions,” allows you to set up a custom mail rule for dealing with junk mail when you click the Advanced… button. We cover setting up mail rules in the “Creating Mail Rules” section of this chapter.

CAUTION: The Erase Junk Mail menu item on both the Mailbox menu and the shortcut menu available from the mailbox area of the Message Viewer window causes any messages stored in your Junk mailbox to be immediately deleted—not stored in the Trash, but gone. This is both a handy way to rid yourself of trash and an easy way to accidentally rid yourself of an important message that was flagged as Junk by mistake.

Next, you can choose certain criteria for messages that should never be marked as Junk. You can exempt mail from people in your Address Book or people in your Previous Recipients list, or e-mail that is addressed using your full name. Exempting people listed in your Address Book and Previous Recipients list is usually safe; however, we find that for whatever reason, lots of junk mailers tend to know our full names, so this option is questionable.

The “Trust junk mail headers in messages” option allows Mail to look at certain e-mail headers that are commonly used by ISPs and mail servers to rate the probability that a message is junk. The results of using this option are mixed depending on your mail server.

NOTE: We leave this option checked since it covers all our accounts; however, if one of your e-mail accounts has its own junk mail quarantine, when a message is released, Mail may still flag it as Junk when it hits the inbox, since the headers that identify it as Junk on the mail server may still be intact.

The “Filter junk mail before applying my rules” option identifies mail as junk before looking at any other rules. This option could prevent rules from running on messages that Mail considers junk. If this option in unchecked, then, unless you specify a custom junk mail action, the junk filter will work after your mail rules are run, thus allowing them to affect all messages.

The Reset… button resets all of your junk mail options and resets all the junk mail training you have done.

Creating Mailboxes to Store E-mails

Besides your inbox and other special-purpose mailboxes and folders that Mail creates for you, it's likely you'll want to create your own to organize any saved messages, as well as notes you store in Mail.

NOTE: In Mail, folders are synonymous with mailboxes. Mailboxes you create will actually appear as folders, and although you can store both mail and notes in them, they are still generally called mailboxes in Mail.

To create a new mailbox, simply select Mailbox >New Mailbox… from the menu bar or select New Mailbox from the menu that appears when you click the + button in the lower left of the Message Viewer window. This opens a dialog box with a text field to enter the name of your new mailbox and a drop-down list for you to choose where you want the mailbox to be created. In general, new mailboxes are stored On My Mac (that being your Mac), which means they are kept locally. If you have access to an IMAP or Exchange mail account (which includes MobileMe and Gmail), then you can also create folders on the remote mail server this way (since IMAP stores your mail remotely). This makes those mailboxes and the items stored within them accessible from any computer you have set up to access that account.

Once you create a mailbox, if you want to change its location, you can do so by selecting and dragging the mailbox where you'd like it. To further add to the flexibility, you can nest mailboxes (i.e., mailboxes can reside in other mailboxes).

In addition to your standard mailboxes, you can also create smart mailboxes in Mail, which will dynamically contain messages based on rules you define. Setting up a smart mailbox in Mail is similar to setting up a smart folder in the Finder. It's good to know that like smart folders, messages added to smart mailboxes aren't moved there; the messages will still remain in their regular mailbox as well.

Creating Mail Rules

Mail rules can help you deal with large amounts of e-mail by automatically performing tasks on individual messages that meet certain specified criteria. To view your rules, go to the Rules tab in Mail's preferences (Figure 10–12).

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Figure 10–12. The Rules tab shows your existing rules and allows you to edit them or create new ones.

The Rules preference tab allows you to view your existing rules, activate or deactivate each of them, and reorder them. The four buttons on the right allow you to create new rules (Add Rule), edit an existing rule (Edit), create a copy of a rule as a starting point for a new rule (Duplicate), and delete a rule (Remove), respectively.

The activated rules will be applied in the order they are listed on either each new message as it arrives or selected messages when Message > Apply Rules (Option-Command-L) is applied. The order of the rules is significant since the last-run rule will have precedence over previously applied rules. Additionally, each rule has the option of preventing further rules from being executed. To reorder your rules, simply drag to put them in the order in which you want them executed.

NOTE: Rules are generally applied to mail in a certain folder, so if one of your rules happens to move a message into a different folder, the following rules will not be processed for that message.

To create a new rule, click the Add Rule button, and a sheet will open for you to begin creating the rule (Figure 10–13).

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Figure 10–13. The rule sheet allows you to fill in the criteria for new rules and edit existing rules.

A rule has three parts: the description (or name), the conditions when the rule's actions are applied, and the actions that will occur when the conditions are met. The description can be any name you want to use to identify the rule.

You can set the conditions so that the actions will trigger when any of the conditions are met or all of the conditions are met. To add a condition, click the + button next to any existing condition, and a new blank condition will appear below. To remove a condition, click the – button next to the condition you want to remove.

You can add and remove actions the same way that you add and remove conditions (using the + and – buttons). Some special actions available are Run AppleScript, which allows you to run any AppleScript, making the possibilities of what you can do here rather immense, and “Stop evaluating rules,” which immediately halts running all further rules for the current message.

ADDING ICAL EVENTS FROM MAIL

Sending E-mail

Sending e-mail is a pretty straightforward task: you create a new message; type your recipients, subject, and message; and click Send. Mail adds a few options that you can take advantage of, such as the ability to use stationery to apply a theme to your message.

Creating a New Message

To start a new message, select File > New Message… (Command-N) from the menu bar, or click the New Message button on Mail's toolbar. This opens a blank New Message window (Figure 10–16).

To start, you must first fill in the To and Cc (and/or Bcc) fields with the names of your recipients and fill in the Subject field with the subject of the message. Also, if you have multiple accounts set up, make sure the message is being sent from the proper account.

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Figure 10–16. Mail's New Message window

NOTE: The To field is traditionally for the primary recipients of a message. The Cc (which stands for carbon copy) field is for including anyone else you want to keep in the loop. The Bcc field (which stands for blind carbon copy) is where you can add recipients that will be unknown to all other recipients, including other Bcc recipients.

NOTE: By default, certain fields, including Bcc, Reply-To, and Priority, are hidden. The small drop-down menu to the left of the From field allows you to reveal these fields, as well as any other header information you'd like to add (via the Customize option).

As you fill in the recipient information, Mail will attempt to autocomplete the names or addresses you are typing using information from your Previous Recipients list, your Address Book, and any LDAP or Exchange address books that are configured and connected. If Address Book has multiple e-mail addresses for a name that you enter in one of these fields, you can click the name to select which e-mail address(es) you'd like to use. Additionally, if you click the Address button on the New Messages toolbar, you will get a list of all the names and e-mail addresses contained in your Address Book.

The From field allows you to select from which of your accounts you'd like the message to be sent. The initial account listed will be the one belonging to your default e-mail address. However, if you are viewing e-mail in a mailbox other than the default mailbox, then selecting New Message will cause that account to be used instead of the default. This has the effect of ensuring that any message you reply to will come from the account to which it was sent. You can alter this behavior in the Composing section of Mail's System Preferences.

After you have filled in the required fields, you can start typing your message in the large text area. By default, the message text is formatted using rich text (which in Mail is HTML). This allows you to style your text using different font styles, colors, and sizes (accessible from the Fonts and Colors buttons on the toolbar or from the various options in the Format menu bar's submenus). Additionally, you may include inline images in your message.

To add an image to your message, you can drag and drop the image file from the Finder into your message, or you can use the Photo Browser built into Mail to browse your iPhoto library for an image to insert.

To add an attachment to your message, you can drag and drop the file in your message, or you can select the files you want to be attached from the dialog that appears when you click the Attach button on the toolbar (or you can select File > Attach File… or press Shift-Command-A).

NOTE: There is a preference for using Windows-friendly attachments. This option is selected by default, and it is likely that you will want to keep it selected unless you are 100 percent sure the person you are sending an attachment to is using a Mac.

When you are done with your message and are ready to send it, just click the Send button on the toolbar, or select Message > Send (Shift-Command-D) from the menu bar, and your message will be sent using the outgoing server set up for the chosen account.

If, for some reason, your outgoing mail server is unreachable, Mail will prompt you to either try again later or try sending the message using one of the other outgoing mail servers you have set up for other accounts. If you want to try again later (maybe you have limited Internet access or SMTP is being blocked), the message will be saved, and Mail will attempt to send the message later.

If you are working on a message and you aren't ready to send it, when you close the message, Mail will ask you whether you'd like to save the message as a draft. If you select Yes, the message will be saved in your Drafts mailbox (if one doesn't exist, it will be created). You can select the message from your Drafts mailbox later to finish and send it or delete it.

Using Mail Stationery

The Mail application in Lion has the ability to apply themes to your e-mail messages using what Apple calls stationery. When you are creating a new message in Mail, if you click the Show Stationery button on the toolbar, a special area will slide open between the header fields and the message text to reveal a selection of stationery.

As you select specific stationery, the stationery will be previewed in the message area. Usually stationery consists of a background, image area, and text area. The text area is where you type your message. In general, the photo areas may be replaced with your own images. To replace the placeholder image with your own image, just drag a new image from the Finder or the Photo Browser into the image area, and the placeholder image will immediately be replaced with your chosen image. Besides the images, some of the backgrounds (such as Birthday Daises) have different options that are available by clicking the background.

NOTE: Stationery items are really just bundles of specially formatted HTML documents and images. Therefore, it's possible to create your own. However, the exact process of packaging them is a bit complex. Mail does allow you to save new messages as stationery so that you can use them as the basis for future messages.

Replying to and Forwarding a Message

Besides creating a new message from scratch, you can also send mail by replying to or forwarding existing messages. The primary difference between a reply and a forward is that a reply will be, by default, directed to the initial sender (and other original recipients if you choose Reply All), whereas a forward is usually addressed to someone not part of the initial e-mail thread.

When you reply or forward a message, the original message is usually included (or quoted) in the reply. The original messages are usually indented and formatted in a special way (as quoted text), leaving room at the top of the message for you to add your own text to the e-mail thread.

NOTE: When you redirect a message, you are not adding to or continuing the thread so much as just passing the message on to someone else as you receive it.

Creating Notes

Mail also has the ability to store notes. Notes are a fantastic way to keep track of just about anything and can be stored right alongside your mail in any mailbox.

To create a new note, just click the Note button on the Mails toolbar, or select File > New Note (Control-Command-N) from Mail's menu bar. This opens a New Note window (Figure 10–17), which is ready for you to start entering your information.

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Figure 10–17. A New Note window in Mail waiting for information

In Lion there is no need to save notes, as notes are continuously saved in the background.

Reading RSS Feeds in Mail

Another feature in Mail is the ability to subscribe to and read RSS feeds. If you set your default RSS reader to Mail (either in Mail or in Safari's RSS preferences), then whenever you select an RSS link, you will be prompted to add the news feed in Mail. Otherwise, you can use options in Safari to subscribe to a feed in Mail or add the URL of an RSS feed in the dialog box that appears when you select File > Add RSS Feeds… from Mail's menu bar.

When you initially subscribe to an RSS feed in Mail, it will appear in the RSS area in the Mailbox column; however, depending on your preferences, when you select a feed, an arrow will appear to the right of it that will bump the feed up to your inbox. This will not only add new RSS items to your inbox but will also notify you when new RSS items are downloaded.

In general, feed items appear and behave as messages, while feeds behave as individual mailboxes. You can even sort your feeds into separate mailboxes to help keep them organized (and read many feeds at once).

If you want to unsubscribe to a feed, you can select Mailbox > Delete Feed… from the menu bar (or Delete Feed from the feed's contextual menu), which will delete the feed and remove any items.

Summary

For many people, e-mail has become a key communication medium for work and play. Apple's Mail application provides a wide range of features and tools for users to get the most out of e-mail, and provides a central hub for contact and event management. With that in mind, in the next couple chapters we will cover Address Book and iCal.

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