Chapter 7

Mail

For many Mac users, e-mail and Web browsing are the two main reasons they use their personal computers. While Web browsing is predominantly accomplished through Safari, the aptly named Mail app is the Mac user’s e-mail client of choice. With Mac OS X Lion, Apple has taken the Mail app to a new level of usability and speed.

Using the full-screen app capabilities of Lion, Mail is now able to organize your mail and focus your attention on the work at hand. If you’re a fan of Mail on the iPad, you’re sure to love the way that the mailbox list can now be hidden to let you see more of your e-mails. Your message list is different as well—a small preview displays a few lines of the e-mail and contact photos for e-mails from senders in your address book.

There’s a new Favorites bar above the messages, providing access to mail folders with a single click. Message headers now display only the sender’s e-mail address, the subject, and when the message was received, giving your e-mails more room on small screens (think of an 11.6″ MacBook Air).

Do you get flustered with long e-mail conversations that are all but unreadable by the time an e-mail has been bounced back and forth a few times? If you do, you’re going to love Mail’s new Conversations feature. With Conversations, Mail groups your related messages and numbers each message in order, making short work of figuring out the order and logic of e-mailed conversations.

Searching through hundreds or thousands of saved e-mails is now easier than ever thanks to search tokens, another new feature of Mail. As I’ll discuss in a few pages, search tokens can be combined to narrow searches to find exactly what you need. Attachments can be searched by name, by content, or by whether a message contains an attachment.

My personal favorite new tool in Mail is the addition of inline controls that appear just above messages that you’re reading. With a click, you can reply to, forward, or delete a message. Those controls disappear when you don’t need them, so they don’t take up any space or detract from the readability of messages.

If you want to clean out your inbox but keep messages for future reference, archiving e-mail now takes a single click. While those e-mails are now in a special archive file, they’re still searchable using a special search token.

Mac users who get their mail, calendar, and address book information from a Microsoft Exchange 2010 server are finally able to use Mail to connect to Exchange, rather than having to use Microsoft Entourage or Outlook for Mac. Exchange users are also able to set their vacation messages from Mail now.

In this chapter, I’ll take you through all of these new features, plus a few others that may surprise you.

Mail Setup and Conversion

Many of the readers of this book are upgrading Macs from earlier versions of Mac OS X to Lion. Fortunately for you, setting up Mail under the new operating system requires just a single click to have your e-mail accounts migrated to the newer software.

If you’re new to the Mac or to using the Mail app, you’ll find that setting up your e-mail accounts to work with Mail is fairly straightforward. As an example, follow along as I set up MobileMe and Gmail accounts in Mail.

Just like earlier versions of Mail, clicking the “postage stamp” icon in the Dock launches the app. Once Mail is up and running, your existing accounts installed under a previous version of Mac OS X are converted to a new format and all of the mailboxes appear in the app.

What if you want to add new accounts to Mail? You’ll find that the process is considerably easier than before. In this example, I’m going to add a Google Mail account to Mail. With Mail launched, select File Add Account. A dialog similar to that in Figure 7–1 appears.

Enter the name of the person to be listed as the sender of e-mails (usually your name), the e-mail address, and the password for the e-mail account. Click the Create button, and a second dialog appears on the screen (Figure 7–2).

With most major e-mail providers, including Gmail (Google Mail), Yahoo! Mail, AOL, MobileMe, and Exchange servers, the e-mail application recognizes the type of server and automatically configures the account for you, as shown in Figure 7–2. If the e-mail provider also has a chat or calendar service, checking the boxes marked Calendars and iChat sets up accounts for iCal and iChat that are linked to the e-mail account. As before, clicking the Create button has an immediate effect. In this case, it causes the account to be added to Mail, and if you requested, accounts are added to iCal and iChat as well.

Like many Mac users, you may have web mail accounts set up with various providers. Safari now recognizes when you’re logging into a web mail page and offers to set up the account in Mail. In Figure 7–3, I’ve entered Safari and logged into a Yahoo! Rocketmail account. The dialog shown in the figure appears at the top of the browser window.

To begin adding the account to Mail (and iCal and iChat if desired), I click the Add Account button. To clarify the services I want to use with the Rocketmail account, Safari now displays a second dialog (Figure 7–4).

If I want to use Mail to send and receive Rocketmail, iCal to display Yahoo! Calendars, and set up iChat to use Yahoo! Chat, I keep the three boxes checked and then click OK. The account is set up with the proper applications, and Mail is ready to roll.

Mail User Interface

Just about every Mac and monitor made by Apple over the past several years has come with a wide-screen display. That means it matches the dimensions of a wide-screen HDTV, with an aspect ratio (the ratio of width to height of the screen) of 16:9.

Mail has been redesigned in Lion to take advantage of all that wide-screen goodness. In Figure 7–5, the Mail app is expanded to take advantage of the full screen on an 11.6″ MacBook Air. On the left, the inbox is displayed as a list of messages showing the sender’s name or e-mail address, the subject of the e-mail, and the first two lines of the message. On the right is the e-mail message itself, and it fills all of the available space from the bottom of the screen up to the toolbar. For messages with attached images or documents, it’s a wonderful way to see all of the content immediately.

This two-column format is perfect if you have only one e-mail address. But what if you have several accounts, all with separate mailboxes? Just above the list of messages you’ll see the Favorites bar. This is where you can place links for mailboxes, notes, and other items, and I’ll discuss it in further detail later in this chapter. By default, the Favorites bar includes a Show/Hide toggle at the far left. If you don’t see a list of mailboxes, click the Show button in the Favorites bar, and a third column appears (Figure 7–6).

As with the Finder terminology introduced in Chapter 2, this gray area is known as the Mail sidebar. When the sidebar is visible, as in Figure 7–6, the Show/Hide toggle button displays the word Hide and does exactly that to the sidebar.

Above the Favorites bar and below the menu bar is the toolbar, familiar to anyone who has used Mail in the past. However, the icons have changed, and there are several that may be strange to you. That’s a good reason to look at the toolbar first.

The Mail Toolbar

The first time you launch Mail on your freshly upgraded or new Mac, you’ll see the default set of toolbar icons (Figure 7–7).

If you forget what these icons are used for, you have two choices. The first is to change your toolbar settings so that the icons are labeled with text. To do this, right-click or two-finger click the toolbar. A small drop-down menu appears, with one of the options being Icon and Text; selecting that item displays the icon function underneath the icon. The second way is to use your cursor to hover over the icon. This displays a light yellow text tip box that describes the function of the icon.

These are the icons from left to right:

• Get Mail: Attempts to receive and send mail from all accounts.
• New Message: Creates a blank message.
• Note: Pops up a small yellow lined notepad into which you enter reminders or short documents.
• Delete: Deletes the currently highlighted message from the mailbox.
• Junk: Marks as spam or junk mail.
• Reply: Displays a reply e-mail addressed to the “reply-to” address containing the original e-mail message or any text that had been highlighted prior to clicking the icon.
• Reply All: Same as Reply, but addressed to all recipients of the original e-mail message.
• Forward: Displays an e-mail with a blank “To” address, containing the original e-mail message or text highlighted prior to clicking the icon.
• Show Related Messages: A new icon in Mail for Lion, clicking Show Related Messages displays any replies and forwarded messages that are related to the currently highlighted message.
• Flag: Would you like to flag certain messages as a reminder to take action on them? The flag icon provides a rainbow of colored flags to choose from. After applying flags, all messages tagged with a particular color are immediately visible under Reminders in the Mail sidebar.

Customizing the Toolbar

If you’re not going to use one or more of the toolbar icons or if you’d like to add a capability that isn’t displayed with the existing icons, you’re in luck. Right-clicking or two-finger clicking the toolbar displays the drop-down menu mentioned earlier (Figure 7–8).

I discussed the ability to add or remove the icon labels on the previous page, but hiding the toolbar altogether is also possible. This is helpful in cases where you may want to maximize the amount of screen space available for messages when using a Mac with a size-limited display. To display the toolbar after you’ve hidden it, select View Show toolbar.

Selecting Customize Toolbar from the drop-down menu displays the palette of icons shown in Figure 7–9.

To add any of these icons to the toolbar, just drag them from this palette to the appropriate location on the toolbar.

On the previous page, I described the purpose of a number of the common icons. Here’s what some of these other icons do for you:

• Archive: Selecting a message by clicking it and then clicking this icon places the message into an Archive mailbox where it is held until you want to take further action. Depending on the type of account you’re using, the Archive mailbox may be local (on your computer) or on a mail server.
• Move: Do you use folders to organize your Mail messages? The Move button provides a quick way to move a selected message into a specific folder by clicking the icon and selecting the target folder.
• Copy: To make a copy of a selected message and then move it to a folder, click the Copy icon and choose a target folder. The message stays in the Inbox folder and is copied to the target folder as well.
• Chat: By default, Mail is set up to display “buddy availability.” If you receive a Mail message from a friend and there’s a small green circle displayed, that means your friend is currently online in iChat. Clicking the Chat icon launches iChat and creates a chat session with your friend.
• Redirect: Have you ever received a message that was intended for delivery to someone else? Selecting the message and clicking Redirect displays a copy of the message. Add a new recipient address and any message you want to pass along, and then send the message on its way. Redirect is a great way to report spam mail to IT departments.
• Sidebar: There’s another way to make the Mail sidebar appear and disappear. Add the sidebar icon to your toolbar, and then click it to toggle visibility of the Mail sidebar.
• Print: Even in this electronic age, it’s sometimes necessary to print an e-mail message. If the Print icon is added to the toolbar, a selected message is printed with a single click.
• All Headers: This icon forces Mail to display all header information in an e-mail. Although most people never need to see this information, it’s useful to IT departments for determining the source of anonymous or spam messages.
• Unread: The Unread icon is useful for displaying only the messages, in an Inbox folder, that have not been read. With a click, all read messages are hidden, which is a wonderful way to focus on incoming mail.
• Read: The Read icon does the opposite of the Unread icon by displaying only the messages that have been previously read.
• Take All Accounts Offline: On occasion, it’s useful to be able to stop Mail from its ceaseless chattering with mail servers. To do so, you need to take all of your e-mail accounts offline, and this icon does so with a click.
• Add to Address Book: If you want to add the sender of an e-mail to your address book with a click, the Add To Address Book icon performs just that task.
• Address: A very helpful icon, Address displays a mini address book (Figure 7–10) so you can find an e-mail address without having to launch the Mac Address Book app. Address books that are stored on your Mac, in iCloud, or on a local Directory Services server on your network are shown, and individual addresses or groups may be added to a message by clicking the To, Cc, or Bcc button.

• Colors: This icon has nothing to do with those flags I discussed a couple of pages ago. Instead, Colors displays a standard Mac color picker.
• Search: The search capabilities of Mail have improved markedly in Lion, and the search field is your gateway to finding messages. If you’re customizing your toolbar and want to add back a missing search field, drag and drop it from the palette to the toolbar.
• Smaller/Bigger: Having problems reading a message in small font size? Adding Smaller/Bigger to the toolbar gives you an instant way to increase the font size (or decrease it if it’s too big) of a selected message.
• Conversations: I’ll talk about Conversations, another new feature of Lion Mail, shortly. This icon is used to toggle the conversation view of any message thread.
• Space/Flexible Space: The last two icons to be discussed in this section are there to add spaces between other icons that you’ve dragged and dropped to the toolbar.

The Message Toolbar

While I’m on the topic of toolbars, I think it’s a good time to discuss another useful set of tools that exist in the Message toolbar. This toolbar appears when you create a new blank message, reply to a message, or forward a message and is at the top of the blank message by default. As with the regular Mail toolbar, the Message toolbar can be hidden if you find that it gets in the way of writing, sending, or reading e-mail. You can also hide or show text labels for the icons and customize the Message toolbar to meet your needs.

Like the Mail toolbar, the Message toolbar contains a default set of icons (Figure 7–11).

From left to right, the Message toolbar contains the following icons:

• Send: When you’re finished writing a new message, composing a reply, or adding text and other content to a forwarded message, clicking the Send icon sends the message to the proper mail server for the account being used.
• Attach: Sending documents in Mail messages is done in one of two ways. First, clicking the Attach icon displays a standard Mac Finder window (see Chapter 2) that is used to choose a file to attach to the document. The second way is to drag and drop a file icon onto your blank message.
• Format: This icon toggles the visibility of the Format toolbar, which is used to format the text in a Mail message. I’ll have more details about the Format toolbar in a minute.
• Photo Browser: Photos are a type of file, so you could think about using the Attach icon to pick an image file and attach it to a message. The Photo Browser gives you a way to actually see those images, much in the way that they are stored in iPhoto. Clicking this button provides access to the standard Mac Photo Browser (Figure 7–12).

• Show Stationery: As with previous versions, Lion Mail provides a selection of virtual stationery for sending unique and colorful e-mails to friends and relatives (Figure 7–13). With a click of the Show Stationery icon, a gallery of stationery included in Mail is displayed.

Clicking any one of the stationery thumbnail images applies that stationery to the current message, and images are selected from your iPhoto library to replace the placeholder images in the stationery template.

As with the Mail toolbar, the Message toolbar is customizable. A right-click or two-finger click displays a drop-down menu that is identical to the one shown earlier on the Mail toolbar. Selecting Customize Toolbar shows you a palette of icons to drag and drop to the Message toolbar. All of them, with the exception of the following four, have been discussed previously:

• Append: On occasion, you may want to include information from an existing e-mail in a new message. This happens automatically when you click Reply, Reply All, or Forward but not when a new message is created. Click Append, and the text of any highlighted message is added to a new unaddressed message.
• Lists: Messages often contain lists of items. To format a list automatically as a numbered or bulleted list, select it and click the Lists icon.
• Link: When typing a hyperlink into a message (an Internet address or a “mailto” link), click the Link icon to add the underlying address to turn the hyperlink into a clickable link. Note that Mail does this automatically when you send a message containing a typed Internet address.
• Rich Text/Plain Text: Plain text is readable by all e-mail recipients, because it contains no special fonts, text styles, and formatting. A small percentage of e-mail recipients cannot read rich text, which does contain special fonts, styles, and formatting. Mail defaults to rich text, but if you need to send e-mail messages in plain text, clicking this icon removes any special formatting.

The Format Toolbar

The Format toolbar (Figure 7–14), which appears just above the To address field and below the Message toolbar in a Mail message, is used to change the font, font size, color, emphasis, alignment, bullets or numbering, and indentation of text.

When writing a message in Mail, the Format toolbar is useful in making changes to the format of selected text. The Format toolbar contains the following icons:

• Font: Clicking the font icon displays a scrolling list of all the fonts currently installed on your Mac.
• Font Size: Whether you want to write your e-mail in 9-point (1/6th of an inch tall) Helvetica or 288-point (4 inches tall) Copperplate, there are many font sizes available for you.
• Color: Sometimes it’s important to call a reader’s attention to a certain phrase in an e-mail, and color is a good way to do that. Clicking the color swatch (indicated by a black square) displays a grid of 144 tiny colored squares to choose from. Clicking any one of the squares changes the color of the text.
• Bold/Italic/Underline: Another way to emphasize text is to put it in bold or italics or underline it.
• Left/Center/Right Justification: This book is left justified, as are most English-language documents. There are situations where you may want to center text, most likely for a header at the top of an e-mail. You might also want to right-justify text in certain cases. The left, center, and right justification icons rejustify text with a click.
• Lists: This button is used to insert bulleted or numbered lists in the body of your e-mail.
• Indent/Outdent: This list has been indented slightly from the left margin, and the indent button does the same to your message text. When you’ve typed an indented paragraph and need to start at the left margin again, click Outdent.

Reading Mail Messages

So far in this chapter, I’ve introduced you to many of the new tools that are at your command in Lion Mail. Now I’ll talk about three new features designed to make reading e-mails much easier: redesigned message headers, Conversations, and hidden quoted text.

Redesigned Message Headers

When new messages appear in your mailboxes, you are notified audibly, and the Mail icon in the Dock displays a small red counter with the number of unread messages. Looking at the list of messages in a mailbox, those unread messages are indicated by a small blue dot on the left side of the message.

By default, your messages appear on the right side of the Mail window with only three lines of information: the name and e-mail address of the sender, the subject of the message, and the date and time the message was received (Figure 7–15, top). The idea here is to give you the important information you need without cluttering up the top of the message.

There’s a light blue link marked Details on the right side of the message. Clicking that link displays more information in the message header (Figure 7–15, bottom), including the person or group it was sent to and the reply-to address (where replies will be sent). As mentioned earlier in this chapter, adding the All Headers button to the Mailbox toolbar and clicking it shows even more information.

Conversations

When I’m working on a project, I often have e-mail “conversations” with my co-workers. Someone starts by sending an e-mail, and I click Reply All and send my views on the topic. Others do the same, and pretty soon we have a long e-mail message containing everyone’s replies. It’s a mess and quite difficult to work backward through the chain of e-mails.

Lion Mail has a new feature called Conversations to help organize these related messages. With Conversations, those related messages are automatically grouped together in your inbox (Figure 7–16). Each message is numbered so that you know exactly which e-mail was first and which replies followed.

There’s another clue that Conversations is at work organizing those threads of messages. In the list view of e-mail messages for a specific mailbox, a small number appears with an arrow pointing to the message body at right (Figure 7–17). This number denotes the number of related messages that are in the conversation.

If for some reason you do not like the way that Conversations organizes related messages, disabling the feature is a simple matter of deselecting View Organize by Conversation.

Hidden Quoted Text

One way that Lion Mail makes conversations easy to read is that it automatically hides quoted text that appears repeatedly in replies so that only the new parts of the e-mail discussion are visible. What if you don’t want to scroll down through all the individual messages in a thread and would actually like to view all of the replies in one message?

In Conversations, there will always be a blue link that says “See More from [sender’s name]” (Figure 7–18).

When that link is clicked, the original quoted text, no matter how many levels deep the Conversation goes, is displayed (Figure 7–19).

If you no longer want to view the quoted text in the conversation, just click another e-mail message and come back to this message later. The quoted text is gone, replaced by the familiar “See More from” link.

Searching Mailboxes

Some of us have a hard time getting rid of e-mail messages.

If you look closely at Figure 7–6, you’ll notice that one of my e-mail accounts has more than 39,000 messages in it. I keep a lot of e-mail that I receive and respond to because I often refer to old messages for stories that I write for The Unofficial Apple Weblog. One of my complaints about Mail in the past is that it did a fairly poor job of helping me search through those thousands of messages to find a specific one.

With Mac OS X Lion, Apple added a much more powerful search engine to Mail. In this portion of the chapter, I’ll explain search suggestions, search tokens, and how Mail now searches attached files.

Search Suggestions

All searches of Mail messages begin in the same place: the Search field in the Mail toolbar. It has the same magnifying glass icon that you may be familiar with from using the Mac OS X search tool, Spotlight.

To begin searching for a specific name or word, start typing into the Search field. As you type, suggestions dynamically appear in a drop-down list. The suggestions are classified into different groups such as “Search messages,” People, Subjects, Status, and Dates.

In Figure 7–20, I’m searching for messages containing the last name of one of the authors of this book: Grothaus. The more letters of Mike’s name I type into the Search field, the more focused the search becomes. When I’m done typing his name, a list of suggestions is neatly displayed below the Search field, such as messages containing the letters grothaus, Mike’s full name, different subjects containing Mike’s last name, and files attached to messages. One of these suggestions may be just what you’re looking for; to use the suggestion, just select it from the drop-down menu.

Several other things happen after you type something into the Search field. First, if you do not select an item from the drop-down menu, the number of items that match your search is displayed just below the Search field. Next, the mailbox that you are currently searching is highlighted in blue in the Favorites bar. By default, the Inbox folder is searched, but you can also select All to look at all mailboxes including Drafts and Sent messages.

For searches that might be used frequently, there’s also a Save button that appears on the far right side of the Favorites bar. The function of this button is to save the search as a smart mailbox for future reference so that any incoming e-mail that satisfies the search criteria is automatically displayed in that mailbox.

Search Tokens

Search tokens are a new feature of Lion Mail that narrow search results with a single click. Whenever you search for a person, a phrase, or a specific subject, the search can be displayed as a clickable token in the Search field (Figure 7–21).

To turn a search phrase into a search token, select that item from the drop-down menu that appears. For names, clicking the left side of the token displays a small drop-down menu that provides a way to narrow the search down to messages from or to a specific person or who are referenced somewhere in a message. The drop-down menus vary from token to token, so if you see a small downward-pointing arrow on a token, be sure to click it to see what search options are provided.

The power of search tokens is that they can be combined to create very focused searches of the mailbox. In Figure 7–21, for example, I was searching for all e-mails from a particular person that were sent in June 2011. If I wanted to widen my search, I could change the date token to 2011. To make the search more restrictive, I could add a third token to add a subject label of “podcast.”

While performing research for this book, I was able to find a number of different token types:

• Name: Drop-down menu displays From, To, Entire Message
• Date
• Attachment
• Subject: Drop-down menu displays Subject, Entire Message

For those readers who also use iOS devices (iPhone, iPod touch, iPad), search tokens are coming your way in the iOS 5 Mail app in the autumn of 2011.

Search Attachments

As you saw in the previous section about search tokens, it’s now possible to display only messages that have files attached. One other new feature is the ability to search attachments by file name and by content.

In the example shown in Figure 7–22, a search has been performed with the attachment search token for any message with an attachment that contains the word Cardinals.

The result of this search consisted of 16 messages with an attached Microsoft Excel spreadsheet that contained the name of the St. Louis Cardinals, so Mail is now able to search the content of a number of different file formats. As noted previously, additional search tokens could be used to focus the search even more, such as to the present year or from a specific person.

Additional Lion Mail Features

There are several more new features in Lion Mail that you should know about. Data detectors have been available for some time, allowing Mail users to click a physical address or phone number to add it to Address Book or to click a date and time in the body of a message to add an appointment to iCal. Now Apple has added several new twists to data detectors to make them even more useful.

Mail also adds a way to view web pages without leaving the Mail app and provides support for Microsoft Exchange 2010.

The Power of Data Detectors

When you receive an e-mail message containing several different types of data, such as a date or time, an address, or a hypertext link, in the body of the text, Mail highlights that data with a gray box with a small arrow signifying the presence of a drop-down menu (Figure 7–23).

Now in Mail, clicking the drop-down arrow for this date and time data detector displays a Quick Look (see Chapter 1) of your calendar for the day (Figure 7–24).

That calendar is indicative of what is actually in iCal for that date and time. Mail is even smart enough to make the change from Eastern Daylight Time to Mountain Daylight Time. To add this appointment to iCal, there’s an Add to iCal button in the upper-right corner of the Quick Look of the calendar.

If the information was somehow interpreted incorrectly by the data detector, clicking the Edit button brings up the standard iCal edit dialog, where you can change the length of the appointment, the start time, the end time, the calendar the appointment belongs on, and the desired alerts.

Viewing Hyperlinks in Mail

Another data detector has been added to Mail. Previously, clicking an Internet address launched your default web browser and opened the link. Now all hyperlinks in Mail messages appear as data detector links as well, featuring the gray box and drop-down disclosure triangle. Clicking the disclosure triangle opens a Quick Look representation of the web site at the Internet address (Figure 7–25).

This feature is helpful because you no longer need to open a web browser to see where an embedded hyperlink in a Mail message is pointing. If you decide that it would be advantageous to view the original page, click the Open with Safari button, and the link is transferred to Apple’s web browser.

Exchange 2010 Support

Up to this point, Mail, iCal, and Address Book have not supported the latest version of the Microsoft Exchange 2010 enterprise mail server. As a result, Mac users on networks using Microsoft Exchange 2010 have been required to install and use Microsoft Office 2011, which includes the Outlook for Mac messaging client.

Mail under Mac OS X Lion works well with Microsoft Exchange 2010, as do iCal and Address Book. One feature that Mac users have been missing for quite a long time is the ability to set their vacation out-of-office messages from Mail. With Lion, that’s finally possible.

Summary

One of the most widely used applications on any Mac is Mail, and with the introduction of Mac OS X Lion, the app gains new ease-of-use and powerful features. Some of the major points to remember from this chapter are as follows:

• The process of setting up Mail accounts is now more automated than before, and you’ll now be asked whether you want to set up web mail accounts in Mail when you visit those accounts using Apple’s Safari web browser.
• The Mail user interface has changed, with new additions to the Mail toolbar, a new Favorites toolbar, and customizable Message and Format toolbars.
• Message headers now show minimal information by default but can be expanded to show additional information about the sender, the recipients, and to whom replies will be sent.
• Conversations is a new view that simplifies reading “back and forth” e-mail threads by hiding repeated text strings and putting all responses into a separate pane in the message.
• Searching e-mail messages is faster and more focused with the new search tokens and the ability to search inside attachments.

Adding appointments to iCal and viewing web sites noted in e-mail messages is now easier with the help of more powerful data detectors and an in-app Quick Look function.