While it’s connecting to the Internet and transferring messages, Entourage reports briefly on its activity at the bottom of the main window. If you’d like more detail, open Entourage’s Progress window, as shown in Figure 10-7, by choosing Window → Progress or pressing ⌘-7.

Figure 10-7. Top: The progress window first appears as a small window with a flippy triangle on the left side. Bottom: When you click it, the window shows you all of the details as it makes a network connection: what server has been checked, the number of messages left to be downloaded, where they’re coming from and how much of each message is left to be downloaded.

You don’t have to check all of your email accounts whenever you want to get mail. Suppose, for example, you’re having a holiday weekend at home and don’t really care to see any email from your work account, but to want to see any messages that come to your personal account.

You can exclude an account (or several accounts) from the “Send & Receive All” routine easily enough. Open the Accounts window (Tools → Accounts), double-click the account’s name, turn off “Include this account in my “Send & Receive All’ schedule,” click OK, and close the Accounts window.

But suppose you usually want to check all accounts, but occasionally want to check only one of them. On such an occasion, choose that account’s name from the Send/Receive menu button on the main Entourage window. (Alternatively, choose the account name from the Tools → Send & Receive submenu.)

Stop pressing a button to check your email. You can set up Entourage to check your email according to a regular schedule. To be sure, this is an advanced feature, which may force you to think, just for a moment, like you’re a computer. But there’s no debating the convenience of receiving messages throughout the day, moments after your correspondents click their send buttons. (On the other hand, some folks enjoy the uninterrupted peace and quiet of their workday, and prefer to take a virtual walk to the post office once or twice a day.)

To create a schedule, choose Tools → Schedules to bring up the Schedules window (Figure 10-8, top). Click the New button in the window’s toolbar, which brings up the Edit Schedule window with an untitled schedule (Figure 10-8, bottom). (If you want to edit an existing schedule—for example, Send & Receive All might be the only schedule you really need—double-click it in the Schedules window.)

In this window, you can set three options: the schedule’s name, when it happens, and what happens. To give the schedule a name, just type it in the Name field at the top of the window.

The When portion of this window lets you determine when a schedule runs, using a pop-up menu:

For Timed schedules and Recurring schedules, you can set the particulars by clicking the button next to the pop-up menu, which opens a window where you can set exact days, hours, and minutes for schedules to run.

By clicking the Add Occurrence button, you can add up to three “triggers” for this automated action. For example, you might set up a Timed Schedule, an At Startup schedule, and an On Quit and schedule, so that, for example, your email gets checked once when Entourage is launched, then every 10 minutes, and once again when Entourage quits.

Now that you have specified when your schedules are to be run, you need to determine what happens when a schedule is run; Entourage can do much more on a timetable than check your mail. Control these options in the Action section of the Edit Schedule window. The pop-up menu has eight options:

Once you’ve selected one of these options, you can also select parameters for it. For example, if you choose Receive News, you can specify which subscribed newsgroups (see Newsgroups) you want to read.

You can add dozens of actions to take place in a single schedule. To add an action, click the Add Action button. A new pop-up menu appears. (To delete one, too, click its line in the dialog box and then click the Remove Action button.) At the bottom of the dialog box, the Enabled checkbox lets you turn this schedule on or off—as does clicking the same-named checkbox in the Schedules window (Figure 10-8, top).

Entourage comes with three prefab schedules you can edit to meet your own ends: Empty Deleted Items Folder, which deletes all messages in the Deleted Items folder; Send & Receive All, which sends all outgoing mail and receives any waiting mail for all the accounts you’ve set up; and Send All, which sends all outgoing mail without checking for incoming mail. You can run these schedules, as well as any you’ve set up yourself, by choosing from the Tools → Run Schedule submenu.

As noted earlier in this chapter, the world’s most common email account types are POP (in which your messages are transferred from the Internet to your hard drive) and IMAP (in which your messages always remain on your mail server rather than your computer). The kind of account you have depends on your ISP.

But like other hip email programs, Entourage can let you use POP accounts almost as if they were IMAP accounts—that is, you can grab your messages without removing them from your Internet server. Better yet, the program can download only the headers of the messages, which takes but an instant, even over a slow (or expensive) connection. Once you have the headers, you can survey the subject lines or the names of the senders, and choose which messages you want to download in their entirety.

This feature is ideal for use when you’re staying in a remote getaway cabin, dialing your Internet account over a slow modem connection, for two reasons. First, you’re spared the tedium of downloading a bunch of messages and attachments you don’t really need while on retreat. Second, the mail stays on the server until you delete it manually; it’ll still be there when you return home, when you can again download the messages, this time onto your main Mac.

Microsoft calls this feature online access, by which it means that you’ll access mail in this account only via the Internet, rather than downloading it to your hard drive. To set up your account this way, choose Tools → Accounts, which brings up the Accounts window. Double-click the account that you want to make available for online access.

In the resulting Edit Account window, click the Options tab and turn on “Allow online access,” as shown in Figure 10-9. You wind up with a new icon in the Folder Items pane: the online representation of your account, bearing the same name.

Figure 10-9. The Edit Account window (left) contains the “Allow online access” checkbox. The icon titled Hopper, located below the list of folders (right), is an online email account. When you select it, Entourage lets you read messages directly from the server without downloading them—particularly useful if you use more than one computer to check email.

Setting up an account for online access doesn’t remove its mail or folders from your hard drive. It just sets up an additional, different way of accessing the account, as represented by a new icon in the Folder List for that account. (Yes, this is confusing.)

To make Entourage check the mail server for new messages sent to this account, click this icon in the Folder Items list—just one click. Entourage starts by downloading only the header information of the waiting messages: subject lines, sender names, date and time the message was sent, and so on. It doesn’t download the messages themselves.

If you see a message whose subject line or sender looks promising, click it. If Entourage’s Preview pane is showing, Entourage downloads the message and shows it there. If not, double-click the message to make Entourage download it and display it in the message window.

Either way, the message also remains on the mail server—that’s the big difference between using the online access feature and using the Send & Receive command for that account.

To delete mail from an online account, select the messages that you want to delete, and then press the Delete key. (Now you see why it’s a good idea to turn off the Preview pane—when you click a message to delete it, you simultaneously tell Entourage to download it if the Preview pane is on the screen.)

The message doesn’t move, but a “deleted online message” icon appears in the message’s Online Status column (see Figure 10-10). When you next connect to that account in online mode, Entourage deletes the message from the server, if you’re still connected to the Internet.

Figure 10-10. Online messages that you’ve deleted still show up in the message list, bearing an icon that looks like a red X. The next time that you connect to an online account, any messages that are marked for deletion will be shown the door. If you change your mind, you can click the deleted online message icon and choose “Leave Message on Server”.

On the other hand, if you change your mind and want to keep a message you’ve marked for deletion, click the deleted online message icon. From the pop-up menu, choose Leave Message on Server, so that the “deleted online message” icon disappears. The message will be there waiting for you when you check your email account in one of the “normal” ways.

For road warriors stuck with slow modem connections, you can tell Entourage to grab only the first portion of a message, so that you don’t have to sit through an hour-long modem connection to download that “You Want It When?” cartoon that your aunt thought was just so funny.

To do this, select Tools → Accounts and then open the account for which you want to limit the size of downloaded messages. Click the Options tab at the top of that window, and then turn on “Partially receive messages over _ _ _ KB.” You can set how much of a message you want to grab (see Figure 10-9). If you decide that you want to download the entire message, click the broken-envelope icon; choose “Receive Entire Message at next Connect” from the menu that pops up (Figure 10-11).

Figure 10-11. Messages that Entourage has only partially retrieved show a half-completed picture of an envelope in the Online Status column.

When you’re in the plane or riding the Greyhound, you probably don’t have an Internet connection. In such situations, you may want to read your email and write replies—but you’ll undoubtedly be annoyed that, every 15 minutes or so, Entourage tries vainly to get online, triggering an avalanche of error messages.

To return serenity to Entourage world, choose Entourage → Work Offline. A checkmark appears next to the menu item and “You are working off-line” appears in the lower right corner of the main window. From now on, you can read and write replies to your email without interruption. In fact, if you click Send & Receive, Entourage asks if you’re sure you want to go online before it attempts to make a connection. (Choose Entourage → Work Offline again to remove the checkmark from the menu item and return to the normal “connect when ready” mode.)

After you’ve received some messages in Entourage, you’ll notice that some of those messages have icons at the left side of their list-view lines. These badges or flags give you useful information about the messages:

Sometimes it’s junk mail, sometimes you’re just done with it. Either way, it’s a snap to delete a message that’s before you on the screen, whether it’s in a preview pane, in its own message window, or just highlighted in the message list: simply press the Delete key. Alternatively, you can:

You can also delete a batch of messages at once by highlighting them or their group header and then using the delete button, menu command, or keystroke.

Either way, the message or messages don’t actually disappear, just as moving a file icon to the Mac’s Trash doesn’t actually delete it. Instead, these commands move the messages to Entourage’s Deleted Items folder. If you like, you can click this icon to view a list of the messages you’ve deleted. If you spot something in there you’d like to preserve, you can rescue messages by dragging them into any other mail folder (such as right back into the Inbox, as shown in Figure 10-13).

Figure 10-13. By dragging an item out of the Deleted Items folder, you can save it from certain doom. On the other hand, you can delete messages by dragging them into the Deleted Items folder.

Entourage doesn’t truly vaporize messages in the Deleted Items folder until you “empty the trash.” You can empty it in any of several ways:

To reply to a message, click the Reply button in the toolbar, choose Message → Reply, or press ⌘-R. Entourage creates a new, outgoing email message, pre-addressed to the sender’s return address.

To save you additional time, Entourage pastes the entire original message at the top of your reply, complete with the > brackets that serve as Internet quoting marks (Entourage indents quoted text in HTML messages). (It’s also a feature you can turn off; choose Entourage → Mail & News Preferences, click the Reply & Forward tab, and turn off “Include entire message in reply.”) Entourage also tacks Re: (“regarding”) onto the front of the subject line, a long-standing convention of Internet email, and prefixes the quoted message with a one-line label indicating who originally wrote it, and when it was written.

Your cursor appears at the bottom of the message area, below any quoted text; you can begin typing your reply. (If you’d rather see your insertion point above the quoted text, choose Entourage → Preferences → Reply & Forward and turn on the checkbox marked “Place insertion point before quoted text.”) You can also do any of the following:

Figure 10-14. If Entourage is acting strangely, or you’d just like to compact its database to make it a smaller, more efficient file, then hold down the Option key while you launch the program to summon the Database Utility.

There are two basic kinds of replies. Create them by choosing commands from the Message menu, Control-clicking (or right-clicking) the message in the list and choosing from the shortcut menu, or by using the toolbar buttons.

Entourage lets you edit a message somebody else wrote. For once in your life, you can edit down some overly loquacious person without hurting his feelings.

Just double-click a message to open it into a window, and then choose Message → Edit Message. (If it’s HTML formatted, it becomes a plain-text message.) Feel free to delete or rewrite the text. When you close the window, Entourage asks if you want your changes preserved. After you click Save, a pencil and notepad icon appears next to the message’s name, a reminder of your meddling.

Some messages are forwarded and replied to about 900 times. With each round, more quoting brackets get added at the beginning of each line. Sooner or later, these messages become almost illegible (see Figure 10-15, top). Fortunately, Entourage can usually clean up a message’s text. It can, for example, make a message’s text all uppercase or all lowercase, increase or decrease its quoting levels (those multiple brackets >>>), or even straighten out curly quotes (which often arrive at the other end of Internet email as gobbledygook).

The most useful of these tools is Rewrap Paragraphs. When you have a badly wrapped message, the Edit → Auto Text Cleanup → Rewrap Paragraphs command (or click the Rewrap Text icon) does its best to remove all those funky line breaks so that the message is clean and legible once again.

Figure 10-15. Top: You can see how forwarding email multiple times can badly mangle the text. Bottom: After choosing Edit → Auto Text Cleanup → Remove Quoting, and Rewrap Paragraph commands, the message’s lines are neat and tidy—though the virus hoax message may still not be worth reading.

Instead of replying to the person who sent you a message, you may sometimes want to forward the message—pass it on—to a third person. You can do that in one of two ways: pass the message along as is, or package it up in an attachment to a new message.

To send a message off just as it came, click the Forward button in the toolbar, choose Message → Forward, or press ⌘-J. A new message opens, looking a lot like the one that appears when you reply. But first you have to address it just like you would any other outgoing message. Once again, before forwarding the message, you can edit the subject line or the message itself. (For example, you may wish to precede the original message with a comment of your own, along the lines of: “Kate: I thought you’d be interested in this joke about Mozart.”) Entourage inserts one-line labels indicating what part of your message is the forwarded content, which helps eliminate confusion.

When you forward a message this way, Entourage puts the insertion point at the top of the message, and inserts labels—“Forwarded message” and “End of Forwarded Message”—to indicate where the forwarded message starts and stops. You can also tell Entourage to use Internet-style quote characters (“>”) before the forwarded text: choose Entourage → Mail & News Preferences, select the Reply & Forward pane, and check “Use quoting characters when forwarding.” (You can also change the starting position of the insertion point from this panel—though be aware that these preferences control replying and forwarding.)

If you have a long message that’s like a document in itself, you might want to keep it separate from the text you’re adding, so you can have Entourage turn the mail into an attachment. This method also keeps the material safe from prying eyes until your recipient chooses to open the attachment. To do so, click Message → “Forward as Attachment”, and take it from there.

A redirected message is similar to a forwarded message, with one extremely useful difference: when you forward a message, your recipient sees that it came from you—just as if you’d written the whole thing yourself. But when you redirect a message, your recipient sees the original sender’s name as the sender; the message bears almost no trace of your involvement. In other words, a redirected message uses you as a low-profile relay station between two other people.

Treasure this Entourage feature; plenty of email programs, including Microsoft’s own Outlook and Outlook Express for Windows, don’t have 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. You might use it when, for example, you, a graphic designer, receive a question from a customer about the sales tax on his bill. You could redirect it to someone in the accounting department, who could respond to it directly just by clicking Reply. You’d then be mercifully insulated from any ensuing discussion of sales tax.

To redirect a selected message, choose Message → Redirect, or press Option-⌘-J. Entourage presents an outgoing copy of the message for you to address. You’ll notice that unlike a forwarded message, this one lacks quoting brackets. You can’t edit a redirected message; the whole idea is that it ends up at its destination unaltered. If you need to make a comment to the new recipient, use Forward or Forward as Attachment instead.

To print a message choose File → Print or press ⌘-P; the Entourage Print dialog box pops up, so that you can specify how many copies you want, what range of pages, and so on. Finally, click Print.

Organizers take note—Entourage lets you create as many new folders in the Folder list as you need. Then, by dragging messages from your Inbox onto one of these folder icons, you can file away your messages into appropriate topics. You might create one folder for family messages, another for order confirmations when shopping on the Web, another for correspondence relating to an important project, and so on. In fact, you can even create folders inside these folders, a feature beloved by the hopelessly organized: your Family folder might have subfolders for each branch of the family tree.

Figure 10-16. Create as many folders and subfolders as you need to organize your email life. Use the flippy triangles to reveal or conceal subfolders. For quick access to your favorite folders, use Entourage 2008’s new Favorites Bar by dropping a folder into it from the folder list. Remove a folder favorite by dragging it off the Favorites Bar. If you don’t see the Favorites Bar—or don’t want to see it—choose View → Show (or Hide) Favorites Bar.

To create a new folder, choose File → New → Folder, press Shift-⌘-N, or choose New Folder from the New menu button on the Entourage toolbar. A new folder appears in the Folder list, sporting the imaginative moniker “untitled folder.” Just type a new name and then press Return.

You can move a message into a folder in any of three ways:

Sometimes you’ll receive an email message 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 1993 through 2006 and sending me a list by email?”)

That’s why Entourage lets you flag a message, summoning a little red flag in the Status column next to a message’s name and—new in Entourage 2008—automatically adding that message to your To Do list. Since all flags are now To Do items, all flags also have due dates. The quickest way to add a To Do flag is to click the message’s gray flag icon in the message list. When you do so, Entourage creates a To Do item with your standard due date. (You can set your standard To Do due date by choosing Entourage → Preferences → General Preferences → To Do List and selecting one of the intervals from the pop-up menu: Today, Tomorrow, This Week, Next Week, or No Date.)

To choose a different due date, select one or more messages, and then click the pop-up menu next to the flag button in the toolbar and choose from the pop-up menu (see Figure 10-18), or Control-click (or right-click) the message and choose from the To Do submenu. If you select Choose Date, the Dates and Reminder window appears. Here you can specify the Start date (when you want the item to appear in your To Do list), the Due date (when the item is actually due), and a reminder (an Office Reminder window that pops up on your screen to help jog your memory).

Figure 10-18. Use the To Do Flag’s pop-up menu to choose exactly when you need to respond to the selected message. If you do a lot of flagging, consider learning the keyboard equivalents listed in the menu (the chevron symbol stands for the Control key). Add a reminder to any flag, mark the item as completed, or clear the flag entirely using the final commands in this menu.

To view the messages you’ve flagged, you can do one of three things: Choose View → Flagged Only to display all the flagged messages in the current folder, click the Flagged search icon (Entourage Functions) in the Mail Views folder at the bottom of the folders pane, or switch to Entourage’s Tasks function (Tasks and the To Do List) and examine your To Do List.

Email messages can be much more valuable when they’re linked to other bits of Entourage information, such as other messages, calendar events, notes, and so on—yet another payoff of having an email program with built-in calendar and address book info. For example, you can link a message to a calendar event; thereafter, you’ll be able to click the link in the appropriate calendar day square to consult the original message (because it contained directions, for example).

Entourage creates some links for you automatically: for instance, when you reply to a message (or forward or redirect it), Entourage automatically creates a link between the original message and your response. That’s how the message history feature works (see Figure 10-19). When flagging a message for follow-up (see Flagging messages), you create a reminder that links to the original message.

Figure 10-19. When you select a message and choose Choose Date from the Flag button’s pop-up menu, besides the date it appears in your To Do List and the date it’s due (top), you can set an Office Reminder to pop up at an appointed time to gently nudge you toward action (bottom).

Chapter 13 has full details on links. In the meantime, here’s a summary that’s specific to email:

In addition to responding to messages, you can link messages in three other ways: by opening the links menu, creating a link to an existing item, and creating a link to a new item.

To remove a link, open the Link To window (choose Tools → Open Links, choose Open Links from the Link pop-up button in the toolbar, or click the link column next to the message in question). Once the Link To window is open, select the link, and then click the Remove button at the top of the window.

You can set one of five priority levels for messages that you send or receive: Highest, High, Normal, Low, and Lowest. Once you’ve assigned priorities to your messages, Entourage can sort them so that the most important messages appear at the top.

To set a message’s priority, highlight its name in the List pane and then choose from the Message → Priority menu. To sort messages by priority, click the Priority column header (the exclamation-point icon at the left side of the List pane). The first time you click, Entourage sorts your messages from highest priority to lowest; the second time, it lists them from lowest to highest importance.

Several factors may be at work if you’re unable to open a file attachment. For starters, your correspondent’s email program may have compressed or encoded the file to make it take less time to send. If you’re having trouble getting a file to open, therefore, your first step should be to drag the attachment’s icon onto that of StuffIt Expander, a free program that you can download from www.stuffit.com.

StuffIt Expander can gracefully decode and decompress just about any compressed or stuffed file, including those with file name suffixes like .sit, .cpt, .hqx, .gz, .z, .arc, .uu, and .zip.

If the file still won’t open, even after being decompressed, then you may be dealing with a file from a Windows PC. Some you can open relatively easily; some require more work, and some won’t work on Macs at all.

The best clue is the three-letter file name extension on the file’s name. For example:

If you were sent a file with a three-letter code not listed here, you may well have yourself a Windows file that can be opened only by a Windows program that you don’t actually own. You might consider asking your correspondent to resend it in one of the more universal formats described above.

Select an email message of the type you’re creating a rule for before you start setting up the rule. That way, Entourage fills in the appropriate text (see step 4, below) as you choose the filtering criteria. Then follow these steps:

Figure 10-23. In this example, if Entourage receives an email message to a specified address—one you set up specifically to collect sales leads, for example—it sends an email reply using the text you create after clicking the Reply Text button (top) and adds the sender’ s address to a special group (bottom) in your Entourage Address Book (see Address Book).

The first thing you’ll see when you create a new email message is the address pane, a pop-up window with four buttons, three address fields, and a list of addresses from your Entourage Address Book (see Figure 10-24). The fields here are labeled To, Cc, and Bcc, each of which has its own purpose:

If you want to send a message to more than one person, click the Add button and type in a second (or third, or fourth) email address, or just press the Tab key or click in an empty area of an addressing box and start typing. As in most dialog boxes, press the tab key another time to jump to the next field (to proceed from the To field to the Cc field, for example).

You don’t have to remember and carefully type out all those email addresses, either. As you type, Entourage compares what you’re typing with the names in your Entourage Address Book. If it finds a match—that is, if you’ve typed tonand your Address Book contains the name Toni Martin, for example, Entourage sprouts a list of that and any other ton matches. The more letters you type, the closer Entourage zeroes in on your intended addressee. Entourage also remembers the last 200 addresses you’ve sent mail to and received mail from that aren’t in your address book, which can be handy when you think of something you’d like to add to a recent exchange. (You can turn this feature off or simply clear out the list in Entourage → Preferences → Mail & News Preferences → Compose if it bothers you.)

You can choose from this list of proposed addressees either by pressing Return when Entourage highlights the correct name, by pressing the up- or down-arrow key to highlight a name, and then pressing Return, or by clicking a name. If none of Entourage’s guesses are correct, just keep typing; Entourage quietly withdraws its suggestions.

Alternatively, you can access your address book by clicking the Address Book button just above the To field (see Figure 10-24).

Figure 10-24. Top: As you type an address, a pop-up menu of matching names from your address book appears. Click the one that you want, press Tab to accept the highlighted name and enter another one. Or press Return to use the highlighted name, close the addressing window, and move to the Subject line. Bottom: Click the Address Book icon in the Address pane’s toolbar, scroll up and down your list of contacts, and drag addresses into the To, Cc, or Bcc panes. If you just double-click a name it goes directly into the To pane. Repeat the process to add more names.

Across the top of the address window are a few handy buttons. Add opens up a new empty row in the current addressing field, where you can specify an additional address. The Remove button removes a selected recipient’s row. Check Names is handy if you don’t know a coworkers email address and you’re connected to your company’s LDAP address directory (see Step 1: Addressing the message) in hopes of turning up the correct address.

If you have more than one account set up in Entourage, a From pop-up menu appears above the message’s addressees. Choose from that pop-up menu to pick the account you want to use to send the message.

Some people, especially in the business world, get bombarded with email. That’s why it’s courteous to put some thought into composing the Subject line (use “Change in plans for next week” instead of “Hi,” for example). Then press the Tab key to make your cursor jump into the large message area. Don’t make your subject too long: remember, most people will see it in a list with other information like your name and the date and time you sent the message, and the subject may get compressed or truncated. If you try to send a message without a subject, Entourage will warn you this isn’t a very good idea, but it’s not a fatal one either. You can go ahead and send it. Entourage will automatically insert “<no subject>” as a subject line. And your recipient’s spam filter may possibly delete it.

After you’ve addressed your message and given it a subject, it’s time to write your message. To do this, just click (or Tab into) the message area and start typing. You can use all the standard editing techniques, including selection, drag-and-drop, and the Cut, Copy, and Paste commands, to rearrange the text as you write it.

As you type, Entourage does something rather wonderful (or alarming, depending on your point of view): it checks your spelling as you go, using a red squiggly underline to mark questionable spelling. To check for possible alternative spellings for a suspect word, Control-click the red-squiggled word; a list of suggestions appears in a shortcut menu. Choose the word you really intended, or choose Add to add the word to the Office 2008 dictionary.

If you want to spell-check a message all at once, choose Tools → Spelling (or press Option-⌘-L) after composing it. (To turn off automatic spell checking, choose Entourage → Preferences → General Preferences → Spelling tab, and turn off “Check spelling as you type.”)

All of this should sound familiar; it’s precisely the same basic mechanism that Word 2008 employs when it looks for spelling mistakes on the fly, as described on Check Spelling as You Type.

When it comes to formatting a message’s text, you have two choices: plain text or HTML (hypertext markup language). Plain text means that you can’t format your text with bold type, color, specified font sizes, and so on. HTML, on the other hand, lets you use formatting commands such as font sizes and bold text.

But there’s a catch: although nowadays nearly all email programs can read HTML-formatted email, they don’t always handle it the same way. An HTML message that looks fine for you may be incomprehensible for someone using another email program. HTML messages can also be much larger (and therefore slower to download on slow Internet connections) than plain-text messages, especially if you include pictures, sounds, or other multimedia elements.

So which should you choose? Plain text lends a more professional, old-hand feeling to your messages—but, more important, it’s the most compatible. Whether your recipient uses a high-end workstation, a Web browser, a cell phone, or a 20-year-old terminal in a dusty university basement, a plain-text message almost always gets through intact. (There are some exceptions: accented characters and language encodings may complicate the issue.)

HTML-formatted messages, on the other hand, may not arrive intact. Your recipient may see a plain-text version of the message, which Entourage includes as a courtesy, but some email programs can’t even display that neatly.

In general, you’re better off using plain text for most of your messages, and sending HTML only when you need it and you’re sure your recipients can see it. To specify which format Entourage uses for all outgoing messages (plain text or HTML), choose Entourage → Preferences → Mail & News Preferences → Compose, and select a format from the “Mail format” pop-up menu.

You can also change formats on a message-by-message basis. For example, if you generally like to send plain-text messages, you can switch one particular message into HTML mode by clicking the Use HTML button to the left and just above the body text area (see Figure 10-25), or choose Format → HTML. Either action activates the HTML toolbar, which you can use to add pizzazz to your messages. This toolbar is broken up into six sections:

Remember: when it comes to email formatting, less is more. If you go hog-wild formatting your email, you may make the message hard to read, especially for people using email programs that interpret the HTML codes differently than Entourage does.

You can also insert pictures, sounds, or movies into HTML email messages. Type your message, place the insertion point where you’d like the item to appear, and then choose the appropriate command from the Message → Insert menu. Entourage asks you to locate and double-click the file you want to insert.

Note that Entourage automatically converts TIFF and PICT images into JPEG format when you add them to HTML messages. If you need your recipient to receive these files unaltered, send them as standard file attachments instead of inserting them or dragging them into the window.

Once you’ve inserted a media item into a message, you can only move it around by inserting Returns and spaces in front of it. To delete a picture, sound, or movie, backspace over it, or select it and then press the Delete key. To remove a background image, select Message → and Remove Background Picture.

Signatures (or “sigs”) are bits of text stamped at the bottom of your email or newsgroup messages. Signatures began as a way to provide contact information without having to type it out in every message. But as online culture evolved, signatures became personal statements. A signature may contain a name, a postal or email address, a memorable quote, or even art composed of typed characters.

To create a signature, choose Tools → Signatures, which brings up the Signatures window. In it, you’ll see something called the Standard signature. You can edit this signature by double-clicking it, or you can create any number of new signatures by clicking the New button. Either way, you get an editing window where you can type your new signature. (Your signature can be either plain text or HTML-based, as described in the previous section.)

Once you’ve created one or more signatures, you can tack them onto every outgoing message or on a message-by-message basis:

You read about receiving attachments earlier in this chapter; sending them sometimes involves a little extra brainwork.

To attach a file or files to an outgoing email message, Microsoft, in its usual fashion, gives you several different methods to choose from:

Once you’ve attached files, their names appear in the message’s Attachments section, seen in Figure 10-26.

Attaching files is the easy part; knowing how to encode those files can be tricky. Not all computers (including the mail servers that transmit messages) can understand Macintosh files. Furthermore, a few email servers still mangle anything that isn’t a plain-text message. Encoding your attachments is the solution to both problems.

Unfortunately, different computers recognize different file-encoding schemes. Encoded improperly, the file turns into gibberish and can’t be opened on the other end.

To make matters even more complicated, files can also be compressed (as StuffIt or ZIP archives, for example) to make them smaller and reduce the amount of time it takes to send and receive them.

Fortunately, Entourage uses an encoding scheme called AppleDouble, which both Macs and Windows PCs can reconstitute. And it compresses your files only if you attach an entire folder (not individual files). It uses ZIP compression in that case, which Macs and PCs can decompress with no trouble.

There may be times, however, when you want to change these options. For example, you may want to turn on the ZIP compression for a single large file. Or you may have trouble sending files to someone using the factory settings, so you want to try different settings.

Figure 10-26. A file’s icon appears in the attachment section of the message window; click the “Encode for…” button below that panel to change the encoding, compression, and compatibility options. By clicking a couple of radio buttons and checkboxes, you can be sure that your recipients can open the attachment each and every time. The “Append file name extensions” is an incredibly valuable option, especially when sending files to Windows fans. If you failed to add the .doc, .xls, or .ppt to the end of their names, Entourage can do it for you at this stage.

To change encoding and compression options, click the gray “Encode for” button just below the Attachments window (see Figure 10-26). A little pop-up window appears where you can change the encoding, compression, and compatibility options:

To remove an attachment, select its icon in the expanded Attachments window and press the Delete key (or click Remove). (Dragging an attachment out of the Attachments window doesn’t remove it from the message. Instead, it makes a copy of the file where you drag it—unless you drag it to the Trash can in the Dock.) You can also remove all attachments in one fell swoop by choosing Message → Remove All Attachments.

Once your message is put together properly, you can send it in any of several ways:

When Entourage finishes sending the message, it disappears from your Outbox, and reappears in the Sent Items folder for your reference. (If you’re a person of steely nerve and impeccable memory, you can turn off this feature; choose Entourage → Preferences → Mail & News Preferences → Compose, and turn off “Save copies of sent messages in the Sent Items folder.”)

The following points are particularly relevant to mailing lists:

Finally, as tempting as it may be to send out flurries of advertising about your products or business using the Internet, it’s a bad idea. Spam isn’t only illegal in many jurisdictions (meaning you can be sued), it’s guaranteed to get your Internet account shut down without notice. It’s fine to keep in contact with current customers via email if they’ve given you permission, but quite another to use the Internet as a means to harass others.