Mac OS X e-mail guide

From hard-core managers who sort through hundreds of messages a day to grandparents who get three messages a week from their kids, everyone uses e-mail, albeit in radically different ways. The various ways people use e-mail have given rise to a surprisingly large number of e-mail programs. A dozen, from companies big and small, now run natively in Mac OS X, and all offer varying combinations of ease of use, flexibility, and power.

We looked at Apple's Mail 1.1 (which comes with OS X), Bare Bones Software's $99 Mailsmith 1.5.3, CE Software's $35 QuickMail Pro 3.1, CTM Development's $49 PowerMail 3.1, Cyrusoft International's $36 Mulberry 3.0a3 (still in beta at press time), MAKI Enterprise's $50 Magellan 3.3, Microsoft Entourage X 10.1 (available only with the $499 Office suite), the free Netscape 6.2 (essentially the same program as the open-source Mozilla 1.0), the $30 Nisus Email 1.6.1, Qualcomm's free or $40 Eudora 5.1.1, Sono Software's $25 Musashi 3.4, and Sugiura's $28 SweetMail. (See "12 E-mail Programs Compared" for details.)

We'll help you figure out which of these apps fits the way you work. To see our top contenders go head-to-head, check out " E-mail Grudge Match: Entourage versus Eudora. "

Transferring Mail

All e-mail programs face two basic tasks: receiving and sending mail. So what's the point of trying an e-mail program that isn't compatible with your Internet service provider (ISP)?

A good e-mail program must handle multiple accounts and support common e-mail standards. Support for receiving mail via IMAP is essential for some people, and for those using POP, support for APOP helps protect passwords sent over wireless networks that aren't secure. (Adrift in acronyms? See "E-mail Lingo" for help.)

The Basics -- All of these programs handle multiple accounts, receive mail via POP, and send mail with SMTP authentication (required by some ISPs). Only Netscape and Nisus Email lack APOP support.

If you use a modem, think twice before choosing PowerMail, Nisus Email, Musashi, or SweetMail, since they can't skip messages larger than a certain size. This ability is helpful if you don't want to get stalled every time someone sends you a big attachment. (The next version of PowerMail, due out by the time you read this, should have this ability.) All the programs performed well when retrieving mail, with one exception: if you receive a lot of mail, avoid Nisus Email. It doesn't let you read downloaded messages while it slowly retrieves new ones.

IMAPping the Internet -- Support for IMAP is less common than support for POP, appearing only in Entourage, Eudora, Mail, Mulberry, Netscape, and PowerMail. By default, IMAP keeps all your mail on a server, with a copy kept locally to improve performance. Mulberry took the IMAP speed award; the others -- except Netscape -- performed acceptably.

Mulberry offers IMAP-related features and options the other programs can only dream about -- although these options can be hard to find in its cluttered interface. They include a disconnected mode that automatically synchronizes offline changes when you reconnect to your ISP, helpful for IMAP users working on a plane, for example.

Proprietary Alternatives -- Some programs let you sign in to proprietary mail systems. Netscape can connect to AOL without using AOL's software, so you can receive your e-mail in your regular mailbox. Likewise, Entourage provides direct access to Hotmail, so you don't have to use Hotmail's Web interface.

Reading Mail

The right e-mail program is one that displays mail, and lets you navigate through it, the way you like. Some people can't imagine using an e-mail program that doesn't let them use the keyboard to switch between messages, for example, while someone who prefers the mouse doesn't care about key commands.

Most programs rely on a paned interface, with one pane for a list of mailboxes or folders, another for messages inside the current mailbox, and a third displaying a preview of the message. You should be able to move between messages in only one action, and you shouldn't have to close, delete, or file the current message and then manually open the next one. Beyond that, no approach is necessarily better than another.

Window Panes -- The three-pane interfaces in Entourage, Mailsmith, Mulberry, and PowerMail are the most flexible and fluid. All can display mail in two or three panes or in separate windows, and all provide multiple ways to navigate through messages. Though Eudora and Musashi provide only message-list and preview panes, each was fast and easy to use, as was SweetMail, which eschews panes entirely. Nisus Email, which uses a single-pane interface, makes you open and close each message manually and is notably clumsy.

Reading in Style -- The ability to display the styled text and graphics in HTML e-mail is increasingly important. Entourage, Eudora, Mail, Mulberry, Netscape, PowerMail, and QuickMail Pro support HTML display; the rest make you open HTML messages in your Web browser.

Thanks to its integration with a Web browser, Netscape offers the best HTML rendering by far, with Mail, PowerMail, and Entourage not far behind. Eudora does fine with simple HTML but has trouble with complex HTML.

Mulberry's HTML support is poor, and it can't display graphics. None of the remaining programs can display graphics either, with the exception of SweetMail and Mailsmith; the latter can display them only in separate windows.

Writing Mail

Reading is only half the battle -- an e-mail program must provide solid writing tools as well. Have you ever labored over an important message, only to see an embarrassing misspelling just as you click on Send? Good writing tools help you avoid such mishaps.

Most programs offer the basic text-editing options you'd expect to find in a Mac application, such as the ability to select words by double-clicking on them. But your e-mail program is often your primary writing environment. Additional formatting tools, a spelling checker, and the ability to add graphics can save you a lot of time. Also important is how successfully the program sends attached files; this depends on the attachment-encoding formats it supports. And since all messages must go to someone, an e-mail program must let you easily address new messages and use its address book.

Sharpening the Quill -- All the programs except Nisus Email (which anticipates that you'll create messages in a word processor) cover the basics: entering and editing text via the keyboard. Mailsmith and Eudora offer the most keyboard shortcuts for moving around and selecting text.

Eudora, Entourage, Mailsmith, and SweetMail offer additional tools for common e-mail tasks, such as quoting (marking parts of the original message when replying to it) and wrapping (adding or removing return characters at the end of lines). Mailsmith again stood out, thanks to its text engine, inherited from Bare Bones Software's powerful text editor, BBEdit.

All the programs except Nisus Email have (or can work with) spelling checkers, but Entourage, Eudora, and Mail win high marks for their inline spelling checkers, which underline misspelled words as you type instead of displaying misspelled words in a dialog box when you select the spelling-checker command. Entourage and Eudora (with the addition of the free TidBits AutoCorrect Dictionary, available at http://db.tidbits.com/getbits.acgi?tbart=06103) can also correct common mistakes automatically as you type.

Customized Paper Clips -- To send a file such as a Microsoft Word document as an attachment, your e-mail program must encode the file -- encoding can be likened to using an envelope to send a newspaper clipping to a friend, rather than scrawling his address on the clipping itself and hoping it arrives.

Widespread support for the AppleDouble encoding format has significantly reduced the severity of problems caused by attachments sent between Macs and PCs, and most e-mail programs now default to AppleDouble. (For details, see "Make Peace with PCs," Secrets, September 2002.) However, it's still occasionally useful to switch back to BinHex (Mac) or UUencode (Unix or Windows) when you send attachments to people using older e-mail programs.

Mail, Netscape, and Nisus Email lose points for providing few encoding-format choices (or none at all), whereas Entourage and PowerMail deserve kudos for clear, helpful interfaces, and for allowing you to compress attachments automatically before sending them, if you have Aladdin's $30 DropStuff or $80 StuffIt Deluxe (888/245-1723, http://www.stuffit.com).

Little Black Books As our friends and relatives, not to mention the businesses and government offices we must all deal with, start using e-mail, we acquire more electronic pen pals daily. A good e-mail program makes it easy to collect and use addresses.

Entourage's address book is by far the most complete. It lets you store postal addresses, birthdays, pictures, and more; categorize and search for contacts; and synchronize address-book data (and calendar events, though not e-mail) with Palm OS handhelds. (Pick up the new Palm conduit at www.microsoft.com/mac/download.) But this information can't be shared -- QuickMail Pro, when coupled with a QuickMail Pro Server, does offer this feature, helpful to businesses that need employees to use a common address book. To save time, Entourage also automatically completes address-book entries as you type -- as do Eudora, Mail, Mailsmith, Netscape, PowerMail, and QuickMail Pro.

The remaining programs offer simple but effective address books, with the exception of Mulberry and Nisus Email. Mulberry's address book suffers from unnecessary complexity, and Nisus Email's overly simple interface works only with a small number of contacts.

Managing Mail

Stored e-mail can be an important record of your business and personal life. Unless you're concerned about a Justice Department subpoena, it's best to file everything away for later reference. You never know when an e-mail may come in handy.

Filing Boxes -- When it comes to creating, renaming, and rearranging folders, four programs stand out. Magellan avoids the concept of folders almost entirely. Instead, it uses "views" to organize potentially overlapping sets of messages that match certain criteria (such as having the same sender). It also provides "folders," views to which you can manually add messages. This is a good approach if you often find yourself wanting to file messages in multiple places, since more than one view can include the same message.

Entourage's custom views are essentially saved searches, a feature also offered by Eudora and Mulberry. Unfortunately, Entourage searches too slowly for views to be useful, and although Eudora and Mulberry are faster, their saved-search features are hard to find. Nisus Email's folder handling and interface are feature-poor and difficult to use.

Seek and Hope to Find -- These programs find messages in different ways. One welcome feature in Entourage, Mail, PowerMail, QuickMail Pro, and SweetMail lets you limit the list of displayed messages by entering a search term in an ever-present search field.

Mulberry offers a similar feature, via a window that provides numerous canned criteria, such as date ranges or messages from the current message's sender. Eudora's approach is faster -- option-click on part of a message-list item to select and group similar messages, such as those from the same person or with the same subject line.

You'll find the best search tools in Eudora. Its fast search tool includes numerous search criteria and a results window that works exactly like a normal mailbox. Entourage and Mailsmith both offer excellent search capabilities, but they could be faster, and they don't let you search in a nonconsecutive set of folders. Bringing up the back of the pack are Mail, Netscape, and Nisus Email, with slow and clumsy search tools.

What if you want to find messages related to a project you did with several people? For more-ambiguous searches, you might want Sherlock-style searching with relevance ranking. PowerMail has long boasted Sherlock-style searching (at the expense of traditional search tools). The most recent version of Mailsmith has this feature as well.

Casting Nets -- A filtering feature brings together mail organization and searching. Most filters just transfer specific messages -- such as those from a mailing list -- into a particular mailbox. A good set of filters can also help you get rid of spam (see "Stop Spam!" Secrets, August 2002).

All of the programs we looked at can move mail into specific mailboxes. (The exception is Magellan -- since its views stand in for filters as well as folders, it does the same job a different way.) But some go beyond that basic functionality. Entourage and Mailsmith take top honors here, with PowerMail close behind. All three offer a wide range of filtering criteria and actions.

Entourage also offers a Mailing List Manager feature, which helps create filters for mailing lists. It would be nice, however, if it helped you change your address, unsubscribe, and search list archives -- as QuickMail Pro does. And Entourage's Junk Mail filter can identify some spam, though it often catches legitimate messages as well. Magellan also offers a spam filter, as will the next version of Mail.

Mailsmith offers an approach called "distributed filtering," which lets individual mailboxes grab the messages they want. Because these filters attach to mailboxes, they can be more efficient and easier to manage. For instance, if you want to keep track of all the e-mail messages you've received about AppleScript -- regardless of which mailing list they came from -- one distributed filter could collect them all in one place, while another filter made sure the individual messages also ended up in mailboxes specific to each list. Plus, Mailsmith supports advanced grep pattern matching in filters, so it can identify messages via patterns of text (see "Filter Fanatic").

Wild-Card Features

Although we've focused on commonalities, some of these programs sport distinctive features.

A Large Retinue -- Entourage is the most unusual of these programs, thanks to its integration with a full-featured calendar and contact database, its ability to read Usenet news, and the fact that you can get it only with Microsoft Office. True to its name, Entourage wants to do everything for you. Netscape is similar: it also provides a browser, a Usenet news reader, a Web-page-authoring component, and instant messaging -- and it's free.

The Workhorse Eudora deals well with large volumes of mail and providing the ultimate in access to occasionally necessary settings. Its unusual features include the unique Eudora Sharing Protocol (ESP), which helps groups keep a shared folder of documents synchronized, entirely via behind-the-scenes e-mail messages. It also offers e-mail-usage statistics and a configurable toolbar.

Not to be missed is Mood Watch, an optional setting that attempts to identify extreme language -- known as flaming -- in incoming mail and as you type. A warning gives you a chance to chill out before sending a message that may offend. Eudora can also read your e-mail aloud, a feature shared only with Mulberry.

A Little Help from Its Friends -- QuickMail Pro works fine with any standard POP server, but if you pair it with a QuickMail Pro Server, you get additional features such as shared address books, shared folders, and server-side filters that filter mail before you download it.

Macworld's Buying Advice

Our top picks are Eudora and Entourage, with Mailsmith and PowerMail close behind. Eudora rules for people who need to manage a lot of mail--nothing else compares to its combination of high-end features and performance. And it's available in three configurations--a free version with ads, a free "light" version, and a $40 full-featured version with

no ads--to fit different needs and budgets. For people who spend their days in Microsoft Office and appreciate Microsoft's efforts at integration, Entourage combines an excellent set of features with an attractive interface. It's included with Office, making it a good value if you're already an Office user and an expensive ($499) option if you're not.

That's not to imply that the rest of the field is just chaff. Mailsmith will appeal to gearheads who aren't into Eudora--its text-handling and filtering tools are superb--though at more than twice the cost of Eudora, it's pricey. PowerMail, though it doesn't stand out in any particular way, is the perfect upgrade for the Mail user who needs just a bit more power. IMAP users should look hard at Mulberry, and QuickMail Pro, when paired with a QuickMail Pro

Server, offers some compelling features for small offices. The path of least resistance for new users is Apple's free, and basic, Mail. A new version with some welcome features should be out by the time you read this.

Whether you receive a few messages a day or a few hundred, there's an OS X-compatible e-mail program out there that will serve you well.

E-Mail Grudge Match: Entourage Versus Eudora

Can't decide between our two top-rated programs, Microsoft Entourage and Qualcomm's Eudora? Each one has strong supporters. Macworld contributing editors Adam C. Engst, author of Eudora 4.2 for Windows and Macintosh: Visual QuickStart Guide (Peachpit Press, 1999), and Tom Negrino, author of Microsoft Office v. X Inside Out (Microsoft Press, 2002), debate common perceptions about the popular programs.

Claim #1: Entourage is better for novices.

Tom: This one's easy. Like any good Macintosh citizen, Entourage doesn't take a lot of effort to learn or use. For example, when I get paper mail, I file it in folders -- Entourage does the same with e-mail.

And because it's part of Office, Entourage shares keyboard commands and menu items with the other programs in the suite. On the other hand, you have to learn how to use Eudora, often by slogging through the manual.

Eudora appears to never have seen the touch of a graphic designer. Look at that button labeled, in minuscule type, Blah Blah Blah. Yeah, I know that it displays the headers of a message, but "Macintosh 101" says that buttons and other interface elements should convey their meaning. All too often, Eudora fails that test.

Adam: Entourage's interface may be prettier, but it wastes valuable screen real estate. The Blah Blah Blah button's purpose may not be obvious until you click on it once, but it's no worse than some of Entourage's buttons. And it's not as though Entourage's approach to viewing headers were good -- you can't choose to see them unless you open the message in its own window.

I've set up lots of novices with Eudora, and they don't have trouble with the interface, because Eudora focuses only on e-mail. With Entourage, the novice user can get lost in the additional address book, calendar, task manager, note-taking utility, and Usenet news reader. Talk about needing to slog through the manual. Oh wait! I forgot -- Microsoft doesn't provide one!

Claim #2: Eudora is more flexible for power users.

Adam: Eudora is the most accommodating e-mail program on the planet for power users or anyone who needs something a little unusual. Need to send e-mail at a future date and time? Need to change the default headers? Want to set Eudora to autosave every two minutes? Eudora can do all that and more.

Although Eudora lets users change almost every program behavior, it doesn't clutter the interface with obscure options. Instead, it makes them available via custom x-eudora-setting URLs that let knowledgeable users help those in need by sending a URL that the recipient can click on to twiddle a setting. (Send an e-mail to x-eudora-settings\@tidbits.com to receive the full list, with descriptions and instructions.)

Tom: Yes, Eudora is an e-mail geek's dream, but it lacks some simpler features. For example, being able to filter mail based on whether the sender is in your address book or in an address group is very useful; you can't do that in Eudora. In fact, Eudora's mail filters are desperately in need of improvement. The problem with Eudora is that much of its power is buried so deep that only the few, the proud, and the darned geeky will ever see it.

Claim #3: Entourage makes it easier to filter out junk mail.

Tom: Junk mail is an annoying problem, and Entourage shines when dealing with it. The built-in, adjustable Junk Mail Filter does a pretty good job of flagging junk messages. It's not perfect, but it's about an 80 percent solution. In addition, Entourage's rules are some of the best in the business; they allow you to filter mail by multiple criteria and perform multiple actions on the messages that meet those criteria.

Adam: The problem with Entourage's Junk Mail Filter is that the user has no way of knowing why some messages >have been marked as spam. That wouldn't be a big deal, except Entourage often incorrectly identifies legitimate mail as spam. I prefer creating my own filters. Though Eudora's aren't as flexible as Entourage's, Eudora can show when each filter was last hit and identify which were applied to any given message (press the shift key when choosing Filters from the Window menu). It's a little more work, but the added accuracy is worth it.

Claim #4: Eudora works faster when searching for old messages.

Adam: Game over, man. Eudora stores your e-mail in text files, one for each mailbox, instead of in a monolithic database, as Entourage does. But despite this, Eudora blows the doors off Entourage in searching speed. In a quick test, searching the same mailbox took 17 seconds in Entourage and 2 in Eudora. This speed is especially useful if you need to search through all your mail. Plus, Eudora lets you select precisely which mailboxes you want to search.

Tom: It's nice to get what you want fast, but search speed is hardly a critical feature -- unless the program is too slow to use or prevents you from working while the search is on. On the rare occasions that I want to search all my mail, I start the search and continue working. When Entourage is done, I click back and get the results. Yes, it's slower, but it's fast enough for most people. Most of the time, though, I skip searching and just use the filter box above the message list. It's not as flexible, but it's quick.

Email Lingo

APOP: POP command, APOP stands for Authenticated POP. When you use APOP, your password is encrypted so it can't be easily captured, particularly beneficial if you use a wireless network in a public place.

HTML: Messages sent as HTML (Hypertext Markup Language) mail can contain different fonts, styles, sizes, and colors, as well as inline graphics, much like Web pages.

IMAP Internet Message Access Protocol): is a method of retrieving e-mail; it stores all of your messages on an IMAP server. You read and respond to temporary copies of messages downloaded to your Mac.

POP (Post Office Protocol): is a common method of retrieving Internet e-mail. By default, it downloads all your messages from a POP server to your Mac for reading and storage.

SMTP (Simple Mail Transfer Protocol): is the standard protocol for sending all Internet e-mail, both from your e-mail program to your mail server and between mail servers. Some mail servers require that your e-mail program send your user name and password-SMTP authentication-before you can send e-mail.

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