E-Mail Survival Guide: Change E-Mail Clients

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Do you find it increasingly difficult to deal with the daily flood of e-mail? Do you wish your e-mail client could share information with other Mac programs? If so, it may be time for you to choose a new e-mail program.

E-mail management is no place for nostalgia—you shouldn’t stick with a client simply because you’ve used it since the first Bush administration. You’re better off basing your choice on the volume of e-mail you receive, the control you need over your e-mail program, and how well the app fits into your workflow.

Changing e-mail clients doesn’t have to be painful. I’ll help you find a program that fits the way you use e-mail, and then I’ll show you how to take your messages and contacts with you to their new home.

Create an E-mail Wish List

Before you can find the perfect fit, you need to understand what features are most important to the way you use e-mail. To help you sort it all out, first consider some of the big issues.

Money Matters If price is your primary concern, you can’t go wrong by choosing an application you already have—Apple Mail. Likewise, if you’ve shelled out money for the Microsoft Office 2004 suite, you already own Entourage.

Spam Protection If you have an e-mail account, you will get spam. Many ISPs and company networks try to filter out the obvious spam before it reaches you. But if yours don’t do that—or if you’re still overrun with the stuff—you’ll want an e-mail client that can take on the task. All the programs we recommend here offer spam filters that learn how to correctly identify incoming spam and that remove it from your in-box. If you receive a lot of spam, you’ll further benefit from a program with sophisticated mail filters, such as those included with Entourage or Bare Bones Software’s Mailsmith. These filters can help you isolate the spam that circumvents your other barriers. (For tips on eliminating spam, see “Win the Spam War.” )

Simplicity Completing day-to-day e-mail tasks shouldn’t require excessive brain activity. If you often receive or create HTML-formatted messages, for example, you should think twice about adopting an e-mail client such as Mailsmith, which makes you jump through hoops to do either. You should also consider the accessibility of the information you need. If you routinely use OSX’s Address Book or iCal, you’ll be happier if your e-mail client does, too.

Manageability Some people keep every message they’ve ever received in one in-box. And that’s fine for very light e-mail users or people who don’t mind weeding through an endless list of messages. But if you receive a lot of mail, you’ll benefit greatly from a program with sophisticated mail filters that can automatically sort and prioritize your incoming messages.

You also may want a client that offers flexible scheduling. Although all e-mail clients can download mail every couple of minutes, only high-end programs such as Entourage and Mailsmith let you create more-complicated schedules—for example, to access a rarely used account only on Tuesdays and Thursdays.

Advanced Control If you regularly receive or send high volumes of mail, you may need something that goes above and beyond the normal call of duty. You might want to use AppleScript, Apple’s native scripting language, to automate some of your e-mail client’s tiresome tasks. Or you may want to be able to add mail headers to your outgoing e-mail messages—a PGP fingerprint header, for example.

Proper Access E-mail is hosted on one of two kinds of servers—POP (Post Office Protocol) or IMAP (Internet Message Access Protocol). POP accounts, which download messages to your computer, are more common than IMAP accounts, which store mail on your ISP’s server. However, many Web-based e-mail services—including Apple’s .Mac and America Online’s AOL—require an IMAP connection. If you use an IMAP account and your client doesn’t support it, the client is useless to you.

Find the Right Fit

OS X users have several options when it comes to choosing an e-mail client. But three programs stand out from the rest in terms of features, reliability, and performance—Apple Mail, Microsoft Entourage 2004, and Bare Bones Software’s Mailsmith 2.1. The kind of e-mail user you are will determine your choice. (For a quick overview of the programs’ features, see “E-mail Programs Compared.”)

The Casual E-mailer

You receive a light to moderate amount of e-mail and don’t spend much time trying to keep it organized, beyond dividing it into folders. You already use (or would like to use) Apple’s Address Book and iCal programs, and you want an e-mail program that can take advantage of them.

Our Recommendation: Apple Mail 1.3.

Why: Apple’s e-mail client has evolved into a reasonably mature application. Mail is accessible enough for beginners and complete enough for people who need to manage a moderate amount of e-mail.

Mail includes all the basic rules necessary to capably route messages to different mailboxes (although the list of rules isn’t as extensive as that of Entourage or Mailsmith). Users who collaborate with others via e-mail will particularly appreciate Mail’s Thread view, which groups messages that are part of an ongoing exchange. But Mail’s scheduling options are extremely limited compared with those in Entourage—you can’t create multiple schedules, and you can’t ask Mail to check your mail less often than once an hour. There is potential for adding more-advanced features; Mail offers solid support for AppleScript and lets you trigger an AppleScript from a mail rule.

Of course, Mail’s greatest advantage is its integration with other Apple applications. You can configure iCal to send announcements of upcoming events through Mail. And you can add contacts to Address Book with the click of a button.

The Office E-mailer

You rely on Microsoft Office to get your job done, and you want an e-mail program that seamlessly integrates into your workflow. You get a moderate to heavy amount of e-mail and you need a way to quickly sort through your incoming messages, pick out the important messages from the not-so-important notes, and file them away in the appropriate folders.

Our Recommendation: Microsoft Entourage 2004.

Why: Entourage offers nearly every feature found in Mail (except integration with other Apple programs and message threading) and many more.

Entourage’s greatest strengths lie in its management features. Its mail rules can filter messages in ways not possible in Mail—for example, you can create rules that apply only to messages formatted as HTML. And its Mailing List Manager greatly simplifies the process of sorting mailing-list e-mail. The program’s Project Center, which allows you to organize contacts, events, mail, and documents by project, is unmatched in any other e-mail client.

Entourage can schedule more tasks than Mail can. It’s also the only e-mail client in this roundup that can trigger an AppleScript from a schedule—for example, to archive messages when you quit the program.

Entourage doesn’t share information with Address Book or iCal. Instead, it offers its own tools for managing contacts, calendars, notes, and more. If you work in a cross-platform office, you’ll appreciate the program’s superior support for Microsoft Exchange Server—server-based software that lets Entourage and Outlook users share contacts and calendars over a network. Entourage is also the only Mac e-mail client that can send and receive Hotmail.com messages by default.

Entourage’s weakest link is its single database. A bloated database can slow down performance, and if it becomes corrupt, you could lose everything. If you choose Entourage as your e-mail client, you should regularly back up Entourage’s Database file (located in your user folder at Documents: Microsoft User Data: Office 2004 Identities: Main Identity).

The E-mail Commander

You’re no e-mail novice. You use e-mail for advanced tasks, such as running a newsletter or managing multiple accounts, and you need to have full access to your e-mail settings. You also want a no-nonsense program that can quickly search and manipulate a high volume of e-mail.

Our Recommendation: Bare Bones Software’s Mailsmith 2.1.

Why: Although Mailsmith is approachable enough for typical Mac users, it tends to appeal to a highly technical—and proudly geeky—audience.

If you’re accustomed to other e-mail clients, you may be thrown off by Mailsmith’s spartan interface and its lack of amenities common in other e-mail programs—for example, support for HTML messages (though you can view such messages in your default browser at the click of a button), support for IMAP e-mail accounts, and an in-line spelling checker.

But for exercising complete control over your e-mail client, Mailsmith’s list of features is hard to beat. Although the program doesn’t search mounds of messages as quickly as Qualcomm’s Eudora—one of Macworld’ s past favorites for advanced users—Mailsmith does a better job of pinpointing the messages you’re after, thanks to its highly configurable search feature. For example, you can search for words that begin or end a text string, or use special grep characters to identify loose patterns of text. And the options for creating mail filters are just as expansive.

Mailsmith offers built-in support for PGP encryption and Michael Tsai’s powerful SpamSieve software—which is superior in many ways to what you’ll find in Mail or Entourage. And if you’re handy with AppleScript, you can automate nearly all of the program’s functions.

Make the Switch

Regrettably, there’s more to switching e-mail clients than just deciding which one suits you. There’s also the sometimes-messy business of moving e-mail and addresses to a new home.

Most e-mail programs have an Import command that automates the process of moving your e-mail, contacts, and other data. But if the Import option doesn’t support your client—or if it doesn’t do a sufficient job—there’s still hope. You can almost always get the job done with a third-party utility or by manually converting your files into the standard mbox or vCard formats. (For details on getting your files into these formats, see “Exporting to Standard File Formats.” )

Here are some guidelines for bringing your old messages and contacts into your new program.

Moving to Mail

E-mail If you’re moving to Mail from Entourage, Outlook Express, Netscape/Mozilla, or Claris E-mailer, open Mail’s Import Mailboxes command (File: Import Mailboxes) and select the appropriate import option. You can also import mbox files that you created in another application. In the Import window, select Other, click on the right-arrow button, and navigate to the location of the mbox files.

Although Mail offers to automatically import e-mail from Eudora, the process is far from ideal—it ignores attachments and removes HTML and rich-text formatting from your messages. Instead, use Andreas Amann’s free Eudora Mailbox Cleaner. This utility correctly transfers messages, as well as filters and nickname files.

Contacts Mail stores its contacts in Apple’s Address Book. You can import addresses from Entourage, Outlook Express, Palm Desktop, Eudora, Claris E-mailer, or Netscape/Mozilla by using the Import Addresses AppleScript.

If you haven’t already installed OS X’s Script Menu (look for a tiny scroll that appears in the Finder’s menu bar), go to your Applications: AppleScript folder and double-click on the Install Script Menu item. Then, from the Finder, click on the newly installed Script Menu and choose Address Book Scripts: Import Addresses.

Moving to Entourage 2004

E-mail Entourage’s Import command (File: Import) will transfer e-mail messages and addresses from Entourage, Outlook Express, Eudora, Mail, Netscape Communicator, and Claris E-mailer. If you’re coming from a different e-mail client or from a different computer, first export your messages as an mbox file, and then drag this file onto the Folders On My Computer entry in Entourage’s Folders pane.

Contacts If you have contacts, calendars, notes, and other bits of data stored in Microsoft Outlook or a personal information manager such as Palm Desktop, you can easily bring them to Entourage 2004 with the help of Paul Berkowitz’s $20 collection of AppleScripts, Export-Import Entourage X. This collection includes more than 50 scripts for moving almost anything into and out of Entourage X and 2004.

If you have vCard files that you exported from another application, you can also import these by dragging them into Entourage’s Address Book window.

Moving to Mailsmith

E-mail When you launch Mailsmith for the first time, it offers to import mail and contact information from a variety of programs, including Eudora, Claris E-mailer, and Mail. If you need to import mail from other clients or want to add messages after the initial import process, you can do so by dragging mbox files into the Mailsmith window.

Contacts You can also import contacts from Eudora and other vCard-compatible applications by exporting them as vCard files and dragging them into Mailsmith’s Address Book window.

Message Received

For many of us, e-mail has become an integral part of the workday and a primary means of keeping in touch with others. Given the variety of e-mail clients out there, you have no excuse for sticking with a program that can’t meet your needs. If it’s time to switch to a better client, this guide will point you in the right direction. But only you can get the ball rolling.

Contributing Editor Christopher Breen pens Macworld’ s Mac 911 column and is the author of Secrets of the iPod , fifth edition (Peachpit Press, 2004).

Microsoft Entourage 2004Apple Mail 1.3.8Bare Bones Software Mailsmith 2.1.2
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