October 8, 2007 (Computerworld)
For many of us, our e-mail client (mail program) chose us rather than the other way around. Apple Inc.'s Mail sits in the dock of every new OS X-based Macintosh. If you're a Microsoft Office fan or liked Outlook Express back in the OS 9 days, inertia may have you using Entourage, Office's e-mail component. Or if you're partial to Web-based e-mail, such as Hotmail, Yahoo Mail or Gmail, you're probably using a browser by default to create, read and respond to e-mail.
But just because you didn't choose your e-mail program before, doesn't mean you can't choose one now. To get an idea of today's best of breed in Mac e-mail, I tried out the current versions of Apple's Mail (v. 2.1), Entourage 2004 (Microsoft) and Thunderbird 2 (a popular open-source e-mail client from Mozilla Corp. and kin to the Firefox browser).
To quickly determine whether a program has the features you need, check the tables and read the accompanying text to learn how well the features work. I've taken a close look at all three contenders in five crucial areas of e-mail client performance -- components and capabilities, creating and sending messages, receiving and reading messages, searching, and message management -- and chosen a winner in each category. I'll also provide tips for switching from one program to another (in case what I found out tempts you away from your current choice), a list of little-known alternative clients and, of course, my overall recommendations.
Components and capabilities
The first question you probably have, and the first set of criteria for distinguishing among these programs, is "What's in the box?" What features are offered -- both core e-mail functions as well as any bonuses?
Mail server support
If an e-mail client doesn't support the types of mail servers you'll be accessing, its usefulness is nil. Most Internet service provider accounts for home and small business users run Post Office Protocol 3 (POP) mail servers. Some Internet providers, such as Apple's .Mac, provide both POP and Internet Message Access Protocol (IMAP). Mail, Entourage and Thunderbird all support POP and IMAP.
If you have a corporate e-mail account that runs on Exchange Server, you won't be able to use Thunderbird unless your account can be configured as a POP or IMAP account. (Ask your network administrator.) Mail and Entourage both support Exchange Server directly.
Entourage users can access and manage their Hotmail accounts without having to launch a browser. (Thunderbird provides Web-based account support via a Webmail add-on, but I couldn't get it to work.)
Ancillary features In addition to handling your e-mail needs, Entourage and Thunderbird have other features that you may find useful (or essential). Because Entourage is "Command Central" for Microsoft Office, it provides the largest number of extras: an appointment calendar, a to-do list, notes and project management.
If your ISP offers newsgroup support, either Entourage or Thunderbird can double as a capable newsgroup reader. However, if you want to receive and read RSS Web site and blog feeds in your e-mail client, only Thunderbird is currently up to the task. Note: It's reasonable to expect that Entourage and Mail will add RSS support in their next versions (see "Coming Soon!").
Components and capabilities winner: Entourage Entourage supports every major type of account and server. Its excellent Hotmail support -- including the ability to check for new messages on a schedule -- is vastly superior to using a browser. Entourage provides an abundance of features that expands its scope beyond that of an ordinary mail client.
Components and capabilities
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Creating and sending messages
When it comes to creating messages, the similarities among the programs are greater than the differences. For instance, regardless of the program you choose, you can compose plain text or formatted messages; use To, Cc and Bcc address fields; select recipients from your address book based on partially typed names or addresses; insert clickable hyperlinks, such as Web addresses, into messages; enclose attachments; specify a message priority; end a message with a saved signature; and create and receive encrypted mail.
You can switch between a plain text and a formatted message by choosing a command. In Entourage, you can also click a convenient button in the message window's tool bar. When composing and editing formatted messages, both Entourage and Thunderbird provide a formatting tool bar. In Mail, formatting options must be selected from less convenient, floating Fonts and Colors palettes.
Special features Thunderbird has two unique send options that you may find useful. First, you can request a return receipt for important messages. When the recipient selects the message for viewing, a dialog box appears with the option to click OK (or Yes) to send an acknowledgment e-mail to the message's author. Second, after installing the SendTools add-on, you can set any message to be sent at a later date and time. For example, you could write a birthday greeting whenever the mood strikes and specify that it be mailed on the appropriate date.
 Thunderbird can ask the recipient to acknowledge receipt of a message. (Click image to see larger view.) |
Entourage can compress attachments (in StuffIt format) within the program; to send a compressed attachment with Mail or Thunderbird, you have to create the archive first.
If you have iChat running and receive e-mail from an online iChat buddy, Mail allows you to reply via chat rather than composing a normal e-mail reply.
Creating and sending messages winner: Toss-up There's no clear winner here, but Mail and Entourage have a slight edge with their ability to resend and redirect messages.
Receiving and reading messages
Each program sports a three-pane interface consisting of an account and folder list, the list of message subjects in the currently selected folder and a preview pane showing the text of a selected message. Mail's reading pane is permanently fixed below the message header list, while if you use Entourage or Thunderbird, you can place the preview pane there or to the right.
Reading messages
Reading is also similar in the three programs. You can view any message in the preview pane or open it in a separate window. You can increase or decrease the size of the message text to make it easier to read. The three programs even support the same keyboard shortcut (the spacebar) for scrolling through lengthy messages.
Creating/Sending messages
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Receiving/Reading messages
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Message threads
Mail and Thunderbird can arrange messages in threads (groups of messages in a folder that have the same Subject). This concept originated with newsgroups, but it's not as useful for tracking e-mail as it is for newsgroup posts, because an e-mail conversation occurs in two places, such as Inbox and Sent Items.
Although Entourage doesn't provide a message thread view, you can achieve a similar result by grouping messages by Subject (something you can do in the other programs as well). In all three, you can also sort messages on several other message attributes, such as who they're to, who they're from, when they were received or when they were sent.
Image handling
Depending on your correspondent's e-mail client, you may receive images as attachments, inserted directly into the message body, or both. (In Mail, for example, when you attach a supported image type, it's automatically inserted into the message body, while Entourage users must specifically choose to insert an image or to attach it.)
When you receive a message with a supported image type in Mail (regardless of whether it's inserted or attached), it's automatically displayed in the message body. Entourage and Thunderbird, on the other hand, take their cue from the sender by default: If the image was inserted into the body, it's displayed; if the image was attached, only its file icon is shown. Both programs offer the option of displaying attached images inline if you prefer, though.
 In Mail, you can view received images as a slide show. (Click image to see larger view.) |
If you occasionally receive batches of photos from friends, you'll love Mail's Slideshow option -- when a message contains supported image types, you can launch them in a full-screen slide show. You can advance the slide show automatically or manually, show images at actual size or fit them to the screen, and display clickable image thumbnails on an index page. You can also elect to add any image directly to your iPhoto library.
Checking for incoming mail
Each program allows you to check for new mail manually or automatically (via a schedule). When checking manually, you can simultaneously retrieve new e-mail from all accounts or check only a particular account. Most users, however, will rely on one or more schedules to automatically check their mail. Entourage and Thunderbird schedules are account-specific; that is, you can set a different checking interval for each account. Mail, however, only allows you to define one schedule that will be used to check all accounts.
When it comes to scheduling, Entourage is the master. First, you can specify which accounts are checked when an automatic or manual Send/Receive All is performed. Second, you can define account groups that are checked together. I have separate schedules for my two ISP accounts (every minute), my two Hotmail accounts (every 30 minutes) and my two Gmail accounts (every hour), for example. You can also define timed schedules that retrieve mail at specific times (such as Tuesdays and Fridays at 9 a.m. and 4:15 p.m.) or recurring schedules that check daily, weekly, monthly or yearly.
Receiving and reading messages winner: Mail
Mail provides several helpful and unique features that make reading your mail more pleasant, such as displaying messages in threads, speaking messages, storing images in iPhoto and displaying image attachments as a slide show. Mail's only significant shortcoming in this category is that it allows only one receiving schedule.
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Coming soon! Although little has been officially announced, Entourage 2008 will feature additional Exchange Server support, including the ability to send server-based "out of office" automatic replies. A stand-alone application called My Day will allow you to view and work with scheduled appointments and tasks without having to launch Entourage. |
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Searching for messages
In addition to creating, reading and responding to mail, it's surprising how often we need to locate an old message. Scrolling through the Inbox or Sent Items is fine when looking for a recent message, but it's woefully inefficient when a message might be in one of many accounts or if you can't recall its approximate date.
Although you can perform a simple search in any of the programs by entering text in a search box on the tool bar, Mail is by far the easiest to use. As when you search with Spotlight, the results show up as you type and display all matches anywhere within each message (including the address section, message text and attachment names) in all of your e-mail accounts and folders. You can also limit the results to matches in the currently selected mailbox as well as to matches in From, To or Subject.
 Just type in the tool bar to conduct a basic search in Mail. (Click image to see larger view.) |
When performing a tool bar search in Thunderbird or Entourage, you first must select an account to search and specify a search object (such as Subject) before typing the search text. Entourage is even more restrictive in that you can't elect to search the entire message, although -- as with Mail -- matches are shown as you type.
To perform a complex search in Entourage or Thunderbird, you specify search criteria in a dialog box. If the search is one you find useful, you can save it as an Entourage Custom View or as a Thunderbird Search Folder. The only way to make a complex search in Mail is to define a Smart Mailbox with multiple criteria. (A Smart Mailbox is a message folder whose contents are dynamically assembled according to the criteria you specify; the messages actually stay in their existing folders.) The result is saved and continually updated until you delete the Smart Mailbox.
 In Thunderbird, as in Entourage, you can combine criteria for a complex search. (Click image to see larger view.) |
Mail and Entourage messages and contact data are indexed for Spotlight, enabling you to search for e-mail and address book information even when your mail client isn't running. However, the specific material indexed differs between the two programs. For instance, Mail indexes the names of attachments, while Entourage does not. You can click any found message or contact record to launch the appropriate e-mail or address book program.
Searching for messages winner: Mail
Searching is greatly simplified in Mail and performs the way most of us want. That is, you type a search string, and Mail automatically searches all parts of every message in all accounts. Unfortunately, unlike Thunderbird and Entourage, Mail does not allow you to save searches so they can easily be repeated unless you turn the search into a Smart Mailbox.
Searching for messages
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Message handling and management
The manual and automatic procedures provided for managing your messages can make using any e-mail client a pleasure or a pain. In other words, can you route, mark, organize and back up your e-mail, and how much effort does it take?
When you add an e-mail account to any of the programs, an account identifier appears in the left-hand pane. At a minimum, each program also provides separate folders within each account in which to store incoming and outgoing messages.
Folders, filters and rules
All programs let you create additional folders or mailboxes for storing messages -- for instance, one for mail related to a particular project, or one for all work-related e-mail. By specifying criteria in a Message Rule (Entourage), a Message Filter (Thunderbird), or a Smart Mailbox or Rule (Mail), you can automatically route particular messages or copies of them to the folder you created.
You can also use rules and filters to perform other actions, such as categorize messages (Entourage), mark them as read (any program), set them as junk or not junk (Thunderbird or Entourage) or send an automatic reply (any program). Note that Entourage supports twice as many action types as the other programs.
IMAP options
Messages from IMAP accounts are generally read directly from the mail server on which they're stored. As such, you normally need an active Internet or network connection to read them. As a convenience, Mail and Thunderbird allow you to store copies of IMAP messages on your computer (providing the same convenience as a POP3 account), enabling you to view messages when you're offline.
Message classification
As the table shows, each program provides several ways for you to classify messages. For instance, you can assign customizable, color-coded labels to Thunderbird and Entourage messages (such as Budget Project, Family or American History Assignments), mark messages for follow-up in Mail and Entourage, or assign a star to messages in Thunderbird to mark them as important.
 Entourage lets you apply customizable, color-coded labels to your messages. (Click image to see larger view.) |
You can manually apply these tags to appropriate messages, or you can create rule or filter criteria to apply them automatically. Once your messages are labeled or marked, you can sort, group or filter them by those characteristics. The labels in Entourage and Thunderbird are particularly useful. To get similar functionality in Mail, you need to buy the $30 MailTags.
Junk mail handling
Every program has a junk mail filter that's applied to incoming mail. Suspected junk is either moved to a special folder or is simply marked as "junk." Thunderbird and Mail can improve their screening abilities through training; as you manually classify messages as junk or correct erroneous junk classifications, each program gets progressively better at the task. Thunderbird can also help protect you from phishing by alerting you to messages that appear to be scams.
Mail includes a special antijunk feature that I've always wished for: Rather than just deleting junk mail, you can opt to send a response from your mail server indicating that the e-mail account doesn't exist! In theory, this tactic should result in your e-mail address being removed from the spammer's mailing list. Unfortunately, spammers generally don't supply real return addresses, so while bouncing these messages may make you momentarily feel good, they won't have any real impact.
Message handling and management
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Message backup
You can save individual messages from any of the programs as ordinary text files. In Entourage, the Export command enables you to back up entire accounts, message folders and other items, such as notes, tasks and calendar events. You can also back up any Entourage or Mail folder by just dragging it onto the Desktop to create a mailbox file. To back up a Thunderbird mail folder, you either need to locate it in the Finder and make a copy or install the ImportExportTools add-on.
Message handling and management winner: Entourage
This category was almost too close to call. All three programs offer excellent tools for automatically handling incoming messages and reducing the influx of junk mail. However, only Entourage provides tools and techniques for easily backing up individual messages, complete message folders and data from its other components, such as appointments and tasks. In an e-mail client, backup is too critical to be relegated to manually tracking down files and copying them in the Finder, as Mail and Thunderbird require.
Making the switch
After digesting all this info, you may decide it's time to try out a new program. When you update your existing program, old messages and contact records are usually imported as part of the process, but switching programs, on the other hand, is not as simple and straightforward. Depending on the programs you're switching between, you may discover that importing your existing data is easy, requires a little or a lot of work, or is downright impossible.
Importing into Thunderbird
Thunderbird can't directly read contact data from OS X's Address Book (used by Mail) or from Entourage. Although Address Book data can be exported in vCard format, Thunderbird can't read those files either. Entourage can export its contacts to a compatible, tab-delimited text file that Thunderbird can import; however, the process of matching the address fields in the exported data to Thunderbird's fields is painful, complex and time consuming. You may find it simpler to first open Entourage's exported address data in Excel, rearrange it and then import it into Thunderbird.
Messages can only be imported into Thunderbird from Eudora or Netscape Communicator. However, you can install an ImportExportTools add-on that enables Thunderbird to read message files in mbox format. While Mail and Entourage can both generate an mbox file by dragging a message folder onto the Desktop, Thunderbird can only read the ones created by Entourage. (Mail creates a folder-based mbox variant that other programs aren't designed to read.)
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Other Contenders
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Importing into Mail
Mail can import address data in Lightweight Directory Interchange Format or text format, handily enabling it to read Thunderbird and Entourage exports. Field matching is relatively easy, and you can specify how any duplicate records are handled: ignore the new record, replace the original with the new record, keep both records, or update the original record with the new information. E-mail is easily imported from Entourage, Thunderbird and many other e-mail clients by simply choosing the mailboxes you want to import. (Tip: To import mail from Thunderbird, choose Netscape/Mozilla.)
Importing into Entourage
Entourage reads exported Thunderbird contact data, and it's easy to match Thunderbird address fields to those in Entourage. Although Entourage can't directly import contacts from Address Book, you can import Thunderbird's exported vCard file by dragging the file icon into Entourage's Address Book pane.
Importing Mail's e-mail couldn't be simpler: You specify Apple Mail as the program from which to import, and its e-mail folders are copied into Entourage. To import Thunderbird messages, you can use the ImportExportTools add-on to export a Thunderbird message folder and then drag it into Entourage's folder list. (Tip: Entourage won't recognize the exported mbox file until you manually add a .mbox extension to its filename.)
Summing up
Mail comes free with every Mac, and Entourage has been a component of Microsoft Office since Office 2001. Both programs are easy to learn, well documented, full featured and pleasant to use. That last is an especially important criterion because most of us spend more time using our e-mail client than almost any other program.
Since you already own at least one of these e-mail clients, why consider Thunderbird? The primary reasons are that it's free, open source, extensible via add-ons and supported by a community of independent developers. Furthermore, it offers some unique features, such as RSS support, return receipts and delayed sending. However, learning to use Thunderbird and its add-ons is severely hampered by the lack of a Help file or coherent documentation.
When you choose Mozilla Thunderbird Help from the Help menu, your browser launches and takes you to the Mozilla Web site, where you're invited to read FAQs or perform a Google search for the information you need. In short, finding answers is considerably more time-consuming than just popping open an indexed Help file. Thunderbird also has the dubious distinction of being one of the few programs I've managed to crash since installing OS X many years ago.
For those reasons, I recommend either Entourage or Mail. Given Mail's capabilities and ease of use, I wouldn't suggest buying Office just so you can use Entourage unless -- like me -- you need a good newsreader, lust after its other components or have many types of e-mail accounts. For example, I use Entourage to manage two ISP POP accounts, a .Mac IMAP account, two Hotmail accounts and a Google Gmail account. On the other hand, if you already own Office, you'll find that Entourage is so central to the suite and so tightly integrated with the other applications that you should definitely give it a try. You may find that you prefer it to Mail.
Steve Schwartz has been a computer-industry writer since the days of Apple II. In addition to hundreds of articles and reviews, he is the author of almost 60 books on a variety of computer topics.
