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Entourage: The Grand Tour

The name suggests you’re a traveling nabob surrounded by fawning minions who smooth your path, handle details, wait upon you hand and foot, and keep adoring crowds at bay. Well, Microsoft Entourage won’t make any plane reservations, mix any martinis, or siphon any cute groupies into your hotel room. But the newest addition to Microsoft’s powerful suite of business productivity applications is certainly a throng of servants, bringing email, a newsreader, contact management, a calendar, a to-do list, reminders, and miscellaneous notes together under one integrated roof, all getting on remarkably well with one another and with the other Office 2001 applications.

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Let’s Get Physical — Entourage’s main window has, by default, a tripartite structure. A list of mail folders scrolls down the left side; click one, and its messages appear listed in the upper right pane; click a message listing, and the message text appears in the lower right preview pane. I find this way of using Entourage, which I call the "single-click" approach, clumsy and frustrating; I feel like a spectator seated behind a column at the ballet, who must keep shifting from side to side to see even part of the stage.

This, however, is not the only way to use Entourage. First, you can suppress the text preview pane. (You can also suppress the folder list, but this would be foolish because you would then be utterly unable to navigate – Entourage provides no separate folder list window or menu.) Second, just about everything except the folder list can be opened as a separate window. This leads to what I call the "double-click" approach. Widen the folder list so you can comfortably see its full width. To peruse a mail folder, double-click its listing to open a separate message list window. To read a message, double-click its listing to open a separate message window. I favor this more Eudora-like approach; others might favor the first approach, or a mixture. In any case, I find the flexibility delightful.

Mail folders aren’t the only thing listed in the mail folder pane. Usenet news servers and subscribed newsgroups appear there; and there are items for your address book, calendar, to-do list (called Tasks), notes, and custom views (saved search criteria). Again, each of these can appear in the right side of the main window or as a separate window.

Neither Rain Nor Snow — Nothing, not even my word processor, is as crucially and constantly present to my daily activities as email. It was with trepidation that I began my preparation for this review with the ultimate sacrifice: I moved completely from Eudora into Entourage. But my fears were groundless. The move was almost painless; Entourage asked what program to import from, then spent an hour copying all my Eudora messages, signatures, and address book contents into itself, perfectly. Importing personalities was slightly less successful, with some attributes not coming over, and although the basics of filters came through, there were a variety of anomalies that required cleanup (though it was still much easier than recreating them by hand). I’m still a bit nervous about how I would return to Eudora later; some things, such signatures, might require a bit of scripting. But transferring a mail folder is easy: drag it to the desktop, change its type to TEXT, do a simple find-and-replace to give each message the proper introductory line and presto, Eudora sees it as a mailbox.

Once within Entourage, I have found the program astonishingly congenial to my way of working with mail. New incoming messages arrive in the Inbox folder, and rules (filters) can then automatically shunt them off to other folders as desired. I can reply to the sender or to all addressees, forward, or redirect; modifying addressees is easy; quoting is beautifully and flexibly handled. I can send an outgoing message now, store it in the Outbox folder for sending later, or save it in the Drafts folder for subsequent modification. Sent messages go into the Sent Items folder, but can be marked explicitly or by rules for copying elsewhere. Deleted messages go into the Deleted Items folder until explicitly deleted for real. I can mark a read message as unread; I can move messages easily between folders. I can have multiple accounts with different default signatures and outgoing headers. I can see full headers or HTML source if I need to. And Entourage boasts a number of tools for formatting and cleaning up both plain and HTML text. In short, Entourage gives me all the tools I need to keep track of my life’s communications without error or impediment.

There are even things about Entourage’s mail handling that I like better than Eudora. A message displays its own history; for example, I might see "You replied to this message on such-and-such a date," with a hyperlink to the reply. Any message list can be quick-filtered using a field at the upper right of the list, thus for example instantly restricting my view of my Inbox to messages from Adam Engst. Signatures appear visibly in the outgoing message, so you know what the recipient will see. Rules can include as many criteria as you like, combined with OR or AND, and as many actions as you like. And an action can be an AppleScript, which brings me to the best news of all: Entourage is wonderfully scriptable, as opposed to Eudora which is scriptable in a uniquely quirky, clumsy, limited way that only someone used to compensating for it for years could love. Scripts can appear in the Scripts menu and a message’s contextual menu, and you can assign them keyboard shortcuts.

On the other hand, Entourage also has some near-fatal shortcomings. Sorting of message lists is primitive; you can sort on only one column at a time, there’s nothing comparable to Eudora’s Option-click trick for bringing together similar messages, and threaded sorting (with related subjects brought together hierarchically) is just plain wrong – the threads themselves are arranged alphabetically by subject, not chronologically, making Entourage quite inadequate for mailing lists. Nested mail folders are poorly handled; for instance, in the menu for moving a message, folders are shown by name alone, without regard to hierarchy, and they appear in the menu only after the first time you’ve chosen Move To Folder and selected the specific folder – and then they appear in an unpredictable order based on most recent use. Searching is a mixed bag: although Entourage doesn’t let you search through any arbitrary set of mailboxes like Eudora, it is quite flexible, and you can save search criteria as "custom views" for instant re-use (and selective archiving – drag a custom view to the desktop save it as a text file). However, some searches, such as "any recipient contains ‘adam’", are outrageously slow (over a minute on my machine). Finally, Entourage relies on a single database architecture that significantly increases your backup needs (since the entire database changes with the addition of a single message) and that provides a single point of failure in the event of disk or file corruption.

All The News That Fits — As military music is to music, so are Entourage’s abilities as a newsreader to those of a dedicated newsreader: it does indeed read news, but that’s all. As already mentioned, Entourage can’t even show threads in chronological order; it goes downhill from there. There is no option to download a particular number of the most recent postings. There is no ability to open postings referred to by the current posting. And so forth. If you’re serious about reading Usenet news, stick with a real newsreader like one of the NewsWatcher variants. If, on the other hand, you dip into Usenet only sporadically, Entourage will probably suffice.

Who’s Who — Entourage’s address book provides two views: a summary view, and a data entry view. The data entry view consists of multiple tabs, each of which offers a plethora of fields: besides name, home address, work address, company name and title, you get as many email addresses as you like (each with your choice of three labels), a wide variety of home and work phone numbers (some with custom labels), birthday, age (calculated automatically from birthday), astrological sign (ditto), anniversary, spouse’s and children’s names, picture, notes, and eight more text fields and two more date fields to use as you see fit. Naturally, you can build complex searches on all these fields, and you can annoy your friends by sending them an address book entry telling all about yourself, as a vCard (.vcf) attachment to an email message. Few email programs (at least Netscape Communicator and Microsoft Outlook in Windows) support vCards, so use them sparingly. Entourage also includes commands for requesting maps or driving directions for any address.

Integration with the rest of Entourage is slick. For instance, as you are creating a new email and start to type who it’s to, Entourage fetches all matching entries from your address book (or from a list of people you’ve recently sent mail to or received mail from, much like Eudora’s History list) and lists them for you to choose from. Also, an address book entry automatically gets a link to every message from or to that person; so to see every message to or from someone, just pick an address book entry and click the window’s Links button.

Integration with the rest of Office is good too. For instance, you can open the Entourage address book from within Microsoft Word. What’s more, as you start to type someone’s name in Word, it consults the Entourage address book and offers to auto-complete the name; such a name is actually a Contact field, and Control-clicking it brings up a contextual menu letting you transfer that person’s email, snail mail, or phone information from the address book into the Word document. Also, as you’re using Word’s Letter Wizard or Envelope Wizard, you can pick an address book entry to slot the addressee’s name and address into the proper place in the new document; and the address book contains a Me entry, which you can automatically use as your return address.

On the other hand, the Entourage address book can’t rival a dedicated PIM or database program. There is no data merge feature for creating a mass "personalized" email. You can use the address book as a source for Word’s mail merge, but you can’t intelligently limit this to a subset of the address book to, for instance, print envelopes to those of your friends who get Christmas cards. The address book can’t export to the Web, or export a subset at all; your only option is to export the whole address book as a tab-delimited file. It can’t even dial the phone. And although you can send people vCards, export tab-delimited files, and synchronize with Palm devices, there’s no networking functionality if you’re used to sharing an address book with other people over a network.

Taskmaster — Entourage calls a to-do list item a "task." A task has a checkbox to show when it is completed, possibly a due date, and possibly a reminder date/time. You can make the due date recur in powerful ways such as "every weekday" or "the third Thursday of every other month;" the task can also be set to regenerate itself automatically for some interval after you mark it completed.

You can view tasks in a columnar list analogous to a listing of mail messages; obviously this list can be sorted and searched, and "uncompleted tasks whose due date is in the future" makes a useful custom view. Still, every serious to-do list I’ve ever used has featured a hierarchical or outline structure that Microsoft would have done better to emulate, difficult though that structure might have been to synchronize down to a Palm device.

A Reminder window will pop up in any Office application (though not at all if no Office applications happen to be running), listing all tasks whose reminder date/time has passed; from here you can open a task, "snooze" its reminder to specify when it should next reappear, or "dismiss" it to kill the reminder altogether. It sounds good in theory, but I find the relationship between tasks and reminders slippery. Dismissing a reminder does not mark a task completed, so you can leave yourself with an incomplete task whose reminder won’t reappear. You can just close the whole reminder window, leaving its tasks’ reminder status unsettled. Changing a reminder’s status within Word apparently doesn’t affect the task in Entourage until you quit and restart. It’s all very confusing, and unless you proactively search each day for uncompleted tasks, a task can pass unnoticed. That’s bad; if to-do items are to be useful, they must remain visibly and insistently pending from creation to completion.

Ides of March — A calendar event is much like a task: it has a date, possibly a reminder, possibly recurrence. The chief differences are that calendar events lack a completion checkbox, and have a starting and an ending date/time (as opposed to a task’s simple due date). You can also have an all-day event that can span multiple days.

Entourage displays calendar events in the calendar window, which is tripartite. In the upper left is a list of tasks and events for today. In the upper right is a mini-calendar interface for specifying a range of time, which can be 1 to 6 days or 1 to 7 weeks. At the bottom, tasks and events for the specified range are displayed in one of three formats: daybook (hourly), for ranges up to a week; calendrical (daily), for multi-week ranges; and list view, which is like the upper-left display repeated for each day in the range that has tasks or events. The calendar window is remarkably good; there’s plenty of drag & drop, the handling of multiple-day all-day events as "banners" is particularly fine, and there is very cute export of a calendar to Web pages.

Still, Entourage’s calendar won’t rival a dedicated calendar program, and its numerous quirks have left me wary and mystified even after weeks of use. An event spanning two days is not shown on the second day. A reminder for a multi-day event won’t appear after the first day. Except for list view, tasks don’t appear in the calendar window at all in advance of their due date; Microsoft has failed to understand that a task due in the future is pending now and needs to appear now. The interface for date entry in dialogs is clumsy and confusing, with tasks and calendar entries strangely requiring two utterly different date formats. The "recurring" checkbox is checked for all tasks and calendar entries even if they are not recurring. You can search for calendar entries, but you can’t limit the calendar display or the exported Web version to the found items. And much like the address book, although you can mail meeting requests to other Entourage users and synchronize with a Palm device, there’s no networking capability that would allow you to share a calendar with other users on your network.

Take Note — An Entourage note is a text snippet. Notes are listed in the Notes window, and can be searched, sorted, and quick-filtered like other items within Entourage. Many Entourage entities have their own notes fields; but a note linked to and commenting on an email message can be useful. There’s no outline or hierarchical structure, though, which makes Entourage useful mostly for basic snippet storage rather than more complex note-taking tasks that require organization.

Grand Unified Theory — Having discussed Entourage’s parts, I wish now to describe how it presents itself as a unity. The key here is that every type of entity (email messages, address book entries, calendar events, tasks, and notes) is a first-class citizen. For example, a search or custom view can include any or all of these types, and all found items of whatever type will appear in the results list.

Further, you can assign to any item any number of categories (labels). This can happen automatically; for example, an incoming email message picks up any categories the sender already has in your address book, and rules can trigger further automatic category assignment. You can also assign categories manually at any time. Then you can filter, sort, and search on categories.

Finally, there are links. You can link any entity to any other entity. Again, this can happen automatically; for instance, incoming and outgoing email messages are linked to the sender or recipient in your address book, a message is linked to its reply, a message is linked to a task created from it. You can create a link manually at any time; an item can also be linked to a file on disk. The result is powerful navigation, because, from an item that has links, you see the links in a pop-up menu or a list window, and can instantly open the item at the other end of the link (if it’s a file, it opens in the Finder). Thus, jobs involving information from hither and yon can be managed easily and quickly.

My one major criticism here is that there is a complete lack of upward navigation, so it’s easy to get lost. For example, I follow a link and an email message opens; but now precisely where am I? The message is in some mail folder, but there is no provision to navigate upward to that folder and see the message in its listing context. Contrast Eudora, where a Finder-like Command-click in a message’s title bar shows where it is in the hierarchy and lets you navigate within the hierarchy.

Last Judgment — If you asked me whether to get Office 2001 just to obtain Entourage, my answer would be "No." Entourage’s mail handling is remarkably good, but not unreservedly better than Eudora or Microsoft’s free Outlook Express, and other aspects of the program range from merely decent to downright poor in comparison with other, dedicated programs; names like NewsWatcher, Now Up-To-Date & Contact, IN Control, and Idea Keeper spring to mind.



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Thus, for those people who will definitely use the other Office 2001 applications, but who already rely heavily on other dedicated programs for email, contact management, scheduling, and note taking, Entourage is mostly a tease. Although its email functionality has few compromises and its integration features are undeniably compelling, the other aspects of the program often aren’t sufficiently fleshed-out to make switching from a dedicated program possible. And from there it’s downhill, since Entourage’s integration and linking become increasingly less compelling as you use fewer of its components.

On the other hand, if you’re going to use Office 2001 anyway, and you’re hoping Entourage will be something you can live with, I’d encourage you to give it a try. Or, if you’re just getting into computers, and own no email, newsreader, or calendar program, Entourage could prove perfectly satisfactory for a long time to come.

With its superb scriptability, its clean, flexible interface, its generous feature set, and its excellent unification through categories and links, Entourage offers a fine integrated system for managing communications, contacts, and time. It’s easy to carp at the Microsoft folks for failing to do their homework in some areas, but let’s not forget to appreciate how much thought and sweat have gone into making Entourage an eminently useful and valuable program. When the team has had a rest, I hope they’ll put some serious thought into improving Entourage’s various parts; when they do, the present version will be an excellent foundation on which to build.

Although Office 2001 is available from some retailers now, its official launch date is 11-Oct-00. The full Microsoft Office 2001 suite costs $500 new or $300 for an upgrade (TidBITS sponsor is taking orders for new versions at $440 or upgrades at $270 – see the sponsor area at the top of this issue for links). There’s also a $100 rebate if you buy the complete version within 60 days of purchasing a new iMac or iBook. Entourage requires a PowerPC-based Macintosh running at least Mac OS 8.1 (Mac OS 8.5 and a 120 MHz or faster processor recommended) with at least 32 MB of RAM (48 MB under Mac OS 9).

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