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Road to Mac Office 2008: Entourage '08 vs Mail 3.0 and iCal 3.0

Entourage 2008

Of course, none of that is going to change in Office 2008. Entourage is never going to become a MAPI Outlook for Mac, and it won't adopt cross platform compatibility with the .ost and .pst files of its Windows cousin. Microsoft does realize that plenty of Mac users in business and educational institutions need to access Exchange Server, so there are regular refinements to Entourage to improve its support. Microsoft is also reserving its Exchange support in Entourage for the $300 version of Office to make sure that schools and business can't get by using the $150 home and education version.

Entourage 2008

The upside to Microsoft using somewhat standard WebDAV for connecting Entourage with Exchange means that alternative clients can also be made to connect to Exchange. Ideally, companies will move to open email servers that don't use proprietary protocols at all. As with previous versions, Entourage 2008 supports POP, IMAP, and Hotmail accounts in addition to its WebDAV support for Exchange.

The user interface for Entourage 2008 has also modernized (above). The program adopts a standard Mac Toolbar, unlike the rest of Office. That means you can customize it using the standard drop down sheet (below). An adjustable iCal-like mini calendar appears in the bottom of the sidebar, and under the toolbar sits a strip that looks and works like Safari bookmarks, allowing you to drag in mailbox folders to create quick access links.

Entourage 2008

The six big icons for email, address book, calendar, notes, tasks, and the Project Center are now smaller, but still work the same way. Rather than displaying your entire Exchange folder or IMAP mailbox as a series of folders in a sidebar as Outlook does, email, contacts, calendar, notes, and tasks all sit behind different pages toggled by clicking one of the buttons. Selecting a mode also changes the toolbar items for that mode.

Conversely, Mac OS X 10.5 Leopard's Mail 3.0 (below) displays your email inbox, Notes, and To Do reminders all in the same sidebar, and also presents an RSS feed reader. Unlike Outlook, when multiple accounts are configured, Mail presents each mailbox folder grouped by section, so for example the inbox has multiple email folders underneath for each account, and the user can choose to view the mailbox individually or composited together in a unified mailbox.

Entourage 2008

Entourage 2008 Email

Entourage sits in between Outlook and Mail; it continues to group each mailbox in a series of folders related by the server they sit on, but extracts each special folder on a separate page so there's more clicking back and forth as you work with different items.

As with previous versions, Entourage presents smart folder mail queries as Mail Views. The new version is also supposed to add improved junk mail filtering and phishing protection by flagging suspicious web links for users. Color categorizing of emails is also featured more prominently than in previous versions.

Entourage has always offered HTML mail text formatting features, but it now offers to assign a background image and color as well as an option to insert multimedia elements (below). The only alternative to HTML mail is plain text. There is no equivalent to HTML email templates offered in the new Mail however, and no easy way to create HTML mails that are more than just formatted text with a colored background and attached files. It also lacks any option like Mail to automatically resize attached photos to save space, nor does it have any option to Quick Look incoming attachments or send them to iPhoto.

Entourage 2008

Entourage does warn you that opening attached files may cause harm and panic, but it did so even on graphics attached to the welcome message, which is particularly painful because Entourage is already displaying the graphics in its inline preview. If they were likely to exploit a buffer overflow and destroy the system, it's too late to complain after dutifully opening them up and rendering them a preview.

Because Entourage stored its mail in a database, it wasn't compatible with Tiger's Spotlight search. Microsoft adjusted the mail store in Entourage to keep a copy of emails as individual files as Mail does in order to enable quick search. The main email store still lives in a database inside of an Identities folder within Microsoft User Data however.

The frustrating problem with this is that in the event of a file corruption, the entire email store is lost. With individual files, a file corruption might only affect one file. Since Entourage constantly writes to the database file, the chances of its being corrupted are high, and seemingly connected to the amount and critical nature of emails stored in it. The idea of using a database is apparently to provide better performance, but this does not seem to have the intended result in Entourage. Another drawback to its email database is that it's more difficult to back up and restore, and it isn't efficient to backup with Time Machine or any other file backup system.

Similar to Mail, you can now attach a To Do reminder to an email. In Entourage, you use the To Do flag menu in the Toolbar to select a due date. Once flagged, the email appears in the To Do list. This is different than Mail, which allows you to create multiple, separates tasks that are linked to highlighted content within an email (below). If you receive a message outlining multiple objectives, you can make each an independently tracked task. Mail additionally allows you to add due date alarms, priority, and assign a task to a specific calendar.

Entourage 2008

Entourage 2008 Address Book

Rather than integrating with the Mac OS X Address Book, Entourage initially insisted on using a separate one. The new version still won't look up addresses in the standard Address Book, but will sync its contacts with Address Book and .Mac. Entourage makes an effort to integrate with Office apps, so if you define your own Me card, Word will use that information to populate some templates.

Maintaining its own address book is a holdover from the classic Mac OS where there was no system repository for contacts. On Windows, Office and Outlook can both have their own address books and Windows doesn't offer its own. While Entourage is designed to accommodate an Exchange Server with an organizational Global Address Book and a user's own Exchange contacts, there's little apparent reason for it to continue to use its own internal contacts.

Mac OS X's Address Book can also sync with Exchange Server, but it may be more convenient to use Entourage to perform the sync using its built in Sync Services support. If you don't use Exchange, or don't want to mix your business contacts with a local selection, you can choose to instead sync your local contacts to Address Book and .Mac.

Entourage 2008

Entourage 2008 Calendar

Prior to Leopard, iCal was so slow that Entourage served as good calendar alternative. Interestingly, the new Entourage 2008 calendar (below) copies a variety of the unique ideas from iCal. Among them is the ability to simply click and drag to create a new event time and its duration. Previously, Entourage had you double click on a date and then set the time manually.

Entourage 2008

The Entourage calendar lets you color-code events by category, but it does not work with multiple calendars at once as iCal does, or subscribe to or import iCalendar files. Categories do allow some sorting and presentation features that are similar to having multiple calendars. One advantage Entourage has over iCal is that you can open settings windows (below) for multiple events at once; the new iCal only presents the details of a single item at once, as a special popup bubble window.

Entourage 2008

Entourage 2008

A Toolbar button allows you to view the To Do List (above), but its presentation isn't very practical, as the To Do List can't shrink down to less than about three inches wide. Similarly, the sidebar of mailbox folders can't be resized smaller than an couple inches and can't be hidden. This severely constrains how much you can customize your view to suit your needs. Beyond the Toolbar, the overall look of Entourage feels a bit unfinished, from the heavy presentation of the calendar to the plastic events with a distracting sheen, to the cramped mini calendar and the loose To Do listing that just takes up too much space. The new iCal really packs a lot of information with clarity into a smaller space.

Entourage 2008

As is the case with Address Book, Entourage's calendar can sync its events and tasks with iCal and .Mac via Sync Services. Leopard's iCal is so much better than previous versions in that it now presents a serious challenge to Entourage. While Entourage 2008 offers a variety of advantages over the past version, it doesn't match the clean design of iCal. For users tied to Exchange, that won't matter, as iCal offers no direct support for Exchange without a third party plugin (noted below). With Sync Services integration however, Entourage users can use it to trade information with Exchange and push changes out to iCal and iSync devices such as phones and iPods.

With Entourage supporting Sync Services and third party tools for syncing iCal to Exchange, it's easy to see why Apple is focusing on replacing Exchange with its new open source Calendar Server offered under the Apache license and as part of Leopard, rather than trying to support the moving target of Exchange from iCal, as described in Apple's Open Calendar Server vs Microsoft Exchange.

On page 3 of 3: Entourage 2008 Notes; Entourage 2008 Tasks; Entourage 2008 Project Center; My Day, My Day; and Entourage vs Mail, Address Book, iCal.