In "Outlook 2001 for Macintosh" (July 2001, InstantDoc ID 21159), I hailed Outlook 2001 for Mac as a good solution for Macintosh users who needed full access to Exchange Server systems. Since then, of course, both the Exchange and Mac landscapes have changed a great deal. We now have Exchange Server 2003 and Microsoft Office Outlook 2003, which together provide a great client-side experience for Windows users, plus the new version of Outlook Web Access (OWA) for Exchange 2003, which improves on OWA 2000. On the Mac front, Microsoft let Outlook 2001 languish for a while after its introduction. As Apple Computer's successive releases of Mac OS X greatly raised the bar for stability, performance, and capability of both the base OS and the applications that run on it, Microsoft updated its Entourage personal information manager (PIM) and email client (part of the Mac Office suite) to run under Mac OS X. Customers began asking for a Mac OS X­native version of Outlook, so Microsoft updated Entourage again to provide partial Exchange support. However, those updates weren't enough to appease Mac users who work in Exchange-based environments. Mac users tend to be a vocal lot who have high expectations for their software and server environments. With the release of Office 2004 for Mac, Entourage 2004 for Mac promises to vastly improve Exchange support. If you have Mac users in your organization, you're probably wondering who can use Entourage, how it works, whether it will satisfy your Mac users, and how it will affect your Exchange deployment. Let's look at the answers to those questions so that you'll be prepared when your Mac users start asking.

Who Can Use Entourage?
The question of who can run Entourage 2004 actually has two answers. First, Entourage 2004 requires a system with Mac OS X 10.2.8 or later and at least 256MB of RAM. These requirements rule out some older Macs, but 10.2.8 is supported on a fairly wide range of hardware. A detailed support matrix at http://www.microsoft.com/mac/support.aspx?pid=exchange compares Entourage 2004 system requirements with those for other solutions (Outlook 2001 for Mac, OWA, the Remote Desktop Connection Client for Mac, and Virtual PC for Mac).

Because Entourage 2004 uses Web Distributed Authoring and Versioning (WebDAV), it requires Exchange 2003 or Exchange 2000 Server; if you have Exchange Server 5.5, you can use it in IMAP mode, but you don't get any of the Exchange support features. Many end users have no idea which version of Exchange they're interacting with, so don't be surprised if you need to tell your Mac users whether Entourage 2004 can actually be used in your environment.

The harder-to-answer question for most administrators involves licensing. Entourage ships in two ways: on the client CD-ROMs included with retail copies of Exchange 2003 and in the Office 2004 for Mac retail package. Entourage counts as a Client Access License (CAL) client, just as Outlook does, so you can freely use Entourage in your organization, provided you have enough CALs (but you'll have to buy the rest of Office, of course, if you need it).

How Does It Work?
A common question in the Mac world has been, "When will Microsoft ship an updated Messaging API (MAPI) client for Mac OS X (i.e., a Mac OS X­native version of Outlook)?" The simple answer is, "Never." As I mentioned earlier, Entourage 2004 uses WebDAV (as OWA 2003 and OWA 2000 do), not MAPI. Although Entourage supports Hotmail, IMAP, POP, and Network News Transfer Protocol (NNTP)—in addition to WebDAV—you'd typically set up Exchange users with what Entourage calls Exchange accounts.

You specify an Exchange account as a collection of several pieces of information:

  • User credentials, including the domain, username, and password.
  • The name or address of the Exchange server. Entourage makes a game effort to determine the actual path to the Exchange virtual directory (although the Entourage online Help doesn't mention virtual directories at all). For most Exchange organizations, the path will be http://servername/exchange, although if your hosted environment sets up multiple virtual servers, you might need to specify the path.
  • The path to the public folder server. This path will often be the same as the mailbox server path, but you can point Entourage to any public folder server you wish; it doesn't pay attention to the default public folder server defined on each Exchange mailbox Store. If you aren't using public folders, you still need to designate this path so that your users will have access to the system free/busy information folder.
  • The path to your Lightweight Directory Access Protocol (LDAP) server. Depending on your Exchange architecture, you might point to your Exchange server (if it's also a Global Catalog—GCserver) or to a separate GC server.
  • Whether the Exchange server requires the use of Secure Sockets Layer (SSL) and the TCP port that Entourage should use when using SSL for communications.
  • Entourage includes an automatic setup assistant that queries DNS to find domain controllers (DCs) and GC servers, then attempts to set up the Exchange account based on what it finds. If your DNS infrastructure is properly configured, this assistant can greatly simplify the setup process for new Entourage installations.

    Will It Satisfy Your Mac Users?
    Once you've installed the Entourage client, you'll find that it provides solid Exchange support, including:

  • Calendar and contact synchronization with the Exchange server. You can synchronize everything, nothing, or information in particular categories (e.g., everything except the family category).
  • Full free/busy support, using the mechanism described in "The Free/Busy Map," September 2004, InstantDoc ID 43152.
  • Delegate support. Entourage lets you act as a delegate to open another user's mailbox or calendar. Instead of using Outlook's display metaphor, Entourage displays all data from the other user's mailbox in a special category named for that person. This feature lets you quickly show and hide the other user's events, but it can be a little disconcerting if you're used to Outlook's display method.
  • Secure MIME (S/MIME) signing and encryption. Entourage doesn't have Outlook's ability to request a certificate directly, so you'll need some other way to enroll your users.
  • Support for the Exchange Global Address List (GAL), including both search and browse functionality.
  • Cool Entourage Features
    Entourage copies some features (such as the reading pane) from Outlook 2003; it also offers some very cool features completely missing from Outlook. Leaving aside the many new features (such as the Project Center) that have nothing to do with Exchange, my favorite addition is Entourage's ability to handle more than one Exchange account. I have three accounts defined, and all of them appear in the same interface (check out the left-hand folder list that Figure 1 shows). You can drag messages between accounts: When you send a message or meeting request, you'll notice a pulldown menu that lets you change the account from which the message is sent.

    As a bonus, if you define more than one Exchange account, you can choose to synchronize all the accounts' calendar and contact data. I keep my home and work accounts (which are in two completely different Exchange organizations) in sync so that both calendars accurately show when I'm free and busy and both my coworkers and family members can book my time. Entourage also includes a conduit for synchronizing its data with Palm OS devices.

    Another nifty Entourage feature is that it implements its own cached Exchange mode that doesn't depend on any server configuration changes; it works just like Outlook 2003's Cached Exchange Mode. Entourage will automatically pull down new mail whenever you're online. You can manually set it to offline mode, and it will automatically go offline for a particular account if it fails to reach the account's server.

    A Few Limitations
    Entourage provides a surprisingly high degree of Exchange functionality, but there are a few things it can't do. These limitations have workarounds, but your users are likely to ask about them:

  • Entourage users can't use public calendar or public contact folders. The Entourage team made the design decision to hide these types of public folders, which will alarm your users if you don't tell them ahead of time. Workaround: Use OWA to access these folders.
  • You can't set up delegate access in Entourage because doing so requires support for the MAPI permissions model. The workaround is to use Outlook to set up delegate access. (The Entourage Help topic, "Set up delegate access in Outlook," explains how to do this.) Because appointing delegates is a fairly infrequent necessity, this workaround is no big deal.
  • You can't create or manipulate server-side rules in Entourage, so you'll have to use Outlook or OWA. Likewise, if you want to set up or change out-of-office messages, you'll have to use Outlook or OWA.
  • Do I Have to Do Anything?

    From an Exchange administrator's perspective, one of the best things about Entourage 2004 is that you have to do very little to support it. If you're running Exchange 5.5, you'll need to upgrade to Exchange 2003 or Exchange 2000 to give your users full Exchange support in Entourage. You'll have to provide Outlook or OWA access for users who need to set up server-side Exchange rules or out-of-office messages or who need access to public calendar or public contact folders. However, most users don't use these features, and for them, the out-of-the-box configuration should work fine.

    The one remaining area of difficulty involves Active Directory (AD). If you let users run Entourage from outside your network perimeter, their message traffic will be protected by SSL, but they won't be able to access your AD unless you publish it outside the perimeter. There are many good reasons not to do this, so most sites don't.

    Overall, Entourage 2004 for Mac is a big improvement over Outlook 2001 for Mac, even though it doesn't maintain strict feature parity with Windows Outlook. It's well integrated with the rest of the Office 2004 suite, it's stable, and it provides the most-often-requested Exchange features for Mac users.