The case for Entourage on Snow Leopard

With last month’s release of Mac OS X 10.6, much has been made about the potential impact of the included Exchange support in Snow Leopard. Many pundits have even gone so far as to say that with Mac OS X 10.6, you won’t need to deal with Exchange clients like Microsoft Entourage, or even the upcoming Outlook for Mac OS X ever again. Exchange support is already in there!

The reality of course, is a bit more complicated. So I set out to do a comparison of the Exchange support offered by Mac OS X 10.6 as compared to the current version of Microsoft Entourage 2008 Exchange Web Services, (EWS) edition. Thanks to the generosity of a Twitter follower named Michael Curtis, I was able to get an account on an Exchange 2007 server that was set up to talk to both Entourage EWS and Mac OS X 10.6.

Note: This is not going to be a “Which is the better client?” argument in the way most people like to do these things. “Better” is too subjective a term to be anything more than a flashpoint for yet another round in the never-ending “Which E-mail Client Rules” war. This is more of a comparison of Exchange feature set and support in each—nothing more.

Setup

If the auto-discovery built in to both products works right, setup is a snap. You point Mail or Entourage at your Exchange server, enter in some basic credential information and the account setup just happens. However, everything does well when everything works right. What happens when the auto-discovery doesn’t work like it’s supposed to?

In that case, Mac OS X 10.6’s separation of applications works against it. Where Entourage only makes you enter the information once, with Mac OS X 10.6, when auto-discovery fails, you have to enter the Exchange account information separately into Mail, Address Book, and iCal—admittedly, not a hardship, but an annoyance that shouldn’t be there. Apple should have provided a function that did something along the lines of: “Hey, I see you’re manually setting up an Exchange account. Do you want me to configure Address Book and iCal with this info as well?”

(Minor point: Both products are far easier to deal with in a case like this than Outlook 2007. For one, you can’t even set up an Exchange account in Outlook; you have to use the Mail control panel. In addition, if, for any reason, Outlook can’t make a good connection to the Exchange server, the setup wizard will not allow you to just enter the information manually.)

So for ease of manual setup, Entourage wins just by having the account setup in one place, so less duplication of work is needed. However, that’s a manual setup. Those work great at home, for one or two people. What about when you want to say, set up 20, 50, 100, even 1,000 Macs to talk to Exchange, and you don’t want to do it manually?

In the area of automating Exchange account setup, Mac OS X 10.6 falls over. There’s no supported way, via either AppleScript or MCX to automate this. In the AppleScript area, neither Mail, iCal, or Address Book allow you to create Exchange accounts via a script. While you can use MCX within Workgroup Manager to set up IMAP accounts in Mail, there’s no direct support for Exchange accounts there, and there’s no shipping support for setting up accounts of any kind in Address Book or iCal via MCX. You can kind of work around this with Address Book if you can bind your Mac to Active Directory, but that’s using Exchange’s LDAP support, and if we’re talking about a home machine, it’s not an option anyway. The only way I can see, out of the box, to automate Exchange account setup in Mac OS X 10.6 is to write directly to a number of plist files or script out the defaults command. That can work, but it’s not the most robust system, and definitely the most tedious way to automate a setup.

How about Entourage? Well, while there’s no MCX support for Entourage in Mac OS X 10.6 by default, this is where the Microsoft Mac Business Unit’s tradition of excellent AppleScript support in Entourage comes in handy. The Exchange Account class in Entourage allows you to script the full setup of an Exchange account, including things like Public Folders, the root Global Address List, (GAL) folder, default out of office (OOF) message, and if the background auto-discover function should run or not. If you’re a sysadmin wanting to automate setup for new employees, or new machines, Entourage is the clear winner here.

Exchange functionality support

So, what about getting stuff done? Setup is interesting, but it’s something you don’t do a lot as a normal user; thus, the appeal of setup automation capabilities is limited to a specific audience. When it comes to the basics—send and receive e-mails, basic meeting setup, finding addresses on the GAL—both applications do well. iCal wins points for letting you look up rooms in the location field of an event, whereas Entourage still relies on the kludgier “you must invite the room” method. Entourage wins points by letting you browse the GAL instead of just doing searches on it. Both let you synchronize mail, events, tasks/to-dos, and notes with Exchange. Entourage adds category sync to that, an advantage in an Exchange environment, where you may be dealing with Outlook users who also use categories.

If all you need to do is access Exchange data from home occasionally, and you don’t have a work laptop or your company isn’t providing you with a remote machine, you’re probably okay with what you get in Mac OS X 10.6. However, an office situation is a different story.

For example, with Entourage, if you bind your Mac to Active Directory, you can use Entourage’s Kerberos support to tie Entourage into Mac OS X 10.6’s Single sign-on support. The result? When you log into your machine, you’re logged into Exchange as well. There’s no need to save or enter passwords in Entourage with Single sign-on—it just works. I’m kind of surprised that Apple didn’t include Kerberos support for Exchange accounts in Mac OS X 10.6, since the company already supports Kerberos for IMAP/POP/SMTP accounts in Mail and CalDAV accounts in iCal. With Mac OS X 10.6, about the only security setting you can control is the use of SSL.

Another area that’s an Entourage win involves Public and Shared Folders. Public Folders, for the uninitiated, are how you can create shared contact folders, calendars, mail folders, task folders, and notes folders in Exchange. Shared Folders are conceptually similar to Public Folders, but handled differently within Exchange.

Mac OS X 10.6’s support here is really uneven. For example, Address Book can use Public/Shared Contact folders but can’t create them, there’s no UI for it. I also had little luck with getting Address Book to see contacts I had added to additional contact folders in Entourage, even though they were visible in both Entourage and Outlook Web Access, (OWA).

iCal supports both using and creating public folders, but on the creation side, it’s not the most reliable thing in the world. iCal can create shared calendars outside of Public Folders, and those seem to work well, so iCal does get some points there. Mail should support Public Folders, but in my tests, it did not. Shared folders seem to work as expected. So, if you are in a company that uses Public or Shared Folders, you’re definitely going to have a better experience with Entourage. If you make use of OOF messages, Entourage provides a way for you to set them within the client, Mac OS X 10.6 requires you to use OWA.

Final thoughts

If all you need is occasional Exchange support (say from a home Mac), you just need the very basics, and your office understands that when you’re at home, you’re going to have highly limited access to Exchange, Mac OS X 10.6 will most likely handle your needs well enough. But if you need anything beyond a really limited set of functionality, or you’re in a corporate environment, then Entourage is the clear winner, at least in terms Exchange support.

[John C. Welch is IT Director for The Zimmerman Agency, and a long-time Mac IT pundit.]

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