Even though Apple builds great products for the consumer, the company often misses the boat with business users. Snow Leopard stands to make serious inroads with Mac users in wingtips and pinstripes with native support for Microsoft Exchange Server. Mail, iCal, and Address Book will all […]

Microsoft Exchange

Even though Apple builds great products for the consumer, the company often misses the boat with business users. Snow Leopard stands to make serious inroads with Mac users in wingtips and pinstripes with native support for Microsoft Exchange Server. Mail, iCal, and Address Book will all be updated to talk directly with your Exchange account and in some cases, may work better than Entourage.

The Long & Winding Road

It’s taken a long time to get to this point, but the Mac has a long history of working with Microsoft. I think a little history is interesting here to show how we’ve arrived at Snow Leopard.

The Mac has had Microsoft Office almost from the beginning (Word and Excel for Mac were first released in 1985). Jaguar added LDAP access to Address Book. Panther introduced Windows Printer Sharing and Active Directory support so that you could log into a Windows Domain from a Macintosh. Tiger introduced Exchange accounts in Mail (though with IMAP access only) along with much improved support for Samba and Windows file sharing. The move to Intel gave us virtualization of Windows apps.

Leopard brought Boot Camp, of course, but this did nothing to help integrate Mac OS X itself into a Windows environment. But under the hood some exciting things were happening. The Address Book and Calendar stores were updated to offer better programmatic access and the Sync Services framework was updated. The result was that Mail and iCal were better at sharing data with each other and we got to-do items that were shared between those two apps. iCal was updated to access outside CalDAV accounts and Mail got Notes that (eventually) were able to sync with the iPhone.

The iPhone OS 2.0 firmware update pushed Exchange integration to new heights because Apple chose to license the ActiveSync technology from Microsoft. This put the iPhone on a level playing field with Windows Mobile devices and Outlook when accessing information stored in Exchange.

Snow Leopard

specs_leopardboxSnow Leopard brings all of this together: integrated email, calendar, and address book (with to-do’s and notes) with access to outside accounts and the ActiveSync technology used in the iPhone. In fact, Apple is touting that the Mac will now have out-of-the-box support for “Exchange Server 2007, something that Windows PC’s don’t have.” The requirement to use Exchange Server 2007 might disappoint some that are still on 2003, but it makes good sense when you consider that 2007 has the new Business Logic Layer that provides a consistent view of your mailboxes from any device and takes a lot of work out of writing client software. In fact, Entourage has been testing a beta version that also requires Exchange 2007 in order to take advantage of this technology to make Entourage behave more like Outlook does on a Windows PC.


Personally, I hope for Entourage to die a slow and horrible death. Having been on the support end of things, I have seen how hard it is to make Entourage work reliably. And when it fails? Look out, because all of your email messages, contact info, tasks, calendar items, etc. are stored in one big database file. Lose that file, and you’ve lost everything. And backing it up with Time Machine means you have copied a multigigabyte file to your backup drive every hour.

Recovering from errors in Mail, where each message is an individual file, is much simpler and it works beautifully with Time Machine and Spotlight because of this file structure. I know there are people that like the consolidated view of all information in one application, but I suspect that this preference comes more from force of habit after using Outlook than any real advantage.

So can Mail, iCal, and Address Book replace Entourage? I think so.


exchange_mailMail provides access to your Exchange account right along any other IMAP or POP3 accounts. As a Mac user, you get all the cool Mac features like data detectors, Spotlight, and Quick Look. I’m impressed that Quick Look can display previews of Office documents even if you don’t have Microsoft Office for Mac installed on your machine. This might be a good reason to give iWork another look.

Quick Look

Quick Look


exchange_icaliCal will seamlessly blend your personal local calendars and your Exchange calendars in one view. I liked how the WWDC Keynote demo showed how iCal could intelligently schedule meetings to avoid conflicts, just like Outlook. And of course it’s still integrated with Mail and Address Book so you can see your to-do’s here or in Mail, and you can auto-fill addresses from Exchange.


Address Book

exchange_contactsOK, contacts are not very sexy, but I do like how you can access the Global Address List from within any app that can talk to Address Book. That means Mail will auto-complete addresses as you type messages and iCal will auto-complete names as you create meeting invitations. I suppose it might mean that other apps like Delicious Library that integrate with Address Book will let you keep track of DVDs that you loan to people at work, even if they aren’t in your personal contact list. I also like how smart groups can blend your personal address book with the Exchange contacts. Very slick.


The Future of Microsoft Office

I see a big problem coming for the MacBU at Microsoft. One of the primary reasons to purchase the full version of Microsoft Office (the only reason?) was to get Exchange support. Now that Snow Leopard will include Exchange support natively, I suspect a lot of people will choose to purchase the Home & Student Edition, despite the language in the license that prevents you from using it for work-related activities. A decrease in revenue would naturally lead to a decrease in funding for future development. Despite my feelings about Entourage, Office is pretty useful. I hope that Apple pushes them a little hard (iWork updates will help too), but I hope they don’t push so hard that Office is abandoned. I have felt like Entourage has languished along for a few years now and if I don’t get my wish for it to just curl up and die, then maybe we can get a better, more reliable Entourage for people who want to use it.

The Future of the Mac at Work

I suspect that despite my enthusiasm, the initial support for Exchange in the first release of Snow Leopard is going to blow. I would advise caution about committing to abandoning Entourage, or a large-scale migration from Windows PCs and Outlook in 2009. The bugs, and there will be bugs, will get worked out though, and 2010 could be a very exciting year for the Mac in the business segment.

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  1. Joseph Awad Friday, June 12, 2009

    I work in an environment that requires encryption and PKI is used for this. Is this supported?

  2. Jon Henshaw Friday, June 12, 2009

    It takes a couple cycles for the corporate world to catch up anyways. So I wouldn’t be surprised if it takes until at least 2011 for larger companies to even consider switching to this as an approved way to access Exchange, let alone switch from PC to Mac. A good example can be seen with Internet Explorer. Many corporations are just finishing up or are still switching over from IE6 to IE7, yet IE8 has already been released. I’m just happy I don’t have to work in corporate hell anymore and I can run and use what I want, when I want.

  3. I used to use the office for mac, but after a while paying for the newer version started taking its toll, so I downloaded NeoOffice which was free and it supported all forms of what I ever needed office for, and on that note I rarely use it anymore. Reason being, I’m the devil of convincing people I know to jump on the Apple Wagon.

  4. I generally agree with this article, but as someone who is an “Office Expert” and long time user who successfully switched to iWork, I think the worries about losing Office are misplaced.

    If you are a hard core business user, you still need Office, but those are not really Apple’s customers right now. Business users use Macs, yes. But the only ones who really *need* Office are the Fortune 500 type of people with the giant knarly Excel Spreadsheets and Visual Basic apps made in the 90’s that their whole company is tied to.

    For the average professional person, small business, home user, educational user, or techie, iWork is a better, more functional, easier to use and cheaper alternative. Switching is hard. The first few weeks will drive you crazy trying to “unlearn” all the stuff you thought you knew about making documents and learning the new keyboard shortcuts, but once you do it you will never go back.

    Office is a gigantic POS that never worked very well. The last good word processor made was Word 5.0 for DOS. Everything since then has been a crapfest.

    1. Reply to Gazoobee 6-12-09

      I’ve used Macs primarily since 1985 and I currently own 3 of them, so I’m no Mac skeptic. But these comments on iWork need a reply. I’m an academic writing a book (not a corporate type) and believe me I’ve tried to abandon Word. But while it’s a crude and ugly tool compared to iWork apps, iWork does not even come close to providing the basic tools that Word provides, and iWork turns out not to be deceptively expensive.

      Point: I need a formula editor for my book. An adequate one comes free with Word. In Pages, an equation editor is a very expensive add-on. It’s probably a better equation editor, but its cost takes away half the price advantage of iWork.

      Point: I purchased iWork 08. That gets me no discount on iWork 09: You have to pay for the whole suite all over again. In 2 or 3 years, iWork would cost me as much as MSOffice, and, while much more elegant, it is still very inadequate, feature wise.

      Point: when I purchased iWork, I was enthusiastic about the nicer graphs and charts than Excel would provide. But they cannot be copied and pasted into any MSOffice document! They are utterly incompatible with any other filetype! It is not realistic to think I can take presentations in any format other than PowerPoint to the conferences I attend. But the graphs I produce in Numbers cannot be used in a PP presentation. Apple has reintroduced incompatible graphics, a problem we haven’t seen for more than a decade. What is especially annoying is that Apple has *deliberately* re-created the old hassle of incompatible graphics. They cannot be serious about corporate use of their apps when they deliberately cripple the apps.

      For all the elegance of the Pages interface, it fails to be any better than Word on the matter of customizable menus. Functions that I need frequently in Word require multi-step drilling down through levels of menus to find them each and every time. There is no means to make lower-level functions immediately available in custom menus. For all Apple touting their ease of use, Pages is no better on this, and in some cases it’s worse.

      Another reason to drop Word is that its master document feature is buggy and prone to corrupting documents, and MS has not fixed it, but rather dropped it from Office 08. (This is a feature that permits treating a series of documents — chapters, for instance — as a single document for purposes of indexing, table of contents, pagination and printing, but still keeping each of those documents a manageable size.) Pages does not even address the question.

      As I said, I really want to dump Word as my word processor for this book, but without a whole lot of basic functions such as indexing, Pages is completely inadequate. Over a couple of years, iWork turns out to be very expensive because you have to keep buying it again and because you have to buy expensive side apps to round out its basic functionality. iWork apps create orphan graphics, so they simply cannot be used for that purpose in any normal cross-platform work situation. That factor alone demonstrates that Apple cannot be serious about making corporate inroads.

    2. Ian,

      If you’re an academic type writing a book, you’re completely crazy for trying to do it in word. Use a typesetting system (TeX / LaTeX being the most popular I’ve encountered in the scientific side of the academic realm) – You’re going to end up paying for someone to remove all of the formatting from MS Word and prepare it for typesetting. Safe method? – write out your text first in a text editor, then worry about things like equations. There are tons of tutorials out there about how to write academic papers and I’m sure you can find an academic cohort that is well versed in one of these systems.

      Long story short, don’t confuse a consumer / “business” grade word processor for a document preperation system. Word has given people some terrible habits (most folks think “I want this text to be bold and centered”, rather than “this is the chapter heading”, and then let the typesetter decide if that’s bold, italic, or purple :)

  5. Weldon Dodd Friday, June 12, 2009

    @Jospeh – this is a great question, and one that I don’t think we know the answer to yet (at least I don’t). Since the Mac can authenticate to an Active Directory domain and implements Kerberos, you might be OK. I have seen problems with some Windows services that are not kerberized though.

    @Jon – Absolutely. I don’t think tons of people will switch over between the September release and the end of the calendar year, but I bet 2010 will see some big deployments. 2011 before it’s mainstream is reasonable.

    @Richard – good point, but people that are tied to Exchange are probably going to stick with Office. You’re not who Apple made this feature for, right? Would you ever use the Exchange support yourself?

    @Gazoobee – thanks for bringing up the points about iWork. After using Excel for about 10 years in a Fortune 500 environment and making some pretty gnarly spreadsheets in my day, I absolutely love iWork for small business and personal use. The whole page layout combined with the spreadsheet is brilliant. Still, the people that are still tied to gnarly spreadsheets are the same ones that will need the Exchange support. I hope that they get a good release of Office and great native support for Exchange on the Mac.

  6. @Jon Henshaw: I agree — I’m one of the few Mac users at my company, and Windows users have just finished upgrading *to XP.* Upgrading (from 2000), not downgrading (from Vista). Also just upgraded to Exchange 2003 in the last year, so that leaves me out of the Snow Leopard-Exchange lovefest.

    That being said (and I’m certainly no Microsoft lover) — I’ve been using Entourage 2008 for work email for quite a while, and it’s really not that bad for mail. I miss out on all the cool Mail features, but as an email client, I find it not lacking. The Rules (filters) are quite powerful, and until I read this article (and found out that Exchange 2003 isn’t supported), I actually wondered if I even wanted to switch from Entourage.

    I think it’s great that Apple is doing this — it’ll really help many companies accept Macs as network citizens, but for the rest of us, we have to wait for our IT people to catch up with the times.

  7. Is Exchange 2007 actually required?!

    Or is it only required to enable that spiffy easy set-up process where you just enter your e-mail address and password? The only time I heard Exchange 2007 mentioned was within the context of making things super easy to configure…I never heard it mentioned as an absolute requirement for functionality.

  8. Exchange Server 2007 is required. The beta for the next release of Entourage also requires Exchange 2007.

  9. Thanks, Weldon, for the excellent overview.

    I’ve heard that MS is going to be removing “folders” from Exchange in the near future – with no plans to support them even in Windows. Curious to see how that plays out.

  10. I would love to switch to Apple’s apps instead of Entourage and probably will. Apple didn’t mention the “Out-of-Office” function but since these are all web services, they shouldn’t be difficult to implement or at least access through the webmail function.

    At least Mail can forward HTML emails and doesn’t store everything inside one huge database.

    And what’s with the purple shading in Entourage? Who was Microsoft targeting Entourage at?

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