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Will Snow Leopard be the end of Entourage?

My jaw dropped.

Right on this page Apple -- Mac OS X Leopard -- Snow Leopard about midway down Apple says:

Microsoft Exchange Support
Snow Leopard includes out-of-the-box support for Microsoft Exchange 2007 built into Mail, Address Book, and iCal. Mac OS X uses the Exchange Web Services protocol to provide access to Exchange Server 2007. Because Exchange is supported on your Mac and iPhone, you'll be able to use them anywhere with full access to your email, contacts, and calendar.

I don't have to ask myself if Apple can pull this off. Of course they can! But with a "free" Exchange solution "out-of-the-box" what does this mean for Microsoft Entourage?

Entourage is falling short

Exchange support for the Macintosh platform has never had parity with Windows. Outlook 98 and Outlook 2001, the only true Outlook clients for Macintosh, were basic versions of their Windows counterparts. Entourage, now in its third version of Exchange support, still lacks many features that customers have been requesting for years.

Switchers, who are adopting the Mac as their primary computer platform after leaving a long-time relationship with Windows, expect something better than what they left behind, especially when they learn Microsoft makes Office for Mac and Windows.

For many folks who have only known the one platform, Office is practically synonymous with Windows. Right or wrong, they expect their experience on the Mac to be similar to what they had on Windows.

Many switchers have expressed their disappointment with Office 2008 for Mac because it simply doesn't do everything Office 2007 and earlier could do on Windows. And when they begin exploring Entourage 2008 they are befuddled to learn that it doesn't support sending Tasks and Notes through Exchange, doesn't support server side rules or doesn't support PST files.

Bring it on!

Competition is good. The fact that Apple is joining the market in Exchange support means that Mac users will not only have a choice of product but the products themselves will have to get better to stay marketable.

Apple has on its side an impeccable flair for design and products that "just work" plus Address Book and iCal data can sync with multiple services. But can Apple do in one new version of Address Book, iCal and Mail what Microsoft hasn't accomplished in three versions of Entourage?

Microsoft has experience on its side, not to mention all the Exchange Server resources and development in-house. It also has stronger AppleScript support and powerful search capabilities, which are needed by power users. Can it continue to offer more Exchange support than Apple to keep it a product in demand?

I look at this two ways:

What should Microsoft be doing to improve Entourage?

While full Outlook parity would be nice I don't think it's necessary for Entourage to be considered the preferred Exchange client. But the following are musts.

  1. Tasks and Notes must work with Exchange
    Mail, calendaring and contacts already work and Exchange users are screaming for these last items. Not only should Microsoft include this support with Exchange, they should include it for non-Exchange (POP and IMAP) accounts as well so that home and small business users can send and receive tasks with each other.

  2. Entourage must support PST files
    While PST files aren't technically an Exchange feature they are an Outlook feature that has no equivalent on the Mac. At minimum, Entourage should be able to import and export the PST file format that is compatible with all recent versions of Outlook. Ideally, it would be able to just use the PST file format.

  3. Sync statuses and metadata with Outlook
    Exchange support needs to consider those who work on multiple computers either at work or between work and home. Read/Forward status arrows, categories and other metadata must sync seamlessly between Entourage and Outlook.

  4. Calendar scheduling should be equal to Outlook
    The Calendar is a core component of Exchange and Entourage should be able to take full advantage of its capabilities such as direct booking of resources, finding first available meeting times and supporting multiple calendars at once. Microsoft should take Apple's lead and provided an overlay view a la iCal.

  5. Entourage needs a non-syncing Work Online mode and an offline mode that syncs the Global Address List
    While on the company network Entourage must offer the ability to not sync and allow immediate viewing of messages on the server. While traveling, users should be able to sync not only their accounts but also the company GAL.

What should Apple do to make Address Book, iCal and Mail the better Exchange clients?

Apple has both the convenience and the inconvenience of starting with clean code. Mail (assuming Mail will be Snow Leopard's Exchange client) is built in XCode but must go through the retrofitting process that Entourage did back in 2003.

  1. Support Kerberos authentication
    Network applications in the Enterprise should be integrated with network services such as Kerberos for single sign-on authentication. Not only does Entourage 2008 support Kerberos but Microsoft Messenger does as well. Integrating iChat with Office Communications Server would be a bonus.

  2. Adopt a three-column view for Mail
    Although this isn't an Exchange feature, it's valuable for the Enterprise road warrior. The three column format is an alternative to the preview on bottom that works well for laptop users with smaller but wide screens who need to maximize their screen real estate. Interestingly the Mobile Me mail view looks very much like Entourage.

  3. Include Public folder support
    I don't see this happening. Public folders is on the Exchange Server 2007 list of de-emphasized features but corporate demand may keep this feature around longer than Microsoft intends.

  4. Include an automatic archive feature
    Apple could surpass Entourage in this area if it would automate moving server-side messages into a local archive that can be readily accessed and modified like PST files.

  5. Market strongly to the education market
    Entourage 2004 Student & Teacher users were surprised that when they upgraded to Entourage 2008 Home & Student that Exchange support was no longer included. The $129.00 price for a new version of Mac OS X is still less than the $149.00 cost of Office without Exchange support.

The recent decision by Apple to license ActiveSync from Microsoft has probably contributed to their entering the Exchange support arena, which can only mean the two companies are probably already positioning their products for different markets. I suspect Apple will gain the education market while leaving Microsoft to handle the enterprise.

The conspicuous statement on Apple's website that Snow Leopard support will be using the Exchange Web Services protocol means that they are onboard with Microsoft's plans to not use MAPI nor WebDAV. Entourage 2008, however, relies on both Exchange Web Services and WebDAV, which means support for connecting to Exchange Server 2000 and 2003 is a potential but not a guarantee.

Comments (12)

Allen Watson said:

Bill, I found the same thoughts (without all the details, since I do not actually use Exchange myself) running through my mind as I watched the "Mobile Me" video on the Apple website. If I have an iPhone, as I plan to soon, and can automatically have that phone and my Mobile Me account synced with Mail and iCal, even as a non-Exchange user, would I want to continue using Entourage? It's a powerful incentive to switch to Apple's products.

Chris Ryan said:

I think it all comes down to user experience. Using Entourage alongside more modern OS X apps makes me feel, every time I'm doing email, like I've taken a time travel trip back to the 1980s. Virtually everything about the app is frustrating, from the ridiculous auto-correct features ("I know better than you what you want to type") to an incredibly confusing tree with no indentation, to just all around working and feeling nothing like a Mac app (I can't even drag an attachment to a an app in the Dock). I can't wait until Mail.app in 10.6. Good-bye Entourage.

Wes Plate said:

The new announcements don't change my love for Entourage. I don't use Exchange and the MobileMe doesn't help since I don't use my .Mac email address but instead email addresses on my own domains (and no I don't want to use iWeb to create my company's web site and then host my domain on .mac).

Entourage is still the best email client, even for us who don't use Exchange.

GL said:

The FRCP changes are really fouling up the whole corporate email world. On the Windows side, PST files will become a thing of the past. Entourage and Apple's email client will both have to support custom managed folders, offline secured synching for mobile users, and the ability to block personal folder usage (PST or whatever flavor you like).

Like it or not, the FRCP and its legal ramifications will impact any business with more than a handful of employees.

Histrionic said:

Just FYI, you can drag one or more attachments to Entourage’s Dock icon. It adds them to a new message if none are currently being composed, or to the frontmost message window if there are one or more already opened.

I have used this all the time in Entourage, both 2004 and 2008.

However, re-reading the previous post, I suppose you’re saying that you’re trying to drag a received attachment from Entourage to another application. I can drag items from received messages to the Dock icons of other apps, but they don’t activate. Dragging from messages I’m sending works perfectly, although I’d wager that’s not a common use case.

Harry Zink said:

Wow, the level of denial in this post is truly fascinating.

> My jaw dropped.

How so? Right after Microsoft turned in the monumental disappointment that was Entourage / Office 2008, and Steve Jobs publicly dissed the entire MacBU on stage at Macworld 2008, it was painfully clear that Apple had both an offing in the wings to supercede Entourage, and no longer had any problems moving ahead with it. Chances are they started on this as soon as it became clear how pathetic Entourage 2008 was going to be.

...and to be honest, I'll shed no tears either for Entourage, or for the inevitable demise / marginalization of the MacBU over this.

> I suspect Apple will gain the education market while
> leaving Microsoft to handle the enterprise.

Wow, denial and lack of clue like this really explains how the MacBU has derailed as it did. Time to take this old horse behind the shed, and put it out of its misery.

Marc Stress said:

I still think there's a ton of life left in Entourage and that Microsoft is not taking advantage of an opportunity to be a _business_ software leader on the Mac.

The new "Me" platform, and all of the "i" software — including Apple Mail — is cute, and works fine for 1-2 users, or for Mom and Dad to put their schedules online for the Grandparents to see when the next soccer game is. However, these are not serious business tools. Me takes the whole thing and wraps it in a pretty web 2.0 package, and brings push to the Mac, but not much more.

When I heard "Out of the box Exchange support" I was read it as a good sign. Maybe, finally, there will be a Mac version of Exchange... that Microsoft/Apple have gotten into another agreement that allows Apple to license the technology for XServe. Call me crazy, but when I looked into my crystal ball, that's what I saw.

Clearly, the Mac doesn't have the density of Windows boxes in business, but there are plenty of business that run PURE Mac environments, and could be dramatically improved if there were real business software solutions in place.

The biggest thing that Microsoft could do for Entourage is to just make it work like Outlook (like Mac Outlook used to) and to get an OS X Version of Exchange, unless that's what's already coming with Snow Leopard. I'd rather not wait that long to find out.

Harry Zink said:

> I still think there's a ton of life left in Entourage

I disagree - Entourage 2008 is done. The MacBU made sure of it.

> that Microsoft is not taking advantage of an opportunity to be
> a _business_ software leader on the Mac.

I wholeheartedly agree, though that statement would have applied more in 2001 and 2004, then now. Nowadays, the only way to say this would be in the past tense - and it's not 'Microsoft', it is uniquely the 'MacBU' within Microsoft that has missed opportunities, again and again.

"The MacBU has not taken advantage of an opportunity ..." and will now be paying the price.

'Microsoft', or rather, the business units dealing with the core business of Microsoft, are very well jumping at the proper opportunities, as the integration of ActiveSync with iPhone (and with the Mail tools of 10.6) shows.

> When I heard "Out of the box Exchange support" I read it
> as a good sign.

So did I - it signifies the end of Entourage, for good.

> Maybe, finally, there will be a Mac version of Exchange...

No, the Exchange support is on the client side - why would Apple include the Exchange server architecture on XServe, which would make no sense. What they WILL provide, is the same functionality as MobileMe provides, that is, push Mail/Calendar/Contacts -- which is all that Outlook using people want.

> Call me crazy, but when I looked into my crystal ball,
> that's what I saw.

You're crazy - it's one thing providing client compatibility for the desktop, but there is no reason for Apple to provide server side functionality, when they have something far better brewing.

MacBU missed their opportunity to aim for an Mac version of Outlook, and they missed that opportunity again when they had to rewrite Entourage for X-Code / Intel compatibility - instead, they just regurgitated all of their old code (many of the bugs we reported under 2004, are still there in 2008, in identical fashion).

So, for all I'm concerned, the MacBU can pretty much go blow itself!

Marc Stress said:

Allright, so it's the Mac Business Unit, and I'm crazy. But, I've got hope —blind though it may be— that Mac users will be able to have enterprise quality calendaring. Really, I don't care if it's with or without Entourage. I just want it, and I want it to work, and I want it on the desktop, not in a web app. It's beyond me to understand why Mac IT directors can't walk to a shelf in the Apple stores and pick up the "Corporate Mail and Calendaring Add-On Pack for OS X Server" and with a couple of clicks, some DNS adjustment have an _enterprise_ calendar and solution.

I'm not so sure that what Apple has brewing is better, and the past 8 years don't point to something better that I can see. Since the launch of OSX, and maybe before, all the Apple software has been focused on the individual, not group and certainly not truly two-way sharing of information. Yes, sharing like look at my pictures, or see my calendar, but not the kind of sharing that people in business or groups need.

Perhaps I over simplified my comments above, but my thought is this. Why *wouldn't* Microsoft license Exchange to Apple? Or, why wouldn't Microsoft create an Exchange OS X? I know that if I could, I would purchase Microsoft SBS MacEdition or Microsoft Exchange XServe (call it what you will) and 10 user packs today. There are hundreds if not thousands of businesses and organizations and departments running and XServe that would do the same, if it was only an option. Spending 6-10k on an Exchange Server with SBS 2003 while I've got a surplus of computing power on my Xserves is not a enticing proposition. Oh, and by the way, I wouldn't have to hire/find/retain additional IT support, or have anti-virus software subscriptions.

Entourage users don't care about shared directories or much else of the Exchange services. We just need real, good calendaring that just works. Not the namby pamby web apps, or desktop apps that have been passed off to us to date.

Now that Exchange support is on the iPhone, it seems like a smart opportunity and much less of a leap for Apple and MS to get this figured out, or for someone —ANYONE— to figure it out. This is an untapped revenue stream for the company smart enough to solve it.

Harry Zink said:

> Allright, so it's the Mac Business Unit, and I'm crazy.

:-)

> But, I've got hope —blind though it may be— that Mac
> users will be able to have enterprise quality calendaring.

Oh, they will be - it just won't be brought to them by the MacBU, despite what they may keep saying (where I'm never sure if they are lying through their teeth, or just hopelessly clueless).

As it stands, the MacBU is hiring, en masse -- it ain't to bring you better calendaring, or a better Enterprise solution - I can assure you of that.

Once Apple realized that the MacBU was just worthless (i.e. once it became clear that Entourage / Office 2008 were going nowhere, there was no reason any longer to play nice -- particularly since, at that point, Microsoft's Exchange group also realized that the MacBU was starting to potentially cost them billions in future business (once more and more Fortune 500s started investigating alternatives, after the disappointment of Office 2008) - so they did the smart thing, and worked with Apple directly.

While I am sure that the MacBU will now desperately try to develop iPhone apps to lend them credibility, it's just more of the same lack of focus - within 24 months, these guys will be a painful memory.

Don't judge based on Apple's past offerings - Snow Leopard, I think, will pack quite a few surprises.. and it won't be Exchange *server* under the hood.

*YOU* don't want *EXCHANGE* server, you want a calendaring solution that works. There is a difference.


Marc Stress said:

You're right, Harry. I don't necessarily want Exchange, but right now it's the only thing that Mac users can point to say "See! We want that!" No one is looking at Lotus or even gCal as good as it is with envy.

I don't care what it is or who makes just as long as it's happening sooner rather than later. I'm running out of band-aids to keep all these things together.

However, the other reason I — for one — keep pointing to Exchange as the standard is just that. It's a standard, and 90% or more of the people I do business with use it.

What ever this magical, mythical Macintosh calendar solution becomes it's got to just work. Like a real business app.

Harry Zink said:

I think the problem here is that you are mixing up 'Exchange' and what it is, but I understand what you are saying -- Ideally, we all need a Mail / Calendaring / Contacts solution, on the desktop, that talks seamlessly to an Exchange server - because, most likely, that's the backend we all have to deal with, and hence multiple band aid solutions.

If you don't already have an Exchange server, and you have an XServe, then all you really want is the FUNCTIONALITY of Exchange, not the actual product - if Apple can deliver that, on the server level, then we all get what we really need, won't we?

Do bear in mind, it's probably no accident that Apple keeps referring to MobileMe as 'Exchange for the Rest of US' -- aside from offering full ActiveSync integration on iPhone, for the Enterprise, they are also offering full MobileMe integration on the iPhone, 'for the rest of us'.

It is therefore not a major stretch that Apple will leverage that development on the Snow Leopard desktop in the same manner -- by not just providing MobileMe 'push-everything' integration, but by also providing the same on the Exchange integration level -- Mail.app already integrates with Exchange, and so does (sort of) Address Book - add iCal integration to Exchange and we have what we want.

For further discussion on more salient points of what your most likely response will be, please e-mail me directly. No reason to flood MacBU stooges with further ideas, seeing as how they are unable to have any on their own :-)

hzink [over at] mac.com

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