Tag Archives: snow leopard

apple, email, exchange, microsoft

Apple Snow Leopard and Exchange: the real story

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Apple’s Snow Leopard (OS 10.6) came out last week, and one of its most hyped features is native support for Microsoft Exchange. Here’s what Apple says:

With Snow Leopard, the Mac is the only computer with built-in support for the latest version of Microsoft Exchange Server. So you can use your Mac — with all the features and applications you love — at home and at work and have all your messages, meetings, and contacts in one place.

What this means is that eager Mac users will be upgrading to Snow Leopard and expecting to be able to connect to Exchange at work with Apple-style “it just works” ease of configuration.

The truth is more complex; and I’m disappointed with both Apple’s publicity and the number of reviews that have simply reported its claims without investigation. That said, it is a tricky subject, and I have some sympathy with Apple, which is doing more or less the right thing at a technical level.

Configuring Snow Leopard Mail to use Exchange

The first thing to understand is that there are myriad ways of connecting to Exchange, including:

  • MAPI, which is Microsoft’s proprietary API
  • IMAP, which is a standard protocol for server-based email
  • ActiveSync, which is a Microsoft protocol used for mobile devices
  • RPC over HTTPS, effectively MAPI over SSL, enabling Outlook to connect from outside the network without VPN
  • Outlook Web Access, a web UI for Outlook
  • WebDAV, now deprecated
  • Exchange Web Services, which communicate using SOAP XML messages

Which of these protocols are actually enabled, and whether they are published beyond the internal network, is a matter for Exchange admins to configure.

The usual generic method to connect to Exchange from a miscellaneous client is IMAP, and this is exactly what Apple supported in Mail before Snow Leopard, and still supports. IMAP works pretty well in my experience, but it is only for email and does not expose any Exchange-specific features.

Snow Leopard adds support for Exchange Web Services (EWS), giving a much richer level of access to Exchange. First snag: EWS is only supported in Exchange 2007, which is why Apple says in its small print:

requires Microsoft Exchange Server 2007 Service Pack 1 Update Rollup 4

Second snag: even EWS does not all the features of MAPI, and some features (notably public folder support) were only added in Exchange 2007 SP2, which has just been released. This probably explains why Mail does not (as far as I can tell) support public folders.

The key thing to understand is that Snow Leopard is not using the same protocol as Outlook and therefore does not have access to the same set of features.

What works and what doesn’t

Let’s assume that you have Snow Leopard and Exchange 2007 SP1. What works and what doesn’t? Based on my experience so far:

  • You will be able to connect on an internal network or VPN, provided that EWS is enabled, which it usually is. You may need to install a digital certificate to avoid warning messages.
  • Mail, Calendar (iCal), tasks and notes in your Exchange mailbox all appear nicely.
  • When outside the network, you will only be able to connect over the Internet if EWS is published externally, which it often is not. You cannot use RPC over HTTPS.
  • There is no access to public folders (note that these are deprecated, but still widely used).
  • It is not possible to send from an email address other than the default.
  • You cannot use Exchange delegation features, such as accessing other mailboxes.
  • Mail will download the entire mailbox; you cannot set it only to download recent items. There is no “online mode” as there is with Outlook.
  • When offline, you can access existing items, but new messages have to be saved as drafts. This is unlike Outlook, which gives you full access to send mail, delete etc, and synchronises on re-connect.

Snow Leopard vs Entourage

You might imagine that Microsoft’s own Entourage product would do a better job than Apple Mail at connecting to Exchange. This is not necessarily the case. The problem is that Entourage 2008 doesn’t use MAPI either. In its first incarnation it uses WebDAV. This proved so problematic that Microsoft quietly released a new Web Services Edition that uses EWS, like Snow Leopard. Even this is a temporary expedient, as the Mac Business Unit has announced Outlook for the Mac. The implication is that it will be closer to feature-parity with Outlook on Windows, though it’s not clear to me whether this means MAPI, or EWS, or who knows what?

My view is that unless you need some specific feature of Entourage, or find that Entourage mysteriously works where Snow Leopard does not, you are likely better off without it. This presumes Exchange 2007, of course. The fundamental reason is that Mail and iCal are nicely integrated with the operating system, whereas Entourage is not so good in this respect; there have also been quality issues with Entourage.

It would be good to see a detailed technical note from Apple and/or Microsoft on Snow Leopard’s Exchange support, how to configure Exchange for it, and any implications for security etc. In the meantime, there is an interesting discussion on Apple’s forums which highlights the issues.

For all its (many) faults, Outlook on Windows remains a better Exchange client than either Snow Leopard or Entourage.

apple, microsoft, windows, windows 7

Apple Snow Leopard: why don’t we all use Macs?

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Last Friday I attended Apple’s press briefing for Snow Leopard, and I’ll be a Mac (mostly) for the next few days as I put OS 10.6 through its paces. For as long as I can remember, I’ve set up my desktop so that I can easily switch between Mac and Windows, so it is no great hardship.

Snow Leopard is a relatively low-key release, timed by accident or design to appear not long before Windows 7 makes its full public debut in October – though many IT professionals are already using the final build. In the unlikely event that you’ve missed the many reports, the headline new features are:

  • Many small refinements and speed improvements
  • Major applications re-written in 64-bit
  • Grand Central Dispatch – OS-level support for easier concurrent programming
  • OpenCL – standard means of using the GPU (graphics processing unit) for general processing, not just graphics
  • Exchange support in Mail, iCal and Address Book

The Exchange support is welcome, though unfortunately it is limited to Exchange 2007. It was already possible to access Exchange in Mail, though the older support (which still exists for pre-2007 Exchange) was based on IMAP, whereas the new support is based on Exchange web services and has richer features.

I use Exchange 2007, and found it easy to set up my account in Mail. Unfortunately I’m missing some Outlook features, such as the ability to choose a different Sender  address, and I’ve found it prone to a few mysterious pauses –  once it went into a sulk for over a minute when I marked a message as junk – but this might be a problem with Exchange web services rather than Mail, who knows? I also have some public folders which appear to be inaccessible from Mail or iCal. Then again – Entourage isn’t as flexible as Outlook either.

Still, I  expect the Exchange support will be good enough for many users, and this will make it easier to integrate Macs into Windows-based networks.

So, here’s a thought experiment. Let’s make an assumption:

  • Most people prefer the Mac operating system over Windows, and prefer the Mac hardware over most PC or laptop hardware.

If that is the case, why do we not all use Macs?  There’s a host of reasons which come to mind, starting with price. I looked at macwarehouse.co.uk and pcworld.co.uk, which are owned by the same group. The cheapest Mac I can find (Mac Mini + keyboard, mouse and display) is currently £536.96, vs £260.86 for a PC; and the cheapest laptop is £645.99 + VAT for a MacBook vs £216.52 for a cheapie PC laptop with Vista Basic. These differences are not small.

Note I am not saying that the Mac is poorer value; that is an entirely different argument.

A second big issue is application compatibility. Although there is no problem that cannot be solved with finding alternatives, or dual boot, or a virtual machine, it is all friction that impedes Mac acceptance.

Third, there is the greater manageability of Windows in a corporate environment based on Windows. This is a form of incumbent advantage, which is hard to break unless the incumbent messes up badly. Arguably Microsoft has messed up badly, though less in the business context than in the consumer context, and Windows 7 will pull back some lost ground.

The above leads me to believe that Snow Leopard is not likely to change the status quo significantly – understanding that the status quo is that Apple is gradually increasing its market share – even granting the assumption I made, which is somewhat controversial. On balance, I consider it more likely that Windows 7 will stem the flow towards Apple, though without a high degree of confidence.

More significant than either factor is the continuing migration towards the Internet. In this respect I’ve argued that Apple is like Microsoft. The Internet is a great leveller; it will reduce the friction of changing operating systems (helping Apple) but also make Apple’s UI advantage less noticeable (helping Windows/Linux/Google), and make it harder to sell expensive desktop software (Microsoft is the bigger loser here I think).

It’s fun to speculate; but I must add that so far Snow Leopard has been a pleasure to install and use. Technically, Apple hasn’t missed a beat with OS X since the first release, and that’s an impressive achievement.