Exchange and Snow Leopard

A guide for those considering switching from Windows/Outlook to Mac for accessing Exchange email, contacts and calendar – focussing on the differences and shortcomings of the Mac. I’m updating it as I find more.

The major business news in Apple’s Mac OS X Snow Leopard release is proper support for Microsoft Exchange. Until now, using Exchange’s mail, calendar and contact suite has been painful and deficient on a Mac – only Entourage worked, and badly. Conosco’s IT support service has tried hard to keep clients away from the experience…

And – a threat for Microsoft in Snow Leopard – Exchange support is free. The necessary desktop programs are built in so Mac users don’t have the fat expense of Outlook. (Factor this into a Mac vs Windows cost comparison and Microsoft is no longer clearly the cheaper option. MS can’t easily respond – Outlook is a key part of Office which is one of its greatest moneyspinners…)

So a breakthrough moment – but does it work? Here are my experiences using Mac Mail, iCal and Address with Exchange. NB this is a switcher’s guide – I’m comparing them with Outlook 2010 on Windows 7 and ignoring the (vast) majority of functionality that works fine on both platforms. If you see any more, let me know.


The most complex area of Exchange – managing multi-user invites causes havoc with every piece of desktop software that’s tried to work with them (except Outlook; most smartphones including the iPhone use MS Activesync and manage fine).

iCal is very slick to use and falls short only in some minor areas. Should be fine for most people.

iCal cons

  1. When you invite groups of people (e.g. ‘Sales’) to an event, iCal shows them only in rolled up form; Outlook allows you to unroll them and see the status of the individuals in a group.
  2. When you add a person to an event and ‘autopick’ the next available time for a meeting with them, iCal assumes that they are unavailable after working hours; Outlook let’s you schedule evening meetings.
  3. iCal shows other people’s busy time as ‘busy’ in the availability picker window; Outlook tells you what they’re doing (as long as you have permission to see their calendar and the event isn’t marked ‘private’). However iCal let’s you view their calendars overlaid on yours with all the non-private details.
  4. iCal doesn’t have categories for events, but you can have different calendars (work, home, etc) which provides a different way to achieve a similar effect.
  5. iCal doesn’t seem to understand ‘new time proposals’ – when an invitee reponds with a different time for a meeting. You can see the proposed time in the email you get, but you have to manually change the meeting.

iCal pros

  1. Multiple calendars – you can overlay work and personal calendars from Exchange, Apple, Google, Yahoo! and more, allowing you to manage complex family lives more efficiently. Exchange and Outlook don’t let you do this. (I don’t have personal experience of this, but plenty of people seem to make it work.)


Mac Mail’s interface is much cleaner and simpler than Outlook’s and a joy to use. Outlook doesn’t actually seem to do much more, but if you’re an advanced devotee you should test Mail before switching.

Mail cons

  1. Outlook has an ‘Ignore’ button that will delete any further messages in the selected conversation. It also has a ‘Clean up’ feature that removes ‘redundant’ messages in a mailbox which I haven’t dared try. Neither of these seem particularly useful.
  2. Mac Mail doesn’t allow you to set your out-of-office message; you’ll have to use outlook web access for this – slightly less convenient that Outlook.
  3. No server-side mail rules with Mac Mail. For those who use them and use multiple computers or OWA, this will be a problem.
  4. “Sending as” from a secondary email address is important for some people who have several jobs. It’s well-established in Outlook and appears to be possible in Mail by adding multiple Exchange accounts, but I haven’t tested this.


No shortcomings so far but advanced users should check Mac Address has all the fields they use in Outlook.

One bug (or deficiency): when you use Mail’s wonderful data detectors to update an Exchange contact with info in an email, the Address book creates a duplicate contact in the ‘On my mac’ contact group instead.


Another minefield for Outlook’s competitors – Tasks can be used for quite advanced project management (if you dare) so you’ll need to test your particular usage in detail. Mac Mail and iCal (they both show Tasks) seem to handle the basic data and synchronisation well.


These seem fine.

General stuff

User interface

Featureless and dumbed down or minimal elegance and practicality? Apple’s user interface design is the antithesis of Microsoft’s and I’ve found the switch liberating – less distraction, less choice, more focus on the content.

Public folders

If you use these, you may have a problem with Mac Mail. I hear that SP2 for Exchange 2007 enables EWS (the mechanism Mac uses to talk to Exchange) for public folders, but since SP2 came out only last week I can’t confirm that.

Data detectors

Hands down win to the Mac – in Mail and other places, the Mac detects address and calendar info and offers a little button that adds it to the appropriate application. So an address in someone’s email footer can be added to their contact record or a date in an email to your calendar. The system does a good job of parsing the data out of unstructured text. Outlook has nothing like this.

Data storage

Outlook keeps all its data in one database file which is the source of most Outlook problems – it often grows to several GB in size, to the point where users inconveniently have to archive data to another file; it makes back-ups slow and tricky; and corruption in the database usually means wiping the data and a tedious re-sync. Snow Leopard’s apps keep their data in individual files – one per mail, contact or event. These shouldn’t cause any problems in back-ups and are included in the Mac’s system-wide Spotlight search – fast and convenient; in extremis you can read them directly from the Finder. The Mac approach is safer and more efficient.

Exchange 2007

You need to be using the latest version of Exchange.