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Wednesday, August 13, 2008, 06:00 am PT (09:00 am ET)

Inside MobileMe: iPhone's Exchange alternative for contacts and calendar

MobileMe's Exchange Server-style push updates for contacts and calendar events on the iPhone is entirely new from the previous .Mac. Here's how MobileMe relates to Exchange, how contacts and calendars work, and what's still missing in Apple's service related to calendar and contact management.

Inside MobileMe series segments

Inside MobileMe: Secrets of the Cloud and Mobile Push (Friday)
Inside MobileMe: Mac and PC cloud sync and mobile push (Saturday)
Inside MobileMe: Apple's Push vs Exchange, BlackBerry, Google (Monday)
Inside MobileMe: iPhone Mail (Tuesday)
Inside MobileMe: iPhone's Exchange alternative for contacts and calendar (Today)

Exchange for the rest of us

Shortly after the launch of MobileMe, Apple admitted that it may have oversold its new service as being an alternative to Exchange. After all, there is no mechanism for instant push from desktop apps to the cloud; Exchange is an always-on groupware server. Apple even pulled its "Exchange for the rest of us" line from its MobileMe marketing. However, the iPhone's calendar and contacts do currently perform push updates in both directions. Make a change on your iPhone, and you should see the update immediately on your Mac desktop and from the MobileMe web apps. 

For iPhone and iPod touch users, that means MobileMe remains an "Exchange for the rest of us." As we noted in the segment on pricing comparisons, MobileMe offers a ground breaking level of service at a very competitive price, significantly lower than hosted Exchange Server plans that deliver far less storage space and don't provide WebDAV file and web hosting at all, nor MobileMe's other data synchronization features between linked computers.  

In terms of reliability, while MobileMe is still less than a month old the new service now seems responsive and usable, although we'd warn users not to expect more from the service than they would from other consumer-oriented online services such as those from Google, Yahoo, or Hotmail. There's still additional features we'd like to see implemented, and Apple intends to invest in regular updates to ensure that the program is "a service we are all proud of by the end of this year." If Apple is able to reach that goal over the next five months, it will certainly accomplish more than just delivering "an Exchange for the rest of us." 

The long road to Exchange

In comparison, Microsoft's Exchange Server began limited internal testing in 1993, and was only launched publicly in the middle of 1996. It would have been a real stretch to describe it as a reliable product anyone could be proud of until at least four and a half years later with the year end release of Exchange Server 2000. 

In the last eight years since, Exchange has seen two major updates, and has now achieved a reputation of being difficult to match in features and broad support. It typically competes against IBM's Lotus (Notes) Domino Server on the high end and Kerio MailServer among smaller businesses looking for a more affordable solution with similar features. 

Where there are many other mail-only servers, the options for comprehensive messaging servers that supply calendaring and contact updates (particularly those that push to mobile devices) are harder to find. That makes Apple's consumer-oriented MobileMe a pioneering new service for the industry, not just Apple. The company still has "a lot to learn" as Steve Jobs recently admitted in response to the high-profile launch problems that dogged its release, but it is well ahead of the game in delivering a service that works for consumers, is easy to setup and use, and is priced affordably.

Contacts and calendar events are specialized emails

Exchange Server pioneered the market for standardized corporate groupware alongside Lotus Notes, which was acquired by IBM in 1995. Exchange intended to adopt the ISO's ITU X-400 standard specification for email messaging servers, but just as Microsoft was bringing it to market, the ISO's IT-related standards bureaucracy was broadsided by rapid new innovation among Internet Engineering Task Force groups. 

The practical IETF working group protocols beat the grandiose technology definitions outlined by ISO committees, leaving Exchange built around a dead-end architecture. Microsoft was forced to tack on an Internet Mail Connector to provide messaging interoperability with other standard mail transport servers on the Internet. While Internet standards quickly emerged on how to pass email between internet servers and to simple email client programs (including POP and IMAP), there were no functional standards that developed around how to pass around calendar and contact information. 

Microsoft invented its own Messaging API, which treated contacts and calendar events as specialized email messages. The contacts and calendar folders in Exchange are simply mailboxes of emails that contain data that are interpreted by Outlook and represented as address book or calendar items. As with most other internal standards originated by Microsoft, the implementation was not intended to be widely interoperable. Instead, the MAPI specification rapidly changed in concert with every new release of Exchange and Outlook, making it difficult for third parties to offer fully compatible replacements to either Exchange or Outlook. 

Microsoft began taking steps away from MAPI when it released Entourage for the Mac as a non-MAPI client to Exchange. It uses standard IMAP to talk to Exchange, which allowed Microsoft to retain the same model of contacts and calendar items as specialized emails while abandoning its oddball message passing system. To talk to mobile devices, Exchange similarly communicates by using semi-standard web updates through Exchange's Outlook Web Access web app rather than trying to spray MAPI commands over the open Internet. This type of connection is referred to as Exchange ActiveSync or EAS. 

Apple and Exchange Server support

In order to make Macs more friendly with enterprise environments using Exchange, Apple has been adding Exchange support features to its desktop Mac OS X apps. Mail has long been able to automate the configuration of an IMAP connection to Exchange (provided the administrators enable IMAP on the server), and Address Book gained the ability to sync local contacts with Exchange via Outlook Web Access (below). Apple has not released support for iCal to directly sync with Exchange, but third party utilities do support bidirectional calendar sync for iCal. Mac OS X Snow Leopard is expected to provide complete, native support for syncing desktop data with Exchange using the same EAS technology Apple licensed for use with the iPhone.

MobileMe


Apple had been leaving Mac desktop Exchange support up to Microsoft with Entourage, but that product is regarded as a poor substitute to Outlook and has not made satisfactory progress in catching up over the last several years. Handling the Mac's Exchange support itself mirror's Apples strategy of supporting Microsoft's Office filetypes in iWork. Rather than being left at the mercy of third party developers, Apple now owns its own implementation of EAS sync with Exchange.

MobileMe uses its own sync technology between Mac OS X desktop apps and the cloud, and uses a unique mechanism for pushing updates down to client computers. The mobile push messaging system for the iPhone is also custom to Apple, although it results in similar functionality to EAS.

On page 2 of 3: iPhone MobileMe contacts; and Missing in contacts.