Internet and Web-based collaborative services

Both Windows Server and Mac OS X Server come with built-in Web servers (Internet Information Server and Apache, respectively). Long-standing comparisons exist between these two systems, and I won't bother to repeat that debate. Beyond basic Web services, however, Microsoft has offered Windows SharePoint Services as a free add-on for some time.

Until now, Apple has not readily embraced collaborative Web tools beyond basic blogging support. Leopard Server promises a greatly enhanced collaborative tool set, including easy-to-configure blog and wiki support. This will be incredibly easy to administer and integrates with directory services very well. So, it appears that these features will be on similar ground, with Leopard having a slight edge in ease of administration.

E-mail, messaging and calendaring

Both Windows Server and Leopard Server ship with basic e-mail capabilities. Advanced messaging and related collaborative tools for shared contacts, calendaring and instant messaging are available from Microsoft in the form of Exchange Server. Leopard Server also ships with a secure instant messaging server -- the Jabber-based iChat Server. Also, shared contacts in Open Directory are available for Mac OS X's Address Book and other products that support LDAP-based contact lookup.

Exchange has always had a leg up in offering a variety of tools beyond e-mail, such as shared calendaring, which users commonly rely upon. Leopard Server's iCal Server, however, is poised to level that playing field significantly. iCal Server is based on the open CalDAV standard and is supported by a number of clients on various computing platforms. Not being directly integrated as Exchange is with Outlook makes iCal Server somewhat more flexible -- as does the variety of e-mail and calendar applications available for Leopard Server clients.

What makes Leopard Server particularly attractive on this front compared with Exchange is that it includes most of the functionality of Exchange without requiring the investment in two server products -- Windows Server and Exchange Server -- and two sets of client access licenses (CAL). Leopard Server does lack shared-note and to-do features, though.

Deployment services

Both Windows Server and Mac OS X Server offer remote deployment and update services. It isn't truly possible to compare them because they are aimed at their respective native client platforms. The closest one could get would be to consider the options for deploying a dual-platform Mac client using Apple's Boot Camp or virtualization tools from Parallels or VMware.

Client management

As mentioned earlier, robust client management features are available to both Windows Server and Mac OS X Server. Like deployment services, they are very much specific to their own platforms. Still, Mac OS X's client management options are significantly easier for new administrators to grasp, and it is often easier to predict how managed preferences will interact with one another than trying to do so for Windows group policies.

Third-party systems and mechanisms for using both Mac OS X Server and Windows Server within a single network -- each for managing the preferences of their native clients -- do exist. The tools implement managed preferences on Mac OS X clients from Windows Server and Active Directory. At this time, however, there are no comparable offerings for advanced management of Windows clients via Mac OS X Server.