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Microsoft’s competitors smell blood in the enterprise waters. They are swarming around NT 4.0 like sharks. And Apple is among the school of circling predators.

Like Red Hat Inc., Novell Inc., Sun Microsystems Inc. and other vendors, Apple Computer Inc. sees a silver lining in Microsoft’s decision to phase out support for NT Server 4.0 at the end of this year.

To capitalize on potentially disenfranchised Windows server customers, Apple is planning on providing an NT migration tool as part of the Mac OS X Server 10.4 Tiger release, due out in the first half of 2005. Built right into the server operating system, the tool also will enable users to migrate from Windows Server 2000 to Tiger, Apple officials said.

The new tool will aid companies in migrating user and group account information from an existing Windows primary domain controller automatically into Apple’s Open Directory. This will allow Tiger Server to take over as the primary domain controller for Windows clients “and even host Windows users’ home directories, group folders, roaming profiles and shared printers,” according to Apple.

Apple, like other Microsoft competitors, believes that not all users of older versions of Windows Server are ready to upgrade to Windows Server 2003, said Tom Goguen, Apple’s director of server software.

Goguen said Apple expects more than a few Windows Server customers to continue to shun Active Directory. They are offering Apple’s plain-vanilla LDAP (Lightweight Directory Access Protocol) directory as an alternative.

And with Microsoft retiring NT 4.0—it stopped supporting client versions June 30 and will stop supporting the server version at year-end—Apple thinks the time is right to try to win the hearts and minds of the disenfranchised Windows Server base.

One analyst said Apple’s got a shot at capturing some attention from NT migrators, but its campaign won’t be an automatic slam-dunk.

Apple’s success in wooing NT customers “is very much up in the air and much will depend on Apple’s actions beyond delivering the NT migration tools,” said Laura DiDio, a senior analyst with the Yankee Group, a Boston market researcher.

“Everyone knows Apple has terrific, albeit expensive, technology,” DiDio said. “In order for Apple to make the short list of prospective NT replacements, it must initiate a compelling promotional campaign that would include catchy marketing and some substantial discounted pricing and great deals on training and support.

“If Apple chooses to initiate an extremely competitive pricing/training promotional deal, then I believe they have the technology and the marketing in place to mount a successful campaign to lure customers away from Windows, Linux and/or Unix. If the price is right, IT managers and C-level business decision makers just may heed the impassioned pleas of their end-users who clamor for more Macs!” she added.

A New York-based systems integrator, who spoke on condition of anonymity, was more skeptical of Apple’s chances.

“I just don’t see Mac OS server competing with Linux or Windows Server,” the integrator said. “There’s the single hardware vendor aspect: Apple is the only supplier of Mac servers. And it’s expensive. The problem is, for the Web server market, the people buying these boxes are ISPs and they want cheap.

“Apple is counting on hardcore Mac shops to buy [Tiger Server],” the integrator said. “But even hard-core Mac shops realize that Linux makes more sense on the server side.”

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