Microsoft last week released a five-year road map for its Windows Server that contains licensing and support requirements experts say are another tactic to pressure corporations to accept the software giant's controversial licensing program.The road map, highlighted by the first ship date announced for the Longhorn Server operating system, lays out a four-year cycle between major operating system upgrades.Next year, Microsoft plans a smaller upgrade of Windows Server 2003, which will add support for features such as\u00a0Trustbridge, directory-enabled middleware that supports the federating of identities across corporate boundaries.The update will require users without maintenance contracts to purchase a new server license. In addition, the update will be bound retroactively to the five-year support life cycle of the original operating system release, meaning users will lose years off the life expectancy of the software and years of free maintenance support.However, the update will be available at no charge to customers with Software Assurance maintenance contracts or corporate Enterprise Agreements.Some say the move highlights the fact that Microsoft is making it tougher for users to reject Software Assurance, a maintenance program that is part of Microsoft's\u00a0controversial annuity licensing plan. When Software Assurance was introduced in 2001, many users determined the program would increase their software costs and rejected it."This will wind users up again because it gives them less and less choice about being on Software Assurance," says Steve Dunton, CTO of activAeon, which develops a tool that analyzes license usage. "Microsoft knows with [Software Assurance] that unless they bring out new software within the three-year life of the contract people won't buy it."With server software development now on a four-year cycle and with Software Assurance contracts covering only three years, Microsoft needs something to fill the gap to appease those on Software Assurance."Software Assurance is a nice side effect of the update. It gives value to people with [Software Assurance]," says Samm DiStasio, group product manager for the Windows Server division.Some customers have complained recently about not receiving new software, and hence no value, from their first Software Assurance contracts for SQL Server and Windows XP, which are set to expire in June.But as with every other major vendor, Microsoft does not guarantee software upgrades as part of its maintenance contracts."If you need [Software Assurance] for these updates, then we are screwed, because we have made a corporate decision not to purchase [Software Assurance]," says George Defenbaugh, manager of global IT infrastructure projects for petroleum company Amerada Hess. He also says purchasing an update and sacrificing two or more years of support doesn't make any sense."Buying Microsoft infrastructure software is like buying a perishable item at the grocery store - once the expiration date hits you better not use it," Defenbaugh says.Some analysts say the support hit and Software Assurance requirements likely will dictate how corporations deploy Microsoft software in the future."It is very unlikely that people without [Software Assurance] will buy the interim release every two years; they will leapfrog between major releases," say Al Gillen, an analyst with IDC.That scenario is what makes Defenbaugh think Microsoft might be polluting a good idea.A long and winding roadMicrosoft last week laid out a five-year road map for its Windows Server, including its first commitment to a ship date for Longhorn Server.Year Server softwareDescription2004 Windows Server 2003 for 64-bit extended systems Single code base for 64-bit chips.Windows Server 2003 Service Pack 1Security, performance enhancements.(Additional Feature Packs)Includes Server Performance Advisor, Virtual Server 2005, Windows Update Services.2005Windows Server Longhorn beta 1First official beta.Windows Server 2003 Update: Code name R2Focus on secure information access and workload optimization.2006Windows Server Longhorn beta 2 Feature set will reflect what will be in final release.Windows Server 2003 Service Pack 2Feature set not yet announced.2007Windows Server LonghornOperating system upgrade featuring .NetWeb services, plus security and management enhancemants.2008 and beyondWindows Server Longhorn UpdateWill likely ship late in 2009 with features that weren\u2019t ready in 2007.Windows Longhorn Service PackUnspecified feature enhancements to Longhorn Update."We have been doing a lot of thinking about our own technology road map," he says. "On the surface what Microsoft is doing is the way we want software delivered - features are optional and we can install them at our leisure. When you have huge releases it is a gut wrench to deploy them. If that can get more modular, then deployment gets much easier. But I won't do that under [Software Assurance]."Others say the update model is a good news\/bad news scenario."It is good they are providing this functionality as it is available, but on the other hand it increases the work we have to do for testing and rollout," says one IT architect with a Fortune 100 manufacturer who asked not to be identified. "Windows Server 2003 will take us two years to roll out, which includes testing against our installed applications."Microsoft says that because the updates will run on an operating system that is already deployed, testing chores should be minimized.One aspect of the update model that could be a saving grace is that while an update will boast new features, it also will include the free Feature Packs that Microsoft delivers after a server operating system has shipped. Users can install those features a la carte and independent of the update release. Features Packs for Win 2003 include Automated Deployment Services, Group Policy Management Console, Rights Management Services and the Server Migration Toolkit. Three others are planned before the end of this year, including the patch management tool Windows Update Services.But the update model does play into Microsoft's effort to define value in Software Assurance, experts say.Over the next two months, Microsoft will see hundreds of thousands of maintenance contracts come up for renewal, which could hold billions of dollars in revenue. The company has said if it gets less than a 10% renewal rate, it might indicate customers don't value Software Assurance.To combat that thought, Microsoft in September added training, support and software tools and home-use rights for Office to the Software Assurance menu."This [update model] could spur sales of Software Assurance," says Steve Kleynhans, an analyst with Meta Group. "The whole thing is for Microsoft to find extra goodies to throw into the pot that don't cost them a whole lot."Microsoft has dabbled with the concept already with less-than-spectacular results.Microsoft Exchange users became upset when Microsoft recently released its Intelligent Message Filter, but made it available only to Software Assurance customers.