The end goal, Ianni and others said, was to get customers running Windows Server or SQL Server on premises or in a data center to transfer those workloads to Azure, Microsoft's cloud-based service.
"Microsoft is saying, 'Invest in our platform and look at Azure,'" Wes Miller, an analyst with Directions on Microsoft, said about Microsoft's ultimate ideal result.
"The strategic endgame here for Microsoft is to get customers into Azure. But they don't want to lose those customers along the way," Ianni said, referring to Microsoft. "They don't want customers to jump ship, from SQL Server to Oracle, say."
Desertions from one ecosystem to another are most likely when product support runs out -- when a change must be made in any case -- whether by upgrading to a new edition from Company A, or switching to the competitor from Company B.
"This is just kicking the can down the road in some ways," Ianni acknowledged. At the same time, Premium Assurance should give companies the breathing room needed to migrate from, for example, Windows Server 2008 R2 to a newer edition, like Windows Server 2016.
"I see this as the first phase in a longer-term strategy to get people to move [server workloads] into the cloud," Ianni said.
Sign up for CIO Asia eNewsletters.