Windows Server gets aboard the fast train

But Microsoft must prove it can pull off sustained rapid release, says analyst

Microsoft must prove that it's able to meet a faster Windows Server release schedule, an analyst said.

"We'll see if they can stick to it," said Jim Gaynor of Directions on Microsoft, about the changes to Windows Server's tempo. "At this point it's aspirational."

Two weeks ago, Microsoft revealed that it will issue upgrades for Windows Server twice each year, once in the spring and again in the fall. (The company implied it would deliver the upgrades in March and September, naming the first two 1709 and 1803 in its now-standard yymm fashion.) Windows Server's release cadence, then, would mimic that of Windows 10 and Office 365 ProPlus.

Gaynor's call for proof echoed a colleague's comments last month. In May, Michael Cherry, also of Directions, used "aspirational" to describe Microsoft's proposed schedule for Windows 10. "For now, I say that this is aspirational, not policy," Cherry said at the time. "They hope to do this [every March and September]. But if they don't, they don't."

The same could be said of Windows Server's schedule.

Missing a Windows Server deadline would have the same kind of domino effect that balking at a Windows 10 release would produce. If Microsoft pushed back upgrade dates after a delayed release, the March-and-September scheme and synchronization with Windows 10 would collapse. But if Microsoft simply resumed the tempo with the next slated release, the delayed upgrade would have to have its support curtailed if Microsoft intends to keep a consistent schedule.

Microsoft had been planning to distribute incremental feature updates for the "Nano Server" installation of Windows Server 2016 two to three times annually, so for that option, the new twice-a-year regime is more clarification than anything. But because Microsoft will, as of September, relegate Nano to container-only use, it will also now begin to refresh the Server Core configuration every six months.

Server Core will become the recommended -- actually, the only -- option for a "headless" installation in data centers as well as Azure, replacing Nano as the latter shifts to containers alone. To continue offering a faster release cadence to users not managing containers, Microsoft had to push Server Core into the same twice-a-year release rhythm as Nano.

Both configurations, Nano and Server Core, will be delivered through what Microsoft calls the "Semi-annual Channel," a label taken from Office, which ditched the "Branch" lexicon last year. (Windows 10 will also adopt the Channel lingo starting this fall.)

Windows Server release cadence Gregg Keizer/IDG

Microsoft's new Windows Server release schedule features two newly-named 'tracks.' Note that the twice-annual upgrades will be under the 'Windows Server' nameplate, minus a year identifier.

Meanwhile, last year's Windows Server 2016 will be maintained with regular security and non-security updates, and will not be enhanced with new features and functionality. Designated as "Long-term Servicing Channel," or LTSC, Windows Server 2016, in its full "desktop experience" model with a client-like GUI, or in the Server Core form, will be supported for the usual 5+5 schedule: five years of Mainstream support, five of Extended -- with the option of an additional six years of paid Premium support.

Gaynor praised the split-release structure Microsoft first assumed last year, then clarified this month. "The bifurcated releases were triggered by different use cases as Microsoft saw them," said Gaynor. Some customers wanted instant access to new components, features and functionality as soon as Microsoft put them into the code; others wanted the traditional long-term stability of a platform that, once deployed, needed maintenance only.

Nano as a container image made for a good strategic fit, Gaynor opined, with the every-six-month upgrade pace justified by the tempo of containerization. "Just look at what's happened with containers in the last five years," he said. Meanwhile, making Server Core available as either always-changing or static also "made sense" to Gaynor because it had taken the place of Nano as the default smaller-footprint installation.

The faster tempo lets aggressive customers "have their cake and eat it, too," said Gaynor.

Cumulatively, those twice-annual upgrades will compose the feature set of the next Windows Server X. In two or three years, Microsoft will put a stake in the virtual ground by christening Windows Server 2018 or Windows Server 2019, built by the iterative process of shipping Server Core updates.

To Gaynor, the changes speak to more than the tactics of how Microsoft delivers Windows Server. What they show, he argued, also reflects the company's strategic, even cultural switch.

"What seems to be changing about Microsoft is that it's willing to change things much faster, to be willing to make mistakes, then to change again. That's going to be good for them going forward."

Assuming the software giant can deliver on its pace pledge. "The proof is in the pudding," Gaynor said of the upgrade beat. "Do they live up to the aspirations? Do they ship solid products? Do they give solid reasons for wanting to do this?"

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