Companies can skip a Windows 10 upgrade, but they have to hurry

Enterprises have a short-lived opportunity to slow the Microsoft upgrade train by skipping one of this year's Windows 10 refreshes, as well as one of the two slated to ship in 2019, according to Gartner and Microsoft's own support scheduling.

Because of a temporary six-month extension of support to the two feature upgrades Microsoft issued last year, corporations will be able to ease into the rapid release slate that the Redmond, Wash. developer has demanded customers accept. "Organizations wanting to deploy only one update in 2018 and 2019 and skip one may do so and have a lesser chance of their PCs falling out of support," said Gartner researchers Stephen Kleynhans and Michael Silver about the support supplement.

Late last year, Microsoft said it was adding six months to the support calendar for Windows 10 1511, the November 2015 feature upgrade, "to help some early enterprise adopters that are still finishing their transition to Windows as a service." The move lengthened support - security patches and other bug fixes - from a standard 18 months to 24 months. In February, Microsoft did the same for versions 1609, 1703 and 1709, the upgrades released in mid-2016, and in April and October of 2017, respectively.

The additional support time - a 33% increase - gives businesses and organizations running Windows 10 Enterprise or Windows 10 Education a maximum of two full years between upgrades. Those customers have been pressing Microsoft for just that amount of time; they felt they would not be able to keep up with a twice-annual refresh cadence, Kleynhans said.

The 18-month support span has proven very tough for enterprises; a year ago, Computerworld spelled out the slim margin of error organizations - as little as two months - had to work with to skip every other upgrade. But it would be feasible on a 24-month support schedule.

"Only organizations with the fastest possible update processes can decide to deploy only one release a year and skip the other without worrying about running unsupported releases," Kleynhans and Silver wrote in an April report. "Organizations would need 'good' processes to deploy two updates each year, as those with 'typical' processes may have trouble eliminating the prior version before support ends."

In an interview, Kleynhans explained the chances of an enterprise handling two updates annually: Essentially zero. "Microsoft's [18-month] support cycle works fairly well if you have a well-run process," Kleynhans said. "But no one really has a tight, well-run process right now. Not customers, not vendors, not Microsoft." It will take all parties, he continued, "a couple of years of cycling" through feature upgrade releases to become proficient with the faster tempo.

So, exactly how would the once-a-year Windows 10 feature upgrading work in 2018 and 2019?

Just skip it

According to Gartner, the combination of the support extensions to versions 1703 and 1709, and what the research firm called "good" processes - meaning the ability to upgrade every six months - creates a scenario where "there is no risk of losing support when skipping alternate releases."

Study Figure 1, which illustrates the various versions, current and future, and their support timelines.

IDG/Gregg Keizer

Assuming an enterprise adopted Windows 10 1709, either as a first-time jump into the Win10 pool or as the usual upgrade process, deployment would have wrapped up in March. (The several steps in each version's timelines were borrowed from Gartner.) Normally, 1709 would have exhausted support in the early spring of 2019, making it very difficult to migrate to 1809 (skipping 1803) without leaving some systems at risk. (The final month of deployment for 1809 would be identical to the final month of support for 1709.)

Instead, the 24 months of support for 1709 gives IT plenty of time to deploy 1809 (again, skipping 1803); there would be little chance that machines would be vulnerable with the extra six months. (Check out the overlap between 1709 and 1809.)

In this scenario, Windows 10 version 1709 would be the SKU (stock-keeping unit) run throughout 2018. Likewise, version 1809 would be run during all of 2019, making good on Gartner's argument that the 24-month support timetable lets enterprises skip every other upgrade.

By the time 1809 nears retirement - unless Microsoft changes its mind again, that would be around March 2020 - version 1903 would have been released, but ideally not deployed. An enterprise would instead look toward Windows 10 1909, which should appear in September or October of 2019. By immediately beginning the upgrade process - two months of testing, two months of piloting, then two months of deployment - of 1909, the company would be able to squeak under the expiration wire of 1809.

The latter maneuver assumes that an enterprise, as Gartner expects, would have sufficiently improved its upgrade processes to complete the testing-piloting-deploying process within six months.

In fact, Gartner saw the six-month support extension offered to versions 1511, 1607, 1703 and 1709 as a breather, one that would let corporations "get much further into their Windows 10 migrations and devise new processes for handling regular feature updates [emphasis added]."

What about a slower IT?

Enterprises with less agile upgrade processes can still take advantage of the temporary situation, Gartner contended.

Those companies, which take twice as long, four months rather than two, for the second and third stages of an upgrade - piloting and deployment, respectively - should have "a moderate but manageable risk if skipping alternate versions," according to Gartner.

See Figure 2, which shows what a firm with "typical" upgrade processes would face.

IDG/Gregg Keizer

This scenario assumes that the enterprise would have just adopted Windows 10 1709, would skip the recently-released 1803, and would deploy 1809 early next year. As in the previous case, the company would get by running just one version (1709) throughout 2018, another (1809) throughout 2019.

Here, the extension of support for 1709 becomes critical, for without it (look at the 18-month mark for 1709) IT would be caught with its pants down on the follow-up 1809, at the end of piloting and before actual deployment began. Sans the extra six months of support for 1709, that would have left corporate PCs unpatched for between one and four months (the time it would take to deploy 1809).

Not good.

The enterprise would have to improve its upgrade processes by the time 1809 neared retirement in early 2020; specifically, IT would need to reduce the preparation and deployment periods for the successor, 1909, from eight months to just four (as shown by the YES version of the 1909 timeline in Figure 2). Failing that, 1809 would fall off support when IT was just at the end of piloting, and before deployment of 1909 (illustrated by the NO version of the 1909 timeline). Windows 10 devices would then be at risk for one to four months.

Again, not good.

Demand 24 months

The relatively uncluttered Windows 10 upgrade path for versions equipped with two years of support has been one reason why Gartner's experts, as well as others, have urged Microsoft to make permanent the temporary timetable of 1703 and 1709, and those versions' two precursors. "Twenty-four months would be better for everybody," Kleynhans told Computerworld.

Microsoft may not be listening, at least not at the moment, because it ended the additional six months of support with the release of Windows 10 1803 in late April. That version comes with 18 months of support.

Kleynhans believes Microsoft will reverse itself. "Gartner predicts that Microsoft will change support for Windows 10 Enterprise and Education to 24 months by YE20," he wrote in the April report, referring to year's end, 2020.

For that prediction to come true, customers will have to put pressure on Microsoft; the say-so of a research firm may carry some weight, but not nearly enough to move Microsoft to change. That the company is susceptible to such pressure has been demonstrated; the extra support for the feature upgrades issued in 2015-2017 is the proof that squeaky corporate wheels get grease.

"Petition Microsoft at the highest levels to set the lifecycle policy for Windows 10 Enterprise and Education to 24 months," Kleynhans said in a bullet-point list of recommendations.