How Windows 10 users can upgrade on their schedule, not Microsoft's

Now that Microsoft has changed the way Windows upgrades are rolled out, it's possible for users to delay updating — within limits. Here's what to do.

windows 10 windows microsoft laptop keyboard update  by nirodesign getty
NiroDesign / Getty Images

Over the last four years, Microsoft has gradually, carefully, slowed the tempo of Windows 10's upgrades.

And customers have rejoiced.

In Microsoft's original planning, Windows 10 was expected to improve itself several times a year, not once every several years. It would be more secure, more helpful, more with it, because it would evolve faster and, thus, adapt to changing times. While earlier incarnations of the operating system stuck to outdated habits for ages, Windows 10 was designed to constantly learn new skills because it would upgrade itself several times a year.

Since September 2018, however, Microsoft has backpedaled. Announcements then and since have made it feasible, sometimes for the first time, for customers to limit Windows 10 upgrades to just one a year. And its most important customers, the commercial operations that run Windows 10 Enterprise, may now be able to stretch the gap between upgrades even longer, to every two years.

Here's how.

Windows 10 Home & Windows 10 Pro, annual upgrades

For the first time, these users have some control over when their PCs jump to a newer version of Windows 10. Credit the April change in Microsoft's upgrade practice that introduced "Download and Install Now" (DaIN) for the new right to ignore a feature upgrade, to establish an annual upgrade cadence.

A quick recap: DaIN lets Windows 10 Home and Pro users request the latest feature upgrade. Because DaIN is a new option, not initiating it means that the PC won't be forcibly upgraded (see exception below). With some restrictions, users will be able to select when their machine receives a refresh.

Microsoft, however, reserved an exception for itself. Saying it needs to keep customers' systems secure - suspecting that left to themselves, users might prefer the convenience of not upgrading over staying secure, in effect returning to the pre-Windows 10 upgrade policy - Microsoft said it would intervene when support for the currently-installed version nears expiration. Although Microsoft has yet to confirm when it will trigger these forced upgrades, it did so four months before the expiration of Windows 10 1803.

Figure 1 illustrates how this will work.

figure 1 july 2019 IDG/Gregg Keizer

A Windows 10 Home user triggers DaIN to obtain 1909 this fall but does not repeat the move. Instead, Microsoft upgrades the PC in the last four months of 1909's support. Because of the overlap of the 18-month support cycles, that means Microsoft will install 2009, 2109 and 2209, making for an annual upgrade.

Annual upgrades are also possible for Windows 10 Pro PCs, whether they're managed or not. The latter, of course, will likely use DaIN, as if it's a Windows 10 Home powered the device.

Managed machines exist in an upgrade purgatory, in that they have some of the upgrade management tools available to enterprise users but must deal with the same shorter 18-month support schedule as consumers. That support lifecycle is the critical factor.

Because an annual cadence allows for just six months of leeway - time to prep for, pilot and deploy the upgrade - there's little room for error on the part of Windows 10 Pro-based shops. A six-month procedure, for example, would be risky, because any kind of delay - on the part of Microsoft in bringing the successor to release status or a snafu on the customer's end - would mean deployment would not be completed before the version being used fell out of support. A faster prep-pilot-deploy plan - lasting, say, two or three months - would provide more flexibility in the schedule.

Figure 2 shows how the two methods - a six-month and a three-month span to test and roll out an upgrade - would look, with the former going annual with the spring upgrade and the latter using the fall's "service pack" refresh.

figure 2 july 2019 IDG/Gregg Keizer

With a three-month process (bottom), a small business could begin deployment of each year's upgrade about 90 days after the debut of Windows 10 Pro 1909; that should be enough time for Microsoft to shake out most of the bugs. Once on this fall's refresh, the company would remain on that schedule, deploying 2009, 2109 and 2209. A six-month procedure (top) - marked in yellow and starting with 2003 - would leave little room for error as the final month of deployment would be synchronized with the last month of support for the predecessor. The business would upgrade every spring, thus installing 2103, 2203 and 2303.

Windows 10 Home & Windows 10 Pro: Is it possible to upgrade every two years?

The math says no. Even the most agile IT staff can't manufacture time. Eighteen months of support leaves Windows 10 Pro six months short of doing the impossible: Upgrading every 24 months.

(An individual running Windows 10 Home, on the other hand, might be more tempted to try this, seeing as how there's just a device or two to upgrade, and while running sans support would still be risky, it might be within that person's tolerances.)

Only shops willing to remain out of support for a half year or more could hazard such a schedule, a dubious scheme at best, career-ending at worst if a patched vulnerability - patched by Microsoft, but not by the customer - ends up exploited and the company is pillaged by criminals.

The most that Microsoft's upgrade calendar can be twisted by Windows 10 Pro environments is by passing over two consecutive feature upgrades, which isn't the same as skipping a second year. But even that shortcut would mean doing without security fixes for a month or more.

Shortening the prep-pilot-deploy process by dumping a step, say, "prep," and jumping directly into piloting as soon as the target upgrade is issued would still require running vulnerable Windows 10 Pro systems for two months. One saving grace: When migrating from yy03 to yy09, the small business could shift one or both preliminary steps - prep and pilot - to the already-out spring upgrade, what with the fall refresh representing a service pack-like release that by definition should be more reliable.

Should is the operative word.

Figure 3 outlines how an SMB might approach skipping two feature upgrades with Windows 10 Pro. (This is for illustrative purposes only: Computerworld, in fact, recommends that a business that values its data foreswear such a risky strategy.)

firgure 3 july 2019 IDG/Gregg Keizer

To gain an additional five or six months on a specific version of Windows 10 Pro, users would have to accept running their PCs sans security patches for at least a couple of months. Frankly, the extra time on a version doesn't seem worth the risk.

Windows 10 Enterprise, annual upgrades

In September 2018, when Microsoft revised Windows 10 support to award the Enterprise version 30 months of updates - for those versions labeled yy09, the Redmond, Wash. company gave large commercial customers an instant path to an annual upgrade, one that didn't depend on their being extremely agile or Microsoft being on time in its releases.

As outlined above, an annual cadence is possible with the 18-month schedule. But, as Gartner put it in a 2018 research paper, the attempt "tied the organization to Microsoft's schedule, with little room for slippage." Instead, the longer support would let enterprises "start their validation and deployment process at any point in the 12 months following the release of an update."

By comparison, a 30-month support lifecycle lets organizations start the prep-pilot-deploy process at almost any time in the year following the release of a fall service pack. Figure 4, for example, portrays the cadence of both six-month and 12-month procedures, and shows not only the annual upgrades but also how much support remains as a safety net.

figure 4 july 2019 IDG/Gregg Keizer

Using a six-month process (top), with two months each devoted to prep, pilot and deploy, an organization can begin at the start of each calendar year and have half the year off from any Windows migrating duties. Larger enterprises, however, may need more time to prep and pilot (two months each) and deploy (six months) and so institute a 12-month procedure (bottom). At that speed, moving from one version to the next becomes a constant job. In both scenarios, the organization opts to stick with the yy09 service packs because only they provide 30 months of support.

Windows 10 Enterprise: Can an every-two-year upgrade be done?

Last year, Gartner analysts said that a biannual upgrade schedule - installing one feature upgrade every two years - is "technically possible" but that it would require "tightly run processes," be "relatively high-risk" and demand "perfect execution every time."

Raise your hand if your organization can do anything perfectly every time. (We thought so.)

At the time, Gartner illustrated the difficulty of a biannual schedule. Computerworld's adapted Gartner's timelines in Figure 5.

figure 5 july 2019 IDG/Gregg Keizer

A six-month prep-pilot-deploy process leaves no room for screw-ups in a biannual upgrade attempt, whether it's begun as soon as the targeted service pack is released (top) or if the organization waits until the start of the new year (bottom). The latter scenario shows how the delay in start time puts the enterprise out of support for the last three months during the upgrade to 2109. That's an unacceptable risk.

Gartner's conclusion? There are more downsides than upsides in a biannual schedule. That pace demands an immediate start to prep-pilot-deploy; because the 30-month support lifecycle is restricted to the fall refresh, that means IT would have to jump on the migration in October-November-December, a quarter already jammed with obstacles, including short-staffed departments and the need to keep everything running during a possibly critical-to-revenue time of year. The analysts also noted that by upgrading every two years rather than every one, each upgrade would be that more jarring to workers as well as that more likely to trigger compatibility problems.

"The biannual cadence should be reserved for devices for which the long-term servicing channel (LTSC) would be desirable, but would be inappropriate for one reason or another," Gartner opined, referring to the static build channel that Microsoft services for a decade with security updates and bug fixes only. "It effectively removes the need for LTSC for many customers, even for selected machines, but does raise some risks."

Windows 10 Enterprise: New major-minor upgrade cadence may make biannual refreshes possible

The possibility of going biannual got a boost in early July when Microsoft announced it was again morphing its upgrade practice and essentially admitted the cadence would be a major feature upgrade (in the spring) and a service pack-style retread (in the fall).

The first instance of the latter - this fall's 1909 - will include, Microsoft said at the time, "a smaller set of enhancements focused primarily on select performance improvements, enterprise features and quality enhancements." It will include few, if any, new features. And those it does contain, Microsoft hinted, might be disabled by default, to be switched on when or if it decides, or perhaps when customers (read large organizations) choose.

Because the fall update will be a service pack - and so almost exclusively bug fixes atop the spring upgrade - it's possible that enterprises can shift some of the usual practices to what's available before the fall's refresh is released.

Take a look at Figure 6, which shows how that might work.

figure 6 july 2019 IDG/Gregg Keizer

The organization adopts 1909 in the first half of 2020 with a six-month prep-pilot-deploy. So far, so good...and normal. But rather than move to 2009 later that year, IT starts prep-and-pilot with 2103, the next year's spring feature upgrade. It can get a head start on adoption of the fall's 2109 because 2109 is a service pack, little more than 2103 reprised. Once 2109 launches, the enterprise kicks off a quick pilot to ensure that everything is as it was in 2103, then does a two-month deployment. The result? A three-month cushion before 1909 falls off support in April 2021. Clear?

The above assumes that the fall updates are as advertised: bug fixes and little else. If that's not the case and there's a significant difference between the spring feature upgrade and fall service pack, the early start to prep and pilot won't work. Neither, then, will a biannual upgrade scheme, at least for most organizations.

Microsoft could make biannual upgrades a snap, of course, with a simple change: Increase support to 36 months for Windows 10 Enterprise's fall service pack updates, twice the length of the spring feature upgrades. The additional six months would provide the buffer enterprises need to craft an unhurried, fully vetted transition. It would also let organizations standardize on the beginning of the year for the prep-pilot-deploy process start date, making it easier to flip between annual and biannual upgrades.

The impact on Microsoft? It would have to simultaneously support a maximum of five versions, not four, but the period when five versions overlap would be just six months long.

Figure 7 shows how a 36-month support lifecycle would look when a business schedules biannual upgrades.

figure 7 july 2019 IDG/Gregg Keizer

Because of the additional six months of support for Windows 10 Enterprise 1909 - pushing its retirement to October 2022 - the business can plan on migrating to Windows 10 Enterprise 2109 at the beginning of 2022, take its usual six-month stretch for prep-pilot-deploy, and still have a three-month cushion to account for delays and snafus.

Copyright © 2019 IDG Communications, Inc.

It’s time to break the ChatGPT habit
Shop Tech Products at Amazon