What Microsoft’s latest Windows 10 update upheaval means

Microsoft’s latest update upheaval will have long-term impact on Windows 10, affecting enterprise and small business upgrade scheduling and pushing consumers to continue working as free testers for the company.

The biggest news from Microsoft’s July 1 announcement about the-until-then-ignored Windows 10 1909 – the second upgrade of 2019, tagged with the firm’s yymm format – was that the company is scaling back feature upgrades, true feature upgrades, to just one a year. What had been the fall refresh would, in fact, shrink to the equal of an old-school “service pack,” last used with Windows 7.

Each spring, Microsoft was implicitly telling customers, it would issue a Windows 10 upgrade filled with new features and functionality; each fall, it would deliver a performance and reliability update based on the spring upgrade. That fall update would essentially be a more polished version of the spring feature upgrade, nothing more, with new features either absent or reduced to a minimum.

But the one-upgrade-a-year-is-enough revelation – as important as that is, what with Microsoft’s harping that its Windows-as-a-service (WaaS) strategy rested on multiple upgrades annually – was not the end of it.

Yes, 30 is more than 18

Changes to the composition of 1909 will not change enterprises’ opinions of the fall upgrade or update or service pack or whatever it’s called: They will still gravitate to it.

That’s because 1909, service pack status and all, is still numbered yy09, meaning that it’s 2019’s only version that comes with 30 months of support for Windows 10 Enterprise and Windows 10 Education, not the measly 18 months awarded to other SKUs (stock-keeping units) like Home, Pro and Pro Workstation.

By supporting Windows 10 Enterprise for 30 months, Microsoft gave its best (and biggest-paying) customers more time to deploy an upgrade, thus more flexibility in when they initiate a migration. More importantly, the 30 months allows businesses to easily upgrade annually. Commercial customers had been calling for a slower upgrade cadence ever since Microsoft unveiled its fast development and release model prior to Windows 10’s debut four years ago. This is Microsoft’s response.

(Even with 30 months of support, it would be difficult for most enterprises to upgrade every two years. See this Computerworld article for details on the agility needed to pull that off.)

Most enterprises won’t care that 1909 and its every-year-after-that successors lack new features. In fact, they’ll like that. Corporations are conservative by nature and the less new shiny in a release, the less re-training, re-testing needed.

The service pack nature of 1909 will also appeal to enterprise, and not because it will remind their IT veterans of pre-2015 advice to wait until the first service pack before deploying a new version of Windows. More on that later, though.

For now, the bottom line is easiest to remember: The fall “upgrade” – 1909 this year, 2009 next, and so on and so forth – will be the preferred version to deploy as long as its support lasts longer than the spring alternative.

SMBs: Dealing with Pro

Small businesses running Windows 10 Pro on some or all of their PCs do not have the refuge of the fall upgrades because that SKU receives only 18 months of support for each version, no matter when released.

Picking the spring or the fall refresh, then, may come down to timing. A company that does the bulk of its business in the year’s final quarter won’t want to risk disruption by upgrading in, say, the late summer or early fall, and so may lean toward the spring update. Likewise, an accounting firm hustling during tax season won’t want to touch their machines after Jan. 1; they might migrate using the fall “service pack” before they get busy.

Most Windows 10 Pro owners will be able to upgrade annually – skipping an intervening refresh – even though support ends after 18 months. (Check out this Computerworld piece for how that’s done, complete with timeline examples.)

If the time of year doesn’t affect the Windows 10 upgrade decision, the slant Microsoft’s just given to the fall update may be the critical factor.

Here’s why.

It’s guinea pigs all the way down

Microsoft rested its rapid development and release strategy on several cornerstones. One was undoubtedly a major concession to commercial customers, those Microsoft has always favored: Not only would Microsoft test Windows 10 prior to release with its own staff (albeit less so than before it purged many of its QC employees) and rely on the millions participating in Insider, but it would rope millions more to field test the upgrade after launch.

That was clear from the schedule Microsoft devised from the start. Windows 10 Home users would be the first to get a feature upgrade – at one time there were to be three a year, but the pace slowed to two almost immediately – and would be forced to run each upgrade. Microsoft controlled when individual PCs installed each upgrade and decided how long they ran it.

Only after time had passed – initially the span was to be four months, but that quickly varied, at least until the implosion of 1809 – would Microsoft give enterprises the green light, telling them the feature upgrade was stable and reliable enough for business use. Over time, much of the formality of that structure vanished, including the separately-named “channels” or “branches” for consumer and commercial. But until recently, the concept remained intact.

That’s beside the point. This is what mattered: Windows 10 was touted as more reliable, with fewer bugs, because non-commercial customers – let’s call them “consumers” – served as unpaid guinea pigs.

Fortunately for businesses, the latest changes to Windows upgrade model hasn’t eliminated the testing that others conduct for corporate users. In fact, the fall upgrade will have been tested significantly longer than earlier Windows 10 updates. (Whether that results in more thorough testing could well be a completely different story.)

Last year, Microsoft kicked off the release of Windows 10 1803 on April 30. Come June 14 – 45 days later – the Redmond, Wash. company declared 1803 fit for businesses, making for the fastest transition yet from consumer-only to enterprise-ready. This year, 1903 hit the street on May 21. Although Microsoft has not nailed down the exact date for 1909’s launch, it has said it’s aiming for September. Let’s say Microsoft starts 1909 delivery on Sept. 17, the third Tuesday of the month. (Microsoft likes Tuesdays for Windows updates of all kinds.)

Those dates mean that 1903 will undergo field testing – with consumers for the most part, but undoubtedly some preliminary prep and piloting by enterprises – from May 21 to Sept. 17, or for 119 days. Remember, 1909 is supposed to be a service pack, with few if any new features. In theory, that means it should have no new bugs and, again in theory, it should be “business ready” from its debut date.

Any delay in upgrading to 1909 by an organization will only add to the testing-by-others total. If Company ZZZ postpones the start of 1909’s deployment to, for instance, Jan. 1, 2020, the upgrade’s field testing period would run to 225 days, or nearly two-thirds of a year.

The key is that the fall upgrade will be a new feature-free – or relatively free – version of Windows 10 that by definition should be more reliable because of the extended time in use.

Consumers…spring forward or fall back?

Unlike commercial customers, who will want to standardize on the fall upgrade/service pack because of its 30 months of support, consumers and very small businesses will have a choice between spring and fall. Each comes with 18 months of support.

But for the 1909 service pack – and its successor – to serve enterprise needs, Microsoft must somehow ensure that large numbers of Windows 10 Home and Windows 10 Pro users select 1903 (and its springtime successors).

The company no longer wields the big stick of upgrade control, however; in April, it gave Home and Pro users the “Download and Install Now” (DaIN) option, which lets those users decide when to upgrade. Do nothing and their PCs will continue to run the installed version of Windows 10. Select DaIN and the latest refresh is deployed.

Although those wedded to Windows 10’s original WaaS standard may think DaIN leads to anarchy, the debacle of Windows 10 1809 – the months-delayed fall 2018 upgrade that Microsoft yanked from distribution – may be a godsend. Because Microsoft appeared to dramatically curtail its then-ordered upgrades to 1809 starting in March, probably realizing that the late release meant butting up against the 1903 follow-up, a larger-than-usual portion of the user base continues to run the older 1803. According to metrics vendor AdDuplex, 58% of Windows 10 users still ran the older 1803 as of June 26, the most recent date when data was collected.

There’s good reason to believe that most of those on Windows 10 Home or working at an unmanaged – or lightly managed – Windows 10 Pro PC, will, first of all, be pushed to 1903 in the next four months as Microsoft exercises its residual rights of forcible upgrades. Secondly, the bulk of those users will probably receive a new upgrade at roughly the same time next year, and each year after.

Even as the firm accepted that users should have a say over when their PCs upgraded to a newer Windows 10, it reserved some control for itself. As a version’s support expiration date nears, Microsoft said, “We will begin updating devices … to help ensure that we keep these devices in a serviced, secure state.” A week ago, Microsoft announced the start to that 1803-to-1903 forced upgrade, citing the Nov. 12 support expiration of the former.

In other words, when users do nothing – do not select DaIN or initiate an upgrade using other means, such as a download image file (in .iso format) – Microsoft steps in and upgrades the PC, as it always did before. Users who, once on 1903, again do nothing, will be upgraded by Microsoft at some point four or fewer months before that version’s Dec. 8, 2020, support termination. The feature upgrade available in August 2020 will be Windows 10 2003, next year’s spring refresh. These users will, then, have run 1803 than 1903 and then 2003.

Because no one in software ever lost their job overestimating user inertia, it’s likely that once on the spring upgrade path, they will stay on it. Doing nothing, after all, is easier than doing something. With the spring annual upgrade set for a majority of consumers and many small businesses, Microsoft will have created a large-enough muddle of guinea pigs to make field testing work for its commercial customers.

Questions, there are always questions

Naturally, there are unanswered questions about the new process, including whether Computerworld‘s analysis of the impacts on enterprise, SMB and consumer scheduling are accurate. As usual, answers may not be known for some time, if ever. But there’s enough information to sketch the longer-term effects of Microsoft once again backing away from its more radical notions of WaaS and reverting to, if not exactly a past process (like service packs) then something resembling that.

• Enterprises will standardize on the fall update because it offers 30 months of support for each version of Windows 10 Enterprise. Everything else remains secondary.
• Some SMBs running Windows 10 Pro may choose between the spring’s full-feature upgrade and the fall’s service pack – for them, support is 18 months no matter which they pick – based on timing during the business year and their stability requirements. Others with more flexibility will want to consider following enterprises to the fall update.
• Starting with 1909, the fall refresh will have been run in real world settings – if not in enterprise environments – for months longer than previous feature upgrades. That, of course, assumes the fall updates are as advertised: Almost exclusively bug fixes atop the spring upgrade. The additional “testing” of the spring update may translate into a more reliable fall upgrade than Microsoft has delivered thus far.
• Windows 10 Home and Windows 10 Pro users will continue to serve as volunteer testers because a majority – of Home, at the least – will settle into an annual upgrade each spring. (It’s unclear whether Microsoft decided on the new major-minor tempo after the disaster of 1809, or simply leveraged it to good effect.) These users will be the ones who uncover post-launch bugs that Microsoft then works to quash before issuing the fall service pack-like update suitable for enterprise. Some in this group, however, will gravitate toward the more reliable fall update. Computerworld believes the latter will be a minority.
• The cadence of full feature upgrade in the spring and the service pack in the fall will, to a great degree, separate the schedules of consumer and commercial customers. The former will tend to upgrade annually to the latest spring update, even if the process doesn’t happen until the summer. The latter will largely adopt an annual timeline, but install the fall refresh.