5 unanswered questions about Windows 10 1909

Since Microsoft gave its Windows 10 update model another violent shake on July 1, Computerworld has tried to parse Microsoft’s meanings and motivations for demoting this fall’s intended feature upgrade — Windows 10 1909 — to little more than a rerun of May’s release.

But while Computerworld was able to decode much of Microsoft’s initial announcements and spell out the likely ramifications for commercial customers, not every aspect of Windows 10 1909 was explainable in the information vacuum Microsoft maintained.

The following five questions remain unanswered. They may not be the only queries, but they’re among the most important to enterprises and IT administrators. Once Microsoft releases 1909 — which should be soon — perhaps some will be resolved.

Is 1909 a one-timer — or the new fall normal?

Computerworld staked out its position earlier: There’s little chance Microsoft invested as much time and energy as it did in creating a completely different kind of upgrade, serviced using a different mechanism than before, only to use the results just once. Doing so would be idiocy when other less costly, less disruptive avenues were available, including skipping the refresh entirely or extending support for, say, Windows 10 1809 or even Windows 10 1903 to cover for the omitted update.

If that’s indeed the case, commercial customers need assurance from Microsoft that 1909’s format and delivery will be the norm for each fall upgrade. Businesses require a definitive schedule and information on an update’s contents — for the latter, at least a sense of the quantity of change — for planning purposes. An ad hoc, seat-of-the-pants servicing model won’t cut it.

That’s exactly why Microsoft codified its upgrade scheme in April 2017 when it told customers it would refresh Windows 10 twice each year, targeting March (really April) and September (okay, October) for the releases.

Then why has Microsoft not spoken up?

We don’t know why Microsoft does things the way it does, although we almost always have common-sensical suspicions. In this case, the most reasonable explanation is that Microsoft wants to gauge how 1909 delivers, or doesn’t, on the concept of a minor upgrade. Assuming it’s satisfied, Microsoft would then tell customers to expect the same, more or less, in the fall of 2020, 2021 and beyond, or as long as Microsoft’s mind doesn’t change again.

Will Microsoft move to a single upgrade annually?

It certainly appears that the company has positioned its Windows update and upgrade model to do that, for there’s little space between an “upgrade” with a smattering of new features and one with no new features. They just tighten the feature spigot that last half a turn to shut it off completely.

Q: So, what’s stopping them? A: Who knows?

It’s clear, for the moment at least, that Microsoft remains committed to a pair of Windows 10 upgrades each year, even if one is such in name only. Whether Microsoft’s stance is due to pride in a promise or for something more tangible is less clear.

A once-a-year upgrade would require more jiggering, not that there’s anything wrong with that (or that Microsoft is against such things; it’s obviously not). The 30-month support lifecycle for Windows 10 Enterprise (and Education) would require shifting to the spring upgrade if the fall’s were eliminated. Labeling might change (what purpose would yy03 have when there was no yy09?), perhaps to Windows 10.21 for the year after next.

Microsoft is the odd man out, so to speak. Other OS makers — notably Apple and Google — have long settled for annual refreshes, whether on personal computers or mobile devices. Experts, ranging from in-the-trenches admins to industry analysts, have either called for or forecast an eventual annual cadence.

Microsoft may well oblige.

Has Microsoft dumped the signaling to commercial customers that a feature upgrade is business ready?

It sure seems that way.

Up to Windows 10 1809, the initially-crippled 2018 feature upgrade delayed by months, Microsoft gave businesses a green light when it (Microsoft) believed the code had been shaken out by early adopters and those forced into installing the upgrade, such as Windows 10 Home users. The business-ready flare went up several months after the upgrade’s debut, between two and a half months on the short end (1803) and four and a half months on the long (1809).

Microsoft hasn’t said a word about Windows 10 1903, which appeared May 21 and so is now four months old.

On one hand — the one that says Microsoft won’t bother with such notifications — there is a host of evidence, from Microsoft’s quashing of the Semi-Annual Channel (SAC) milestone that marked an upgrade’s reliability for commercial customers to its harping at enterprises to begin their upgrade process as soon as the code launches (rather than wait several months). On the other hand — a much smaller hand, by the way — Microsoft at one point did say it would continue to offer this good-to-go declaration.

“We will continue to communicate for future releases the transition from targeted to broad deployment status,” promised John Wilcox, a Windows-as-a-Service (WaaS) evangelist, in a March 28 post to a company blog. (In that post, Wilcox also announced that 1809 was suitable for “broad deployment,” Microsoft’s euphemism for ready to run for business.) Since then, silence.

Fine and good, but what does all this have to do with Windows 10 1909?

Time for more conjecture. (It would be nice if Microsoft just told its customers what’s up, or soon to be up, but for some reason that’s verboten at Redmond.)

Because 1909 is a cumulative update of 1903 — for those old enough to remember, a “service pack” in earlier Microsoft-ese — and its contents are, in fact, identical to a fixed-up 1903, 1909 has, theoretically, been as well tested as has 1903. And Windows 10 1909’s target release, Microsoft said in early July, would be September, whose end is quickly approaching. Even if that’s delayed into October, the launch of 1909 would be within days of any business-readiness alert for 1903 that Microsoft might give this late in the process.

The two — 1909 as a tested 1903 and the former’s imminent release — make it likely that Microsoft treats the launch of Windows 10 1909 as the milestone for commercial customers to install the year’s feature upgrade. The company may not come out and say as much (or it might if it makes good on Wilcox’s pledge) but it will almost certainly allude to a go signal in whatever phrasing it uses in a blog post or somewhere on the Windows release health dashboard.

How can we tell whether an update is for 1903 or the newer 1909?

IT administrators have voiced concern about the cumulative update approach for Windows 10 1909, particularly after Microsoft outlined how the numeric labels would be identical until they weren’t.

For example, the Sept. 10 update — the month’s Patch Tuesday collection — for 1903, labeled “KB4512941,” was also delivered by Windows Update to any Insider beta tester who had shifted to Release Preview ring to try out 1909.

Normally, each version of Windows 10 gets a differently-marked update on, say, any given Patch Tuesday. For instance, Windows 10 1809’s Sept. 10 update was labeled “KB4512578” and 1803’s as “KB4516058.”

But Windows 10 1903 and 1909 will share a KB stamp when, assuming the latter launches before Oct. 8, when Microsoft issues that month’s Patch Tuesday update. Confusion!

[If your head doesn’t hurt by this point, you haven’t been paying attention.]

Once an organization has 1909 in place — probably through upgrading from a pre-1903 version of Windows 10 — it will have to keep in mind that the KB designations for the two are identical. As long as it’s assigning the cumulative update to machines running one of those two versions, however, it won’t matter, as the contents (remember) of the update for each are identical.

(This assumes that a company has some PCs on 1903, some on 1909; a common occurrence.)

Microsoft could alleviate some of the bewilderment by better explaining how the cumulative update process works on end points, whether Windows 10 Pro or Windows 10 Enterprise. Perhaps that will happen at the same time it rolls out 1909.

Will Microsoft initially defer 1909’s new features? If so, will it let enterprises control the deferral or even permanently disable them?

Windows 10 1909 has been tested differently than past upgrades: Initially, Microsoft fed the update to Insider participants with the new features switched off. Later, it first enabled the features — they’re neither large in number or in import — for a portion of the pool, then for all. (The mechanism, Microsoft has said, is a small “enablement package” downloaded from Windows Update “that turns on the 19H2 [1909] features.”)

But Microsoft has never said whether 1909 will ship — either as a cumulative update for 1903 or in its larger form for upgrading from pre-1903 versions — in the same way.

Arguments abound for off-by-default.

Testing of 1909 has been significantly less than for previous upgrades — and for the upcoming Windows 10 20H1, which should be called 2003 next spring unless Microsoft blinks at that numeric tag — because it’s been limited in time (only since July 1) and in the number of testers (the usual Fast Ring testers have been kept banging on 20H1/2003). It would behoove Microsoft to enable the new features in 1909 by stages, which it can do in its current format, as a way to limit possible damage due to unforeseen problems.

And if Microsoft in fact utilizes Windows 10 1909 as the business-ready version of 1903 (see “Has Microsoft dumped the signaling to commercial customers that a feature upgrade is business ready?” above), setting new features to off would also mean companies would not have to test or prep for them. Instead, they’d be dealing with the changes baked into Windows 10 only up to and including 1903’s, just as if they’d migrated to that version.

(The difference for Windows 10 Enterprise and Windows 10 Education customers, of course, is the 30 months of support for 1909 versus the 18 for 1903.)

If Microsoft inhibits 1909’s new features at launch, it’s unclear when it will turn them on. Will all go live at once or will Microsoft flip the switch on some now, others later? How will it decide that? Microsoft needs to answer these questions and more.

For instance: Can enterprise IT admins control the delivery of the enablement package — Microsoft’s term, not Computerworld‘s — to Windows 10 1909? Will Microsoft cede oversight here? A move like that would not be unprecedented, as admins can already bar employees’ access to some Windows 10 bundled apps. But it would still be a significant surrender of responsibilities; Microsoft, like virtually every software developer, has always…always…implicitly told customers that it knows best what they want or need (even when soliciting feedback, as Microsoft does through Insider; the company, after all, decides what feedback to accept, what to reject). Giving admins the right to make those decisions, especially if the decisions are granular — feature by feature, for instance — could be revolutionary even if was not at the beginning.

Without proof, and based on nothing but a hunch founded on years of following Microsoft, Computerworld has more confidence that IT admins will be able to defer 1909’s new features’ appearance than that they will be allowed to cull some features as they accept others. The latter will probably be a GPO (group policy object) too far.