Like any proud parent, the company wanted its offspring to succeed in life, to have opportunities galore. Go to an Ivy League college, land a good job.
To Microsoft, Windows 10 would be different than, better than, the other kids. It would improve itself several times a year, not just once every several years. It would be smarter, more helpful because it evolved faster and, so, adapted with the times. While its older siblings remained mired in their outdated habits, Windows 10 would rapidly learn new skills because it upgraded itself multiple times each year.
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If Apple boasted that its OS X, later renamed macOS (like that fooled anyone), was smarter than Windows because it upgraded annually, Microsoft could brag that its Windows 10 was three times smarter than macOS because it morphed three times a year.
Over the last nine months, Microsoft has so altered Windows 10's effective upgrade cadence - the practical rate at which users will upgrade - that it's no more ambitious a parent than Apple.
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Enterprise and the annual Windows upgrade
The earliest days of Microsoft's plans for Windows 10 have been well-trod, here and elsewhere.
Although Microsoft touted a three-times-a-year pace for feature upgrades before Windows 10's mid-2015 debut and backed that up with a first upgrade just four months after the debut, the company quickly retreated from the tempo, first informally - the second upgrade appeared more than eight months after the first - then officially. In April 2017, Microsoft committed to a twice-annual schedule - one in March, the other in September - to put some regularity in the process, something enterprise customers demanded.
In 2017 and 2018, Microsoft hewed to the schedule, producing and delivering two feature upgrades each year - 1703, 1709, 1803 and 1809, all in the firm's four-digit yymm format - even though it monkeyed with support lifetimes during that span.
The latter, especially the September 2018 change that extended support for each fall's upgrade - those tagged as yy09 - to 30 months from the then-standard 18, upended the effective cadence for Windows 10 Enterprise customers; it gave them a way to easily assemble an annual upgrade schedule, one that didn't rely on Microsoft being exactly on time in its releases or their being among the most agile of companies.
And enterprises will vote with their feet, so to speak, by deploying the yy09 upgrades each year, said Gartner. "The extension of support to 30 months for the annual 'xx09' feature updates reduces disruption and increases organizations' flexibility to plan by enabling an annual update cadence, rather than a semiannual one," the research firm's Stephen Kleynhans and Michael Silver wrote in a report last year.
In theory, an annual cadence was possible with the 18-month schedule. But, as Gartner put it, the attempt "tied the organization to Microsoft's schedule, with little room for slippage." The recent delays of 1809 and 1903 showed the futility of assuming Microsoft's schedule would not slip.
"This new extended support window enables organizations to start their validation and deployment process at any point in the 12 months following the release of an update," Kleynhans and Silver said.
Which was adapted from a Gartner illustration, shows how annual upgrades would work when an enterprise began a six-month process at the start of a year, say, for example's sake, 2020. (The six months are a combination of two-month periods for preparation by the IT staff, piloting on a small number of systems and then deploying the upgrade to all eligible machines.) Note that each spring's upgrade, the ones pegged as yy03 with 18 months of support, are skipped.
Enterprises that require six months to wrap up an upgrade can reduce their Windows 10 pace to once a year without any trouble.
illustrates an annual upgrade, but with a process which extends over 12 months, perhaps in a much larger organization where deployment takes much longer.
Even large organizations that need a year to do an upgrade can get on an annual upgrade train with the 30-month support lifecycle of Windows 10 Enterprise. Note, though, that timing is tighter in this scenario: The company is finishing deploying the upgrade just three months before the prior version runs out of support.
In each case, users will remain on a particular feature upgrade for 12 months (assuming their place in the update queue doesn't change). Enterprises could initiate the process at virtually any time in "Year 1" (or 2020) and still manage annual upgrades from that point forward, each year at or around the same date.
Consumers get annual upgrades too
Others working on Windows had to wait until this year, nearly nine months after enterprises got their break, for relief from Microsoft's punishing hustle-hustle-hustle schedule.
In late May, with the release of Windows 10 1903 and then last week with updates to 1803 and 1809, Microsoft began adding a "Download and install now" option to Windows 10 Home (and presumably Windows 10 Pro as well) that lets users decide when to upgrade the OS. Unless "Download and install now" - DaIN for short - is chosen, Microsoft said, the latest feature upgrade won't be downloaded and installed.
Windows 10 Home users have never had this kind of control over when a feature upgrade arrives, or whether one lands on their PC at all. For the first time, those customers will be able to skip a feature upgrade and adopt just one each year, even though their Windows support lifecycle has remained frozen at 18 months for each upgrade.
The Windows 10 Home user has two ways to use DaIN: Call on it themselves or let Microsoft take control.
Microsoft take control? What?
Redmond gave itself a backdoor when it handed over DaIN. Saying it needed to keep customers' systems secure - implying that users might prefer the convenience of not upgrading over staying secure - Microsoft said it would intervene when support for the currently-installed version neared expiration. "When Windows 10 devices are at, or will soon reach, end of service, Windows Update will continue to automatically initiate a feature update," the firm said.
How this will work. A user, perhaps one of the millions whom Microsoft will forcibly upgrade from 1803 to this year's 1903, decides to trigger DaIN in early 2020, when 1909 is the current version.
A Windows 10 Home user lets Microsoft upgrade her PC, which the company does in the last four months of its support. Because of the overlap of the 18-month support cycles, that means Microsoft skips an upgrade for the user.
The user then does nothing, upgrade-wise. So Microsoft steps in during the last four months or so of 1909's support, which on a calendar would be during the end of 2020 and beginning of 2021. Because of the way each upgrade does or does not overlap the previous version - again, look at Figure 3 - that means Microsoft would skip 2003 and instead install 2009, the fall upgrade.
From that point - assuming the user doesn't intercede - Microsoft would upgrade the user's machine at the same time each year going forward. The next upgrade? Version 2109, delivered and installed in late 2021 or early 2022.
But DaIN also allows users to be extremely flexible in when they upgrade and what they upgrade to.
With the DaIN option, users can adopt every upgrade, skip one to upgrade just once a year, or combine the two approaches in a pick-and-choose method. Some limitations continue to apply, notably that Microsoft reserves the right to forcibly upgrade when the version is close to support retirement.
How a user might manage a Windows 10 Home PC with DaIN. The user, one of the minority who were given the problem-plagued 1809 earlier this year, decides to pull the DaIN trigger in late 2019, upgrading from 1809 to the just-out 1909, skipping 1903 (not shown) entirely.
A Windows 10 Home user triggers DaIN to get 1909, decides to upgrade to 2003 in the fall of 2020, but then gets on the annual upgrade ride starting with version 2103. It's not as confusing as it sounds. Really.
Rather than wait for Microsoft to upgrade a PC - which would mean an upgrade every fall - the user decides to switch to Windows 10 2003, the upgrade slated for release April 2020. The PC runs 2003 for about seven months before DaIN is triggered, this time to grab Windows 10 Home 2103 during its first month of availability. (The light yellow and light green in Figure 4 show the last four months of the current version's support, and the corresponding four months that Microsoft would forcibly upgrade a PC.)
From then on, the user can rely on DaIN at the start of each spring's upgrade to skip each fall's refresh.
SMBs: How Pro can go annual
Windows 10 Pro users are stuck in a kind of 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.
The latter might be what kills Pro as a viable business operating system. (Keeping Pro at 18 months is just one of many ways Microsoft pushes commercial customers to run Enterprise and pay for the latter in an ongoing subscription.) The support timeline can be tight - too tight - for a company with significant numbers of Pro PCs.
But by using the management tools Pro provides - upgrade deferrals, primarily - IT administrators can still get to an annual refresh of Windows 10 ... as long as the process doesn't take too long.
In a six-month upgrade process, a small business relying on Pro-powered PCs can, just barely, move to an annual schedule by skipping a refresh. Anything longer than that six-month procedure, though, is really risky, as it would mean deployment would not be completed before the version being used fell out of support. And if Microsoft's release schedule slipped, well, then all bets would be off.
Still, it's possible.
With a six-month upgrade process - two each for preparation, piloting and deployment - an organization running Windows 10 Pro can get to annual upgrades, but just barely. Note that the last month of deployment is the same month that support ends for the version being replaced.
A very small organization with just a handful of Windows 10 Pro PCs should not need six months to upgrade. Instead, its process would look either identical or very much like that of the consumers running Windows 10 Home. In this case, timing is much less critical.
With just a two-month process, the small business is able to start deployment about 90 days after the launch of Windows 10 Pro 1909, enough time for Microsoft to shake out most of the bugs. With relatively few machines, deployment can easily be done within one month, giving a two-month cushion before support dries up.
A lighter deployment load makes moving to an annual upgrade with Windows 10 Pro easier, as the small business should be able to pilot and install an upgrade within two months, letting it delay the start by 60 days and having the same amount of cushion at the end before support expires.
The Gartner analysts - Kleynhans and Silver - obliquely noted the problems for Pro posed by the 18-month support, making annual upgrades possible only with a tight turn-around. "Re-evaluate the business case for Windows SA/E3/E5, if you're running Windows 10 Pro," the pair of analysts wrote in their report last year. The "E3" and "E5" they mentioned referred to subscriptions which provide Windows 10 Enterprise.