FAQ: Windows 10, now with more upgrade skipping

It's possible for companies to maneuver around Microsoft's upgrade schedule for Windows 10, and skip some updates if they want. Here's how.

Senior Reporter, Computerworld |

Corporate customers have repeatedly told Microsoft to put the brakes on Windows 10's runaway upgrade train.

We know that because Microsoft has steadily increased the time it will support each Windows 10 feature upgrade. Originally envisioned as just 12 months, support was first boosted to 18 months, then extended to two years - first for the 1511 feature upgrade, then for its three successors: 1617, 1703 and 1709, the refreshes released in mid-2016, and April and October 2017.

And last week, Microsoft upset the support cart again by pushing support out to 30 months for the upgrades released each fall.

The additional support effectively repealed the regimented schedule of the past and voided Computerworld's recommendations about skipping every other refresh to reduce the upgrade churn.

But new challenges replaced those Microsoft had invalidated with more support. To illustrate how the new scheduling affects businesses - which are now rushing to meet the January 2020 deadline set by Windows 7's retirement – we've gone back into the Windows' software-as-a-service timeline to reveal what options enterprises have.

New feature upgrade timetable. Each feature upgrade goes through a multi-step process that generates the 18 or 30 months that Microsoft now promises to provide security patches and other bug fixes.

Each upgrade is numbered in Microsoft's yymm format; 1803, for example, or 1809. Once an upgrade is completed, Microsoft issues it to devices assigned to the Semi-Annual Channel (Targeted), the release track mandated by Windows 10 Home. Over the next several months (shown in blue and green in the following figure), Microsoft feeds the upgrade to an increasing number of devices, monitors telemetry and feedback, and then quashes the inevitable bugs that users uncover. Think of Targeted as the upgrade's shake-down cruise, done before the real paying customers - businesses - get their hands on the code.

In Microsoft's perfect world, businesses also immediately install the Targeted version on a small number of PCs to test the upgrade and validate the firm's applications against the build (or identify those applications that will not work, or not work with full efficiency).

Only after a feature upgrade has run the consumer testing gauntlet does Microsoft certify it as business-ready. After several months - the time varies, but has been shortening of late - the theoretically-more-stable-and-more-reliable build is re-labeled as simply Semi-Annual Channel (SAC). There is no re-release at this point, no difference between SAC (Targeted) and SAC either, except for the changes Microsoft may have made due to feedback as users (consumers) absorbed the latter. In fact, the boundary between SAC (Targeted) and SAC is entirely one of labeling or, at best, a temporal border: They're the same thing, just differently named for different moments in time.

Enterprises will be piloting SAC (Targeted) and SAC with subsets of the device base (shown in green in Figure 1), but once IT signs off - and Microsoft gives the thumbs up - the company will begin to deploy the upgrade (shown in red). The time necessary to deploy the upgrade will vary by customer, but Computerworld (based on prior Microsoft guidance) illustrated a four-month span. YMMV (Your Mileage May Vary).

Microsoft now supports twice as many feature upgrades simultaneously. Initially, when support was limited to 18 months per upgrade, Microsoft supported only two upgrades at the same time. Then, for a few months, Microsoft bumped three upgrades - 1607, 1703 and 1709 - from 18 to 24 months to give enterprise customers a respite. That extension made it much more likely that IT staffs could skip an upgrade and still maintain an up-to-date OS that received patches.

However, in May Microsoft confirmed that Windows 10 1803, aka "April 2018 Update," would receive the standard 18 months of support, not the 24 of its predecessors. Enterprises were back to where they began.

Now, with the 30 months of support for all fall feature upgrades - those titled xx09 - but just 18 for their spring colleagues (the ones marked xx03) - the simultaneous support matrix is more complicated.

If N equals the latest upgrade, say, 1809, then Microsoft will support a maximum of N+1 (next year's March release, labeled 1903), N+2 (1909, 2019's fall upgrade, or 2003, the following spring release) and N+3 (2020's fall release, or 2009) at the same time. The amount of support overlap fluctuates depending exactly when the comparisons are made.

For example, in July 2020, 1809 will still be in support, as will 1903 (albeit two months from retirement), 1909 and 2003 (in its fourth month of support). Figure 2 illustrates how the four consecutive upgrades would all qualify for support at the same time.

Select a different month of 1809, though, and while four upgrades will still be supported simultaneously, they will not be the same versions. In December 2020, just a few months before retirement, 1809 will be joined by 1909, 2003 and 2009. What happened to 1903? It expired three months prior, that's what. Refer to Figure 3 to see how this will work.

Endless upgrading. Because of the timing of Windows 10 feature refreshes, businesses that adopt each one will be upgrading an average of every six months, no matter how long each version is supported.

Surprisingly, Microsoft seems to expect that some customers will continue to do that, even with the added support of each fall's upgrade. "All future feature updates of Windows 10 Enterprise and Education editions with a targeted release month of March (starting with 1903) will continue to be supported for 18 months from their release date," wrote Jared Spataro, the marketing exec for Windows and Office, in a Sept. 6 post to a company blog. "This maintains the semi-annual update cadence as our north star and retains the option for customers that want to update twice a year."

Windows 10, now more flexible. Previously, enterprises could increase the interval between upgrades only by robbing Peter to pay Paul: Because of the hard-and-fast 18-month timetable, lengthening the time PCs remained on an upgrade meant shortening the lifespan of the one that followed.

The same still applies, but with 30 months of support there's all that much more elasticity to the schedule.

(Note: Computerworld's unconvinced that enterprises will bother deploying the spring feature upgrades - those identified as xx03 - with their 18 months of support. That's why the scenarios outlined below assume that companies rely on the xx09 upgrades only.)

In the simplest example, an organization that finished deploying 1809 in that upgrade's 10th month could stay on the version until July 2020 - 12 more months - before migrating to 1909. Check out Figure 4 for how this would work. Note that the last four months of 1809 correspond to the four months of broad deployment for 1909.

Version 1903 would be skipped entirely; it would make no sense to shift to that version when it was within three months of going belly-up.

Figure 5 shows a different tack and illustrates the flexibility that the longer support allows. Here, the enterprise runs Windows 10 1809 to the last minute - March 2021 - before moving to 1909. That means 20 months, almost two years, on the same version. (Again, the last four months of 1809 correspond to the four months of 1909's deployment.) In this scenario, there would be 12 months of support coming to PCs running 1909 after the migration - one year, but just barely.

That's the difference between the first and second scenarios: Once extended to the end of 1809's support, Windows 10 is stuck, forced to repeat the same cadence in the future. To "back up" the migration so that a company can again, as it did with 1809, run an upgrade for 14 or 16 or even 20 months after deployment, IT would have to run a "short" version.

Figure 6 spells out that dilemma. After running through all support for 1809, the IT staff pushes PCs to 1909. Rather than run on the latter for 12 months, the enterprise stays on 1909 for only 6 before beginning another migration, this time to 2009. That last move then restores upgrade flexibility, since there will be 17 months of support remaining on 2009.

Notice, though, that the two test-pilot-deploy periods - the 10-month spans for 1909 and 2009 - overlap: The four months of deployment in 1909 would take place at the same time as testing and the beginnings of piloting for 2009. Some organizations might find it tough to execute such hustle.

Sure, you can skip one. But two? Can you? Unlike under the old regime, skipping an upgrade now - almost certainly those marked xx03 - can be done, and without any real sweat. (You just saw how in the section above.)

But what about skipping more than a single upgrade? Possible?

That's an important question: 40% of the IT professionals who responded to a questionnaire this summer said that Windows 10's feature upgrades should be issued only every two years. And a sizable number asked why the survey lacked an option for an even slower tempo. (Just 11% said that they preferred the current twice-annual cadence.)

Skipping two upgrades isn't difficult; there's plenty of time. The problem is that the destination upgrade would be one of the spring xx03 versions supported for only 18 months. Hitching yourself to one of those would be like grabbing onto a drowning man; you might stay above water for a bit, but you'd likely get dragged down in the end.

But bypassing three future feature upgrades - skipping an 18-month version, a 30-month, and another 18-month before landing on a 30-month upgrade - takes real agility.

Figure 7 shows the narrow window, no pun intended, available for just such a maneuver. An organization keeps its devices on 1809 until December 2020, four months before support retirement, then starts deployment to Windows 10 2009, skipping 1903, 1909 and 2003.

Look closely at the timeline for version 2009; it doesn't begin with the standard 2-4-4-month timeframe (for testing, piloting, and deploying). Because version 2009 will have launched in September 2020, the enterprise would have to shorten testing to one month (the blue section) and piloting to two months (green) to allow deployment its usual four months.

With this fancy dancing, the enterprise puts itself on a two-year cycle, adopting 2018's fall build, followed by 2020's fall refresh. Bottom line: It's reduced upgrades by 75%.

Now, that's progress.

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