State of the Union: Microsoft's Windows 10 Upgrade Strategy

    

Since Windows 10 was released with much fanfare as the 'last Windows', Microsoft has made many changes to its servicing model, terminology, and support schedule — causing much confusion among its customers, IT admins, and C-level executives.

One could say that change is a constant with Windows-as-a-Service, and not only with its much smaller, continuous updates. In just over 4 years and 7 feature update releases, Microsoft has repeatedly changed the naming conventions for updates as well as how long they will be in service for, and has extended the EOL dates and support windows — which, initially, they said they wouldn't do.

Because it is so easy to lose track of what is going on, here is a quick recap and some recommendations on how to move forward.

Windows10StateOfTheUnion2019

Decision Time Is Now

Now is the time to make your long-term strategy on Windows 10, whether your organization is already on Windows 10 or you are still on Windows 7, because:

  • Windows 7 extended support ends in January 2020.
  • The support lifecycles are set (for now) on 18 months for the spring update and 30 months for the fall update.
  • The 1909 fall update is now more of a service pack, with few or no new features.

So, let's review what has happened so far with Windows 10 before talking about timing and migration strategies.

Quick History On Windows 10

When Windows 10 was first released in July 2015, Microsoft's original aim was to have 2-3 feature updates a year. However, 2015 and 2016 only saw one release each. It wasn't until 2017 that Microsoft settled into a twice-a-year spring and fall update release schedule, even if they did release late most of the time.

In the very beginning, Microsoft released every new upgrade first as Current Branch (later renamed Semi-Annual Channel (Targeted)) and four months later as Current Branch for Business (later renamed Semi-Annual Channel) — deeming the release enterprise-ready.

But enterprises didn't adopt Windows 10 as fast as Microsoft had hoped — although it is now installed on over 900 million devices. Large organizations struggled to keep up with the pace, settling on no more than one update a year. Microsoft, desperate to move them to Windows 10, extended the support window of fall releases to 30 months.

In addition, a few months ago, the rumor mill kicked around a few different scenarios about what is happening to the twice-a-year release schedule, as this year's fall release 19H2 looks like more of a service pack than a feature update.

For more information, check out Juriba's timeline of Windows 10 versions.

What Is The Status Quo?

Right now there are several tracks for Windows 10 updates. With the above-mentioned new changes, enterprises have these decisions to make:

  • Update every six months (fall and spring update)
    • This option is suitable for organizations who have embraced Evergreen IT fully throughout their IT.
    • Organizations will have adequate processes, tooling, and methodologies in place to manage this upgrade pace easily (as Business as Usual).
    • This option allows them to get the latest feature updates as soon as they become available.
  • Update every year (fall update)
    • This option will be pursued by most of the larger organizations.
    • Enterprises will have finished evaluating, testing, and piloting before the fall update is released, and then will move into broad deployment.
    • As the fall updates receive 30 months of support and they start testing up to 6 months before, they essentially have 3 years.
  • Update every two years (fall update)
    • Some organizations, especially those with a large number of critical legacy LOB and custom applications, might consider migrating every two years by moving onto the fall update.
    • Theoretically, you could split your organization into two waves, which would mean about half of your machines would be staggered to the next release.
    • Unless very tightly managed, this could result in chaos as it means maintaining duplicate images, application versions, and much more.

Please note: There is the Long-Term Servicing Channel (LTSC), which doesn't need to be updated for 10 years, but as it isn't feasible for broad deployment in enterprises, we will not discuss this option.

What This Means For The Future

No matter which direction you choose, one thing is clear: Microsoft has departed from big bang migrations every few years and embraced an Evergreen IT management approach that requires smaller, more frequent updates. This mantra is not only deeply embedded in Windows 10 (as the name Windows-as-a-Service suggests) but also in other products, such as Office 365, Windows 10 Server, SCCM, Intune, and others.

But there is a dangerous pitfall that enterprises forced to make a decision could fall into: By allowing enterprises 30 months of support and making this year's fall update (and potentially future ones) more service pack-like with few to no new features, organizations who have struggled so far to depart from their big-bang ways could use this as an opportunity to upgrade every 2-3 years.

Devices that don't have the latest features could be missing integrations and enhancements that make processes faster, take up less memory, and run more efficiently. Also, while a device might, on paper, have the proper specifications to handle the newest version, if it has been 2 years since the last update, it could cause a slowdown that will cost your organization time and money.

Delayed upgrades also increase the learning curve of the refreshed OS because several feature update versions have gone into this update, so the change is more dramatic than if it's made incrementally. And it can be demotivating for your employees to be using an older OS than they do at home.

Employee efficiency is another key issue when operating on an older OS. Besides the features added to the new Windows 10 version, the user experience is also improved. These improvements are based on user testing and feedback about how real-world people use the OS. An older version could have significant UX issues, causing frustration and loss of time in your employees.

Conclusion

Evergreen IT will become the new norm for all organizations — sooner rather than later — and companies who realize it and adapt accordingly will have a significant competitive advantage. As with any major undertaking, this transformation will take strategic planning, right methodology and tooling, organizational restructuring, a change of mindset, and full C-level buy-in. Keep that in mind as you consider how you will move onto Windows 10 and as you design an efficient upgrade methodology for the future.

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