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It's been more than two-and-a-half years since Microsoft released Windows 10, its Windows-as-a-Service OS. Thanks to a free upgrade option for consumers and tremendous security improvements, adoption generally has been faster than any other Microsoft operating system.

However, enterprise adoption has been slower than hoped for — partially due to the constant changes and confusion around the update release and end-of-life dates, branching/servicing name changes/deletions, as well as a change in major (feature) update frequency to better align with the Office365 release cycle and so forth.


But now, it seems that Microsoft has finally settled on a Windows 10 release and support roadmap, apart from the recent announcement to extend support for versions 1607, 1703, & 1709 for an additional six months for enterprise and educational customers to accommodate the current needs of larger organizations. Microsoft had previously granted the six-month extension to version 1511.

While the support roadmap still might not be set in stone, IT professionals must know one thing: The speed with which enterprises will need to update has picked up significantly. Whoever doesn't get with the program, will risk running thousands of users on unsupported and potentially unsecure versions of Windows 10.

Quick Windows 10 Servicing Primer

Before we look at the roadmap in more detail, just a quick Windows 10 Servicing Model refresher: The new Windows-as-a-Service roadmap consists of feature updates twice a year, one in March and one in September. Each update receives an official name (e.g., Fall Creators Update) and version number (e.g., version 1709) that is year/month of release.

In addition to those major updates, Microsoft will publish monthly quality and security updates. All updates are cumulative, so you can upgrade at any point in time to the latest version. Starting with at least 1709, each new version will receive 18 months of support (barring extensions for enterprises) starting from the day it was first released into the Semi-Annual Channel.

Why is January 2020 Such A Critical Date?

With Microsoft's shift to smaller feature updates twice a year, March and September, instead of a whole new version of Windows every 3-4 years, enterprises will have to adapt to the new update cadence — a much faster pace than they are used to. This means they have to juggle many more release dates and end-of-life deadlines. Because there have been so many moving parts, we decided to create a list of all the important impact dates for you to consider until January 2020.

Why that date? Because the extended support for Windows 7 is due to expire then, and since most enterprises migrated from XP to 7, skipped Vista and Windows 8/8.1, they will be upgrading from Windows 7 to Windows 10 within this 24 month period.

The Windows 10 2020 Roadmap

The following dates are our interpretation of how Microsoft will handle their updates in the future, based on information trickling out of Redmond. In a separate blog post, we will explain our reasoning in more detail. So, without further ado, let's get out your calendars, as here come the most important dates concerning Windows 10 until 2020:

*Please note on deployment — All versions in the future will only have 18 months of service, with both mainstream and enterprise (barring the extensions granted) support ending at same time. For more information, read up on the Windows 10 Servicing Timeline here.


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As you can see from the next 24 months ahead, there will be a lot of moving parts which require adequate and timely management. But rather than trying to defer updates, organizations are well-advised to keep closely aligned with Microsoft's new servicing roadmap — as it keeps your organization more secure and productive. 

Our recommended first steps are to learn more about how to use deployment rings to better time your Windows 10 rollout and how to set up a repeatable process using an automated IT Transformation Management tool like Dashworks

Download Definitive Guide to Alleviating Your Windows 10 Branching Headaches

Barry Angell

Written by Barry Angell

Barry is a co-founder of Juriba, where he is focused on using his experience in IT migration to help drive product strategy, pre-sales and service delivery. He is an experienced End User Services executive that has helped manage thousands of users, computers, applications and mailboxes to their next IT platform. He has saved millions of dollars for internal departments and customers alike through product, project, process and service delivery efficiency.

Topics: Windows 10/Desktop Migration