According to the just released Adaptiva 2018 Windows 10 Enterprise Impact Survey, only 40% (instead of the expected 52%) of organizations have reached their half-way milestone in their initial Windows 10 migration by now.

The biggest hurdles they are experiencing are a lack of time, e.g., IT staff priorities, loss of employee productivity (61.9%), application compatibility (50.24%), as well as the cost of staff, hardware, application licensing, testing and packaging, and infrastructure related to the OS upgrade (41.7%).

While almost all enterprises are feeling the pressure of having to complete the upgrade as soon as possible, may it be because support is running out on Windows 7 or because of the advanced security capabilities, many have procrastinated as long as possible.


However, this is only partially due to the obstacles with the initial migration, because they know, as soon as they are on Windows 10, the relentless upgrade clock starts ticking! And by the way, the same goes for switching away from Exchange and onto Office 365 ProPlus.

Today, I want to clear up some of this confusion by quickly describing the changes before talking about the impact this will have on your application management strategy.

The Most Important Windows 10 Servicing Model Changes In 2017/2018

Keeping up with the complexity around Microsoft’s ever-changing release and support model for Windows-as-a-Service and Office 365 can leave you confused because there is a LOT to consider (e.g., the looming end-of-life deadlines, uncertainty about release dates of new versions, multiple terminology changes, and more-or-less synchronized schedules between Windows 10 and Office 365) and even more outdated and false information floating around! If you are constantly feeling you are behind the proverbial 8-ball with Microsoft’s Windows 10 Servicing strategy, you are not alone.

So, let’s get this sorted out.

One of the biggest announcements that Microsoft made was back in April 2017, when the software giant announced that it will synchronize its Windows 10 feature update release schedule with its Office 365 support update timeline. This means updates are delivered twice a year, in March and September, with each update receiving 18 months of support.

This cleared up a lot of confusion and scheduling mess. However, the order didn’t hold for long. In November of 2017, enterprise and educational customers received extended support for the Windows 10 Anniversary Update (Version 1511). This extension — until April 10, 2018 — makes it almost 2 years of mainstream support, and almost 2.5 years of enterprise support.

In February of 2018, enterprise and educational customers also received 6-months of additional support for Windows 10 versions 1607, 1703, and 1709. This increased the support period for these versions from the new standard of 18 months (20 for version 1607) to 24 months (26 for version 1607).

Windows 10 Servicing Options For Enterprises

Traditionally, large organizations would take at least 18-24 months to upgrade to a new version of Windows, so having to migrate your entire estate to two new versions a year might be too daunting. Therefore, large organizations are scrambling to come up with a different deployment strategy to slow things down a bit.

Basically, you have three options:

  • Splitting your organization into two or more waves and staggering your Windows 10 deployment so that the first group gets version N as soon as it is released, the second group gets version N+1, and so on. Very quickly, you will run parallel environments as well as parallel deployments, so if you are going this route, you need to have an IT Transformation management tool that allows you to keep a tight lid on everything.
  • Going completely Business-as-Usual with your upgrade deployment. As new devices are purchased or break-fix events happen in your organization, the OS is upgraded in a complete Business-as-Usual mode. However, the Evergreen IT approach requires a tight Evergreen application management strategy as well as automation to kick off workflows that let you know which assets are due to be migrated.
  • Skipping every other feature update. A lot of enterprises that I recently talked to have decided to skip every second Windows 10 version and only deal with one upgrade a year. While this theoretically makes sense, you are now dependent upon Microsoft shipping new updates on time and you risk bigger disruptions if your upgrade process takes longer than planned, as the majority of your users will run out of support before you can upgrade them.

The optimal way to roll out these continuous updates depends on your unique situation, but due to this faster pace of Windows 10 feature upgrades, they all have one thing in common — they all require a completely different approach on how we manage our IT assets, may they be hardware or application lifecycles.

Impact On Application Packaging & Testing

Regardless of which path you choose, you will soon find that your application management must be organized in a strategic and scalable manner and managed very closely to allow fast and continuous application testing and packaging.

Instead of one focused, big-bang application packaging and testing effort with a scaled up team and dedicated project resources, your team will now be required to test applications at the drop of a hat, determine which are business-critical or used by the majority of users right away, and have an automated workflow-driven process in place that continuously churns out ready applications.

To achieve this, these six steps are crucial:

  • Rationalize and normalize your application portfolio as much as possible to minimize the number of applications you have to package and test.
  • Categorize your applications by importance and risk (e.g., business-critical, high, medium, and low impact) and by usage (How often used? What’s the % of users for this app?).
  • Define which applications must be tested and how often (e.g., business-critical apps or applications used by 60% of your end users must be tested on every new version of Windows).
  • Define documentation requirements for all your applications (e.g., source mediums, business owner information).
  • Centralize your app management. I cannot stress enough how crucial it is to store and manage your application documentation, executable files/packages and other related data/mediums in a central repository.
  • Create a project framework and define automated workflows that streamline your packaging and testing process by routing the app through from your initial certification and documentation creating stage all the way to release.

When setting up your Evergreen application management process, keep in mind that it needs to minimize manual work and resource overhead (e.g., Access Capture spins up a virtual machine and triggers an email to the application owner with username and password which will be wiped clean as soon as the testing is completed and the app routed to the next step). Furthermore, the process must be down- and upgrade-able as your workload changes from day to day.

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