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Windows 10 Pilot = Key to Success

With the free upgrade deadline for Windows 10 approaching on July 29, more businesses are thinking about migrating to that desktop OS version. But the vast majority of commercial concerns — particularly those with thousands of users and OS licenses — already obtain Windows from Software Assurance or Volume Licensing contracts. They aren’t under the same time pressure to take advantage of “free” upgrades because they pay over the life of their contracts anyway. For such organizations, the real concern is to make sure that key applications and services work properly in Windows 10. They don’t want production desktops and environments to be adversely affected by its rollout and deployment. That’s why initial testing and experimentation in the form of a Windows 10 pilot program can play an important role.

Now’s a Good Time for a Windows 10 Pilot Program

Moving from an old runtime regime to a new one is a demanding task. It takes considerable time and effort, and inevitably ends up costing money. But even for organizations that jumped onto Windows 8 (and market research says there were precious few of them), Window 10 will probably be a necessary migration. That’s because Windows 10 introduces a new model for upgrades and updates, which will keep coming at regular, fairly closely-spaced intervals from now on. That’s in stark contrast to a new major version once every two or three years since Windows NT made the scene in the mid-1990s, now over 20 years ago (Windows NT 4.0 appeared in 1996). Many commercial concerns and large organizations adopted an informal “every-other-release” migration plan in the past because of the time, effort, and expense involved. But it seems that Windows 10 is a matter of “when,” not “if,” for most outfits simply because it’s slated to stick around for a long, long time.

That makes 2016 a great year for organizations that haven’t already started piloting Windows 10 in-house to get going. Organizations can track behind the leading edge of Windows 10, which is simply called the “Current Branch” and represents the most current release of Windows 10 (Version 1511) plus the most current cumulative update and all subsequent interim updates (Build 10586.218 as I write this post). The first milestone after that is called the Current Branch for Business (CBB) which is also based on Version 1511, but which currently rests at Build 10240 at the moment. It’s designed to support staged deployments of new features to match scheduled rollouts typical in most production commercial environment. It tracks about 90-180 days behind the Current Branch, to give organizations time to test and vet upcoming updates, and to plan workarounds for updates that won’t work if put into production. The last stage in the branch structure is the Long Term Servicing Branch, which tracks one year or longer behind the Current Branch, and receives no new features but gets security and other updates necessary for proper operation. It’s aimed at factory floor machinery, POS systems, automated teller machines (ATMs), and other tightly-managed and locked-down systems.

The real bleeding edge is the Insider Preview Branch, which tracks new features as they appear (and which may never go into production).
[Source: TechNet: Windows 10 servicing options]

Despite the appeal of hanging back as far as the Long-Term Servicing Branch, most businesses will be served best by focusing on the Current Branch for Business. Power users and those working on Windows 10 evaluations going forward should stick to the Current Branch for a more forward-looking take on upcoming Windows 10 stuff. But only non-production machines should ever play host to Insider Preview releases.

At the same time, the Windows 10 pilot program can also try out new PCs. This might include some of the latest hybrid 2-in-1 devices (tablet + keyboard such as the Surface Pro 4 or Surface Book) or latest generation laptops (such as the Dell Latitude 13 7000 series). Ditto for desktops (something with a 1151 socket, a Skylake CPU, and an NVMe SSD). This is also a great opportunity to dig into Microsoft’s Azure Active Directory, which provides seamless integration for Office 365 via Azure AD accounts. Interested admins will find lots of cool new features and functions to play with.

The Perpetual Windows 10 Pilot Gets Underway

The most important aspects of any pilot program are to assess the impact of migration on key line-of-business applications and services, and to determine what must change (and what can be maintained) while keeping workers productively and constructively engaged. This also means testing deployment tools, provisioning and rollout tools and methods, and getting everything ready to take into the field. It will actually turn into an ongoing process that happens continuously going forward, because working with Windows 10 means keeping a forward-looking pilot project constantly engaged to track upcoming changes and releases from the Current Branch (or Insider Preview) that will ultimately propagate into the Current Branch for Business.