Should you migrate to Windows 10 in 2016?

miguel angel aranda windows 10
Credit: Miguel Angel Aranda

Should 2016 be the year you migrate to Windows 10 and Microsoft’s new model of windows as a service? What are the factors in deciding if you should upgrade your users to Windows 10 this year?


In my previous article I looked at the marketing and hype surrounding the release of Windows 10 in its first six months. Microsoft have vaunted the rapidity of the rollout so far (4 times faster than for Windows 8), the fastest of any OS so far, and that over 200 million users are already on the new operating system according to Yusuf Mehdi, of Microsoft. He goes on to say that 76% of their enterprise customers are in active pilot.

This week I will look at the pros and cons of doing an enterprise upgrade to Windows 10 in 2016, so that you can begin to form a clearer picture for yourself of whether you want this year to be year that you do this upgrade.

matti mattila upgrading to windows 10 Matti Mattila

The push from Microsoft

The rapid rollout of Windows 10 is, of course, due in large part to it being given away free to users of Windows 7 or 8. Furthermore, the penetration of Windows 10 among home users will probably increase dramatically this year as Windows 10 will become a recommended update in 2016. The majority of Windows’ home users have their system configured to automatically download and install recommended updates and so with this move Microsoft will go beyond the early adopters and address the majority of Windows users who have not made a conscious decision to upgrade.

Potentially, it is not just home users who will find themselves automatically updated to Windows 10. Microsoft state that the only systems excluded from the automatic update are Enterprise and RT and embedded versions of 7 or 8, or machines serviced through WSUS (Windows Server Update Services). Domain-joined systems that have eligible versions of Windows and aren’t WSUS managed will be updated if automatic updates are turned on.

If you have non enterprise versions of Windows 7 or 8 in your environment that are not controlled by WSUS, and you want to avoid them being automatically upgrade to Windows 10, then you need to use one of the methods described by Microsoft.

Since the November Threshold update of Windows 10, Microsoft considers it enterprise ready and, according to Myerson, we are entering "the Renaissance of the Enterprise PC." Tools like Windows Update for Business will give IT complete control over the update process of all Windows devices in the Enterprise. The message from Microsoft is clear. Windows 10 is the future and they want everybody to be on it as quickly as possible.

portal gda
Portal GDA

Why going for it this year could be a good choice

Microsoft’s aggressive pushing of Windows 10 to home users will, of course, provide some benefits to the enterprise environment. Potentially a large percentage of corporate users will have familiarity with Windows 10 before you perform your rollout, so you may be able to count on a lower impact on your support desk when you the rollout is complete than you would normally experience with an OS upgrade. A survey of your user base during planning could allow you leverage this.

Various features of Windows 10 will also appeal to many of your users. The Cortana search engine, virtual desktops, the action center, the support for touchscreen, the battery saver functionality, the ability to setup file histories, and the ability of Edge to cast to DLNA and Miracast devices are all interesting new features that may appeal to the corporate user.

If you’re buying new hardware based on Intel’s Skylake architecture, then you should deploy Windows 10 by necessity, as Microsoft will only provide Windows 7 or 8 support on this architecture until July 2017. Mobility devices based on Qualcomm’s 8996 chips, or computers using AMD’s Bristol Ridge, and Intel’s future Kaby Lake, however, will not have Microsoft support for Windows 7 or 8 at all.

If you progressively upgrade hardware, then you will find yourself with a heterogeneous OS environment unless you upgrade legacy machines in line with your new purchases. If your strategy is to purchase new hardware running the same version of Windows as your current systems and upgrade later, then you’re going to have to finish your upgrade by July 2017.

From a management and technology perspective, Windows 10 offers interesting security management features. Active directory access for Azure Cloud, for instance, will help alleviate an ongoing concern of the insecurity of mixing desktop and web identities, where users can be tempted to re-use corporate passwords, potentially compromising them. With built-in biometric and two-step authentication possibilities, Windows 10 also gives a better toolkit for securing the user environment.

Finally, enterprise data protection will give us the ability to protect key corporate data, while allowing the user freedom on non-corporate data.

couldnt update to windows 10

And why it may not be

Upgrading an OS is driven by many factors: is support running out? Does the new version provide significant improvements for our users? Does it increase security and simplify management? Does it facilitate mission-critical projects that can’t be done otherwise? In other words, are there urgent pain spots that can be solved by the upgrade? If you cannot answer this question with a “yes,” then  where is the urgency to migrate in 2016?

Then there is the question of readiness. Can we budget the upgrade this year? Gartner estimated XP to Windows 7 costs of about $1000 per user, and while those costs were probably exaggerated, there is no denying that a Windows migration is an expensive endeavor.

The big question is, though, “is Windows 10 ready for the corporate environment.”  Evidently, Microsoft will say yes, but history has shown that Windows versions don’t tend to be stable enough until they’ve gone through a first service pack. Can we consider the November threshold update a valid service pack? While it seems to qualify, it was also strewn with issues. Many users reported the update got stuck (anecdotally, of the 9 machines I have at home, that I’d migrated to Windows 10, 4 got stuck and one refused to update at all, eventually causing me to do a clean install). It deleted certain non-Microsoft software, and changed default applications. Ultimately, we are still talking about an OS that has been in general release for less than six months. This seems like a very short period to allow for thorough checking of issues, compatibility with legacy hardware and software, and creating the confidence that we can give the migration a go.

A report by Adaptiva of 127 IT professionals conducted online claims that 63 percebt of companies are planning to migrate important number of machines to Windows 10 this year. This report has been given wide coverage in the press, including some exaggerations that say things like “63 percent of enterprises are planning to move their systems to Windows 10 by the end of this year.” Personally, I take such reports with a pinch of salt and a survey of 100 IT people isn’t going to be a major factor in my decision. However, if there really is a rush to Windows 10 this year then there is a risk to be considered in making your decision to migrate. Internal resources are often not enough to perform such a migration. If, indeed, two thirds of the companies in the world are all looking to migrate at the same time, then the pressure on such resources will push up prices, making it potentially much more expensive to migrate in 2016, then waiting until the pressure has eased.

In the end your decision to migrate or not to Windows 10 in 2016 should be, as usual, driven by business concerns. If you have compelling reasons to upgrade, then that’s fine. Make sure, though, that you’re not being unduly influenced by media and press reports.

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