In the past, there was a certain longevity tied to Windows desktop releases. Generally speaking, Microsoft only released new Windows versions every few years. In contrast, Microsoft has more recently adopted a semi-annual release schedule for Windows 10. This means that Microsoft provides a major feature update twice each year. While there is something to be said for not having to spend years waiting for new Windows features, Microsoft’s current approach to Windows 10 releases complicates the deployment planning process.

Before the new, Windows 10 way of doing things, deploying a new version of Windows required a massive amount of effort. This effort wasn’t so much tied to the physical deployment process, although that could sometimes be complicated too; rather it was the pre-deployment testing that was so time-consuming. New Windows releases were notorious for breaking applications, and so extensive testing was required to determine which applications would and would not work with a new Windows release.

Extensive compatibility testing? A thing of the past

Now that Microsoft has moved to a semi-annual release cycle, it has become at least somewhat impractical to perform extensive compatibility testing before deployment of each release cycle. Being that the testing process can take months to complete and that Microsoft releases new feature updates twice a year, a company could almost justify having full-time employees who are dedicated to preparing for the next Windows semi-annual release.

Some organizations have gotten around the challenges of pre-release testing by simply tossing caution to the wind and abandoning the testing process altogether. The rationale behind this approach is that even after the upgrade, their desktops will still be running Windows 10. If an application worked with Windows 10 before a feature update, it should theoretically continue to work after the update is complete. Although this strategy does seem to work more often than not, it is not without its risks.

So what is an organization to do? Thoroughly testing new Windows feature updates can be expensive and time-consuming, while skipping the testing process introduces unnecessary risks. Up until now, a lot of companies have tried to find a middle ground by using one of two strategies.

The first of these strategies is to do basic, rather than exhaustive compatibility testing on the new Windows feature release. While it is true that this approach doesn’t deliver the same peace of mind as comprehensive compatibility testing does, it gives the organization a chance to test its most critical applications and to look for any obvious problems before deploying a new semi-annual update.

Back to basics

The second middle-ground strategy that is sometimes used is to not deploy every new feature update that Microsoft releases. An organization might, for example, choose the deployment one new feature update per year, or perhaps the deployment of a new feature update every 18 months rather than attempting the deployment of every new feature update that Microsoft releases. The advantage of using this approach is that it gives IT pros a lot more time to test updates, and it does not bog down the IT department the way that more frequent testing might. The disadvantage to this approach, however, is that besides missing out on new features, deferring feature updates can complicate an organization’s patch management strategy.

So as you can see, none of the strategies that I have described are ideal. There are significant pros and cons associated with every one of these strategies. Recently, however, Microsoft has introduced a new option that has the potential to address this issue once and for all.

Enter Desktop Analytics

Microsoft’s answer is to allow a machine-learning algorithm to handle the compatibility testing for you. This solution, which was only recently made available through public preview, is called Desktop Analytics. Desktop Analytics is a cloud-based service that integrates with System Center Configuration Manager, and will eventually also work with Microsoft Intune. Its job is to use artificial intelligence to assess your organization’s update readiness before you attempt to deploy a Windows feature update. Desktop Analytics is an expansion of the already existing Desktop Analytics’ job is to compile an inventory of the applications that are being used throughout your organization, and then determine whether or not those applications will be compatible with the latest Windows feature release.

On the surface, this approach sounds a lot like the way that Microsoft has done things in the past. After all, Microsoft provided application inventory and compatibility tools even in the days of Windows XP. However, there are a couple of key things besides the use of artificial intelligence that makes Desktop Analytics different from some of the tools from the past.

First, Desktop Analytics looks at both the applications and the device drivers that are being used throughout your organization. It compares that list to the applications and device drivers that are being used by other Microsoft customers. If issues are identified, the software provides advice on how you might be able to work around the issue.

The second key difference between Desktop Analytics and some of the tools that Microsoft has given us in the past is that Desktop Analytics works to simplify your Windows pilot deployment. The idea is that even if Desktop Analytics tells you that all of your organization’s software is fully compatible with the next Windows feature release, it is still a good idea to do some compatibility testing, just to make sure. As previously discussed, however, comprehensive compatibility testing can be expensive and time-consuming. That being the case, the Desktop Analytics tool recommends specific machines for use in pilot deployment testing. Its goal is to find the smallest possible number of machines that collectively represent every application and device driver used throughout your organization.

What you need to run Desktop Analytics

Desktop Analytics has the potential to greatly simplify the preparation for new Windows feature releases. To use Desktop Analytics, you will need an Azure account, and you will need a supported Windows 10 license subscription. Microsoft includes Desktop Analytics with Windows 10 Enterprise E3 and E5, Microsoft 365 F1, E3, and E5, Windows 10 Education A3 and A5, Microsoft 365 A3 and A5, and Windows VDA E3 and E5.

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