In late June I was approached to record some short technical overview videos on Microsoft 365 Business, and now that they are recorded and published, it’s time to review them, and provide some additional resources and any important updates since the content was created. This is the second video in the series, the focus is on assessing existing environments.

This is a fairly broad topic, so a few decisions were made including to only mention tools that were easily available from Microsoft, and even better if they provided long term value. Both of the tools that were mentioned, the Microsoft Assessment and Planning Toolkit, or Windows Analytics met the first requirement, but for a cloud focused organisation the clear long term winner is Windows Analytics. This tool not only gives you a current inventory of your PCs and their readiness to upgrade to Windows 10 Pro (remember, this is a series on Microsoft 365 Business, so we usually aren’t looking at Windows 10 Enterprise or Education editions, which Windows Analytics also supports).

Some of the hurdles you will need to overcome initially with Windows Analytics are that you need to attach an Azure subscription to your Microsoft 365 Business Azure Active Directory tenant, which can be done pretty easily through CSP or even a pay as you go account. Pay as you go requires a credit card number, but if you are only using Windows Analytics those costs will be zeroed out at the end of each month. If you are going to be leveraging more Azure services (my guess is you will, but that’s something I can focus on in a later post), then the CSP path makes more sense.

Once you’ve got the Azure subscription set up, the next steps include setting up Windows Analytics, which I have traditionally done through the Operations Management Suite portal, but need to get used to leveraging the functionality natively within the Azure Portal as the OMS functionality moves across. Add Upgrade Readiness as a solution, and then you need to start enrolling the target devices. For your Windows 7 and Windows 8.x PCs, there’s a script you need to customise and run, and for Windows 10 devices you can do it through a Group Policy or Local Policy (if domain joined and pre-Intune enrolment) or you can enrol devices through Intune with an MDM policy, which makes more sense for a cloud first organisation.

This raises the question, why would you enrol the Windows 10 Pro devices if they are already running Windows 10 Pro? Well, that’s an easy one, you will start getting insights into readiness for the latest Windows release, e.g. upgrading from 1709 to 1803. You can also enrol the devices into the Update Compliance solution which allows you to get a snapshot of security updates that are deployed or needed. There are also a host of additional capabilities that Windows Analytics solutions can provide, including letting you know what versions of Office and other apps are currently deployed, the compatibility of existing hardware, software and drivers, and much more.