upgrade to windows 10At the time of writing this, Windows 10 is pushing about seven percent of market share. And while it’s outclocking its predecessors at this point in their releases, many IT shops are uneasy about pulling the trigger. We’ve generally seen the hesitation stemming from the change in how the upgrading and licensing will work work and how painful the process is of getting users to adapt. Microsoft has also said that Windows 10 will be the last operating system upgrade that you can buy. Everything OS related from here on out will get incremental updates. So, new can be scary.

Windows 10 Licensing, What the What?

Here are some good, in-depth articles from our licensing specialist Seth on Windows 10:

In short, if your business has qualifying licenses of Windows 7 Professional, Windows 7 Ultimate, or Windows 8.1 Pro, you can upgrade for free. If you have the Enterprise licensing of Windows 7 or 8, you must have Software Assurance to upgrade for free. (Find out more about Software Assurance and whether or not you should get it with your Microsoft licenses here.)

If you are not sure what type of license for Windows you have, there is an easy way to determine that. If your version of Windows says Enterprise at the end, your company has a Volume Licensing Agreement with Microsoft. If your version says Pro, it is a retail version that came with your system from the manufacturer or was bought at a retail establishment of some sort (also called OEM). If you are really unsure of where you stand when it comes to your Windows licensing, give us a call and we can figure it out together. Given the mixture of OEM licensing on some machines, mixed with any volume licensing you may have purchased in the past, it could get confusing pretty quickly.

Three Ways to Upgrade Your Environment

You’ve got options when it comes to upgrading your organization to Windows 10, and like any good consultant will say, which one you should go with depends. Your upgrade method will depend on the number of users, your licensing, your geographic locations, and your information security practices…just to name a few factors. So, I’m going to lay out the three ways you can go and some basic rules of thumb, but if you have questions about which route to take, you can email us or call.

Windows Deployment ToolKit

This kit allows you to quickly create a provisioning package to use to customize each device without having to reimage. You can download it here.

You’ll probably want to go this route if you have a large-scale environment and you want to use a tool like System Center to push out the changes and updates. It is also prudent to use if you are creating a base image for all machines and you are looking for an easy way to deploy one standard image across multiple machines.

Windows Media Creation Tool

With the Windows 10 Media Creation Tool, you can load everything you need on a flash drive or burn it onto a DVD and go workstation to workstation to upgrade. This method is best for smaller environments, since it’ll take a bit of manual work. You can download the Windows Media Creation Tool here.

In-Place Upgrades

And, lastly, you can just push Windows 10 through the in-place upgrade function. Eligible Windows 7 and 8 machines should get two pop-up notifications, the first of which to set up their reservation of Windows 10. Microsoft is doing this to help spread the release over time. The second message that will pop up from the notice to start the download process. If your Windows 7, 8, or 8.1 machine is behind on Windows updates, it will make you install all of the Windows updates that are needed before it will even prompt you for the ability to reserve your copy. The option to reserve a copy comes from Windows update itself. You can go this route and let each user be the master of his or her own destiny, or you can run the in-place upgrade on everyone’s machine yourself.

Important Things to Note

If for some reason something goes sideways during an upgrade, don’t worry, it should revert back to a backup of the machine before the upgrade started. I haven’t seen any data loss occur after a failed update. That being said, after a machine is upgraded to Windows 10, you might want to check for that backup because it might still be saved on the drive and could take up considerable space — in some instances, 20Gb. The way to find these files is to do a disk cleanup and then run it again looking to “Cleanup System Files.” If you’re happy with the upgrade and feel safe, go ahead and delete it so you can get that space back. Keep in mind that once you do that there is no turning back. You are on the version of Windows 10 you installed.

Happy updating! Send us an email or give us a call at 502-240-0404 if you have any questions about your licensing or what upgrade method is best for you.