Windows 10 Free Upgrade Deadline of July 29th is coming quickly!If you haven’t started your deployment plan already you may end up paying for your procrastination.

If all of your workstations are licensed using SA or included Windows 10 upgrade media, then you may be able to procrastinate a little longer. However, if you have a stockpile of Windows 7, 8, and 8.1 systems using OEM copies of Windows, you may want to pull out the calculator and start adding up the cost savings of jumping on the free Windows 10 bandwagon.

By the numbers, let’s use some round estimate numbers for a quick estimation:

  • Small business 20 systems at $200 per license is $4,000 in licensing cost saved
  • Medium business 50 systems at $200 per license is $10,000 in licensing cost saved
  • Larger business 200 systems at $200 per license is $40,000 in licensing cost saved

Hopefully that helps put into perspective why you need to go, go, go now!

Granted, you can’t just jump in headfirst without proper planning. Here are some of the items you need to review:

  • Windows 10 hardware requirements
  • Software compatibility with line of business applications
  • End user “what’s coming” schedule/communications/training sessions
  • Tested backups of your systems
  • Full deployment plan
  • End user training sessions

The most common questions that come to mind are:

“Can I roll back to my original operating system?” Yes. When you upgrade, the installation will automatically back up your system, giving you a restore point that is accessible to you for 30 days. Learn more about Windows 10 Recovery Options.

“When I use the free upgrade to Windows 10 and my system crashes a year later causing me to reload from scratch, will I have to buy Windows 10 again?” No, according to MS support forum and FAQ:

Once you’ve upgraded to Windows 10 using the free upgrade offer, you can reinstall or perform a clean installation on the same device. You won’t need a product key to re-activate Windows 10 on the same hardware.”

“When I use the free upgrade to Windows 10 and change out my motherboard or hard drive will it be recognized as a new system? Will I have to buy Windows 10 again?” That depends on what is changed, but if significant system hardware is changed just like any other previous Windows license it may require reregistration and, in some cases, a new license.

For more information on Windows 10 help, here is a Microsoft support article that also includes some helpful information for end users.

Okay, I’m onboard, so how do I get started?

Go to Microsoft’s Specifications site and review.

To test, I would recommend picking out systems you have already cleared as ready to upgrade. Create and test a full backup of the system (a great method for this is to use the Veeam Endpoint protection). Microsoft will include a 30-day rollback option, but I always like to have a backup for my backup. Then go to the Microsoft site to download your installation media.

If the update to Windows 10 has already downloaded to your PC and is prompting for installation, you can install immediately or schedule the upgrade.

Upgrade and test everything. Once you have confirmed and sufficiently tested everything, document any changes for end users and deploy to the rest of your site. Don’t forget the end users need to test and document items they struggle with. It will save you and your end users frustration later.

My final tip is the most common problem I have experienced that delays the installation is the update screen hangs during installation, like below:

Windows 10 Free Upgrade Deadline of July 29th is coming quickly!

Run the Windows Update Troubleshooter in the background to fix the issue.

If you need help with your Windows 10 free rollout, you can send us an email or give us a call at 502-240-0404!