Still undecided about Windows 10? Here's how to reserve that free upgrade

The July 29 deadline looms. Here's what you need to know to reserve your free upgrade, even if you're planning to stick with Windows 7 or 8.1 for now

Still undecided about Windows 10? Here's how to reserve that free upgrade
Credit: flickr/Robbie Biller

As we count down to the end of free upgrades to Windows 10, many of you have asked if you should reserve your free upgrade by installing Windows 10 on your Windows 7 or 8.1 PC before July 29, then roll back to your original version of Windows. My short answer is probably not.

If your Windows 7 or 8.1 system works well and you don't see anything in Windows 10 that particularly rings your chimes, there's nothing wrong with sticking with the devil you know. Microsoft may be making it hard to keep Win7 and 8.1 machines up-to-date, but it's still on the hook to supply security patches for Win 7 SP 1 until Jan. 14, 2020, and for Win 8.1 Update 1 until Jan. 10, 2023.

That's a contractual obligation. Those dates aren't going to fade into oblivion next week.

If you're the kind of person who has to have the latest technology -- phones, cars, watches, refrigerators -- you've probably already jumped at the upgrade. But for everyone else, the change deserves some skepticism, particularly in light of Microsoft's hell-bent push to convert the world.

For those of you who haven't been following along, the key is something called a digital license (formerly known as a digital entitlement), which Microsoft stores on its servers. The digital license says you (identified by a Microsoft account) have a right to run Windows 10 on a particular system.

There are still many unanswered questions about digital licenses, but for upgrade purposes, if you have a "genuine" version of Windows 7 SP 1 or Windows 8.1 Update 1 running on a PC, upgrade that PC to Windows 10, and log in to that upgraded PC with a Microsoft account on or before July 29, Microsoft is supposed to remember -- forever -- that the PC has a genuine license for Windows 10.

You can subsequently go back to Windows 7 or 8.1 (or install Ubuntu, turn it into a Chromebook, or run DOS 3.2 for that matter) and as long as you don't change the motherboard, the machine will forever be Windows 10 "genuine."

To reclaim the license, all you have to do is install Windows 10. If Microsoft's servers don't recognize the system, you can log in to the Windows 10 changeling with your anointed Microsoft account, and it'll be activated -- in theory. We don't have a lot of experience with digital licenses tied to Microsoft accounts, but if the logon doesn't work that easily, activation is a phone call away.

About a billion people are probably wondering: If you aren't ready to switch to Windows 10, why not hedge your bets, claim the free upgrade for your PC, then go back to running whatever operating system you like? First ask yourself: Is it worth saving the $119 retail price of Windows 10 to spend all this time and effort reserving a free upgrade -- especially if you aren't really keen on upgrading? After all, there are plenty of perfectly valid reasons why you might never want Windows 10 on your PC.

But if you're sitting on the fence, you might want to at least think about upgrading to Windows 10 using a Microsoft account -- even if it's a fake one you don't use for anything else -- then roll back to Win 7 or 8.1.

If you decide to make that leap, you have three options:

1. Upgrade and pray. That's the approach Microsoft recommends -- and the one you're funneled into with all of the "Get Windows 10" folderol. You can start the upgrade manually by signing in to Win7 or Win8.1 with a Microsoft account, venturing to the Windows 10 download page, choosing Upgrade this PC now, and following the prompts. Once Win10 is installed you can in theory, and within 31 days, roll back to the operating system you once had. Unfortunately, the rollback doesn't always work, which is why very few experienced Windows graybeards recommend this approach.

2. Swap out disks. If you're adept at swapping out hard drives, have an extra hard drive handy, have an activation key for Win7 or 8.1, and don't mind booting once from a USB drive, this is the cleanest and easiest option. Start at the Windows 10 download page and choose "Download tool now" to create a bootable USB drive. Turn off your PC, unplug the current C: drive, stick in the new C: drive, boot from the USB, and install Win10. Microsoft has full instructions for activating the new copy of Win10 with your old Win7, 8, or 8.1 product key. As long as you don't mind physically swapping the disks, this is a very reliable method for keeping the old and new versions separate. If you change your mind, just turn your machine off, unplug one drive, plug in the other, and you're clean as can be.

3. Make a full image backup. If you don't relish the thought of plugging and unplugging hard drives, this is a reasonable alternative. I'll avoid the religious debates by saying both Acronis True Image ($30) and Macrium Reflex Free work well. Both will require a substantial amount of free space on your hard drive -- enough to hold a full image of your C: drive -- and you'll have to create "rescue media" to restore the drive image. Jason Fitzpatrick at How-To Geek has the full details. Once your C: drive is backed up, you can play with Windows 10 till the cows come home. If it all goes shiny side up, restore your original drive from the backup.

Don't forget: as I said earlier, Microsoft will continue to provide security patches for Windows 7 SP 1 until Jan. 14, 2020, and for Windows 8.1 Update 1 until Jan. 10, 2023. You shouldn't feel pressured into upgrading right now. My guess is you'll want a new computer before your current version Windows starts rolling in the sand.

But if you really want to spend the time and energy needed to hedge your bet -- and save $119 in upgrade costs should you decide one day to assimilate into the Win10 borg -- now you know the tricks.

To comment on this article and other InfoWorld content, visit InfoWorld's LinkedIn page, Facebook page and Twitter stream.
From CIO: 8 Free Online Courses to Grow Your Tech Skills
Notice to our Readers
We're now using social media to take your comments and feedback. Learn more about this here.