Why You’ll Want to Upgrade to Windows 10 This Week

After months of pushing us to upgrade to Windows 10, Microsoft is cutting off the free upgrade on July 29th. Let’s review the facts and dig into both why and how you should upgrade today.

Microsoft warned us Windows 10 would be free for only a limited time. After months of bugging us, Microsoft will be cutting off the option for a free upgrade on July 29th, just five days from today. Even if you’ve decided to keep your current operating system, read on, and I’ll explain why you should upgrade today and; how you can both upgrade AND keep your old operating system. Confused? Keep reading.

Should You Upgrade? Maybe.

Your PC has been working fine under Windows 7 or 8, so why rock the boat? Andre makes some excellent points about keeping your PC just the way it is. Clients I work with tell me horror stories about upgrading to Windows 10. Since I do computer repair for a living, I usually only hear about the problems. If you’re upgrading from Windows 8, I never see problems. Microsoft is so confident Windows 8 users can upgrade they guarantee your computer can handle the upgrade.

same upgrade service

People love free stuff- just ask the food samplers at your warehouse store. When it’s time-limited, people have a call to action. That doesn’t mean they should, though. People started worrying about Windows 7’s retirement date when Microsoft retired Windows XP. You’ll have until 2020 for Microsoft to fully end support for Windows 7. End of support isn’t a fair reason to upgrade to Windows 10 this week.

Microsoft added an interesting curve ball: digital entitlement. Once you upgrade to Windows 10, your computer’s hardware is automatically activated. That lets you download and reinstall Windows 10 at any time. That’s a game changer from Microsoft.

Why Digital Entitlement is Awesome

With the average Windows 7 or Windows 8 machine, reinstalling your operating system is an all-day affair. First, you put in the operating system, assuming you can find the disks. If you can’t find the disks, you can download a generic version and then call Microsoft to activate it. Microsoft recently made it harder to find old versions of operating systems, though there are a few tricks.

After you install those operating systems, you’ll wait to do all the updates. You’ll need to do that with any Windows version, but the older the operating system, the more updates you’ll have.

Photo by Matti Mattila - http://flic.kr/p/x5sJjM

Photo by Matti Mattila

Then you have drivers. Those tiny pieces of software enable the hardware on your PC. Even if you have the disks from the manufacturer, those drivers probably need an update. Many times those just show up as generic icons. If you knew what they were, you could download the software. Third-party programs help with this, but the hunt takes time.

Enter Windows 10 digital entitlement: you download Windows 10 and install it. Microsoft tracks the hardware and automatically activates the license. Since it’s new, it has most of the latest drivers. I rarely see hardware that Windows 10 can’t update after a few tries. An all-day affair now just takes a few hours.

Getting Digital Entitlement and Keeping Windows 7/8

After installing Windows 10, Microsoft gives you 30 days to change your mind and return. For people that felt forced into upgrading 10, that rollback is a lifesaver. To get your digital entitlement, install Windows 10 and then roll it back to your current version.

Again Andre points out that this rollback has glitches. It’s as reliable as Windows; we’ll just leave it there. In my experience, a bad Windows 10 installation has problems rolling back. That makes sense. If the operating system isn’t working right, it’s probably not going to roll back correctly.

You have a few other options instead of rolling back from Windows 10, but it requires prep work, and the clock is ticking. They’ll also require a little more technical skills than just pressing install.

Before You Start

You should be backing up your computer anyway, but it’s particularly important in this case. A few false moves, and you could erase everything. Since this can render your computer useless, you should plan for downtime. If your hardware has problems, they’ll show up during an operating system install. The typical failures I see are due to failing hard drives.

Option 1: Clone Your Drive

To clone your existing drive, you’ll need an external hard drive to clone your system. This clone, by definition, is an exact backup of your system. If all you care about is digital entitlement and don’t intend to move to 10, install Windows 10 on the clone and just never use it. In the future, however, you are entitled to the upgrade should you ever want to make the move for free.

What is a hard drive?

Option 2: Install Windows 10 on a Spare Drive

You’ll have to feel comfortable opening up your computer to try this idea. Pull out your existing hard drive and put in a blank one (or any drive you’re okay erasing). This drive could be a cheap refurbished drive or a drive you pulled out of an old machine. You don’t have to use this installation; you just need to use it long enough to activate the license.

To do this, you’ll need to create an offline installer on a USB flash drive or DVD. After you boot off that installer, it’s going to ask for your Windows 10 key. Microsoft lets you use your Windows 7 or Windows 8 license for this. Type in that key, and Windows 10 will use that as part of digital entitlement.

When you’re done with Windows 10, you can get rid of the drive or keep it around. Microsoft doesn’t care since they’re tracking your license. If Microsoft detects major changes to your hardware, they might ask you to activate it again. Usually, the size of your hard drive doesn’t make a difference.

Option 3: A Fresh Start With a Clean OS

Sometimes a clean start is the best way to go. If your computer’s more than a few years old, it’s probably collected a bunch of junk. All those Flash updates add up! Hard drives have a limited life span. Starting your computer with a new hard drive, even a mechanical one, will make it feel faster. You’ll have just what you need on your computer, eliminating junkware and successive updates. This option would be the time to consider moving to an SSD if your budget and space requirements allow it.

The process would be the same as option 2, just keep that spare drive in the computer and use your existing drive as a backup. If you don’t like Windows 10, you can then clone your Windows 7/8 installation onto your Windows 10 system. That’s option 1, just reversed.

The Value Of Old Hardware

Windows 7 has been out for about seven years, so a ton of old hardware can run it. Search your basements and garage sales; the odds are there’s a Windows 7 machine out there. Now is the time to install Windows 10 on it to get digital entitlement.

People upgrade their computers even when there is nothing wrong with the old computer. That old computer might have slowed down or got so infected with viruses it wasn’t worth fixing. Instead of recycling it, Windows 10 digital entitlement lets you reuse it.

As mentioned earlier, starting a Windows 7 or 8 installation from scratch is a hassle. With Windows 10, you can easily get a clean start with all the drivers you need. If you can’t use it yourself, that Windows 10 system can be used by someone else. Donate the computer somewhere along with that clean, freshly installed Windows 10.

Time Isn’t On Your Side

I hate to rush you, but July 29th is fast approaching. You’ll need to make a decision soon and get to work. If you wait, you can always buy a license for Windows 10, but you’ll pay full price.



  1. Andre

    Excellent article Dave. Its a great project which not only encourages backing up your system, but can save you $119 if do decide you want to switch to Windows 10.

  2. carmen

    Since I’m not ready to make the switch, I burned Windows 10 to a DVD after following the prompts on the Windows 10 pop-up. With the deadline approaching, I’m feeling anxious, thinking the DVD won’t work when I want it to (since I don’t have a lot of experience burning DVDs).

    I just tested out the DVD and with auto-play, I get the screen: Do you want to allow the following program to make changes…Program Name: Microsoft Windows….E:\setup.exe
    1. Based on that, does my Widnows 10 DVD appear to be working?
    2. Do I still get the “digital entitlement” mentioned above if I wait a year to install, using my DVD?

    • Dave Greenbaum

      You have to install, make sure it activates, and roll back to get digital entitlement.

  3. holdum333

    Excellent blog! Thanks friend! Also excellent reply Dave Greembaum. You are right on target. Once you get the digital entitlement, you’re home free!
    PS Way to go Kansas. I’m a old Okie countryboy. That makes us neighbors my friend!

  4. holdum333

    Sorry I’m late responding to this blog, but like the old saying ” Never to late to respond to a good blog”
    Actually I just now made that saying up LMAO.
    Thanks Dave! You are appreciated my friend. keep the good blogs coming friend!
    Okie from Muskogee!

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