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Microsoft Operating Systems Are Crazier Than Trump Tariffs

We’re finally seeing closure on the craziness of Windows 11 taking the reigns from Windows 10. I don’t honestly know how I feel with the exception that this has been the craziest transition I’ve been through. Between the hardware requirements constantly changing and the chaos of dealing with how to keep software and settings on people’s new computers, this has been the craziest ride Microsoft has given me.

Over the past 20 or so years I’ve been doing this through retail, Microsoft has given me plenty of reasons not to have hair. I thought it would be fun to outline the operating system transitions I’ve experienced over the last bunch of years. Luckily I have most of my hair even though it’s covered by a baseball cap most of the time.

When I first started this business Windows 95, 98 and Me were the current operating systems. Pretty much any system that was compatible with Windows 95 would also be compatible with 98 and Me. The problem at the time was it took a solid 2-3 hours to install one of these operating systems between prepping and formatting the drive, actually installing Windows and hunting down all the drivers.

Customers were eager to have their old PC’s upgraded to Windows Me, only to find out that Me was plagued with little bugs that the previous two versions didn’t have. Many customers had us downgrade a week after upgrading them. I never knew how to handle that seeing as though they had already paid for my labor plus the upgrade license. So, I performed the downgrade for free.

Windows 2000 was the next iteration which caused major issues for us and customers. It was around this time that I setup a few large servers in the shop to store customers’ data while we performed the upgrades. Upgrading from 98 to 2000 required all the data to be stored somewhere, then upgraded, then the data migrated back.

We took hours of time and gigabytes of storage backing up files, reinstalling and moving files back. Bear in mind that in the early 2000’s solid state drives didn’t exist and most were IDE interfaces which were extremely slow. In any event, at the end of the day customers were left with an operating system that was completely different and not compatible with most of the software they already owned. It was a mess.

Luckily Microsoft decided to refine 2000 and re-badge it XP. It’s fair to say all of the software that worked on 2000 systems was fully compatible with XP. It was also nice to see a familiar layout just with a prettier color pallet. Oddly though, we had many customers reach out to have the colors changed to the drab 2000 style they were used to. At the end of the day Windows XP was nothing more than a prettier 2000.

For some reason Microsoft decided to create Vista. They went from two versions of XP to six versions of Vista. Hardware requirements changed drastically. Though it technically ran on older hardware, most people used the opportunity to purchase new computers that were more compatible with Vista. Microsoft made the upgrade easy by offering an upgrade license from XP to Vista which meant we didn’t have to break the bad news to customers that they had to reload software.

People absolutely hated Vista. I think 2006 marked the most downgrades my little company had ever done. People who purchased Windows Vista licensed computers were asking us to downgrade them back to XP. It sounds easier than it was. I just recently recycled hundreds of custom XP CD’s. It seems like every downgrade required a custom installer plus another 2-3 hours to finish the job. There were many nights I would stay very late to finish my work.

A fan favorite was Windows 7 which was luckily a very easy upgrade from Vista. Install the CD or USB stick and with the click of a few buttons customers’ computers were back to a classic look and feel they were used to. No more nag screens asking about account control, just a good old fashioned start button.

But wait, Microsoft had another thing coming! They created the abysmal Windows 8 that everyone couldn’t wait to have – then hated it once they got it. Again, they made upgrades really easy. I remember talking to my employees about how confusing it was to use with each corner doing something different and the required swipes from the left or right. Microsoft missed the mark by predicting people would purchase touch screens and forgetting that most of their customers were businesses.

Very shortly after the release of 8 they released 8.1 which brought the start menu back. Even though it still had the weird corner clicks and slide out menus, Windows 8.1 included a start menu. Woo Hoo!!!

8 and 8.1 were active for such a short amount of time I kept only one set of CD’s and tossed the rest. Windows 10 was released earlier than planned to quench the burn that Windows 8 had caused in Microsoft’s backside. Windows 10 brought back the traditional feel of windows and gave people the option of a touchscreen with normal buttons and desktop icons. It was truly a streamlined version of Windows 8 with a normal workflow. And yes, Windows 10 is identical to Windows 8 with a different graphical interface.

And now this brings us to 2021 and the introduction of Windows 11. Right smack in the middle of the pandemic I was slapped in the face with a new operating system that came with very specific hardware requirements. TPM security chips, processor requirements, secure boot and UEFI. Add to that 11 only comes in a 64 bit flavor (10 came in 32 and 64 bit). My first thought was, “how am I going to upgrade customers who have older equipment?” It was tough but I figured it out.

Using a little bit of the knowledge I picked up back in my XP downgrade days combined with a fair amount of traditional code, I mastered transitioning people from their old Windows 10 computers to brand new Windows 11 machines while keeping most of their software and settings and all of their data. Quite honestly it’s the most work of all the upgrades and downgrades I’ve done over the years, but with solid state drives the jobs go fairly quickly.

Jeromy Patriquin is the President of Laptop & Computer Repair, Inc. with locations in Gardner and Greenfield MA. Feel free to reach out to him at LocalComputerWiz.com.