Windows 10 Free Upgrades Ending: Correcting One of Microsoft's Biggest Mistakes

By Rob Enderle May 10, 2016

Back in the early days of Microsoft the company made a critical strategic error that didn’t come back to bite them in the butt until last decade.  They finally corrected the problem, and that means there is good and bad news in regard to your Windows 10 upgrade.  The bad news is it stops being free, the good news is you’ll never have to pay for an “upgrade” again once you move to Windows 10.  

Confused?  Let’s see what I can do about that. 

Microsoft’s Big Mistake

Like a lot of young and amazingly successful companies, Microsoft got a tad arrogant in the 1990s and seemed to believe too much of their media coverage, which argued it could do no wrong.   Everybody makes mistakes and Microsoft made some big ones.  But, because they were so well regarded, the few of us that were trying to point out those mistakes were largely disregarded. 

One of the biggest mistakes was to take their partners for granted.  One of the most painful events to watch was how they treated 3-Com, who had aggressively oved to OS/2 at Microsoft’s insistence while Microsoft was planning to separate itself from OS/2 and when 3-Com complained, Steve Ballmer went on record basically telling them something to the effect they “needed to grow up”. 

But with operating systems there is a symbiotic relationship, and the reason that Microsoft was able to beat Atari, Commodore, Apple and IBM was because of their large number of PC partners.  But, as it was with 3-Com, they tended to treat these partners increasingly poorly.  One of the worst behaviors was to effectively separate the operating system cycle from the hardware cycle.  You could increasingly buy a new version of Windows at an upgrade price and put it on your old hardware, removing one of the primary reasons why people might otherwise buy a new PC. 

Increasingly that meant Microsoft, rather than aggressively supporting AMD, Intel, and NVIDIA advancements focused on assuring backward compatibility so they could sell more copies of Windows and this contributed sharply to the PC sales stall we are now experiencing.  Windows Vista and Windows 8 were changed for reasons other than selling new PCs and they sucked. 

Apple never lost track of the need to update the software in-line with the hardware, and Apple users generally refresh their hardware more quickly and have historically been happier with the result. 

Windows 10 was created to fix the mess of old versions of Microsoft’s OS in market and it is currently on over 300M PCs and after July 29th of this year, if you don’t get the upgrade (with one noted exception), you’ll be “S.O.L.” because Microsoft is effectively exiting the upgrade business.  

The Exception

The Exception is for those folks who, because of a disability, have to use some of the unique accessibility software in market.  Some of that doesn’t yet work with Windows 10 and, for those people alone, they’ll generally be provided with a free upgrade when or if their software becomes compatible. 

Going Forward

Going forward the only way you’ll get an upgrade to a new operating system is if you buy or build a new system with the hardware that the upgrade requires.  You’ll get patches, and what we used to call minor upgrades, for free as part of your initial purchase so you won’t be buying any more discounted upgrade products.  If you’ve bought a new PC recently you likely have found it behaves much more like a Smartphone or tablet in that your files are brought down from OneDrive and your apps come down from the Windows store (if you bought them there, suggesting you should buy them there). 

After Windows 10 the operating system will increasingly be tuned for the more advanced hardware coming from AMD, Intel, and NVIDA making sure you get more of the value you paid for and creating a bigger incentive to buy a new PC because there will be far more pronounced benefits in terms of performance and capability version to version.  Much more similar to what you would currently see in a Smartphone, Tablet, or even a TV.  

Wrapping Up: 

This showcases that even when a decision is institutionalized, like the decision to charge for upgrades and disregard the needs of PC vendors to sell PCs, it can be corrected.  Yes you’ll likely have to buy a new PC more often than you currently do going forward, but you’ll also get more of what you are paying for and, if Apple is any guideline, you’ll actually be happier with the result and the PC venders will be healthier and happier.  

Alone this won’t restore the PC market to its former glory, to do that we’ll need the PC vendors to step up and create some even more amazing PCs, but it is a huge step in the right direction.   You might want to take a look at some of the new hardware in market particularly if yours is over seven years old.  A lot has changed for the better and, over the next 7-10 years, thanks to this, it is going to change even more dramatically.   And, this is the interesting part, you’ll likely be really glad it did.  

Don’t forget though, the clock is ticking and if you want to upgrade to Windows 10 and get current after July 29th, the price goes from free to around $110.   So, if you haven’t moved, you again might want to consider it.   Just saying…




Edited by Maurice Nagle

President and Principal Analyst, Enderle Group

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