The moment I almost forget what a pain Windows 10 is, this message pops up on my PC. Why did you have to ask me this question again, Microsoft? Why must you remind me of my suffering? All the details of what I have experienced are too much to cover in a single blog, so I will do my best to focus on the big issues. As such, I won’t be whining about Windows 10 not consistently recognizing my finger, but that is a common theme here.
Nor will I spend the time rehashing various feature disruptions associated with forced updates to the degree that they deserve. Most notably, Bitlocker comes to mind, but I cannot bring myself to go there in any significant detail. Suffice it to say that when I lost access to my encrypted Bitlocker drive due to an update, the documented fix required reinstalling an older version of Windows 10 to recover my data. I chose to buy another hard drive since it was less complicated and time-consuming.
At one point in January of this year, I estimated that the combined dysfunction of Windows 10 and Office 365 had cost me at least two full days of productivity for my own system, never mind other people that I provide support to. In that month alone, I personally spent over an hour a day on average dealing with issues that you would never see on a Windows 7 PC running a non-365 version of Office.
As an IT professional with thirty years of experience, I can honestly say that the Windows 10 operating system (OS) may be the most intrusive and unreliable OS ever created by Microsoft. Computers and operating systems are intended to make our work lives more efficient and less challenging, not less efficient and more challenging. On a regular basis, Windows 10 and its cohort, Office 365, thwart productivity through seemingly incessant and meaningless updates performed in the almighty name of compliance and security.
Even the most basic functionality of turning off your computer is challenged by the HAL-like behavior of this OS. On my way out for a recent Thanksgiving road trip, I attempted to shut down my PC (four times). Each time, my PC appeared to shutdown it came back on again. It was clearly going to do this ad infinitum, which led to a few expletive laden Google searches like, “Windows 10 will not $&%#ing shut down!”
This is not the first time I have seen this particular issue in Windows 10 or similar quirky bugs like the black screen issue, so my patience was tested. Eventually, I rediscovered and used the “hold the left-shift key and shutdown” method to wrestle my insubordinate PC into submission, then for good measure I actually unplugged it too. Let’s see you restart now, Windows 10! Thankfully, it didn’t.
Sure, this OS looks good on the surface, and in some ways it is better than its predecessor, but there are some major drawbacks. For example, trying to use an app arbitrarily deemed as “not stable” or “incompatible” results in Windows 10 uninstalling that app without users’ permission. Windows 10 won’t necessarily remove the app as soon as you install it, but when Windows applies updates again, it will remove the offending app and does not notify users.
Want to postpone an update or set the time updates are supposed to occur? … Go ahead. There are settings for that, but whether you go through the exercise of configuring those settings or not, Windows 10 pretty much seems to do whatever it wants to do when it wants to. I feel like I have lost control of my computers that run Windows 10. Microsoft is in charge of them now and decides when and how I can use them.
If you have a critical online meeting, work that needs to be done right now, or a plane to catch, you can almost count on Windows 10 attempting to update or do some other thing that doesn’t need to be done at that exact time. I don’t know how it does this, but it does. It could just be that it is always doing an update. In a nutshell, if you are familiar with the printer in the movie Office Space, Windows 10 is that printer.
Given my experiences, recommending this OS to anyone before they felt that they truly needed to move to it would be willfully irresponsible. That said, I suspect there is a small contingent of users that Windows 10 helps stay out of trouble. I know some of those people, but the masses should not have Windows 10 on their computers when there are other more reliable – as defined by computers that do what you want them to do when you want them to do it – alternatives.
Many of my financial services customers have likely moved to Windows 10 or plan to move to Windows 10 in the future. For those businesses where compliance and security are paramount, staying the course on an aging OS like Windows 7 will become more difficult, given that Windows 10 is widely perceived as being more secure.
Understandably, for corporate use Windows 10 may just be a desktop environment that is used to gain access to a more secure and redundant cloud environment. As such, the pain points I describe related to Windows 10 could be less of an issue for these users. However, consigning users to Microsoft’s decisions about how they can use their PCs at any given time is scary.
Ultimately, the path Microsoft is on with Windows 10 is either headed toward total authoritarian rule over personal computer systems, or toward the eventual demise of Microsoft’s stranglehold on the PC OS market in favor of a more agreeable and obedient operating system.
By way of disclaimer, I am using Windows 10 Professional, but know that Windows 10 Enterprise LTSB, which will soon be renamed to LTSC in 2019, follows the more traditional release policy and is not updated with the frequency of Microsoft’s other versions of Windows 10. Based on my experience to date with Windows 10 Professional, the Enterprise LTSB product would probably be a much better user experience. Also, related to Windows updates, my advanced options are set to Semi-Annual Channel (Targeted) with the option to defer feature updates by up to 180 days and security updates by up to 30 days. I realize that I could gain a greater level of reliability and reduce the problems I experience by changing to the straight Semi-Annual Channel, which would delay feature updates by an additional 4 months. My opinions are the result of using Windows 10 as both my primary desktop and notebook OS for the past two years.
About the Author: Kevin Shea is the Founder and Principal 
Consultant of Quartare; Quartare provides a wide variety of technology solutions to investment advisors nationwide.
For details, please visit Quartare.com, contact Kevin Shea via phone at 617-720-3400 x202 or e-mail at kshea@quartare.com.
Windows XP was a mainstay at many financial services firms for nearly a decade. In keeping with the Microsoft Lifecycle Support Policy, support for Windows XP and similar aged software must eventually end. You can learn more about the policy 
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