How Do You Solve a Problem Like Windows 10?

Yes, it has actually happened.  The title of this article is a callback to The Sounds of Music.  My ex-girlfriend (who will not be reading this article) would be proud.

On October 4th I wrote an article called Windows 10 1809: What’s New.  I was all excited.  Two days later I wrote 1809 Recalled.  Microsoft has since re-released the semi-annual release of Windows 10… and has once again recalled it.

Microsoft has flip-flopped on a particular issue over the last fifteen years, and it is now coming back to bite them.  I remember being upset as a community leader when the MVPs were not invited to beta-test Windows 7.  With Windows 10, they essentially laid off many of their dedicated testers and decided to rely solely on the community to test the semi-annual releases of the flagship operating system.  Guys, that is not what I meant.  A compromise would have been to allow the community to test it, while still doing internal testing as well.

So here we are, a couple of days from November, and the September release of Windows 10 is not out yet.  Is that a bad thing?  I don’t know… I have read a few interesting articles and have to agree that the semi-annual channel may be a bad idea; would it be such a disaster to release a new Windows once a year instead of twice?  Tell me, please… was anyone complaining when there were the operating system was on a three-year cycle?  Were throngs of corporate users picketing in the streets of Redmond waving signs that said ‘Down With Windows 7! We Want Windows 8!’  I spent a great deal of time in Redmond during those years, and I do not remember any such protests.  In fact, from what I can tell, corporate customers were so happy with Windows 7 that most of them never deployed Windows 8, and to this day many of them (41.59% of users according to a survey released in March) are still on that OS, three years into the Windows 10 era.

If we are unsure about this, let’s take a quick gander at what great new features we are thrilled about in Windows 10 1809:

  • Windows Explorer Dark Theme
  • Right-Click to Open Linux Shell
  • Clipboard History
  • Game Bar
  • Game Mode
  • Battery Level Indicator for connected Bluetooth devices
  • Data Usage Monitor for different networks
  • HD Color on Windows Settings page
  • On-Screen Keyboard SwiftKey Intelligence
  • 157 new emojis

Is there anyone else who thinks that, with regard to recent Windows 10 updates, the most important emoji of all seems to be this one?


I have been a Windows user for over thirty years.  I believe I have used every single version since Windows 1.0 was released.  It took until Windows XP Service Pack 2 to start getting used to the feeling that my operating system was going to be stable and 100% usable.  It took until Windows 7 for me to start getting used to Windows being the cool kid’s OS, and that Windows was starting to be the basis for a secure, well-managed desktop environment.  With Windows 10 I was happy that I would continue to receive incremental improvements every six months… that is, until now.

Yes, I said it.  There may have been hiccoughs along the way, but Windows 10, which I have been using since its release, has been good to me.  Yes, I know, there are people who were unhappy when the Control Panel disappeared from the Windows Context Menu… but it was still there, if you looked for it!  Like so many of you, I am upset every time something that I’ve been doing the same way since Windows 2000 has suddenly changed… but a) you can’t stop progress, and b) if you really like doing things the old way, there’s usually a way to do it! (Click the Start Menu and type Control Panel… see what I mean?)

That brings us to the autumn of 2018… and the new release of Windows 10 is not deleting your shortcuts; rather, it is deleting your data.  Not only from your computer, mind you… Oh no, that would be too soft.  It is deleting cloud data as well!  You remember the cloud… Where Microsoft and everyone else has been swearing up and down that you should be storing your data, because nothing is ever lost from the Cloud?  Yeah, there… Say goodbye, unless you have a recent and reliable non-Cloud backup.

Is this all happening because Microsoft’s community testers (Windows Insiders) are unreliable?  No.  The Insiders reported this issue months ago.  The problem is with how bugs are prioritized; if not enough people voted for your bug, it gets lost at the bottom.  Not important.  Irrelevant.  Would this be the case if Microsoft still had an in-house professional engineering team devoted to full-time testing of real-world scenarios?  Probably not.

The Windows Insiders are not to blame; even if they never reported the problem they are not to blame.  President Harry Truman had a sign on his desk at the White House that said The Buck Stops Here (pictured).  He was the president, and whatever his people may have done, it was his responsibility.


Likewise, whatever Microsoft’s testers may find, they do not work for Microsoft.  It is incumbent upon Microsoft to release a reliable program, even if their community testers do not find every bug.  With that said, it is unconscionable that the Windows Insiders actually did report this bug, and Microsoft did nothing about it.

Someone at Microsoft decided that we need a new release of Windows 10 every six months.  They are breaking their backs to release a new version of the operating system on that schedule, and rather than miss their target they have now a number of times released a product before it was ready for prime time.

Andrew Orlowski wrote a great piece for The Register last week called Memo to Microsoft: Windows 10 is broken, and the fixes can’t wait. I read this piece with great interest because so much of what he writes mirrors my own opinions.  Read the piece, and you will understand what so many of us have been feeling.  It is time for Microsoft to admit that there is a problem, and to address it.

Okay, we get it… Microsoft wanted everyone to be on Windows 10, and they have moved heaven and earth to make that happen.  They have spent a few iterations getting this wrong, but they seem to have finally come up with a coherent, stable release/support cycle.  I don’t particularly care for it, but they didn’t ask my opinion so there it is.  By the new calendar, Windows 10 1709, which was possibly the last really good and stable release, will be supported until April 14, 2020… about a year and a half from now.  Because of the diminishing QA, Windows 10 1803 was not extremely well received, and Windows 10 1809 is still missing in action.

Let’s assume for a minute that with the crap show that has become of Version 1809, no company with an even slightly conservative Director of IT will touch it, even if it was released tomorrow with $10 bills attached to every deployed instance.  That means that if a company skipped Version 1803 – either because of issues, or simply because they decided to skip a version – then the next scheduled release that they would be looking at is Spring of 2019… and since Spring releases going forward (according to the newest calendar) will only be supported for 18 months from the date of release, most conservative corporations will really be looking at the Autumn, 2019 release… with Autumn releases getting 30 months of support instead of 18 months.

Okay, let’s say the Contoso Corporation (you see what I did there?) opts to skip from Version 1709 to Version Autumn, 2019.  That means that from the release date of the new version they would only have six months to run all of their tests and then to deploy the new operating system to every desktop, laptop, hybrid, and tablet in their organization before the End of Support date of April 14, 2020 comes around.  If Contoso has 500 endpoints and 25 applications that won’t be a problem.  If Contoso has 70,000 endpoints and 250 applications… well, there’s going to be a problem.

So what is the solution?  Well for one thing, Microsoft has to a) recognize that this is a problem; b) mitigate the current situation in a way that will allow Contoso (and all of the real companies out there) some breathing room; and c) Fix the underlying problem and stop making us feel like unpaid beta-testers.

I stopped beta-testing operating systems with Windows 8.1.  It isn’t simply because I stopped being a Microsoft MVP; I lived on the bleeding edge from Windows 2003 through 2015, and frankly I grew tired of it.  I like having a stable operating system to work with, and I find I am more productive for it.  I have, however, deployed each version of Windows 10 the day that it was available to me, and it is only by the grace of a broken USB key that I deployed Version 1809 to a Windows to Go key that day, rather than to my production machines.  That USB key has since been re-provisioned to Version 1803, and I don’t have any plans to upgrade it (or my production machines) any time soon.  Leading Edge is okay… Bleeding Edge just hurts.



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