Whenever you get something for free, you should take a second to consider what it might entail. The upgrade to Windows 10 seemed like an easy way to get away from the mess of Windows 8.1, but it also meant that the beloved Windows 7 wasn’t going to be a long-term plan.

People jumped ship in record numbers, making Windows 10 incredibly successful if you count “how many free users upgraded to get away from broken things Microsoft has no interest in fixing” as a success metric, which Microsoft did, of course, as would any corporation. Those upgraders were about to find that not everything was greener on that side of the grassy hills wallpaper, and the somewhat forced upgrades in Windows 10 would come with some significant issues.

These have introduced a wide range of issues over the years of varying severity. Some caused boot loops and BSODs until the update was removed, which is annoying but fixable. Others deleted user data, which is unforgivable, and caused Microsoft to delay one feature upgrade by over six months. Things started to get better after a series of lawsuits that made Microsoft (eventually) add ways to pause updates, but the damage was already done in some cases.

6. The endless reboot loops of August 2015

KB3081424 was a doozy

When you take the stance that forced updates will happen, you have to ensure that nothing happens with those updates, especially the first update after your new operating system launches. Unfortunately for Microsoft, the update pushed in August 2015 caused several huge issues. Many users found that their PCs were stuck in an endless reboot loop, caused by orphaned or corrupted user profiles in the registry, left over from earlier upgrades, stored in the following registry key:

HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion\ProfileList

One fix was to delete any old user profiles from that key and try the update again. Eventually, Microsoft released KB3081436, which fixed the issue for most users, but some users still had similar boot-looping problems even after that. Not the best start to Windows 10 and its forced update system, and it reignited the conversation around user agency, testing of updates, and reliability.

5 Windows 10 October 2018 Update version 1809 deleted user files

Yeah, this one was not ready for prime time

On the list of things not to do when pushing out updates, deleting user files is high on the list, if not the top entry. With the second of the bi-annual Windows 10 major updates in 2018, that unforgivable error happened to many users, causing Microsoft to pause pushing the update to anyone. But it wasn’t just lost data that this update brought; it also had a longer list of bugs:

• Broke built-in apps and features (including Mail, Edge, Calendar, and News)
• Caused boot loops, failed installations, and system freezes
• Incompatibility with some Intel audio drivers caused widespread BSODs
• The update was blocked from installing on some newer Intel CPUs and the affected systems were stuck without future updates

It took Microsoft and the small army of Windows Insider testers until March 2019 to fix most of the issues with the October 2018 update, and it started rolling back out widely then. That’s nearly half a year of troubleshooting, and nearly to the next bi-annual release window. To say this was a bad update would be an understatement. It should never have gone out at all.

4 An update in March 2020 caused multiple major issues

KB4535996 brought boot issues, frequent BSODs, and plenty of other bugs

In February 2020, an optional feature update brought woe to the many users who opted to install it. Among the litany of problems were boot hangs, black screens, systems that wouldn’t boot at all, and a bug that caused many users to get logged in with a temporary profile, losing their Start menu, documents, and other personal touches. Gamers reported stuttering, slowdowns, and delays in launching apps, some hardware (specifically USB sound cards) stopped working altogether, VPNs broke, and many other issues, including reports of missing data or emails.

There were also widespread reports of enterprise fleets with hundreds of PCs suddenly starting to BSOD after the update. Microsoft’s Visual Studio code signing tool broke and stopped developers from releasing product updates, which Microsoft quickly fixed. The easiest fix was to uninstall the update since it was optional and block the PC from downloading it again.

3 An update in May 2023 was bricking PCs

KB5026361 had a lot to answer for

In May 2023, an update that was supposed to increase the security and reliability of Windows 10 did nothing but. On the same day, Microsoft also broke VPNs in the update for Windows 11, but the Windows 10 update was much more mischievous. These ranged from the dreaded BSOD to the update getting stuck partway through and boot looping, linked to a corrupted “Bootcat.cache” file. Some affected PCs couldn’t boot at all, effectively “bricking” them.

The pain didn’t stop there. There were issues with AMD’s RAID Drivers, TPM issues for anyone using ESET Full Disk Encryption, broken policies in ESET Endpoint Antivirus, an inability to open Outlook attachments, and issues with copying files on shared drives. The Taskbar went unresponsive on some systems, Wi-Fi drivers broke, and other peripherals had problems.

2 In October 2020 a pair of updates crushed many systems

KB4579311 and KB4577671 seemingly brought more issues than they fixed

Windows 10 and its forced update policy would strike again, with many users unable to install this update even though the system would repeatedly try. Some unfortunate hardware configurations got BSODs and other boot issues for their efforts, and some systems progressively slowed to a halt until the updates were uninstalled.

Windows Explorer would randomly crash, printers, HDMI outputs and audio hardware would stop working, and many third-party devices stopped working completely. That was traced to a new driver signature enforcement flag that made old or improperly signed drivers unusable, which took longer to fix than some of the issues here. Doing an in-place repair install to remove the update was the only fix for many users until Microsoft and third-party device manufacturers figured out which drivers needed signing properly and fixed the issue.

1 Windows 11 forced as a ‘feature update’

Nobody asked for this one

In October 2021, some Windows 10 users who searched for updates were greeted by a banner that said Upgrade to Windows 11 is ready—and it’s free! Remember what we already talked about with free upgrades? Yeah, it went down as well as expected, with many of the offered PCs unable to upgrade to Windows 11 for various hardware reasons. Microsoft also forced the PC Health Check App onto Windows 10 computers, which was used to check the hardware on the computer and tell the user (and presumably Microsoft) which parts needed upgrading to get the new operating system. Microsoft would also aggressively advise users to upgrade to Windows 11 over the next few years, even going as far as to put an advert in the Windows 10 installer.

Updates are supposed to make your PC better, but that doesn’t always go to plan

Apart from the sneaky upgrade to Windows 11, the Windows updates on this list are only a small section of the many update packages that went smoothly without widespread issues. Without security updates, your PC might be at risk, and skipping bugfixes could stop you from enjoying your favorite apps or games.

The problem here is that forced updates aren’t always appropriately tested, even with the millions of Windows Insiders who get early builds of features. And when your PC won’t boot after an update, it’s not comforting to know that you’re in a small group of users when you only want to know how to get your computer working again. The fix requires a little manual effort each month, as you can pause Windows updates just before the second Tuesday of each month, which is the day major updates get released. That way, you can ride out the first wave of updates and see if any big issues crop up. It just sucks if you forget, or if you were one of these Windows 10 users before the ability to pause updates was introduced.

Posted on: August 3, 2025, by : Bhavin Thakkar