Most Infamous Computer Operating Systems And IT Services

One of the ultimate goals of any IT software or service is that it should work so well and with so little friction that a user barely notices that it is there.

Logically, this means that the opposite is true; if you are acutely aware of the program you are using, that typically means that something is wrong with it or that it has not been as intuitively designed as it should be.

This is even more important for the piece of software at the heart of your computer: the operating system.

A good operating system such as Windows 10 or Mac OSX, whilst not without flaws, will allow most people to get on with their working day without relying on constant support tickets.

By contrast, the following operating systems either suffered from limited features, unpleasant unreliability or were based on poor fundamental ideas.


In the early 2000s, before the iMac provided a usable alternative, almost every single computer user in the world would use a version of Windows, and that left many people clamouring for an alternative that was not connected to a company mired in antitrust litigation.

The solution appeared to be in the form of Linux, but whilst in 2023 there are plenty of easy-to-use and highly compatible Linux distributions to choose from that could be installed or even used from a USB stick, but in 2001 it was much harder to reliably install Linux, especially as a dual-boot computer.

Enter Lindows, Inc., a Debian-based commercial version of Linux advertised to work with Windows applications, but this approach went so badly that the concept was abandoned within months.

First of all, Microsoft almost immediately sued them for trademark infringement, in a case that Microsoft somehow lost, earning Lindows $20m in exchange for changing their name to Linspire.

The bigger problem was that Lindows/Linspire’s main selling point was built around WINE, a Windows compatibility layer that now works very well and as of 2008 has better backwards compatibility than Windows itself, but was in a very early stage in 2001.

It was too unreliable to be a reasonable selling point and given that WINE was open source, not worth buying either.

After a brief period of being bundled with budget laptops, Linspire’s original company folded, although it still exists as a free distro today.

SCO Open Desktop

Once infamously described as Open DeathTrap by its own developers, SCO Open Desktop was designed to be a 32-bit Unix-based system with a GUI in 1989, which would have been groundbreaking for the time.

The problem was it had atrocious unreliability, which often manifested in ridiculous crashes and core dumps happening with exceptional regularity.

Windows ME

Whilst Windows has had its fair share of poorly received versions, from the confusing multi-system mess of Windows 8.0, the sluggish and unwieldy Windows Vista (pre-Service Pack 2) and the almost useless Windows 1.01.

However, by far the most infamous was Windows ME, the final swansong for the Windows 9X line that had made Microsoft a monolith, but also a system that was so plagued with reliability issues that it lasted just 11 months before Windows XP immediately and completely replaced it.

Infamously difficult to upgrade from Windows 98, with poor compatibility with hardware and such incredible unreliability that even the new System Restore feature could crash.

It was a strange in-between release that was sandwiched between the capable business-orientated Windows 2000 and the world-dominating Windows XP.

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