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Worst Microsoft Products of All Time

by Ossiana Tepfenhart 3 years ago in product review

Microsoft may be the leader of the PC world, but that doesn't mean they haven't had serious problems with products in the past. Take, for example, the worst Microsoft products in history...

Microsoft has made quite a few amazing products over its history.

There was the revolutionary Windows 95 OS that took the world by storm during the 90s. Windows 7, too, remains one of the most popular PC operating systems in recent years. Xbox users will also tell you that they love Microsoft products because they can make a great video game system.

Sometimes, though, the company of Bill Gates' fame misses the mark. In fact, there have been some seriously colossal flops over Microsoft's existence. Though executives would hope that you've forgotten them, a quick look back at the worst Microsoft products of all time will be a good reminder as to why people hate this company with a passion.

Windows 10

Though there have been a number of operating systems that have been called the "worst Microsoft products" of all time, few have bombed as badly as the most recent incarnation of Windows.

This OS actually started to get outrage after it started to install itself on peoples' Windows 7 and 8 PCs without permission. It kicked off the "Windows 10 is a virus" rumor, and to make matters worse, kept badgering people to download it like a malware site would.

Windows 10 is very hard to control and has become one of the least user-friendly interfaces in recent years. To get it to act like a normal computer, users have to stop updates that happen automatically, stop having automatic restarts, and also force the computer to be okay with Google Chrome.

Did we mention Windows 10 also has ads involved in it from time to time?

Needless to say, a lot of people are now downgrading their computers to Windows 7 because it actually allows users to control their experiences with the program. We can't blame them. It sucks that much.

Windows 8

The other major operating system flop you'll hear about on lists of the worst Microsoft products out there is Windows 8. Windows 8 was an OS that was meant to be a laptop operating system that also worked on mobile devices. The idea was great, but the execution was pretty awful.

Windows 8 had no starter toolbar, very few good apps, and also had an obnoxious "tile layout." The entire system was so terrible that it was not useful on tablets or laptops. It also was the operating system that was featured on one of the other major Microsoft flops out there...

Windows Phone

While it could be argued that almost any Windows mobile device will suck, it's hard to suck as bad as the Windows phone line did. This line of "smart" phones weren't really smart as much as they were developmentally delayed—literally.

Two years prior to the iPhone's release, they would have turned the world upside down. By the time they actually showed up on the market, they were old hat and the competition blew them away.

Speaking as someone who had a Windows phone, the app market was the worst. Instead of Pokémon Go, Windows phone users got to play Pokémon Pokédex App. In other words, every good app you would want didn't exist on these things.

The abysmal Windows phone app market, along with the atrocious Windows 8 OS, meant that it was really dead on arrival. At its peak, just over 2 percent of smartphone owners had a Windows phone.

Microsoft tacitly withdrew itself from the phone market within a matter of years.

Microsoft Zune

Okay, enough bashing on Windows for a bit. Let's talk about the iPod explosion of the 2000s. During the mid-2000s, everyone wanted an iPod. They were the top mp3 player on the market, followed by SanDisk Sansas.

Microsoft tried, and hoo boy, did they try, to make a comparable product. What they came up with was the Microsoft Zune—one of the worst Microsoft products of the decade.

Technically, there was very little wrong with the Zune. It played mp3s. It was just very large, clunky piece of plastic that could barely do its job. Microsoft just expected people to roll with the brand name... but people didn't.

Just like with the Windows phone debacle, Microsoft quietly exited the mp3 player game. Perhaps that was for the best, right?

Microsoft Kin

The Microsoft Kin was the first precursor to the Windows phone, and somehow, it managed to be an even crappier foundation to a crappy product. The Kin was a line of two different phones—Kin One and Kin Two.

Both Kins were able to do some light social networking but the fact was that they ended up being total failures. The two phones were totally software-locked, and that meant no third party software could be made to expand the Kin's functionality.

This wouldn't have been so awful if it wasn't for the fact that the software sucked. Oh, and it was also 2010. This meant that the iPhone was already out for about three years and did everything better by a factor of, probably, 10 million.

To give you a full idea of how awful this quasi-moronic phone was, Verizon had carried them for a short time of only 48 days before they realized it was a horrible decision. After 1 1/2 months, they took all the Kins and quickly threw them out. They were WORTHLESS.

The Kin didn't just make the list of one of the worst Microsoft products in history. It basically raised the bar of suck.

Hotmail/MSN/Outlook/Live Email Accounts

You know how you can tell if someone has a Google account? They have a Gmail account. It's nice and uniform like that. Gmail also has good spam filters, great security, and an easy to use layout.

Microsoft, on the other hand, does not have that advantage. In fact, one of the worst Microsoft products out there is all the different email services included with Microsoft services. In fact, all of their email services are notoriously easy to hack and have terrible spam filters.

To make matters worse, there's zero uniformity. Having a Microsoft email means you can have an account that's could take forms like:

Confusing? You betcha! That's why people avoid these email addresses at all costs. To make matters worse, certain email addresses end up acting as a "Microsoft Passport" and track your data.

If you lose your "Passport" to a hacker (which is easy to do), you can get locked out of your accounts to other things. It's a nightmare, to say the least!

Windows Genuine Advantage

Windows Genuine Advantage is one of those things that made almost every PC user scream in rage. Windows Genuine Advantage was the way Microsoft shielded itself from copyright issues when users started to download Windows 2000, Windows 98, and Windows XP.

This thinly-veiled product was nothing more than copy protection that would shut down the operating system if you didn't enter the right validation code or serial number when you were installing the Windows OS.

The only way to unlock your OWN computer after making a mistake on installation was to call up the Windows center and ask for forgiveness. To make matters worse, false positives for copyright infringement also popped up. Even if you did everything right, you'd still have problems.

All things considered, this remains one of the worst Microsoft products ever made—not to mention one of the biggest wastes of money ever.

Internet Explorer

Okay, maybe at one point this was an okay internet browser, but by the time that IE saw its last run, Internet Explorer sealed its fate as one of the worst Microsoft products in recent years. It's hard to fully explain what was wrong with this program until you used it yourself.

First off, it was buggy—like, really buggy. Errors happened all the time. IE was notoriously bad with allowing cookies and malware to download themselves onto computers, which didn't bode well with users, either.

By the time 2006 rolled around, all people used this browser to do was download Chrome or Firefox. Ouch, right?


Oh, oh dear. Bing.

Bing was the biggest flop in Microsoft's history. It was supposed to be a competitor to Google, but much like the Kin, was released too many years too late. Along with being a piss-poor search engine, it just looked awful.

Going on Bing means you get a busy search engine that's literally smeared with more 90s ads than a vaporwave music video. The worst part about Bing is that it still looks like it's from 1995, even though it's 2018.

It's an eyesore that delivers terrible results more often than on-point results. However, that's not even the worst aspect of Bing from a business perspective.

Microsoft actually pays users to search using Bing because their engine is so badly botched and requires a better algorithm. Most people who use Bing do so because they're paid, or because Bing doesn't filter out porn results like Google does.

To this day, Bing remains one of the biggest tech flops of all time.


If you used Microsoft Word during the 90s, you already remember this annoying, unhelpful bastard. Clippy was a paperclip that spoke and had the magical power to make your computer freeze up every time it offered you help.

Designed as a friendly tool to make computers less intimidating for new users, Clippy was supposed to help people get the hang of Word. Unfortunately, it'd help with all the most inane aspects of Word by telling you what to do and force you to click it to go away.

Clippy wasn't just annoying, he was one of the worst Microsoft products of the 90s. When they decided to do away with Clippy, the world rejoiced and it got a little brighter.

Microsoft Bob

Microsoft Bob was a graphical user interface program that was designed to help older folks and young kids learn to use computers back in the 90s—and it did so with the same kind of "flair" that Clippy did.

Bob ran on Windows 3.1, 95, 98, and XP. It was a major failed experiment that was supposed to help people feel more comfortable with computers. The problem was, it was a program you had to load onto the OS, and then would have to work around.

After you get onto Bob, you would have to search around an animated house just to do basic tasks. At times, the program was even more confusing than the standard GUI or MS Word.

The user experience was nothing short of aggravating. Online explorations of Microsoft Bob basically illustrate everything that's wrong with Microsoft during the 90s.

Patronizing and totally unnecessary, Microsoft Bob was one of the worst Microsoft products ever created.

product review
Ossiana Tepfenhart
Ossiana Tepfenhart
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Ossiana Tepfenhart

Ossiana Tepfenhart is a writer based out of New Jersey. This is her work account. She loves gifts and tips, so if you like something, tip her!

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