The Windows Version That Almost Killed Microsoft

What's the worst Windows version you've

ever used? Me? No contest. Vista by a

large margin. Windows 8 and 8.1. If they

didn't exist, that god-awful Metro UI

wouldn't have existed either. 11. Barely

anything that I've used in the past

survived this dumpster fire. I've been

on Windows since 3.1 all the way to 11.

And none were as bad as ME. ME pushed me

over to full-time Linux. I never went

back. I was in Greece visiting family

and I needed to use a computer. My

cousin's husband boots up the PC and I

see the WindowsME splash screen. He just

shook his head and said, "Bad Windows."

Microsoft has released roughly a dozen

major versions of Windows over the last

three decades. Some of them changed

computing forever. And some of them were

so catastrophically bad that they cost

billions of dollars, set the industry

back years, and made millions of people

voluntarily downgrade to the thing they

already had. This is bad tech history,

and today we're ranking every terrible

version of Windows. All the way from

pretty rough to how on earth did this

ship. Now listen, I'm not ranking these

by how old they are. I'm going to be

ranking them by how much damage they

did, how many people they screwed over,

and how badly Microsoft fumbled. So,

let's go.

Let's talk about Windows 8. The iPad was

eating Microsoft's lunch. Tablets were

the future. So, Microsoft's Galaxy brain

move was, "What if we made a desktop OS

that works like a tablet?" Windows 8 was

supposed to unify the tablet and desktop

experience into one seamless interface.

They removed the start button, which was

the most iconic piece of UI in computing

history. You know, the thing that

literally says start, that was gone and

replaced with a full screen tile

interface that made zero sense with a

mouse and keyboard. Your grandma who

just learned where the start button was,

well, congratulations. She's going to be

calling you once again. Now, the entire

OS felt like it was fighting you. If you

wanted to shut it down, good luck

finding it. If you wanted to access

settings, there are now two settings

app. You have the desktop version and

the tablet version. And sometimes they

would actually contradict each other.

Windows 8 apps ran full screen only on a

desktop in 2012. Just imagine running a

calculator that takes up your entire

27in monitor. Here's the thing, though.

Under the hood, Windows 8 was actually

fast. It was really fast. Multiple

people in that Reddit thread pointed out

that despite the trash gooey, 8 and 8.1

were extremely lightweight and speedy.

Now, Windows 8's problem wasn't

engineering. It was a strategy fail.

Microsoft misread the market and bet the

entire OS on a tablet future that didn't

happen on desktops. The engine was fine,

but the steering wheel was on the

freaking roof. Businesses refused to

adopt it. Enterprise stayed on Windows 7

like it was a life raft. And PC sales

tanked. People actually stopped buying

computers because the new ones came with

eight. So, Microsoft panic shipped 8.1,

which added the start menu back and then

rushed Windows 10 out the door with a

we're sorry energy that was almost it

was kind of endearing really. Now, this

is Steven. He's the guy who championed

Windows 8. Where did he go? Gone from

Microsoft within weeks of the launch

because Windows 8 was a terrible idea

executed competently. It ran fine. It

was stable. It was fast. The problem was

entirely that Microsoft forgot that they

were making an OS for people with mice

and keyboards. And the next three, let's

just say that they aren't strategy

failures. We're talking different

flavors of how the hell did you ship

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After Windows 10 was supposedly the last

version of Windows ever, Microsoft

announced Windows 11 in 2021. It was

going to be incredible, I tell you.

Fresh UI, better gaming, and an entirely

new direction. But here's the harsh

reality that we realize, though.

arbitrary hardware requirements locked

out hundreds of millions of perfectly

good PCs quite literally overnight. You

needed a specific CPU generation and TPM

2.0. Microsoft said it was about

security. But here's what actually

happened. Dell's COO went on the record

saying 500 million PCs are too old to

run Windows 11. And then Michael Dell,

yep, that's the actual guy, the Dell

guy, got on an earnings call and told

investors to get excited about quote,

"The next major PC refresh cycle that

Windows 11 requirements were about to

trigger." Dell, HP, Lenovo. They're all

projecting sales growth directly because

Microsoft made your 3-year-old PC

obsolete on paper. Microsoft gets new

license revenue, the OEMs get new

hardware sales, and you get to spend

$800 on a computer that you didn't need.

And then came the updates. Now, I made

an entire video about this, and if you

care to check it out, it's on the

channel. You would know that if you're

subscribed, by the way. 2025 alone had

tons of major update failures. The first

mandatory update of 2026, brricked

machines on arrival. What was

Microsoft's official fix? Uninstall the

update. And the feature creep that

nobody asked for, co-pilot shoved into

everything. You had recall,

screenshotting your desktop, ads in the

start menu, AI in the calculator. I'm

going to say something not controversial

at all. Nobody asked for AI in the

calculator. One Reddit user called it

the laziest version of Windows ever

released. Said everything good about 11

was made by third party developers and

actually not even Microsoft. Listen, the

story isn't over yet. 11 might climb

this list, but it hasn't earned the top

spots yet because at least it boots, at

least it runs. The next two can't always

say that.

Okay. Can we talk about Windows Vista?

We should probably talk about Vista. All

right, buddy. It's time. Vista was

supposed to be the next evolution of

Windows. It was 5 years in development,

which is actually the longest gap

between releases at that point. It was

originally codenamed Longhorn. It

started as this almost wildly ambitious

OS that was going to reinvent

everything, the file system, the

graphics, the security, the works. And

then after 5 years, you could say that

expectations were through the freaking

roof. People were excited. It needed

more RAM to run the desktop than most

people's entire computers had. The

aeroglass interface, a transparent

glassy look, that was the entire selling

point. It brought mid-range PCs to their

knees. Listen, I also have to mention

that driver compatibility was an

absolute massacre. Printers didn't work.

Webcams didn't work. Sound cards didn't

work. You had millions of peripherals

that were fine on XP and then suddenly

were useless. Microsoft rewrote the

entire driver model and told hardware

manufacturers, "Hey bud, good luck with

that. Have fun." There we go. And then

there was the UAC, the user account

control. Every single action triggered a

permission popup. If you open a program,

you'd get a pop-up or change a setting.

You'd get a pop-up. If you look at your

computer wrong, yeah, believe it or not,

probably get a pop-up. Apple ran an

entire ad campaign just dunking on

Vista. You guys remember those Mac

versus PC ads with Justin Long?

>> Mac is asking a question. Cancel or

allow?

>> Allow. He's part of Vista, my new

operating system. PCs have a lot of

security problems, so he asked me to

authorize pretty much anything I do. You

are coming to a sad realization. Cancel

or allow? Allow. That was free money.

Microsoft made their competitors

marketing for them. It was a total show.

Okay, settle in because this is where

Vista goes from bad product to an actual

scandal. Microsoft created a Windows

Vista capable sticker program for OEMs.

They slapped it on budget laptops that

could technically boot Vista. Could now

could they actually run it? Absolutely

not. They would choke on Arrow, but the

sticker was on the box, so people bought

them thinking that they were getting the

full Vista experience. And then

Microsoft got sued. And here's the best

part. Internal emails came out where

Microsoft's own executives called the

program misleading. And one exec even

wrote that his own dad bought a capable

laptop and it was basically unusable.

When your own leadership is getting

scammed by your own sticker, I think

it's safe to say that you have a

problem. All right. Now, in the midst of

all this chaos, Windows XP refused to

die. Businesses demanded downgrade

rights. Downgrade to XP actually became

a selling point for brand new computers.

I mean, just dude, imagine marketing

your product by saying, "Don't worry,

we'll put the old one back on." Vista

ended up becoming something that people

bragged about avoiding. You had multiple

Reddit users in the thread that I shared

proudly saying that they skipped it

entirely. Now, Microsoft eventually

shipped Windows 7, basically Vista, but

it works. And then the world moved on.

But Vista's reputation was so toxic that

to this day, calling something the Vista

of anything means, well, it means it's

terrible. But there's one version that

makes Vista look competent. And this

one, this one's personal to me.

Now, before I get into the history, I

need to tell you something. I didn't

just research Windows Millennium

Edition. I lived it. It's Christmas

morning. I'm a kid. My dad, who knows

absolutely nothing about computers, got

me my first PC. Thanks, Dad. Not the

family computer. My computer, the one

that I could call my own. It was a HP

Pavilion 6736. Now, he had no idea what

operating system was on it. He had no

idea what caliber of software he was

blessing me with. All that he knew was

that his kid wanted a computer and he

got one and it came with WindowsM.

Now listen, I mainly played Starcraft on

that thing and every time I'd get deep

into a match, me would find a way to

remind me that stability was a luxury

that I had not earned. Now Dad, if

you're watching this, I love you. The

thought was incredible. But the

operating system was a war crime. It was

the year 2000. Ah, yes, the Millennium

Edition. The name alone tells you that

Microsoft thought that this was going to

be special. better multimedia, easier

networking, system restore for the first

time. The future was finally here.

Windows ME is by nearly universal

consensus the worst operating system

Microsoft has ever released. And it's

not particularly close. It crashed

constantly, not sometimes has issues. It

crashed like you're lucky to get 20

minutes of uptime crashed. Blue screens

were so frequent that people joked that

me stood for mistake edition. Microsoft

removed real mode DOS support, which

meant a huge library of existing

software and games just stopped working

overnight. They ripped out compatibility

for modernization and replaced it with

nothing. Let's talk about system

restore. By the way, this was the one

headline feature that didn't work

reliably. One Reddit user said running a

restore point actually corrupted their

entire OS. The safety net had a hole in

it. The networking was fragile. USB was

broken. Drivers fought each other for no

reason. and it was built on the ancient

Windows 9x kernel and Microsoft tried to

duct tape modern features onto a

foundation that couldn't hold them. You

remember that Reddit comment from the

opening? Let me give you the full

version. This is fun. So, this guy was

visiting family in Greece. He needed to

use a computer and his cousin's husband

takes him to the office, boots up the

PC, and our guy sees the WindowsME

splash screen. and his cousin's husband,

who barely spoke English by the way,

just looked at the screen, shook his

head, and said this bad windows. Very

bad windows. That's the review. Five

words. It transcended language barriers.

You didn't need to speak English to know

that me was garbage. It was universally

understood. Now, listen. Here's what

makes me truly unforgivable. Microsoft

released Windows 2000, a stable,

professional, well-built OS on the NT

kernel the exact same year, 7 months

earlier. They had the technology to make

a good operating system, but they chose

to ship me to home users instead because

they wanted to keep consumer and

business product lines separate. They

knowingly gave home users the worst

product. People like my dad who just

wanted to buy his kid a computer for

Christmas. ME was on shelves for about 1

year before XP replaced it. 1 year,

Microsoft could not run away from it

fast enough. It's crazy. Emmy was so bad

that it forced Microsoft to merge the

consumer and business Windows lines

permanently. XP was built on the NT

kernel, the good one from Windows 2000,

and it became the most beloved version

of Windows ever made. PC World named

Windows ME the worst tech product of all

time. I'm not talking worst OS, worst

tech product of all time in the entire

history of consumer technology. They

decided ME was the single worst thing

ever sold to people. One Reddit user

said that they've been on every version

of Windows since 3.1 and nothing was as

bad as ME. Another said that Emmy pushed

them to Linux fulltime and they never

came back. That's not a bad review.

That's quite literally a restraining

order. Okay, let's talk about some

honorable mentions, shall we? The last

one is my favorite. A version of Windows

8 for tablets that couldn't run Windows

programs. That's the product. The

Surface RT was Microsoft's iPad killer

that did less than a laptop and somehow

less than an iPad. They wrote off $900

million in unsold inventory. In 1995,

Microsoft released a UI that replaced

your desktop with a cartoon house. You

clicked on furniture to open programs.

It shipped with a talking dog named

Rover. It lasted a year. Its only

lasting contribution to society is Comic

Sands, which is arguably a worse legacy

than the product itself. GREAT JOB. AH,

YES. the Windows phone. Microsoft spent

$7.2 billion buying Nokia's phone

business, then killed it. The Tiles

interface was actually kind of great,

but the app gap killed it. Microsoft

literally paid developers to make apps

and they still wouldn't come. So, let's

pour out a ball's energy. RIP to the

Windows phone. We hardly knew you. Okay,

so here's the pattern. This is the

actual point of the video, by the way.

Every terrible version of Windows failed

for the exact same reason. Microsoft

prioritized what Microsoft wanted over

what users needed. Me, they wanted to

keep the product line separate. Users

needed stability. Vista, well, they

wanted to flex with Arrow and ship

something, anything after 5 years. Users

just wanted their printers to work.

Windows 8, they wanted to chase the

tablet market. Users just needed a start

button. Windows 11, they want your data

and AI integration. Users need updates

that don't brick their PCs. Every time

that Microsoft listens to users, they

make something great. XP, Windows 7,

Windows 10 eventually. But every time

they chase a corporate strategy instead,

well, surprise, it ends up with

disaster. And the internet agrees on

this. Go read any forum, any Reddit

thread, any comment section. The answers

are always the same for names. The

consensus is real. And if I missed

anything or you want to actually me, let

me know in the comments down below. And

Windows isn't alone, by the way. The

tech industry is littered with products,

companies, and decisions that looked

great in a boardroom and then fell apart

the second that real people touched

them. Now, if you made it this far in

the video, please do me a favor and hit

subscribe. We are going deep on the

biggest flops in PC hardware and

software, and there is a lot of material

to cover. So, drop a comment with your

worst Windows experience because I know

you've got one. Everyone's got one. And

if you actually used Windows ME on

purpose on an HP Pavilion 6736, no less,

just know you're not alone. It builds

character, allegedly. This has been Bad

Tech History. Thanks for watching. We'll

see you next time.