The Long Road from Windows 3.11 to Windows 11

There was a time when you had to tell your computer fairly precisely what you wanted it to do.

You typed cd.. to move up one directory, switched to the floppy disk with A: and to the big, actually floppy disk with B:. You knew AUTOEXEC.BAT and CONFIG.SYS, and if you were unlucky, you learned things about IRQs that no reasonable human being should ever have needed to know.

Eventually, we had mice, too – the kind with a ball underneath. It reliably collected dirt from your desk until the pointer moved only vaguely in the direction you wanted it to go. So you took the ball out, scraped the grime off the little rollers – and the mouse was repaired.

There was no USB. Certainly no Wi-Fi. Networking was something for people who apparently had far too much spare time.

Not everything was better back then.

But at least the computer still knew which one of us was the computer.

Just how much that has changed became very clear to me recently when, several decades later, I tried to install WinAmp.

Not some obscure hacking tool. Not software for controlling a uranium enrichment facility. WinAmp – a music player that has been around since roughly the Stone Age of digital audio playback.

Windows 11 had a clear opinion on the matter:

The administrator has blocked this application.

That surprised me.

Because I am the administrator.

With earlier versions of Windows, I knew a perfectly understandable procedure for situations like this. Windows issued a warning. Windows required administrator privileges. You entered a password or confirmed a security prompt – and by doing so, you accepted responsibility for what you were about to do.

I can understand that.

An operating system should absolutely warn me when I may be about to do something stupid. It is perfectly entitled to say:

“This software is old.”

“The signature looks suspicious.”

“We don’t know the publisher.”

“If you run this and smoke starts coming out of your computer afterwards, please don’t claim we didn’t warn you.”

All right.

But Windows 11 told me that the administrator had blocked the application and offered me exactly one course of action:

Close.

No administrative confirmation. No conscious acceptance of the risk. No “Run anyway.”

Just: No.

So there I was, the owner of my computer and administrator of my operating system, sitting in front of my own machine and being informed that I had forbidden myself from doing something.

Without bothering to tell myself beforehand.

That takes some doing.

Of course, all of this is for our own good. That is one of the more interesting phrases of our time anyway.

Software gets “simplified.” Afterwards, you search for functions that used to be visible behind three dots, a submenu and an option called “Show more options.”

You could apply the same principle to buildings.

“Where are the door handles?”

“We simplified them for you.”

“Then how do I get into the next room?”

“The adjacent room has been classified as potentially unsafe. The administrator has denied access.”

“The adjacent room is the bathroom and I REALLY need to get in there!”

“Please contact your administrator.”

“I AM the administrator, damn it!”

“That is what you believe.”

Perhaps there is a fundamental misunderstanding here about what usability actually means.

A task does not become easier simply because you hide the controls required to perform it.

A door without a visible handle is not a simplified door.

It is a door whose handle you now have to find.

You can take this principle to its logical conclusion – all the way to the safest toilet in the world.

A toilet whose lid cannot be opened has enormous advantages. It uses less water, needs cleaning less often, blockages are virtually impossible, and wear and tear approaches zero.

A fantastic product.

There is just one problem: it is the safest toilet in the world – and completely useless for the purpose for which it was built.

The same applies to many other things. A car lasts considerably longer if you never drive it. A book remains pristine if you never read it. Action figures retain their collector’s value if you leave them sealed in their packaging.

Sausage and cheese lose virtually all of their resale value after being used for their intended purpose.

And yet we eat them.

Apparently, when it comes to sausage and cheese, we still understand that a significant part of the value of something made to be used lies in actually using it.

The same is true of computers, by the way.

My computer could probably remain almost brand-new for many years if I switched it off and left it sitting in a corner.

Unfortunately, I bought it to work with it.

That seems to have become a surprisingly demanding requirement.

I do not want to romanticise DOS, either. I am not one of those people who believe everything used to be better.

Anyone who ever fought to free enough conventional memory just to get some program to start knows that the past had perfectly good reasons for becoming the past. We juggled drivers, IRQs and serial ports and knew things about our computers not because they were particularly fascinating, but because otherwise the damn sound card refused to make a sound.

There is plenty of that I am very happy to live without.

I have no desire to exchange USB for floppy disks, regularly dismantle my optical mouse to scrape dirt off tiny rollers, or once again regard 620 kilobytes of free conventional memory as a personal triumph.

Progress is wonderful.

As I write this text, I am discussing its wording with artificial intelligence. In the days of DOS, I would probably have regarded that as science fiction.

Which is precisely why we should not confuse progress with change.

A new feature can be an improvement. Removing a feature can also be an improvement. But if something that used to be easy becomes more difficult or impossible, it does not magically become progress merely because the version number has increased.

Despite all its inconveniences, DOS had one remarkable quality:

It obeyed.

If I entered a command and that command existed, DOS executed it. If something did not work, I might get:

Bad command or file name

That was not particularly helpful.

But DOS was inconvenient; it did not lie. It did not say:

“You have forbidden yourself from doing this.”

Perhaps that is a peculiar form of progress.

Computers used to fail sometimes.

Today, at least they explain to me that it is intentional.

There are other areas where I certainly do not want the technological past back, either. In the old days, for example, you could safely shout at your computer. You could threaten to switch it off, pull the plug or send it to the scrapyard, and the machine would accept all of this with the stoic composure available only to devices that cannot understand a word you are saying.

Today, we have voice control.

So anyone who angrily shouts at their computer, “If you do that one more time, I’m switching you off!”, should be prepared for the possibility that it may reply:

“Shutting down.”

Progress also means having to watch what you threaten your computer with.

And sometimes a single wrong word is enough.

A friend of mine had voice-controlled lighting in her home. In the front part of the apartment, the relevant command was “lamp”; in the back, it was “light.” It worked beautifully – as long as you remembered which word belonged to which part of the apartment.

Mix the two up, and you might suddenly switch on the light in the room where her partner was trying to sleep so he could be rested for work.

That did not make the technology bad.

In fact, it did almost exactly what it had been told to do.

It just was not always what the person had meant.

Perhaps that is a useful description of quite a few technological problems – and a good place to ask what we actually hand over to our tools when we let them do work for us.

Technology saves us work. That is precisely why we build it.

With the device in my pocket, I can find my way through an unfamiliar city, look up the opening hours of a pharmacy, learn the basics of glassblowing or find out how to turn a tree trunk into a board and then plane it flat.

In the past, I might have needed a street map, a telephone directory, a library and perhaps an expert for all of that.

Today I can carry all of it around on one small device.

That is wonderful.

But convenience is not free. Sometimes we do not pay for it with money, but with redundancy, knowledge and our own ability to act independently.

People used to know at least a few important telephone numbers by heart. Today, the phone takes care of that. It is far more convenient – until the screen breaks and you discover that you can no longer call even the people whose numbers you urgently need.

Music is much the same.

A younger friend once mocked me for still owning audio CDs.

“How old are you?”

A few weeks later, the hard drive containing his music collection failed.

I really tried not to grin.

I am afraid I was not entirely successful.

I asked him why he had not at least made a backup and, with as much solemn seriousness as I could muster, pointed out that there are companies capable of recovering data even from failed hard drives.

Unfortunately, their prices tend to start at roughly the point where recovering a private MP3 collection has already lost all contact with economic reality.

The lesson is not that we should all start buying audio CDs again.

The modern solution is called a backup.

That is the crucial point.

Progress does not have to mean throwing old possibilities away. We can enjoy the advantages of the new while still asking:

What could the old technology do that might still be worth preserving?

A good tool saves me work.

It should not take away my ability to function without it.

And that brings us to a larger question that goes far beyond backups. For a long time, technological development was associated with a great hope: if people only had access to enough knowledge, surely they would become more reasonable.

Today, we carry a considerable portion of humanity’s accumulated knowledge in our pockets. Within seconds, we can find scientific publications, compare historical sources, read specialist information or learn how people on the other side of the world think about a problem.

Human beings have not suddenly become reasonable as a result.

Alongside knowledge, rumours, lies, propaganda and conspiracy theories now travel around the world in seconds as well.

With the same device I can use to learn how glass is blown, I can also convince myself that contrails are part of a conspiracy, that “foreigners” are responsible for my misfortunes, or that extraterrestrials probably already have plans for us.

Anyone looking for knowledge can find more of it than ever before.

Anyone looking for confirmation of the greatest nonsense imaginable is remarkably likely to find someone offering that as well.

Perhaps the mistake was assuming that knowledge and judgement were the same thing.

With artificial intelligence, we are now repeating this debate in an intensified form.

Some expect it to solve almost all our problems; others fear machines that will eventually take control.

There is no need to invoke the Terminator.

The more immediate questions are quite sufficient.

AI can help us think. It can organise information, explain connections, formulate objections and point out things we may have overlooked.

But it can also be used to produce convincing false reports, fake images, imitate voices or reinforce people in believing precisely what they wanted to believe in the first place.

The tool does not decide what we use it for.

A hammer can drive a nail. It can also be used to destroy something.

A screwdriver can turn a screw. It can be misused and cause injury to oneself or others.

Pliers increase the strength and capabilities of our hands – and can pinch those same hands remarkably effectively.

That does not make us regard pliers as evil.

The more powerful a tool becomes, the more important competence, judgement and responsibility become in using it.

Artificial intelligence adds another dimension: it does not merely amplify physical power. It can amplify intellectual and communicative power. With its help, one person can produce texts, images and voices in a short time that would once have required considerable effort to create.

That opens up tremendous possibilities.

And tremendous possibilities for nonsense.

More information does not automatically create better judgement.

And more artificial intelligence does not automatically create more human reason.

As I write this text, I am using artificial intelligence myself. Several systems, in fact. I ask them for possible formulations, compare versions, disagree with them, delete things, add things and make the decisions.

I could also ask them to do all the thinking for me.

That would undoubtedly be more convenient.

Whether the resulting text would be any wiser is another question.

Perhaps one of the most important skills in dealing with new technology is therefore not to hand over to it the very thing it is supposed to help us with:

our own judgement.

For situations in which our judgement is still functioning perfectly well but our patience is not, there used to be programs whose social value we may have seriously underestimated.

One of them was called “Stress Reducer.”

It allowed you to do things to your screen virtually that, for financial and various other good reasons, you would be better advised not to do to a real computer.

You could smash windows with a hammer. Fire paintballs. Release termites across the desktop. Set things on fire. Or take a virtual machine gun and explain to the currently active window exactly what you thought of its user interface.

The window got holes in it.

The monitor did not.

The computer survived.

The house remained standing.

The user found peace.

Looking back, this strikes me as a remarkably sophisticated safety concept.

Microsoft should consider including Stress Reducer with Windows 11 by default.

Not as a game.

As a system component.

When Windows announces for the third time within an hour:

“The administrator has blocked this application.”

a window should automatically appear:

We have detected that you may be experiencing dissatisfaction.

Please select:

Hammer
Flamethrower
Termites
Paintballs
Chainsaw
Machine gun

Below that:

[Start Troubleshooter]

This button should, of course, be greyed out.

We would not want to confuse the user unnecessarily.

Behind all this nonsense, however, lies a serious question: how much decision-making should a technical system be allowed to take away from its user?

I absolutely want my operating system to protect me. I do not want to install malware accidentally. I want to know if a file is suspicious. I want to be warned if a decision might have consequences I do not fully understand.

But warning and forbidding are not the same thing.

Neither are protection and paternalism.

Security is not the same thing as control.

A good tool expands the possibilities available to its user. A good security system helps that user make informed decisions.

It explains.

It warns.

It asks.

And eventually, it accepts the answer.

The alternative is technology that no longer merely assists but increasingly decides for itself what its user is allowed to do.

At that point, a tool slowly becomes a guardian.

Because in the end, there is a human being sitting in front of the computer – even if, occasionally, the error really is sitting in front of the screen.

The computer is not sitting in front of a human being.

Perhaps that is the real lesson of the long road from Windows 3.11 to Windows 11.

We have made computers more powerful, more convenient, more connected and more secure. We have replaced hard drives with SSDs, floppy disks with networks, ball mice with optical sensors and AUTOEXEC.BAT with systems whose internal workings users hardly need to know anything about anymore.

Most of that is progress.

And I do not want to turn it back.

But progress should empower people, not disenfranchise them.

That applies to operating systems just as much as it does to smartphones, voice control or artificial intelligence.

The crucial question is not whether a technology is old or new.

The question is whether it serves its purpose – and whether the human being using it remains the one who gets to decide.

In all of this, we should not lose one of the oldest and most important characteristics of a personal computer:

It belongs to the person sitting in front of it.

And if that person is the administrator and explicitly says:

“I want to run WinAmp.”

then perhaps a revolutionary improvement in usability would simply be:

Run WinAmp.

If that is technically impossible, I still have one constructive alternative to suggest.

Stress Reducer.

With a machine gun.

Virtual, of course.

We would not want to damage the computer.

We still need it for Linux.

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