20 Years of Microsoft UI Crimes

Microsoft has been an innovator in many fields. User interface design, not so much.

Matthew MacDonald
Jun 25 · 10 min read

The world of software is full of interesting twists and turns. Consider Microsoft, a trillion-dollar company that’s dominated computer desktops for nearly a generation. Despite having built some of the most successful software products in history, Microsoft’s vision for user interface design has always been a little… shaky.

That’s not to say that Microsoft UI is uniformly awful (it isn’t). But Microsoft does have a long tradition of inconsistency. For years, they’ve veered from one design trend to another, innovating in one area, shamelessly copying in another, and frequently reversing direction — all while somehow still keeping in place some very dated bits of graphical interface.

Everyone who’s had a career working with Microsoft products has their own favorite UI horror stories. Awkwardly worded errors messages, false choices, graphical features that only make life more complicated—the list goes on. We aren’t talking about abject failures like Microsoft Bob and Clippy, but about the bad design choices that infiltrate their way into good products. With apologies to Microsoft, here are my personal sore spots.

1. Fancy window chrome

It should be self-evident that window chrome (the OS-supplied styling around every window, which includes the title bar and frame) should be clean and consistent. After all, you want people to focus on what’s happening inside the window. The details around it are for function, not showmanship.

As obvious as this seems, Microsoft has oscillated between clean and usable window chrome and fancy glitz more times than I can count. One of the worst examples was the candy-colored buttons and bulging borders introduced with the Windows XP Luna theme. Detractors called it “Fisher-Price Widows.”

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There’s none more blue than the Luna style in Windows XP

Even in 2001, heavy gradients were already looking dated — after all, tech companies had just spent the last few years removing them from their logos. And although it was possible to switch off the Luna style, it was impossible to customize it in any meaningful way. Custom colors weren’t allowed, leaving users to choose from exactly three equally ugly color skins. The one place you could get additional skins was in Microsoft Plus! — the only product in the Microsoft family that gets an exclamation mark in its name (which neatly sums up the reaction of a modern computer user to its boatload of graphical chintz).

The custom border chrome in Windows XP was also responsible for a generation of bad screen captures. The problem was that the rounded corners of Luna-style windows allowed the background to show through. However, the standard Alt+PrtScn command still grabbed an exact rectangle that didn’t respect the slightly curved window. The result was unexpectedly filled-in corners.

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The corners of Luna-style windows are curved

Windows XP was hardly the first or last time that Microsoft tried to jazz up their window chrome. In slightly more modern times, Windows Vista brought us the Aero Glass effect, which let blurred content show through the edges of window frames for no discernible reason at all. At the time, reviewers speculated that the purpose was simply to shame people into buying the latest graphical hardware and (hopefully) upgrade their computers and Microsoft software along the way. Like Luna, Aero Glass was soon abandoned.

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Aero Glass — another frill in search of a reason for its existence

Even if you think design schemes like Luna and Aero Glass are harmless, there’s a deeper flaw taking root. Over the years, Microsoft’s hastily added design frills never stay consistent for long. Some apps follow one standard, others obey another. Desktop menu-based software is replaced by Windows store apps — but only partly. The classic Windows look is replaced by the Metro design language, which is quickly replaced by the Fluent design standards — at least for the time being. As a result, the Windows operating system always looks half-finished, like a house in the middle of an expensive renovation. In my less optimistic moments, I wonder if Microsoft’s most lasting contribution to UI design is this, an enduring mishmash of software that never quite meshes together, but never goes away.

2. The Office ribbon

Microsoft’s backward compatibility is legendary. When SimCity contained a critical bug that passed unnoticed in DOS but was bluescreening test versions of the new Windows operating system, they coded around it by adding special SimCity-detection code to the OS. When Microsoft needed to compete with leading spreadsheet software Lotus 1–2–3, they dutifully copied its leap year bug. And when Microsoft tried to update Internet Explorer, the curse of standards-loving web developers everywhere, they gave it a thick layer of kludges called quirks mode that kept old sites looking the same.

With this keep-it-working-at-all-costs approach, it’s all the more surprising when Microsoft changes something big. And the introduction of the ribbon in Office 2010 was something very big. After all, Office was a key pillar of Microsoft’s business dominance (second only to Windows at the time). Yes, the ribbon had its own backwards compatibility layer — it kept old shortcuts and menu access keys working — but for people used to hunting through layers of submenus, the ribbon changed the experience dramatically.

For those who had the time to temporarily sacrifice their productivity and learn an entirely new command layout, the ribbon was actually a solid improvement. But it wasn’t without flaws. One issue was the ribbon’s thick space-hogging layout, which seems out of step with a modern generation of widescreen laptops that have more width than height. (Happily, users who don’t want to waste screen space can just collapse the ribbon down to a narrow strip.)

A more serious issue is the way the ribbon alters its layout when you resize the window. Less fancy toolbars just drop their extra items into an overflow menu. But the ribbon subtly rearranges everything as it shrinks. If you’re a casual user, that means you’re faced with learning a new layout every time you switch to a different screen or device.

The problem is that the ribbon is simply too smart for its own good. UI design isn’t just about logical arrangement and having the right features at your fingertips, it’s also about consistency and expectation. Move things around, and you violate those expectations — and shatter the trust of your users.

3. The tyranny of non-resizable windows

In the early days of Windows 3.1, there were two main types of window borders. Resizable borders allowed you to expand a window, so you could see as much content as your screen allowed. Fixed borders, by comparison, were locked in place. They were easier for programmers to design (because they never changed), but less flexible.

Fast forward a few decades and… not much has changed. There are still fixed window borders, lazy programmers, and plenty of places where you can’t see all the information you’d like to see because the window stubbornly refuses to grow bigger than a postage stamp.

Consider the age-old import media wizard in Windows, which lets you quickly transfer pictures and videos from digital cameras. The problem is that the box that shows the destination is hopelessly small. I’m forced to click the Browse button every time, just to check if I’m about to put content in a folder named 2020 or 2019.

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Import to where exactly?

The end of the world this isn’t. But often user experience succeeds or fails in the little details. And in Microsoft’s oldest products, many of these details have been slipping past for years. There are dozens of annoying fixed windows scattered through Microsoft’s most popular software. Consider the stubbornly fixed Font dialog box, which appears in Word, Excel, and PowerPoint and shows a scrollable list that’s just a few items tall:

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After 25 years, why not make room for more than 5 fonts at a time?

Yes, in most scenarios savvy users will pick the font they need from the ribbon, which provides a much longer drop-down list. But the Font dialog box is just one example of a familiar juxtaposition that stands out in Microsoft software, between carefully tooled design elements (like ribbons) and old, mostly ignored relics from the past.

4. The long clicktrail

The long clicktrail is a task — usually an easy one — that requires many more steps than it should. If you’ve ever had to click your way through a series of modal dialog boxes, letting them stack up one at a time on each other until you finally get to the sub-sub-window that has the option you want, you’ve seen the long clicktrail. But for the most part, it’s become such a familiar part of the Windows ecosystem that experienced users simply accept it.

There are no shortage of examples. For example, say you want to change the AutoCorrect options in Excel. No problem, right? First, choose File → Options to get to the multitabbed Excel Options window, which is stuffed full of useful settings. But the options you want aren’t actually here. Instead, you need to click the Proofing tab, then click the AutoCorrect Options button to show the AutoCorrect dialog box. Oh, and there’s another button here, named Exceptions, which pops open yet another dialog box on top.

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A stack of dialog boxes

If this seems like a few harmless extra clicks… well, not quite. The Excel Options window is a proper part of the modern Office UI. It’s resizable and scrollable, which makes it easy to work with. The AutoCorrect options and exceptions should be here — there’s no shortage of space, and that way you could save some clicks and see more entries at a time. But the AutoCorrect dialog boxes are fossils from the past, frozen at an artificially tiny size that dates back to Office 95.

If you suspect I’ve cherry-picked an intentionally awkward example, then you need to spend more time hanging out with Office. Despite the fact that Microsoft launched a review with Office 2010 that was supposed to revise every old and potentially problematic window, these old dialog boxes are everywhere. Try changing the document template in Word for a particularly nasty stack of dialog boxes.

The long clicktrail is at least partly a side effect of Microsoft’s exceedingly conservative design. In other words, if the UI isn’t screaming out to you that it’s broken, don’t fix it. And there’s good reason to fear making even small changes with massive products like Windows and Office, because these changes can have ripple effects. When the product is localized or ported to other versions, these ripple effects can eventual lead to an obscure bug in, say, the Turkish language edition. (This isn’t as far-fetched as it sounds. Microsoft faced exactly this sort of problem many times on its way to global domination in the 1990s.) In other words, the too-common result of Microsoft’s success is UI paralysis.

5. Active desktop and other gimmicks

Should a Windows desktop look like the crafting aisle at a discount store? For the first 15 years of the Windows operating system, the ability to trick out your computer with personalized details was a major selling point.

A lot of the excitement was simply because you could. Making your computer play Thus Spoke Zarathustra when it booted up was the 1990s equivalent of picking a custom ringtone in the first generation of smartphones. And as Windows became more sophisticated and hardware became more capable, the frills expanded beyond custom icons, mouse pointers, and desktop backgrounds to include gimmicky effects that no one needed, like in-your-face menu animations and — my personal pet peeve — active desktop.

Active desktop was an IE-powered feature introduced with Windows 98 that would let you replace your ordinary desktop background image with a web page with dynamic content, JavaScript, and even animation. The problem was that this feature exceeded the abilities of plenty of computers of the day. Before it was retired in Windows Vista, active desktop had the opportunity to crash plenty of computers.

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If you used Active Desktop, you know this message

Active desktop is the most obvious examples of gimmicks for gimmicks’ sake, but it was only one installment in a series of showy but mostly useless features. But at least the short-lived 3D fishbowl screensaver craze (which Microsoft chased in the last version of Microsoft Plus) only kicked in when the computer was idle, making it relatively harmless. By comparison, active desktop was all cost and no benefit, which is the worst sort of UI frill.


Of course, Microsoft has plenty of excellent designs as well, many of them poached from competitors, but then fortified with good ideas of their own. I’ll go to my deathbed defending the modular VS Code environment, which is as comfortable as well-worn easy chair. But even the occasional gem can’t erase the memory of Microsoft’s years of UI crimes.

Have you suffered from one of Microsoft’s UI crimes? Drop it in the comments below! And for a once-a-month email with our best tech stories, subscribe to the Young Coder newsletter.

Young Coder

Hack. Code. Think. Stories about science, tech, and programming.

Matthew MacDonald

Written by

Teacher, coder, long-ago Microsoft MVP. Author of heavy books. Join Young Coder for a creative take on science and technology. Queries: matthew@prosetech.com

Young Coder

Hack. Code. Think. Stories about science, tech, and programming.

Matthew MacDonald

Written by

Teacher, coder, long-ago Microsoft MVP. Author of heavy books. Join Young Coder for a creative take on science and technology. Queries: matthew@prosetech.com

Young Coder

Hack. Code. Think. Stories about science, tech, and programming.

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