For decades now, Raymond Chen has been posting to his blog The Old New Thing about various technical Microsoft quirks, occasionally venturing into Unsung territory. Last week, Chen shared a nice remembrance of Tony Krueger, a person responsible for implementing the red squiggly underlines in Word:

Tony worked on Word 1.0, 1.1, 2.0, then on Word for OS/2 and Word for Mac, then returned to Word 6.0 and several versions beyond that. He probably holds the record for “most versions of Word shipped.” […]

Tony made the spell checker much more unobtrusive so that it didn’t interfere with your foreground work. And when it found a problem, instead of waiting for you to trigger a spell check, it immediately drew red squiggles under potentially-misspelled words (and later green squiggles under potential grammatical errors). […]

Today, there are red (and even green and blue) squiggles in nearly every word processor, and often outside word processors. Tony did it first. The next time a red squiggle catches one of your mistakes, say thanks to Tony. I think he’d appreciate it.

Read on for some fun celebrity encounters, and even a touching comment from Krueger’s father. Another person adds that a “PM named Diana” and another Microsoft employee, Jim Walsh, might have been the people who designed the feature.

Chen doesn’t name it specifically, but it’s my understanding that the red underlines were named Spell It (meh), and appeared in Office 95 in 1995. Steven Sinofsky confirms it on his blog, adding “The red squiggles were simply reflective of a proofreader’s style of mark (also one of the early uses of color in the interface).”

As far as I can tell by looking at various screenshots and photos of boxes, the feature wasn’t advertised at all. It was only mentioned more explicitly a few years later in Office 97:

When taking screenshots, macOS at some point followed iOS and introduced a “floating thumbnail,” which serves as a proxy of the screenshot you just took – you can drag it somewhere, open it to annotate, etc.

The thumbnail is a nice gesture. The problem is that I rarely do the things it enables, so the thumbnail is now an extra thing to deal with and dismiss. And you have to dismiss it, because inexplicably on macOS the floating thumbnail is diegetic, meaning it itself can be screenshotted. And this happens, routinely, if you do a few screenshots quickly in a row – the screenshotting tool literally ruining your screenshots. “You had one job,” &c.

(“Diegetic” is perhaps my favourite pretentious word. It generally stands for “in-universe.” If characters in a movie are listening to the song, that song is diegetic. If the song is just for the viewer as part of the soundtrack, that song is non-diegetic.)

You can turn off the thumbnail, but then outside of the sound – which is unreliable for other reasons – there is nothing else to tell you the screenshot was taken. And I think it’s good to have some sort of a confirmation, especially since the screenshot shortcuts are so harrowing.

Now, on Windows, when you press the equivalent (Windows key + PrtSc key), this happens:

I think this is better. It’s elegant, unmistakably recognizable as a screenshot, gone immediately, and a cute skeuomorphic nod towards old cameras.

4096 is a Russian UI artist (I just made up that title) who creates interesting audio-visual mashups. Here are some of the best ones:

Interfaces of rhythm games (like Guitar Hero):

Windows startup sounds, incl. fun hi-def reimagining of their splash screens:

Windows error messages:

If this looks like fun, check out the rest of their work, including Windows 95 mobile and the art of blank VHS tape boxes.

As a Mac user I naturally focus on that platform, but Windows 11 has had its own share of problems – and that list has grown so vast it’s hard to know where to start.

So let’s pick it up at random, with a post by Thom Holwerda with a great title “You can actually stop Windows Explorer from flashbanging you in dark mode”:

One of the most annoying things I encountered while trying out Windows 11 a few months ago was the utterly broken dark mode; broken since its inception nine years ago, but finally getting some fixes. One of the smaller but downright disturbing issues with dark mode on Windows 11 is that when Explorer is in dark mode, it will flash bright white whenever you open a new window or a new tab. It’s like the operating system is throwing flashbangs at you every time you need to do some file management.

I find the videogame-inspired nickname darkly – I’m sorry! – funny, but the problem is real. It looks like this (video via windowscentral.com):

It’s not a problem unique to Windows 11 – just the other night I saw this on Wikipedia on my iPhone, exacerbated by the delayed reaction of Liquid Glass buttons spastically adapting to the changing background:

But there is something about this that feels a notch more important than other visual and layout issues.

I think this is because dark mode is a contract – we’ll lower the brightness, and we’ll let your eyes rest. There’s a physiological part to it: a sudden flash of light when your eyes are not expecting to it can be actually physically painful. I think it’s worth thinking about it and futureproofing and sanding dark-mode views especially at their edges: loading states, error messages, signing in and logging off areas. The “flashbang” analogy is very apt, and especially so on bigger screens.

Just a few hours after writing about floppy disks, I stumbled upon a bona fide floppy icon in the Bluesky’s iOS app, anno domini 2026:

I imagine this, in a nerdy view deep inside settings, might be more of a fun nod, but it made me curious – does Word still use a floppy icon?

Yes, it does! Right next to the icon-less AutoSave toggle, deep within a veritable kowloon walled city of interface elements.

And yet, maybe I should chill with the jokes – NN/Group revisited the save icon in July of last year and surprise! People still understand them.

83% of participants associated the floppy disk icon with saving. […] Another 13% described this object literally with responses such as “disk,” “disc,” or “this is an SD card for storing information.” These responses were not coded as “save,” but still suggest familiarity with the image.

What a fascinating journey! The icon didn’t change at all, but its perception went from being a literal representation of a familiar object, to a skeuomorph once floppies were replaced by hard drives, to then a symbolic representation of physical media in general (a lot of people think it’s an SD card – or perhaps even that floppy disks and SD cards are one and the same), to increasingly just an abstract symbol that represents saving as a concept, registering similarly to the circular arrows for syncing, and an arrow pointing south for downloading.

NN/Group is itself kind of a floppy disk, trying to walk a fine line between their legacy and reinventing themselves. They’re dismissed by many as old-school, academic, boring enterprise software aficionados, relics of a different era. I see some of that and often disagree with them, but I also sometimes appreciate their rigor, reliance on user studies, and outright dismissal of fashion in UI design. I want to revisit their site in more detail and see how I feel about it today, 30 years after Jakob Nielsen’s books rocked my world.

A good 22-minute video from XDA about the debacle that was Windows Vista and the corrective measure that followed, Windows 7:

It taught me many things and it clarified that things were more complicated than they seemed. Windows Vista (widely seen as failure) perhaps wasn’t so bad, and 7 (quoted by many as the best Windows ever) was not that far away from Vista, down to its internal version number being 6.1 to Vista’s 6.0.

It’s also interesting to reflect on this today, when macOS is having its own Vista moment.

There is also a follow-up video on Windows 8, the possibly most consequential Windows release of that era, with product decisions that reverberate still today.

Main takeaway: An entire book could be written and a lifetime of lessons learned from Microsoft’s “.1” releases.

One thing I really admired in earlier versions of Windows was the thing that was also its weak point: the keyboard orientation.

I miss the old tradition in Windows where many commands had underlined letters, and you could simply press Alt and that letter to jump to it:

If I remember correctly, eventually this got simplified so that the underlines were only there when you held Alt (although I bet there was an option to keep showing it all the time).

Opening Windows 11 today, it feels like the system got less elegant. I can still press Alt and stuff happens, but it doesn’t look nearly as good or tightly integrated, and the two alternate entry points (Alt and the keyboard shortcuts) become muddled:

In the meantime, on a Mac, in various places apps reinvent the wheel by their own thing.

I just saw this in Nova, the code editor, which is very thoughtful; those shortcuts only exist within this dialog (and one wonders if they couldn’t just be letters without modifiers)?

A little more old-fashioned from Photoshop, and the same question: could they just not be digits, without requiring ⌥?

Previously, I mentioned yet another idea from DevonThink.

I appreciate these gestures toward moving faster via a keyboard, but I wonder if we lost something that already used to work well in old Windows.

Wes Fenlon at PC Gamer:

Every so often, a wonderful thing happens: someone young enough to have missed out on using computers in the early 1990s is introduced to the Windows 3.1 “Hot Dog Stand” color scheme.

I can’t figure out whether Gruber’s take (“That’s Microsoft.”) is also a subtle jab at Apple in the year of Liquid Glass.

Also, great first comment under the original post:

I assume “Plasma Power Saver” served an actual purpose - it was intended for users of “portable” machines having a gas plasma display. Early ones were monochrome (orange) and I guess the actual color hue didn’t matter so much as the intensity.

Early plasma displays were genuinely fascinating.

I just got my first Windows laptop in ages, and a little nervous to dig in, given the burgeoning reputation.

(My secret: I used to admire Windows in the 3.x and 9x and 2000 era because I always thought its keyboard operation was a lot better than Mac OS’s.)