“How can I delete and add to library at the same time”

An absolutely eviscerating 18-minute walkthrough of Apple Music for macOS Catalina, from a few years ago. More funny than anything else, but a reminder to test the “boring” edges of your app – like a state with a lapsed subscription, or coming back after a few months.

There’s no way to drag and drop. […] If I want to add this to here, I have to go through this bullshit, and when I do, it takes seconds again.

Also, an ode to a well-functioning back button, and well-behaving loading states. Those things add up so quickly.

(My debugging brain understood what populated the confusing History entries – I bet it was the early play sequences that went through a bunch of stuff without playing.)

“Ugly in a way that’s pretty”

I gave a talk about the craft of pixel fonts at Config last year, and this fresh YouTube video by Noodle seems to be a great and quirky companion to the whole issue of “how did pixels look on old CRTs,” including many examples from modern games.

⌘-P ⌘-S

A really interesting convention I just spotted in DevonThink that shows the shortcuts as soon as you hold ⌘, although it feels a bit clunky and cheap in execution.

(The main worry here for me would be that it’s distracting if you already know the shortcuts. I haven’t noticed it disappear if you use it, but maybe it does after a while.)

“OK cool now we can ship the game phew. But why did this EVER work?”

Tom Forsyth wrote about a fun bug in a Half-Life 2 reissue, of a particular flavour I have never heard before.

So I started it up, selected new game, played the intro section. It’s a fairly well-known section - you arrive at the train station with a message from Breen, a guard makes you pick up a can, and then you have to go into a room and... uh... I got stuck. I wasn’t dead, I just couldn’t go anywhere. I was stuck in a corridor with a guard, and nowhere to go. Bizarre.

“Especially helpful during live shows”

Fascinating quick walkthrough of Strudel on TikTok from DJ_Dave (sound on!). Sometimes you see an interface and you immediately just sense how efficient and fun and powerful it is, without ever touching it.

Very bretvictorian in a way. Also related: a recent video from Benn Jordan walking through obscure music software used by Aphex Twin.

“And then the system crashes”

From Nina Kalinina’s excellent revival of a forgotten 1983 GUI, a discovery of a hilarious accessibility bug:

VisiOn loves to beep at the user. It beeps every time a menu option is chosen or an on-screen button is clicked.

If you are tired of the noise, you’d appreciate that Application Manager has an option to replace the sound with a “visual beep”. It is implemented as a flashing area of 32x16 pixels around the mouse cursor. Every time the flashing is about to happen, an image “below” the cursor is preserved in RAM to be restored after the “visual beep” is over. However, the memory allocated for this bitmap is never freed. It takes between 200 and 1000 clicks to fill the RAM with useless copies of the mouse cursor, and then the system crashes.

If you have never heard of VisiOn, The Digital Antiquarian has a fun walkthrough that also happens to be the first chapter of an excellent series about the history of graphical user interfaces.

“Never criminalize pride in craft.”

From Jeff Veen:

It reinforces my belief that teams need a culture that values attention to detail when building products. Tiny annoyances so often get neglected as we rush to ship, but the consequences accumulate, souring the whole brand. It’s not a long journey from “Ugh, these AirTags…” to “Apple has lost their way…”

But in my experience, those rough edges seldom go unnoticed by someone, somewhere, who was unable to stop the momentum of a product release for such an “insignificant” flaw. Or, even more consequentially, they did not feel it was safe to do so.

I want to quote so much of this essay, so I’m going to do just that.

I’ve always felt that culture is made of the accumulation of small acts of gracious leadership: acknowledging moments of bravery during a retro, teasing out a reticent comment during a product review, and on and on. It can come from other places too, but it is most effective when it comes from the top.

If you’re leading a team remember: Never criminalize pride in craft.

Dec 4, 2025

“More nuanced, more expert, interaction design skills”

Scathing from John Gruber:

I think the fact that Liquid Glass is worse on MacOS than it is on iOS is not just a factor of iOS being Apple’s most popular, most profitable, most important platform — and thus garnering more of Apple’s internal attention. I think it’s also about the fact that the Mac interface, with multiple windows, bigger displays, and more complexity, demands more nuanced, more expert, interaction design skills. Things like depth, layering, and unambiguous indications of input focus are important aspects of any platform. But they’re more important on the platform which, by design, shoulders more complexity.

A great read – harsh, but deserved. It’s good to punch up. I don’t have a lot of context on Alan Dye, but the parts that resonated the most was appreciation of the craft of interface and interaction design for complex things. iOS has had occasional sprinklings of great interaction design, especially in its physics-based gestures that blossomed since iPhone X. macOS feels abandoned in this regard, with even hard-won victories like fast Finder and great user preferences deteriorating.

Dec 4, 2025

“Fight my way through it all again”

From my friend Robin Rendle:

But here’s what modern UI design looks like: There’s always a confusing title; it doesn’t quickly tell me what to do or what it wants me to understand; beneath that there’s a subtitle, explaining the title again; beneath that there’s several sentences that restates the title and subtitle but simply jumbles all the words around to make it justify its existence; then the button—there is always a button—and it asks me to “Confirm” or “Apply” but as to what I’m confirming or applying I have absolutely no idea unless I go back to the text and fight my way through it all again.

Kept nodding through this whole essay. I don’t love nervous user interfaces that share their own problems and insecurities with their users. I love confident interfaces that know exactly what to say, and don’t outstay their welcome.

Dec 4, 2025