I keep thinking about MacCharlie, this strange product from 1985 that turned the original Macintosh into a dual-purpose machine that could also run software by its chief competitor, early PCs:

I’m fascinated by it because it almost feels like cargo culting: “hey, PCs are big and ugly, so if we make a Mac big and ugly, it must turn into a PC.”

Of course, there was more method to this madness, and two alien cocoons wrapped around the Mac and its keyboard actually have the correct technology, but still – what an absolutely soul-sucking experience: an ugly on/off switch, ugly disk drives, ugly, slightly misaligned elements, ugly, ill-fitting, slightly off-color plastics, even ugly colors for key legends.

(Okay, I liked one thing – the embossed Dayna logo matching the Apple’s.)

This was not a novel idea. Those kinds of matryoshkas happened to computers before, and are still happening to computers today:

There even exists a concept of a “naked robotic core” – devices designed specifically to welcome more infrastructure around them. Here’s an example from the professional cine camera world…

…but your smartphone with MagSafe is gesturing toward this idea, too.

This is not limited to hardware, and it is in software where things get really interesting to me. Here’s a thing I saw the other day when installing some keyboard modification software:

The top is the native macOS interface. The bottom, including those arrow tendrils, comes from the interested app, trying to walk me through the process using some overlaid coach marks.

Or, this is something I saw on my Windows laptop. Putting aside none of this was what I gave consent for – again, top is native, bottom comes from McAfee:

Those adornments, whether “white hat” (like the keyboard tool), or “gray hat” (like the McAfee), all feel equally desperate and hopeful.

Desperate, because if this is the best idea, there are no good ideas. You can almost feel developers gritting their teeth, saying “I can’t believe we have to do this.”

Hopeful, because – well, you’re skating where you hope the puck will remain. At least the hardware, once mounted, cannot morph into something else. But the software appendage you create doesn’t really know how the host organism will evolve. Even a singular word change in the original UI can throw everything out of balance. This is no software proprioception where you control both sides of the equation and can re-synch them when either needs to evolve.

Okay, I imagine if you think ahead enough, and have an appropriately vivid imagination, and a robust QA process set up so you can react immediately when the host changes its UI from under you, you might get something passable.

But I think it will be hard. Sure, McAfee’s pop-up didn’t even try so its approximation of the “Enable extension” button is basically laughable – but CustomShortcuts did, and even then, the rounded corners and the shadows don’t quite match.

I think this is the foundational disadvantage of this kind of an approach. I imagine there are much worse and more nefarious “black hat” examples than the McAfee callout I showed above, but even without that, shoddy facsimiles of things are all around us – fake text messages from fake support centers, fake smartphone pop-ups telling you to update your OS – and we learn not to trust them. And this kind of UI inevitably starts as a shoddy facsimile. You can pull it, with effort, to be something better, but it will never forget its roots.

Here’s another “white hat” example:

This is from Raindrop. Again, you can sense some pretty understandable desperation as presumably iOS doesn’t allow you to add the highlighting and annotating commands to its top toolbar – hence additional, bottom toolbar.

I consider Raindrop a generally well-made app, but you can immediately feel a certain maccharlieness of it all here – what was mismatched plastics in the 1985 is mismatched liquid glass effects in 2026.

And, on top of all that, once in a while, disaster strikes: