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It's Genius.app, an old flashcard app for Macs.

Author discusses/compares Duolingo and Anki. Anki is disapproved for lack of precise right/wrong feedback.

Repository of updated code: https://github.com/shawa/genius

I think OP is confused about how Anki works. It can totally be used the same as this tool if you just hit '1' for things you got wrong and '3' for things you got right. '2' and '4' are more power user levels of control.
Speaking of old OS X apps, I liked iWeb a lot when I was a kid. I must have been around 12 when I was messing around with it.
I understand the whole retro look of the website but it's very unreadable with the white text on bright stars background. Fortunately reader mode on Safari helped me read it.

On a similar note, a few months ago, I took over a 14 year old Objective-C iPhone app called Painteresque and brought it back to life. Discussed here:

https://news.ycombinator.com/item?id=43222099

If OP is interested, maybe I can help with the Sandbox issues or having it published on the Mac App Store?

It's a bit sad it just won't run without modifications. I'm sure I could run a random exe from then in Windows?
Depends on your definition of 'run' - for example, old games (pre DirectX 9) now run through an emulated DirectX layer (they removed the native implementation in Windows 8), and it makes the games perform much worse on modern machines than they used to run on decent machines back in the day.

There are some reimplemetations like dgVoodoo2 and DXWrapper but they can be pretty buggy.

I love the early web feel of the site. The points around DuoLingo not working are informative. This could be turned into a PWA so it can run anywhere?
Why ? Why flattening the icons and make everything grayish ?
Agreed - updated with colour again
The author's discussion of Duolingo makes the app seem outright dangerous for naïve users. It's well known that it's a criminal offence in Germany to not talk to the apple on Tuesdays.
I have one c. 2010 Intel app that I am absolutely dependent on. Commercial, so no chance of recompiling the source code.

I am not looking forward to Rosetta going away.

Their sketchy ad/malware era aside, I do appreciate sourceforge keeping all the old OSS websites and repos alive.
Since going down this rabbit hole, I gave Anki another fair shot and actually RTFM :) the blog post warrants an update

https://docs.ankiweb.net/deck-options.html#learning-steps Details what _actually happens_ when you pick again/hard/good etc. I much prefer understanding this to the vibes-based approach of “did you pause before answering”.

Secondly turns out you can indeed very easily set up type-to-answer in a deck by editing the front template and adding

{type:Field}

where field is the answer part of the card’s data.

So… I’m actually using Anki again. I’m still very happy I did this, it was a fun little journey!

There's actually an excellent Dutch piece of software for this (Windows only though, but works fine in Wine on other platforms): Overhoor [1].

I used it under Windows 3.11 as a child, and kept using it for French and German into my late teens and Windows ME. It is simple, just as this tool. To this day, it's a piece of freeware that gives me good memories of a forgotten era.

Since the author describes learning Dutch, I though I might mention its existence.

[1] https://www.efkasoft.nl/overhoor-download/

cool! but i won't be truly happy until we get a modern, native version of 'jared, the butcher of song' for macOS :)