Comment by Jach
I frequently try to mention how Java with JRebel is the closest to the Lisp experience I've found with non-Lisp, it's more dynamic feeling than so-called dynamic languages. Having something like the condition system being ubiquitous would be golden. (I'm aware there is a Java port though I never got around to playing with it and it doesn't solve the problem of other people's code not using it..) My last big job involved a giant app server that would take minutes just to restart if you had to do it, JRebel saved so much time by making things much more reloadable including support for a lot of other libraries' quirks and in general a lot of Java-isms like things configured with XML. Looking under the hood at the JVM you can see traces of Lisp everywhere, like class loaders are just (load)s, it's easy to believe the quote about dragging C++ programmers halfway to Lisp.
Then there's things like rr (https://rr-project.org/) that also seem largely ignored by old unix systems people, despite being exactly appropriate for that environment.
Still, having the whole language available via REPL as Lisp does when you hit a break or error makes up for a lot of weaknesses in the rest of the debugging experience.
I haven't met the individuals like taeric but I do find it plausible that something has been lost for developers whose main experience is in highly separated cloud-oriented systems, whether they go as far as micro-services or not. When you don't have full end-to-end debugging and have to correlate everything with trace ids in logs, and also if policies prevent even getting a debugger hook in production, I can see how one would be less motivated to learn about debugging tools to begin with. (On the other hand you're encouraged to have better logging, and often that's enough to figure out a problem, no need to have a running application.)
Agreed on your last paragraph. Really all of your post. I would oddly find myself arguing against people trying to make a complicated step debug mock setup to simulate the deployed environment when looking for bugs. A general socratic approach to the behavior you were witnessing was a valuable way to find bugs.
To me, the connected debugger was far more interesting as a development tool than a debugging one. Despite the name.