This is a very cool conversation, for some reason, I always found debugging tools to be fascinating bits of tech. I do have to admit though, that my first read

This is a very cool conversation, for some reason, I always found debugging tools to be fascinating bits of tech. I do have to admit though, that my first read of your post was wrong tough, I read it as "debuggers used in embedded" like JTAG stuff, OpenOCD, etc. but you mean it as, if I read this right "debuggers embedded in the runtime/program" stuff like Python, or GDB server running on system right?