You mean 90's Linux?
My experience is: On Windows, for most enduser use cases (and this absolutely excludes anything dev related), I would expect the user to get by without touching the CLI. In fact, I would assume that any given application will expose all of its functionality only through a graphical UI. For me, on Linux, the opposite expectation applies.
It's either crashdump or nice error message. If not I just increase loglevel to find the actual problem.