I can run Simon 2 either directly from Windows or with DOSBOX.

1) When I do it from Windows, the game plays fine, but there is no voice-over or other sounds, even though the music is there. This is so despite the setup where I can find devices for both sound and music. More upsetting, the game crashes frequently when crossing between areas, exiting or entering the map. It is otherwise stable. This reminds me a lot of the crashes with Grim Fandango, which had a patch that made that game run well on modern machines with fast CPUs. It may be an issue here.

2) When I run Simon 2 with DOXBOX, the setup screen for sound looks all garbled. When I do manage to pick some options there, SIMON2.BAT still won't run. I get this error:

rsptrflt E:\GAMES\SIMON2\SIMON2CD E
Illegal command: rsptrflt.

(RSPTRFLT.EXE is a file in the game's directory.)

What to do? If it makes any difference, I installed the game from CD, but it has never been asked for or required for anything since.