if the file plays when i run it with chuck filename.ck, and all kinds
of fun sound things happen, doing the same with --loop running in one
dos box, and chuck +filename.ck in another dosbox should make all
kinds of fun audio things happen as the tutorial suggests, however, no
audio things happen at all.

That's a bit disapointing, then, that should really work.

What happens instead? Do you get any errors at all? Or other output? Do other commands like the "status" one that should also interact with the running VM work? (see "chuck --help" or the manual for the exact options that you have) When you write "+filename.ck" , do you mean you used it like that, without the space? It should be like this;

chuck + myfile.ck

so with a space.

Because you mention a "dosbox" I assume you are on Windows. If this is somehow related to how differend commandline sessions on your OS interact then it would also be quite helpful if you could mention what exact version of Windows you are running. It could be that some of the more recent versions of Windows were "improved" in some way that makes things stop working, for example.

Yours,
Kas.