Hi Rob,
It may be worth checking that winamp is the default player for audio.
1. press windows key and x.
2. cursor up to apps and features, press enter.
3. you may need to shift tab once, to the list, and arrow down to
default apps, and press enter.

4. tab three times, to default music player, if it is not winamp, press
the button, and from the nex dialogue, select winamp and press the
button.
If winamp is already the default, press alt f4 to close the default apps
and features settings window.

see if winamp plays files when you press enter on the files you want to
play.
If not, we need to look further.

Joe

t