I'm new to Foobar (got fed up with Winamp) and I have a question. I have a playlist and Foobar is set to play randomly. But when I open the playlist, it always plays the first song on the playlist and not random. How can I fix this?

core => resume playback after restart

it will resume the last song you listened to

What if I just want it to play a random song? I have it set as my alarm clock to wake up to, and I don't want to listen to the same song/resume song every morning.

hum, the song will restart where it has stopped.. consequently, I don't see the problem..

You won't listen to the same song as you will listen to your track until its end and then it will be a new track (a random one)

example:
playlist

A
B (song after A)

Z (the random song)

H (random after Z)

if you listened to A, then stop, restart, you will listen to A where you had stopped (could be the end, start, etc of the song) at the end of A, you will listen to Z, then stop, restart, you will listen to Z and then to H etc..

I just tried the option. Turned it on, saved, closed the player, re-opened the player and it played the first song. So it didn't work.