I requested two songs right after each other - "Pinocchio's Villiage Haus - loop 5" and "He's a Pirate." When it came time to play the first song it played fine.. but He's a Pirate never played (I did see it in the "coming up" status). And it doesn't even show that I ever requested, actually. Hmm.
But it did take my points and what not (I can see the regen status), so I at least know I did requested it. Here's a picture for reference.
