Both of them are set to "Yes". Is this causing the problem?
What I actually prefer is that whenever I click on a playlist, RockBox will bring me to the playlist and show me all songs within the playlist. I will then choose one of the songs and songs after that song will be played randomly; similar to how Iriver firmware works... What should I do to achieve this?
EDIT: I shifted my playlists to the Playlists folder in the root directory of my player. This allowed me to choose the songs I want to play first but now, RockBox is not shuffling the playlist ie. it used the same arrangement of songs all the time. What gives?