Studies which I carried out recently of users of digital music players revealed that the element of randomness plays a role in influencing the user experience (UX). Apart from being generally positive, some users even report rich experiences such as serendipity. I propose a field study to further explicate the phenomena. In doing so, I aim to produce a theoretical framework which will provide a richer characterization of the randomness-influenced UX. This will add to our understanding of UX and may serve to inform designers of interactive systems on how randomness can be used as an innovative design resource for supporting rich and novel UX. Author Keywords Randomness, Design, User Experience, Digital Music. ACM Classification Keywords H.5.3 Group and Organization Interfaces, H.5.5 Sound and Music Computing.