It has become a commonplace to observe that the economic and cultural significance of live music has increased, while the sales of recorded music have declined. With a sense of relief people observe that the physical experience of live music attendance remains vital under conditions of rapid digitalization. This observation runs the risk of neglecting the actual challenges faced by the live music sector. In fact, live music organizations are also competing for the attention of the consumer in the dynamic entertainment landscape of a digital society. Meanwhile, many small music venues and musicians operate under precarious conditions. This chapter provides an overview of contemporary challenges in the live music sector and discusses potential solutions.