This chapter explores some philosophical quandaries facing the natural law outlook, with particular emphasis on the prospects for a natural law account of human rights. The chapter begins by considering challenges to natural law’s reliance on the notion of human nature. It then examines the role of time in natural law theories, focusing on the question of whether natural law changes. Next, the chapter looks at the place of rights in the natural law tradition, critically discussing the suggestion that the notion of rights is at odds with the core themes of the natural law outlook, before considering what natural law has to offer to human rights theory. Finally, I turn to the place of God within natural law theories, raising the issue of whether natural law assumes a theistic worldview. I argue throughout the chapter that a hermeneutic and historicised view of natural law, which sees it as shaped by and discovered through human social practices, holds important advantages in responding to each of these challenges.