Self-tracking tools are often built around the assumption that tracking the “right” health variables will lead to actionable insights and greater control over one’s health. Yet, it remains unclear how these assumptions hold up in contexts marked by uncertainty, unpredictability, and frequent fluctuations in health needs. We explore this question in the management of enigmatic diseases—conditions such as fibromyalgia, Crohn’s disease, and endometriosis that are poorly understood and highly individualized. Through interviews with 23 participants living with disparate enigmatic conditions, we examine goals, motivations, and how tracking practices evolve across different disease states. Our findings show that tracking was strongly shaped by shifting needs, with goals emerging, evolving, or being abandoned in response to health fluctuations. Tracking was often double-edged: at times empowering, fostering a sense of control, but also frustrating, leading to self-blame and negative views of everyday activities being tracked.