Self-tracking and personal informatics offer important potential in chronic condition management, but such potential is often undermined by difficulty in aligning self-tracking tools to an individual’s goals. Informed by prior proposals of goal-directed tracking, we designed and developed MigraineTracker, a prototype app that emphasizes explicit expression of goals for migraine-related self-tracking. We then examined migraine patient experiences in a deployment study for an average of 12+ months, including a total of 50 interview sessions with 10 patients working with 3 different clinicians. Patients were able to express multiple types of goals, evolve their goals over time, align tracking to their goals, personalize their tracking, reflect in the context of their goals, and gain insights that enabled understanding, communication, and action. We discuss how these results highlight the importance of accounting for distinct and concurrent goals in personal informatics together with implications for the design of future goal-directed personal informatics tools.