This paper presents a conceptual synthesis on why patient-led pathfinding is essential for the development of clinically stable digital health and AI-enabled systems. It argues that persistent failures in healthcare digitalisation are not primarily technical, but structural, arising from misaligned system incentives, disrupted clinical workflows, and insufficient legitimacy. Building on the Clinically-Grounded Systems (CGS) series, the paper positions patients as uniquely capable of leading early system pathfinding without institutional or professional conflicts of interest. It shows how patient-led grounding enables professional alignment, legitimate governance, and safer integration of AI as a downstream clinical tool rather than a primary driver of change. The paper is intended for clinicians, health system leaders, policymakers, patient organisations, and researchers working at the intersection of healthcare, digitalisation, and artificial intelligence.