Forrester’s new Total Experience Score, Brand Experience Index (BX Index™), and Customer Experience Index (CX Index™) ratings for eight health insurers in Singapore reveal that the good brand perceptions among noncustomers do not align with the poor quality of experiences among existing customers. We also identify the key drivers of BX and CX, the top levers of trust, and the emotions that impact brands’ ability to win and retain customers. CX, marketing, and digital business leaders can use these findings to understand their market dynamics and how to improve customer loyalty.