As climate-related hazards intensify, integrating Anticipatory Action (AA) with Climate Risk Insurance (CRI) has become increasingly essential for strengthening disaster preparedness and resilience. Yet these approaches have largely evolved in parallel, shaped by different operational logics and institutional incentives. Drawing on 11 expert interviews across the humanitarian and insurance sectors, this study analyses the opportunities and constraints of linking CRI with AA systems. Findings reveal that while both sectors recognize the value of pre-arranged financing mechanisms to enable early action, significant barriers remain. These include misaligned trigger mechanisms, uneven data quality, limited operational readiness, and persistent affordability gaps that constrain scale and sustainability. The study highlights how differing risk lenses – actuarial precision in insurance and adaptive, people-centred decision-making in humanitarian practice – shape the feasibility of integration at multiple stages of the AA cycle. The paper concludes with recommendations to strengthen data-sharing systems, develop context-specific trigger designs, and embed CRI within national social protection and disaster risk financing frameworks. Overall, the study provides one of the first cross-sector analyses of CRI-AA integration, offering actionable insights for advancing climate-resilient risk management.