Rapid digitalization has heightened exposure to cyber risks for organizations and individuals, and technical controls alone cannot ensure complete protection. Cyber insurance complements security investments by transferring residual risk and enabling post-incident recovery; however, adoption remains weak. This study examines the technological challenges constraining cyber-insurance uptake and prioritizes them to guide managerial and policy action. Using an exploratory qualitative design, we convened a nine-member expert panel spanning IT security, risk management, cyber-insurance practice, and information security research to elicit and refine barriers. The resulting eight challenges were ranked with the Analytic Hierarchy Process (AHP) based on expert pairwise judgments. Findings show the dynamic nature of cyber risk, scarcity of historical loss data for quantification, and innovation-driven resource constraints as the most influential impediments, while integration complexity, cascading interconnections, non-standard assessment frameworks, baseline verification, and general threat evolution contribute comparatively less. The study contributes an expert-validated prioritization that clarifies where limited resources should be directed- data generation and sharing, capability building, and standardization and offers actionable insights for insurers, regulators, and enterprise buyers seeking to unlock cyber-insurance adoption in emerging market contexts.