The Cayman Island’s reinsurance sector has expanded sharply over the past five years, raising the stakes around how reinsurers structure financing and manage risk. The Cayman International Reinsurance Companies Association (CIRCA), the jurisdiction’s trade body for commercial reinsurers, addressed those themes at the latest event in its Reinsurance Insights series.
The event was titled Reinsurance in Motion: Financing, Modelling and Managing Risk in a Changing World. It was held at Camana Bay Cinema and sponsored by Conyers and Lewis & Ellis.
Derek Stenson and Tommy Tuohy (pictured third and fourth from the left), partners at Conyers, presented on reinsurance financing. Their session examined the practical considerations involved in structuring financing transactions for Cayman reinsurers. That included matching commercial objectives, regulatory requirements, transaction timelines and legal structures early in the process.
Regulatory alignment has taken on added weight as Cayman pursues US qualified jurisdiction status, which would reduce collateral requirements for reinsurers transacting with US cedents. Only seven jurisdictions currently hold that status, and Cayman would become the eighth if its application succeeds.
Financing structures also face new scrutiny directly from US regulators. Actuarial Guideline LV, adopted by the NAIC in August 2025, requires asset adequacy testing for asset-intensive reinsurance transactions above set reserve thresholds. The first reports under the guideline are due in April 2026.
Matt Stahl (pictured first from right), vice president and principal at Lewis & Ellis, presented separately on modelling and reserving. His session examined how changing risk environments are challenging traditional modelling and reserving assumptions.
The session title referred to risk environments in which historical loss patterns no longer reliably predict future outcomes. Stahl addressed the growing importance of combining analytical tools with sound judgment and governance.
Stephen Conway (pictured first from left), vice chair of CIRCA’s Social & Outreach Committee, said the series helps members “learn from industry experts and share knowledge.” He said the discussions help keep the jurisdiction connected as the industry changes.
The sessions come as Cayman’s reinsurance sector expands at pace. The number of licensed reinsurance companies nearly doubled from 58 in 2020 to 113 in 2025, according to Cayman Islands Monetary Authority data.
Total premiums written in the sector rose to US$30.2 billion from US$9.3 billion over the same period. Total reinsurance assets grew 341% to $101 billion, driven largely by record US annuity sales pushing insurers toward offshore reinsurance capacity.
That combination of faster growth and closer regulatory scrutiny explains why financing structure and modelling assumptions have become harder to get right for Cayman-domiciled reinsurers.
