Insurance/reinsurance in Cayman Islands


Campbells 'very knowledgeable team' is led by Alan Craig and advises insurance managers on the formation, licensing and ongoing operation of captive insurance entities that are established in Cayman. The practice also has extensive experience advising Cayman-domiciled reinsurers on formations, IPOs and day-to-day matters, assisting life insurers with overseas presences, and handling catastrophe risk mandates. In a recent highlight, the team advised Automobile Dealers Mutual Insurance Company on the re-domestication of AMIC Holdings from Cayman to the US. Alistair Walters is an insurance litigation specialist.

Practice head(s):

Alan Craig

Other key lawyers:

Alistair Walters


Appreciated for its length of service within the sector, in-depth knowledge of Cayman law and good commercial sense‘.

The strength of Campbells is the years of experience that its attorneys have, especially in dealing with insurance matters‘.

Alan Craig is a go-to lawyer for legal guidance in Cayman‘.

Key clients



Island Heritage

Pan-American Life Insurance

Investors Trust

Guardian Life

Global Captive Management

Artex Risk Solutions

Caribbean Catastrophe Risk  Insurance Facility

Guardian Insurance

Strategic Risk Solutions

Beecher Carlson

Fidelity Insurance

Eastern Alliance Insurance Group

Crum & Forster

Cottingham & Butler

Guy Carpenter & Co

Innovative Captive Strategies

Work highlights

  • Advised Pan-American Life Insurance Company of the Cayman Islands on compliance issues.  
  • Advised Strategic Risk Solutions, a global captive manager, on the restructuring of an innovative security structure for the pooling of capital support payments.
  • Assisted Innovative Captive Strategies and Global Captive Management with the establishment of a group captive named Delta Indemnity Group.


Conyers has notable expertise in insurance-related M&A, regulatory advisory work, transfers by way of continuation to Cayman, catastrophe bond structures, insurance litigation and insurance financing matters. In recent work, the team advised Topsail Reinsurance on the establishment of a new reinsurance platform in Cayman, which utilises a segregated portfolio structure focusing on short-tail lines of business. Derek Stenson, who specialises in insurance, reinsurance and structured products, joined from Walkers in 2018, and counsel Rob Humphries was recruited from Bedell Cristin in 2019. Kevin Butler leads the firm’s Cayman office and Paul Smith is recommended for contentious matters.

Practice head(s):

Kevin Butler; Derek Stenson

Other key lawyers:

Rob Humphries; Paul Smith


Conyers has made significant advancement in the sector with its recent hire of Derek Stenson‘.

Key clients

Advantage Life & Annuity Company

Aetna Life And Casualty (Bermuda)

American Specialty Insurance Company

Cayman Islands Insurance Association

Cigna International Corporation

Coinbase Insurance Company

Controlled Risk Insurance Company

Corporate Risk Insurance Company

Cox Reinsurance

Lennox Reinsurance

Liberty Specialty Markets Bermuda

Limestone Insurance Company

MetLife Global Benefits

MP Reinsurance

Sapphire Reinsurance Company

Saxon Motor & General Insurance Company

SDA Annuity & Life

Topsail Reinsurance

Tower Hill Re

Work highlights

  • Advised Aquiline Capital Partners on its acquisition of independent insurance brokerage, Relation Insurance Services, from private equity firms Parthenon and Century Equity Partners.
  • Advised Assurant, a global provider of risk management products and services, on the Cayman aspects of its acquisition of TWG Holdings.
  • Assisted Controlled Risk Insurance Company with ongoing legal and regulatory issues.

Maples Group

Maples Group's practice encompasses insurance-related M&A and corporate matters, regulatory compliance work, the licensing of insurers, managers and brokers, capital insurance issues, catastrophe bond work and other special purpose insurer, reinsurance and corporate advisory matters. The firm's litigation team also assists with insurance-related disputes. Group head Tim Frawley handles the formation of new insurance companies, insurance-related corporate and regulatory advice, substantive insurance law, and alternative risk transfer structures; John Dykstra is highly regarded for catastrophe bond transactions; and Abraham Thoppil focuses on insurance regulatory matters, licensing work, restructuring mandates, insurance M&A and motor vehicle insurance.

Practice head(s):

Tim Frawley

Other key lawyers:

John Dykstra; Abraham Thoppil


The firm’s staff is professional and makes itself available for discussions‘.

Key clients

United Insurance Company

Signature Insurance

Scottish Annuity & Life Insurance Company (Cayman)

Cayman First Insurance Company

Oxbridge Reinsurance

Nassau Re

Crosswinds Re

Island Heritage Insurance Company

Brac Insurance Associates

Magni Re

Nomadic Insurance

Work highlights

  • Advising Knighthead RE on insurance and corporate issues regarding proposed new initiatives.
  • Advised Nomadic Insurance on proposals and policy wording.​
  • Provided insurance regulatory advice to Assured Guaranty.


Walkers' insurance and reinsurance practice is focused on the establishment and licensing of life and non-life insurers and reinsurers; financing and collateral arrangements; M&A, restructuring and portfolio transfers; compliance and corporate governance issues; insurance contractual reviews; regulatory due diligence; and alternative risk transfer structures. Lucy Frew is global regulatory and risk advisory group head.

Practice head(s):

Lucy Frew

Key clients

Phoenix Group

Work highlights

  • Acted as Cayman counsel for Phoenix Group on the successful onshoring of Phoenix Group Holdings from Cayman to the UK.