When CIRCA launched ReConnect in April 2024, there was no dedicated reinsurance conference in the Cayman Islands. Three years later, the event is set to welcome more than 700 delegates from at least nine countries to the Ritz-Carlton, Grand Cayman, on 16-17 April. Conor Kearney, CIRCA’s Marketing Chair, speaks about the conference’s evolution, what’s new for 2026, and what attendees can expect to take away from the event.
ReConnect is now in its third year. What was the idea behind the reinsurance conference when it was launched?
ReConnect was created to fill a distinct gap. Cayman’s reinsurance sector was evolving quickly, with rising international interest, but lacked a dedicated senior-level forum. There was also limited international understanding of Cayman’s reinsurance environment and regulation. The conference aimed to address both, offering access, context and factual discussion based on real market practices and supervision.
From the outset, the intention was to create something distinct from larger, more traditional conferences. ReConnect is not a trade show and not sales-led. It is deliberately curated for a senior, informed audience and structured around substance rather than scale.
It also supports CIRCA’s broader role. We aim to promote clarity and informed dialogue around Cayman’s reinsurance framework. That role is particularly important right now, given the increased external focus on the sector and the need to discuss how the regulatory framework operates in practice.
How has the conference changed since that first edition in 2024?
Feedback from previous years consistently highlighted the value of candid, substantive exchanges among regulators, policymakers and industry leaders, particularly on supervisory expectations, capital and regulatory frameworks, and cross-border alignment. Delegates also pointed to the ability to engage directly with decision-makers as a key differentiator from larger, more transactional events. That feedback has directly shaped the 2026 programme.
The most significant structural change this year is the expansion to a full two-day format, with a clear distinction in purpose between the two days. Day One is focused entirely on Cayman. The Discover Cayman sessions provide practical, detailed discussion on licensing pathways, capital requirements, regulatory engagement and what it means to operate in this jurisdiction. Day Two broadens the lens to global reinsurance and capital markets. That structure reflects both the continued development of the conference and the growing maturity of the conversations around Cayman reinsurance.
The Discover Cayman sessions have expanded and moved to the larger Royal Ballroom, with an additional panel. The programme includes more than 40 speakers and moderators, over 45 sponsoring organisations, expanded exhibitor space, a dedicated networking area, and, new for 2026, a conference app giving delegates real-time access to the agenda, speaker profiles and networking tools.
What do the attendance numbers tell us about the trajectory of the event?
Attendance has grown steadily each year. The inaugural conference in 2024 drew just over 400 attendees. In 2025, that rose to approximately 650. For 2026, we expect more than 700 delegates, with over 540 already registered, representing more than 157 companies across at least 9 countries.
The audience is well balanced with approximately 50 per cent Cayman-based delegates and 50 per cent international participants from markets including the United States, Bermuda and Europe, representing both the Life & Annuity and Property & Casualty sectors. That mix supports practical, cross-border discussion between those operating within Cayman and those engaging with the jurisdiction globally.
What role does ReConnect play in the broader development of Cayman’s reinsurance sector?
ReConnect brings together industry, regulators, policymakers and capital providers in one place, enabling direct dialogue about how the market operates in practice. The ability to have those conversations in Cayman, with the people directly responsible for operating and supervising the market, is what gives the conference its particular value.
Cayman’s reinsurance sector is evolving, with a focus on long-term capital, effective risk management and alignment with international standards. The conference reflects that in both its audience and its content. It is visible in the breadth of participation as well as in the programme of panel discussions, which have a clear focus on operating models, supervisory expectations, governance and how Cayman operates within a global market.
Why does it matter that the Cayman Islands hosts its own dedicated reinsurance conference, rather than relying on representation at international events?
It matters because Cayman offers a well-established, internationally aligned regulatory and operating environment, supported by a deep professional ecosystem, and the only way to fully understand that is to experience it.
Hosting ReConnect here allows participants to engage directly with regulators, understand supervisory expectations in context, and connect with the local service providers and market participants who make the jurisdiction work.
We want delegates to see that Cayman is a sophisticated, well-governed, globally integrated reinsurance hub.
What are the highlights of the 2026 programme?
Day One centres on the expanded Discover Cayman sessions, which have been broadened significantly in response to delegate demand. The sessions provide practical guidance on Cayman’s evolution in financial services across funds, captives and reinsurance; how to establish and operate a Cayman reinsurer; and the development and future direction of Cayman’s regulatory framework.
Day Two opens with a keynote address from André M. Ebanks, Premier and Minister for Financial Services and Commerce. Another highlight will be a featured conversation with Cindy Scotland, OBE, Chief Executive Officer of the Cayman Islands Monetary Authority, moderated by Derek Stenson of Conyers. This will be a great opportunity to hear directly from the head of the regulator about the issues shaping the market.
Panel sessions will cover regulatory and actuarial trends in global reinsurance; offshore jurisdictions in a global context; private assets in the insurance ecosystem; geopolitical developments and their macroeconomic impact; climate resilience and public-private partnership models; and the practical adoption of AI in (re)insurance.
What are the themes you expect to generate the most discussion this year?
There is no single headline theme, but there is a clear direction. The programme focuses on how reinsurance markets are evolving in practice. The relationship between long-term capital, private assets and insurance liability structures is one of the defining debates in global reinsurance at the moment, and it runs through a significant portion of the Day Two agenda. Regulatory alignment, how Cayman’s framework sits within and engages with the international supervisory architecture, remains central. There is also a focus on climate risk, governance and the applied use of data and AI.
Underlying all of that is something more specific to Cayman: ensuring that discussion about the jurisdiction is grounded in fact and reflects how the regulatory framework operates, particularly in areas where there is increasing external scrutiny.
What is the one thing you want delegates to leave with?
A clear, practical and evidence-based understanding of how Cayman operates and the role it plays within the global reinsurance market. The key takeaway is that Cayman is an internationally aligned and well-regulated reinsurance jurisdiction. It operates within a proportionate, risk-based, principles-based framework aligned with international standards, supported by active supervision, ongoing regulatory engagement, and the depth of a well-established financial services ecosystem.
What makes ReConnect different is that this understanding comes from direct engagement with the regulators and practitioners who operate in and supervise the market.
ReConnect 2026 takes place on 16-17 April 2026 at The Ritz-Carlton, Grand Cayman, Cayman Islands.
Registration and full agenda: Reconnect.ky
