2023 Annual Report

The progress made in 2023 would not have been possible without the support of all our customers, brokers, underwriting program partners, shareholders and staff. Thank you. I would also like to thank my fellow board members for their determined support of the management team and the priorities and goals they set and have now achieved. I would be remiss not to express my gratitude to Sharon Ludlow, who served as Interim Chair for the first half of 2023 and steadfastly led the Board through some challenging times. I very much look forward to working with the Board, Scott Egan, and the entire SiriusPoint team to deliver on our vision and ambition.

Our progress in 2023 was hard won. As you know, our main focus in 2023 was to become a profitable (re)insurer via disciplined underwriting, with laser focus on our profitable books of business, while reducing volatility in our underwriting portfolio, and capitalizing on favorable underwriting conditions. We have also reduced volatility in our investments and are producing strong and stable investment returns for the company. This measured approach culminated in a record year in operating income.

During the past year, we have also concentrated on building the foundations for continued success. We're now concentrating on building fewer but stronger relationships with our key partners. The rationalization of our program relationships is aligned with our 'underwriting first' strategy and cultivates further stability in our performance. SiriusPoint has built strategic partnerships with a select group of specialist managing general underwriters and programs with targeted distributions around the world, which allows us to leverage their expertise and our balance sheet.

Finally, the banner 2023 year would not have been possible without the truly 'One SiriusPoint' team. It's the unwavering dedication and solution-driven mindset of the SiriusPoint team that defines our people and our culture. Under the steadfast leadership and vision of Scott Egan - supported by his leadership team and driven staff - we look to seize the growth opportunity at SiriusPoint as we strive to become a best-in-class (re)insurer.

Bronek Masojada

Chair of the SiriusPoint Board of Directors

To achieve that goal, we are in the midst of an ambitious transformation, relentlessly implementing the significant changes that need to happen to make our vision a reality. Our focus remains on executing against our three strategic goals: simplification, reducing volatility, and profitability.

But we are not there yet. Big moves require big change. At SiriusPoint, we are achieving our turnaround strategy via cross- functional collaboration with our empowered leadership team and incredible staff. Transformation is not just a discipline; it is an experience of profound change together.

The great news is that SiriusPoint's balance sheet and capital ratios are stronger than they have ever been since the company formed through a merger in 2021. Our 2023 results are evidence that our turnaround strategy has positively impacted all parts of our business. This is exemplified by five consecutive quarters of underwriting profit, our reduction in catastrophe losses, and our organic capital generation.

S&P's revision of our outlook from negative to stable was a momentous milestone for the whole team - and an emotional moment for me personally. It was an important external validation of the progress we have made as a Company, and an important acknowledgement of our underwriting discipline, prudent growth, our great management team and all the hard work of our staff.

After a year in the role of Chief Executive Officer, I could not be prouder of the progress SiriusPoint has made. 2023 was not the destination for us and I feel confident, but not complacent, as we move into 2024. We know there is more to do, we are excited and committed, and I look forward to the progress we will continue to make.

Our purpose and vision for SiriusPoint

In April 2023 we rolled out a new purpose and vision for SiriusPoint. Our purpose is to provide security and resilience in an uncertain world, and our vision is to be recognized as a top insurer and reinsurer using deep risk capabilities to protect our customers. Our purpose and vision are both inspirational and aspirational, and our values are at the heart of the Company.

None of us want to be part of an average company, and our ambition is to be among the industry's most respected and reliable insurers and reinsurers.

We will achieve this by blending our essential components - talent, expertise and data - to provide intelligent risk solutions. Getting behind our purpose and vision and making them a reality is how we will differentiate ourselves in the market. The work has already begun, and we are determined to build on our actions in the year ahead.

Measurable improvements

It is our people that differentiate us from others in the market, and their hard work, determination and dedication is already delivering results. Together we have demonstrated measurable improvements to the business, and the aim now is to keep the momentum so we can continue to build both capital and cultural resilience.

In 2022, SiriusPoint was an outlier and radical change was needed. Our performance was poor and our volatility high. But we put a transformation plan in place to become a profitable underwriter. We decided to work with fewer and stronger partners, we worked hard to reduce the uncertainties on our balance sheet and within our risk framework. We set out to build stronger teams with deeper expertise.

Tangible results

We have spent the last year building a stable platform for 2024 and beyond, and our financial performance is starting to match the level of effort our colleagues are putting in to making our business a success. Highlights of 2023 include:

• Record full year retuon equity at16.2%, 10.2% excluding one-off adjustments.
• Record underwriting income of$250 million, record combined ratio of 89.1% (core business), record net service fee income of $50 million, and record net income of $339 million available to common shareholders.
• Fifth consecutive quarter of positive underwriting results.
• Fourth consecutive quarter of positive net income.

• Another quarter of positive capital generation across all the three areas: underwriting, strategic investments, and investments.
• Closing a Loss Portfolio Transfer with$150 million of capital released on S&P model and Bermuda Solvency Capital Ratio benefit of >15 ppts. The transaction is transformative for SiriusPoint, drawing a line under business that we have discontinued and further strengthening our balance sheet.
• S&P Global changed our ratings outlook from negative to stable.
• Investor confidence has more than doubled our share price.
• Further progress on rationalizing our equity stakes in managing general agents and programs.

SiriusPoint has made impressive progress against our stated initiatives. All three of our business areas - underwriting, the fee income from our consolidated underwriting partnerships, and our investment returns - are producing strong organic capital generation. Our customers have felt the progress, and we thank them for trusting us while we work to become best-in-class.

The Company's transformation has been driven by the quality and capability of the expertise within our business, aligned with strong client and broker relationships. We can confidently say that the turnaround, heavy-lifting transformation part of our journey is behind us. We are now driving forward with purpose, intent and true clarity about the best-in-class business that we want to be. In 2024, we still have some refinement to do as we grow and build on the progress we have made. Our healthy balance sheet and diversified business portfolio will act as a springboard towards a profitable 2024 and 2025, during which time we'll continue to strive to deliver even higher returns for our shareholders.

Building our culture

Culture is key to creating a sustainable, performance-driven organization. Our collaborative 'One SiriusPoint' ethos is designed to fully integrate our global businesses and bring our purpose, vision and values to life. This cultural initiative is starting to permeate through the business and drive better performance and outcomes, benefitting our partners and stakeholders.

At SiriusPoint, people matter. Building the right team and the right mix of culture, opportunity, approach, leadership, and inclusion is essential to attract and retain talent. We have seen some staff changes over the course of the year and thank those that are no longer with the organization for being part of our journey, and welcome those that have come on board. We are building a track record of success at SiriusPoint and have attracted strong talent who contribute to the success of our Company.

We are also supporting our local communities and will continue to build on our philanthropic efforts in each of our regions, championing those causes that are important to our employees.

Technology investments

SiriusPoint has invested in technology. We have made progress in simplifying, modernizing, and ensuring the architecture of our technology platform is more scalable, which has resulted in measurable operating efficiencies. Significant investments have also been made to strengthen our cybersecurity and leverage the Cloud and SaaS platforms to drive innovation. We have also built a robust platform to more effectively use data and analytics to make better decisions and develop risk solutions for our clients and the market. This work will continue into 2024 and beyond.

Underwriting first

We have had another quarter of strong underwriting results with underwriting profit for the core business at $250 million for the full year. These latest results are further evidence that our underwriting strategy is taking us to where we want to be. We must build on this progress; we want to be leaders in our specialisms and will not settle as midtable performers.

SiriusPoint restructured its underwriting platform last year to support the future shape of its business, strengthen underwriting results, and align the Company's operating platform with its business portfolio.

While portfolio remediation at SiriusPoint International was core to our transformation and reduction of underwriting volatility, the restructured business is a key part of our growth plan and franchise. The team trades across the globe utilizing SiriusPoint capabilities out of our offices in Stockholm, Zurich, Liege and London, including Lloyd's of London. Our International business launched an MGA Centre of Excellence to deliver an efficient and

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NEW APPOINTMENTS

This year we have continued to strengthen the team with many high-quality, senior external appointments including:

• Trecia Sigle as Global Head of Claims in February 2023
• David Rees, joined as Head of London US Casualty in July 2023. David was later promoted to Head of Casualty, London
• Linda S. Lin joined SiriusPoint as Chief Legal Officer in July 2023
• Habib Kattan as Global Head of Ceded Reinsurance in August 2023
• Anthony Shapella as Deputy Chief Underwriting Officer in September 2023
• Stephen Smyth as Head of Marine, October 2023
• Alex Hardy as Director of Sales & Distribution, Nov 2023

INTERNAL PROMOTIONS INCLUDE

• Peggy Huang appointed as Chief Investment Officer
• Nestor Lopez appointed as Chief Information and Technology Officer
• Tom Leonardo appointed as Global Head of A&H

collaborative onboarding experience for new partners. The approach mirrors our North American structure and enables operational efficiencies and access to expertise across the Company's global platform, allowing partners to benefit from the 'One SiriusPoint' ethos.

We have reduced our property catastrophe exposure on our international platform, which allowed us to successfully navigate catastrophe season. We are also working with Lloyd's of London on our future growth plans.

Partnerships

We are strengthening and establishing strategic distribution partnerships with both existing and new program partners, which are core to sustaining our underwriting profitability and aligns with our specialisms and risk appetite. We onboarded nine new partners in 2023 including Air Centurion (US), Applied Surety Underwriters (US), Eaton Gate (UK), and Nordic Marine Insurance (EU).

Our consolidated program and MGA revenue was up 10% in the last year. Our net service fee income was $50 million and grew 37% year over year, with the service margin at 21%. We will continue with the rationalisation of our smaller equity stakes. Our MGA and program stakes are at 26 as of year end 2023, down from 36 at full year 2022. MGAs and programs will continue to play a key role in our strategy, but we don't have to own distribution to provide underwriting capital to our partners.

The way forward

While we have made great progress, I can reassure you there is no complacency with the results we have achieved so far and our work at SiriusPoint is far from done.

We know success is not a straight line and that it takes time and hard work, but we have the will, talent, and determination to build on the transformation of our business. Our continued aim is to reduce volatility, simplify operations into a fully integrated 'One SiriusPoint', and focus on profitability to deliver value for our stakeholders.

I would like to end by expressing my gratitude once again to our stakeholders for your ongoing support. I am deeply appreciative of the loyalty of our valued customers and partners - we will continue to serve you with the expertise and responsive, collaborative and solutions-driven mindset you have come to expect from us.

Finally, I would like to extend a special thanks to all my colleagues at SiriusPoint for their exceptional dedication, integrity and resilience. I look forward to further successes over the next

12 months as we strive to be best-in-class.

Yours sincerely,

Scott Egan

Chief Executive Officer

In 2023 we delivered record net income of $339 million, achieved a 16.2% annualized retuon average equity and delivered $50 million of cost savings ahead of schedule. This contributed to a consolidated combined ratio of 84.5%, an improvement of 11.9 points year on year, and we expect to build on this performance.

We continue to remain conservative with regards to volatility. Our underwriting first approach remains unchanged, and we will continue to prioritize underwriting profits over premium growth in 2024.

Reduced volatility in underwriting

We delivered a combined ratio of 89.1% for our core business which was supported by 5 points of one-off reserve releases linked to the LPT we announced in 2023. Excluding the LPT benefits and other one-off items, our adjusted core combined ratio stood at a record 91.2%. This is an improvement of 10.4 points against our 2022 figures and demonstrates the impact of the decisive portfolio actions taken during the last 18 months.

The core combined ratio has been supported by both loss and expense ratio improvement, with the loss ratio improvement helped by lower catastrophe losses, which were $14 million for the full-year 2023, a 90% reduction from $138 million a year ago. This ties in with our 1-in-100 year event PMLs, which are considerably lower now at around 5% of common shareholders' equity, down from 11% at second quarter 2021 just after the merger.

PML for 1-in-100 year event 1,2

$ numbers in USD millions

1. PMLs are on a per occurrence basis for 1-in-100 year events, net of restatements and after-tax. PMLs are an estimate based on industry standard catastrophe modeling with proprietary adjustments. [2] Within this chart, Q4'23 relates to 1/1/24, Q2'23 relates to 7/1/23, Q4'22 relates to 1/1/23 and Q2'21 relates to 7/1/21