There have been no material changes to the risk factors previously disclosed in our 2025 Annual Report, except as set forth below. On June 4, 2026, we completed our previously announced acquisition of Vantage (the Vantage Acquisition), and Vantage and its subsidiaries are now consolidated subsidiaries of the Company. As a result of the Vantage Acquisition, we are now subject to risks relating to the specialty insurance and reinsurance business conducted through Vantage. The risk factors set forth below under the caption “Financial Risks” amend and restate in their entirety the corresponding risk factors in the 2025 Annual Report; the remaining risk factors set forth below are new. The following risk factors should be read in conjunction with the risk factors disclosed in the 2025 Annual Report. RISKS RELATED TO THE VANTAGE ACQUISITION The Vantage Acquisition involves substantial integration risks, including diversion of management attention, potential disruption of our existing operations, challenges integrating systems and internal controls, and loss of certain Vantage personnel, any of which could prevent us from realizing the anticipated benefits of the transaction and materially adversely affect our business. The successful integration of Vantage's specialty insurance and reinsurance business into our operations is critical to realizing the anticipated strategic and financial benefits of the Vantage Acquisition, and there can be no assurance that the integration will be completed on the timeline we expect or that those benefits will be realized fully, in part, or at all. The Vantage Acquisition and related integration activities will continue to require substantial time and attention from our senior management and other key personnel, potentially diverting resources from our day-to-day operations, existing strategic priorities, and other business opportunities. We have limited prior experience operating in the specialty insurance and reinsurance industry, and we cannot assure you that our operational, financial, or administrative infrastructure will be adequate to manage the expanded operations of the combined company. Integrating the information technology systems, financial reporting and accounting processes, internal controls over financial reporting, actuarial systems, tax reporting and compliance systems, and other compliance programs of two distinct businesses is inherently complex and time-consuming. Although Vantage's subsidiaries, including its Bermuda subsidiary, are expected to be treated as U.S. taxpayers, integrating their tax reporting functions into our consolidated U.S. tax profile and coordinating that status with Vantage's continued obligations under Bermuda insurance regulation, may involve transitional complexity and cost. Any disruption, deficiency, or material weakness arising from the integration of Vantage's systems and internal controls could impair our ability to report our financial results accurately or on a timely basis, expose us to regulatory scrutiny or civil liability, and adversely affect the market price of our securities. Our ability to realize the benefits of the acquisition also depends on retaining certain key underwriting, actuarial, and claims personnel, whose specialized expertise and client relationships are impactful to the ongoing performance of Vantage's business. In addition, since the announcement of the Vantage Acquisition, Vantage has experienced changes in several senior leadership positions. Although we believe Vantage’s new leadership brings substantial relevant experience and strong counterparty relationships, the loss of such personnel and the potential for continued uncertainty associated with the acquisition could negatively impact the business. RISKS RELATED TO OUR INSURANCE OPERATIONS The Company conducts specialty insurance and reinsurance operations through Vantage and its subsidiaries. The following risks relate principally to those operations and are in addition to the other risks described in the 2025 Annual Report. HHH 2026 FORM 10-Q | 71 Table of Contents Vantage has a limited operating history, and its prior results may not be indicative of future performance. Vantage was founded in late 2020 and accordingly has a relatively short operating history. Its loss-development patterns, pricing assumptions, reserve estimates, and underwriting models are based on a thin historical data set as compared to longer-tenured insurance carriers, and the results Vantage has achieved in recent years may not be representative of future results. Vantage has also experienced rapid premium growth and continues to expand into new product lines and distribution channels. Entry into new lines of business or products entails risks that may not be apparent at the outset, including the investment of significant time and capital, the possibility that the marketplace does not accept new offerings, increased liability exposure, and the risk that our personnel, systems, and controls may not scale effectively. If Vantage is unable to manage these growth-related risks, or if its limited operating history proves to be a poor predictor of future loss experience, our business, financial condition, results of operations, and cash flows could be materially and adversely affected. Vantage’s insurance results depend on the accuracy of its underwriting, and inaccurate risk assessment could materially harm the Company’s business. Vantage’s profitability depends on its ability, and the ability of the managing general agents and other producers with which it transacts, to accurately assess the risks associated with the insurance and reinsurance business it writes and retains. This requires reliance on the judgment and experience of underwriting personnel, on actuarial and catastrophe-exposure models, and on data supplied by insureds, brokers, and third-party vendors. If Vantage misjudges the nature or extent of the risks it assumes, or if its models fail to capture all material exposures (including unmodeled accumulations and emerging coverage issues), it may fail to charge risk-adequate premium, may experience actual losses that materially exceed its probable maximum loss estimates, and may suffer adverse reserve development. Any of these outcomes could materially and adversely affect our business, financial condition, results of operations, and cash flows. Vantage’s reserve for claims and claim expenses may prove inadequate. Vantage establishes reserves for the estimated ultimate cost of all reported and unreported claims, including the related cost of adjusting those claims. These reserves do not represent an exact calculation of liability; they represent management’s estimate, based on actuarial analysis, of what Vantage expects ultimate settlement and administration of claims will cost. Because Vantage has a limited operating history, the historical data on which these estimates are based is limited. Emerging claim and coverage issues, changes in judicial interpretation of policy terms, changes in legislation or regulation, social-inflation trends, changes in claim-handling procedures, inflation in repair and replacement costs, and many other factors could cause actual ultimate losses to differ materially—and adversely—from current estimates. Any material increase in Vantage’s reserves would reduce earnings in the period the increase is recorded, erode statutory capital and surplus at Vantage’s insurance subsidiaries, and have a material adverse effect on our business, financial condition, results of operations, and cash flows. Vantage depends on third-party reinsurance, and Vantage may be unable to obtain it on acceptable terms or to collect amounts due from reinsurers. Vantage cedes a portion of the risks it underwrites to third-party reinsurers in order to manage its exposure to large losses and accumulations. The availability, scope, and cost of reinsurance depend on market conditions that are largely outside our control, and may change materially following catastrophe losses, changes in reinsurer appetite, or broader capacity contractions. If Vantage is unable to renew expiring reinsurance contracts on acceptable terms, to enter into new reinsurance arrangements, or to expand coverage as its book grows, its net loss exposure could increase. Vantage may then choose to reduce its underwriting commitments, retain greater net risk, or accept reinsurance terms that contain coverage exclusions or other limitations that leave gaps in protection that may expose Vantage to greater risk and greater potential losses. In addition, purchasing reinsurance does not relieve Vantage of its underlying obligations to its policyholders or ceding companies, so any inability to collect amounts due from reinsurers could adversely affect our financial condition and results of operations. Vantage therefore remains exposed to the credit and performance risk of its reinsurers. A reinsurer may withhold payment due to disputes over coverage, refuse to pay due to insolvency or financial distress, or otherwise fail to perform. Although Vantage regularly monitors the financial condition of its reinsurers, a significant reinsurer failure or a broader deterioration in the reinsurance market could materially and adversely affect our business, financial condition, results of operations, and cash flows. HHH 2026 FORM 10-Q | 72 Table of Contents Vantage’s business depends on its relationships with independent agents, brokers, wholesalers, and program administrators. Substantially all of Vantage’s products are distributed through independent retail agents, brokers, wholesalers, and program administrators. These intermediaries generally own the policyholder relationship and the related “renewal rights,” meaning that Vantage’s ability to retain and grow its book depends on its continued ability to attract and maintain favorable relationships with them. Further, Vantage is also dependent on the relationships its program administrators maintain with the agents and brokers from whom they source their business. These relationships may be terminated at any time, and there can be no assurance that compensation, service, product offerings, or financial-strength ratings will remain competitive. Any deterioration in Vantage’s distribution relationships, the loss of one or more material intermediaries, or the failure of a program administrator or managing general agent to operate within the underwriting authority granted to it could materially and adversely affect our business, financial condition, results of operations, and cash flows. In addition, Vantage could be adversely affected if the distributors with whom it does business exceed their granted authority, fail to transfer collected premium to Vantage or breach their obligations to Vantage and expose Vantage to liability. Vantage and its insurance subsidiaries are subject to extensive regulation, including risk-based capital and statutory accounting requirements. Vantage’s insurance and reinsurance subsidiaries are subject to extensive regulation by regulators in each of the jurisdictions in which they are domiciled or transact business, including U.S. state insurance departments, the Bermuda Monetary Authority, and other non-U.S. regulators. These regulations govern, among other things, licensing of insurers, agents, brokers, third-party administrators, managing general agents, reinsurance intermediaries, adjusters and other producers; capital, surplus, and risk-based-capital requirements; investment and underwriting limitations; affiliate transactions; the payment of dividends or other distributions from regulated subsidiaries to their parents; enterprise risk management; market conduct; financial reporting by Vantage’s U.S. insurance subsidiaries on a statutory-accounting-principles (SAP) basis; and changes in control. Insurance regulators have broad discretion to suspend, deny, or revoke licenses, require additional capital, impose corrective actions or fines, temporarily suspend a company from carrying on some or all of its activities or impose other penalties, and to subject insurers to supervision, rehabilitation, or liquidation. In some instances, where there is uncertainty as to applicability of regulations, Vantage follows practices based on its interpretations of regulations or practices that it believes to be generally followed by the industry, which may turn out to be different from the interpretations of regulatory authorities. The laws and regulations applicable to Vantage’s insurance operations, and the manner in which regulators interpret and enforce them, are subject to change. SAP and components of SAP are continuously reviewed by the National Association of Insurance Commissioners (the NAIC) and state insurance departments, and the NAIC has proposed and may continue to propose changes that, if adopted, could have negative effects on insurance industry participants. These changes, or changes proposed by other regulators, could include changes to investment and reserve valuation requirements, surplus requirements, dividend limitations, and risk-based-capital frameworks. Compliance with these requirements may limit Vantage’s flexibility to operate and grow its business, may restrict the ability of Vantage’s insurance subsidiaries to distribute cash to the Company, and may increase the cost of doing business. Failure to comply with applicable laws and regulations, or failure to maintain required capital and surplus, could subject Vantage’s subsidiaries to penalties or to the loss of authority to write new and renewal business, any of which could materially and adversely affect our business, financial condition, results of operations, and cash flows. Court or regulatory decisions affecting policy coverage, exclusions, or limitations, and insurance-related litigation, could increase our losses. The terms of insurance and reinsurance policies, including coverage grants, exclusions, and loss limitations, are subject to interpretation by courts and regulators. From time to time, courts have nullified, narrowed, or refused to enforce policy exclusions or limitations, and legislatures have enacted laws that retroactively modify policy terms or bar reliance on particular exclusions. Vantage’s policy wordings are intended to define and limit covered risks; however, an adverse judicial or legislative outcome could expose Vantage to claims and indemnity payments materially in excess of those it priced into the relevant policies. As is typical in the insurance industry, Vantage is also exposed to litigation arising from claim disputes under its policies and to other general commercial and corporate litigation. So-called “social inflation”—the trend toward larger jury verdicts, broader theories of liability, and litigation funding—can drive claim severity above historical patterns, particularly in casualty lines, leading to the potential for significant judgments. The outcome of any individual matter is inherently unpredictable, and adverse outcomes or trends could materially and adversely affect our business, financial condition, results of operations, and cash flows. HHH 2026 FORM 10-Q | 73 Table of Contents Competition in the insurance and reinsurance industry is intense. Vantage operates in a highly competitive specialty insurance and reinsurance environment that includes both domestic and international carriers, many of which have greater financial, operational, distribution, and brand resources than Vantage. Competition affects Vantage’s ability to price its products at risk-adequate rates, retain existing accounts, underwrite new business on favorable terms, and achieve target operating results. Increased competition, including new market entrants and the deployment of alternative capital, could reduce premium rates, depress retention, and limit growth opportunities, any of which could materially and adversely affect our business, financial condition, results of operations, and cash flows. The insurance industry is historically cyclical, which may cause Vantage’s results to vary materially from period to period. The property and casualty insurance industry has historically been cyclical, alternating between “soft” markets characterized by excess underwriting capacity, price competition, and falling premium rates and “hard” markets characterized by capacity shortages, increased premium rates, and improved profitability. This cyclicality is often more pronounced in the excess-and-surplus-lines market in which Vantage participates. We cannot predict the timing or duration of changes in the market cycle, which depend on factors largely outside our control, including the actions of competitors, general economic conditions, the frequency and severity of catastrophes, and capital flows into and out of the industry. As a result, Vantage’s gross written premium, underwriting profitability, and overall results may fluctuate materially from period to period, and past results should not be considered indicative of future performance. Catastrophic events expose Vantage to large insured losses and may increase the cost or reduce the availability of reinsurance. Vantage is exposed to insured losses arising from natural and man-made catastrophes, including hurricanes, severe convective storms and tornadoes, windstorms, earthquakes, hailstorms, wildfires, floods, terrorism, riots, and pandemics. The frequency and severity of catastrophic events are inherently unpredictable, and changing weather patterns and climate change may increase both. A single catastrophe or a series of catastrophes could result in insured losses materially in excess of Vantage’s estimates and could exhaust the reinsurance capacity Vantage has secured. Catastrophes can also cause widespread market disruption that increases the cost, or reduces the availability, of reinsurance for subsequent periods. As described elsewhere in the 2025 Annual Report, the Company is also separately exposed to physical damage from catastrophes at its real estate properties; the risks described in this factor are distinct and relate to Vantage’s insured-loss exposure. Vantage’s investment-portfolio results are subject to equity-price, interest-rate, concentration, and other market risks, and adverse investment results may coincide with underwriting losses. A significant portion of Vantage’s revenue and earnings derives from its investment portfolio, which consists primarily of short-term U.S. Treasury securities (including cash equivalents) and common equities, and which may also include other asset classes. The performance of this portfolio is subject to a variety of risks, including liquidity risk, equity-price risk (including market volatility and declines in the value of common equity holdings), concentration risk (to the extent the portfolio holds a limited number of equity positions), interest-rate risk (including the effect of rate changes on the fair value of Treasury holdings and on net investment income), credit risk (to the extent applicable), sovereign and political risk, and risks arising from extreme weather, geopolitical events, and other catastrophic conditions. Realized and unrealized investment losses, reduced net investment income, and impairments may occur, and may occur at the same time as significant underwriting losses, compounding the adverse effect on our business, financial condition, results of operations, and cash flows. A downgrade or withdrawal of Vantage’s A.M. Best financial-strength rating could materially impair its ability to write business. A.M. Best and other rating agencies assign financial-strength ratings to insurance and reinsurance companies. These ratings reflect the rating agency’s assessment of the insurer’s ability to meet its ongoing obligations to policyholders and are an important factor in the decisions of brokers, reinsurers, and insureds regarding whether to place business with a particular carrier. A.M. Best has assigned Vantage’s principal insurance subsidiaries a financial-strength rating of A- (Excellent) with a positive outlook. A.M. Best periodically reviews this rating and may revise it downward, place it under review, or withdraw it based on its assessment of factors that include balance-sheet strength, operating performance, business profile, and enterprise risk management. A downgrade or withdrawal of Vantage’s financial-strength rating could cause distribution partners, reinsurers, and insureds to place or accept business with more highly rated competitors, could increase the cost or reduce the availability of reinsurance to Vantage, and could limit or prevent Vantage from writing new HHH 2026 FORM 10-Q | 74 Table of Contents and renewal contracts. These risks are distinct from the risk of an adverse change in our corporate credit ratings, which is addressed separately in the 2025 Annual Report. Vantage manages alternative reinsurance platforms and segregated-account vehicles, which exposes Vantage to additional regulatory, and counterparty risks. Certain of Vantage’s subsidiaries provide management and administrative services to AdVantage Reinsurance Bermuda Ltd., a collateralized insurer and segregated-account company that constitutes an alternative reinsurance platform operating as part of Vantage’s partnership capital unit. In providing these services, these subsidiaries owe legal duties and obligations, including reporting obligations, to the vehicle and, indirectly, to third-party investors that provide capital to its segregated accounts. The management of these structures is subject to complex and evolving laws and regulations, and a failure of personnel to adhere to established policies and procedures—even if inadvertent—could result in regulatory action, contractual liability, or other losses. In addition, Vantage’s ability to write certain lines of business depends in part on the capital provided by these third-party investors, and the loss, alteration, or reduction of this capital support, or Vantage’s inability to attract additional capital for new or existing segregated accounts, could reduce Vantage’s fee income and limit underwriting capacity. Any of these outcomes could materially and adversely affect our business, financial condition, results of operations, and cash flows. National and global economic conditions, including inflation, recession or the perception that recession may occur, and national and international socio-political events, could materially and adversely affect Vantage’s business. Factors, such as business revenue, economic conditions, the volatility and strength of the capital markets, and inflation may affect Vantage’s ability to receive the appropriate rate for the risk Vantage insures for its policyholders and may adversely affect the number of policies it can write and its opportunities to underwrite profitable business. Inflation and increased international trade tariff-related loss costs could significantly impact Vantage’s claims severity across multiple lines of business and cause adverse reserve development. An economic downturn could also lead to increased credit and premium receivable risk, failure of reinsurance counterparties and other financial institutions, limits on Vantage’s ability to issue new debt, reduced liquidity, and declines in Vantage’s investments' fair value and financial strength ratings. These potential events and other economic factors could adversely and materially affect our business, results of operations, financial condition, and growth. Ongoing wars and conflicts continue to impact global economic, banking, commodity, and financial markets by exacerbating ongoing economic challenges, including inflation and supply chain disruption, which influence insurance loss costs, premiums, and investment valuation. Changes in U.S. international trade policies and tariffs, particularly with large trading partners like Canada, China, and Mexico, could increase loss costs for materials and parts used in certain claims. FINANCIAL RISKS The Company is dependent on the operations and funds of its subsidiaries, including The Howard Hughes Corporation and Vantage. The Company has no business operations of its own, and the Company’s only significant assets are the outstanding equity interests of its subsidiaries, including The Howard Hughes Corporation (HHC) and Vantage and its subsidiaries. As a result, the Company relies on cash flows from its subsidiaries, including HHC and Vantage, to meet its financial obligations, including to service any debt obligations that the Company may incur from time to time in the future. Legal and contractual restrictions in agreements governing future indebtedness of any of the Company’s subsidiaries, as well as the financial condition and future operating requirements of any such subsidiaries, in each case, including HHC and Vantage, may limit such subsidiaries’ ability to distribute cash to the Company. In addition, dividends and other distributions from Vantage’s insurance subsidiaries to Vantage, and ultimately to the Company, are subject to insurance regulatory requirements administered by the Bermuda Monetary Authority and U.S. state insurance departments, which limit such distributions to amounts derived from earned surplus (or comparable measures) and may require prior regulatory notice or approval. If HHC, Vantage, or any of the Company’s other subsidiaries is limited in its ability to distribute cash to the Company, or if the earnings or other available assets of the Company’s subsidiaries are not sufficient to pay distributions or make loans to the Company in the amounts or at the times necessary for the Company to meet its financial obligations, then the Company’s business, financial condition, cash flows, results of operations, and reputation may be materially adversely affected. HHH 2026 FORM 10-Q | 75 Table of Contents Tax increases and changes in tax rules may adversely affect our financial results. As a company conducting business with physical operations throughout North America, we are exposed, both directly and indirectly, to the effects of changes in U.S., state, and local tax rules, as well as changes in Bermuda tax laws, regulations, administrative guidance, and interpretations applicable to us. Taxes for financial reporting purposes and cash tax liabilities in the future may be adversely affected by changes in such tax rules. We are also subject to U.S. tax rules of particular significance to international insurance and reinsurance groups, including the base-erosion-and-anti-abuse-tax, and related-person-insurance-income rules. These rules, and the related U.S. Treasury regulations and Internal Revenue Service (IRS) guidance, Bermuda laws and regulations, and related guidance or interpretations issued by Bermuda authorities, are subject to change (in some cases on a retroactive basis), and any such change could adversely affect our effective tax rate, our cash tax obligations, or the structure of our intercompany insurance and reinsurance arrangements.