Howard Hughes Holdings Inc.

We continue to maintain a strong balance sheet and endeavor to ensure that we maintain the financial flexibility and liquidity necessary to fund future growth. As of June 30, 2026, we had $2.6 billion of cash and cash equivalents, including cash held at Vantage, $515.0 million of undrawn capacity on our Secured Bridgeland Notes, and $970.3 million of undrawn lender commitments available to be drawn for property development, subject to certain restrictions.

Cash Flows

Operating Activities Each segment’s relative contribution to our cash flows from operating activities will likely vary significantly from period to period given the changing nature of our development focus and the timing of condominium and land sale closings. Our operating cash flows consist of the following (1) condominium deposits received from contracted units and proceeds from condominium closings offset by other various cash uses related to condominium development and sales activities, (2) revenues from MPC land sales offset by development costs associated with the land sales business and acquisitions of land that is intended to ultimately be developed and sold, (3) recurring contractual revenues from operating leases, and (4) post-acquisition operating cash flows attributable to Vantage, primarily related to insurance and reinsurance premiums collected, reinsurance recoverables, fee income, and investment income, offset by claim payments, ceded and retro reinsurance payments, and underwriting costs.

Net cash provided by operating activities was $277.1 million in the six months ended June 30, 2026, and net cash used in operating activities was $47.7 million in the six months ended June 30, 2025. The change in operating activities of $324.8 million was primarily due to an increase in cash provided by condominium towers, primarily due to the closings at The Park Ward Village in the current period, an increase in the cash provided by Vantage in the post-acquisition period, and an increase in MPC land sales, partially offset by a decrease in cash provided related to higher proceeds from the sale of MUD receivables in the prior period and an increase in MPC development expenditures.

Investing Activities Net cash used in investing activities was $357.5 million in the six months ended June 30, 2026, and $122.7 million in the six months ended June 30, 2025. The $234.8 million increase in net cash used in investing activities was primarily due to $1.6 billion of cash used for the Vantage Acquisition, net of cash acquired, and $1.1 billion of cash used to purchase equity securities in the current period. These increases were partially offset by $2.3 billion of cash received for the sale of fixed maturity securities in the current period, and an increase in cash received of $119.3 million for the sale of properties, primarily due to the sale of two multifamily properties in The Woodlands in the current period, compared to the sale of two land parcels and a retail space in Ward Village in the prior period.

Financing Activities Net cash provided by financing activities was $1.3 billion in the six months ended June 30, 2026, and $970.6 million in the six months ended June 30, 2025. The $377.9 million increase in cash provided by financing activities was primarily due to $1.2 billion increase in proceeds from mortgages, notes, and loans payable, primarily related to the issuance of $1.0 billion of new unsecured notes and a $300.0 million mortgage secured by Downtown Summerlin in the current period, as well as $997.4 million of net proceeds from the issuance of Series A Preferred Stock in the current period. These increases were partially offset by a decrease in cash provided of $862.9 million related to net proceeds received in the prior period for the common stock issuance to Pershing Square, a $906.8 million increase in cash used related to principal payments on mortgages, notes, and loans payable, primarily related to the repayment of $750 million of existing unsecured notes in the current period, as well as an $18.6 million increase in deferred financing costs and bond issuance costs related to these transactions.

Short- and Long-Term Liquidity

Short-Term Liquidity In the next 12 months, we expect to continue to drive meaningful value creation following our transition to a diversified holding company.

From our real estate operations, we expect our primary sources of cash to include cash flow from MPC land sales and condominium closings, cash generated from our operating assets, first mortgage financings secured by our assets, and deposits from condominium sales (which are restricted to funding construction of the related developments). We expect our primary uses of cash to include condominium pre-development and development costs, debt principal payments and debt service costs, MPC land development costs, other strategic developments costs, and general operating costs.

From our insurance operations, we expect our primary sources of cash to include premiums collected from policyholders, investment income earned from our investment portfolio, recoveries from reinsurers, proceeds from the sale or maturity of investments, and if needed, available borrowings under Vantage’s Revolving Credit Facility. We expect our primary uses of cash to include payment of claims, premiums ceded to reinsurers, commissions and other policy acquisition costs, and general operating expenses. Cash flows from operations may be impacted by the timing of premium collections, claim payments, and changes in reinsurance balances. Actual claim payment patterns may differ from current estimates due to a variety of factors, including the size and timing of individual losses, changes in the legal and regulatory environment, and broader economic conditions. The Company currently intends to reposition Vantage’s investment portfolio to include cash, short-term U.S. Treasury securities, and publicly traded equity securities. In June 2026, the Company began implementing this strategy by divesting a significant portion of its available-for-sale fixed maturity securities and initiating investments in equity securities. The Company expects to divest the majority of its remaining available-for-sale fixed maturity securities prior to the end of 2026.

We believe that our sources of cash, including existing cash on hand, will provide sufficient liquidity to meet our existing obligations and anticipated ordinary course operating expenses for at least the next 12 months.

Long-Term Liquidity We expect our long-term sources and uses of cash for our real estate and insurance operations to continue to align with those mentioned above.

For our real estate operations, we expect long-term operating cash flows to increase over time as a result of increased MPC land sales driven by price appreciation, rental revenue growth and continued condominium sales. These cash flows are expected to be reinvested into the real estate business to fund development opportunities, which are capital intensive and will likely require significant additional funding, if and when pursued. We currently expect that any additional funding beyond those sources listed above would be raised with a mix of construction, bridge, and long-term financings, or by entering into joint venture arrangements. We cannot provide assurance that financing arrangements for our properties will be on favorable terms to us or occur at all, which could have a negative impact on our liquidity and capital resources. In addition, we typically must provide completion guarantees to lenders in connection with their financing for our projects.

For our insurance operations, we expect cash inflows to grow over time through the optimization of underwriting profitability and investment strategies. Insurance operations generally provide liquidity as premiums are received in advance of the payment of related claims, although the period between the occurrence of a claim and settlement of the associated liability may extend for many years. The Company’s investment strategy is managed to establish a level of cash, investments, and expected future cash flow that will be able to meet foreseeable payment obligations. The Company’s ability to deploy cash held at the insurance-subsidiary level for long-term uses is subject to various limitations and considerations, including the timing and uncertainty of claim payments, regulatory capital and solvency requirements applicable to its insurance subsidiaries, and restrictions on the ability of such subsidiaries to pay dividends or other distributions to the parent company. While management believes that existing cash flows, invested assets, and other available sources of liquidity will be sufficient to satisfy long-term obligations, the ultimate amount and timing of claim payments may differ materially from current estimates. In addition, the Company must maintain sufficient liquidity to support its insurance liabilities and meet policyholder obligations under a range of stress scenarios. As a result, a significant portion of insurance-related cash and invested assets may not be readily available for discretionary uses.

The Series A Preferred Stock issued by HHH to Pershing Square is convertible into equity interests of Vantage if not redeemed by the end of the seventh fiscal year post-transaction. HHH has the right, but not the obligation, to redeem the Series A Preferred Stock over the next seven years. Refer to Note 3 -Pershing Square in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information.

To the extent real estate operations generate excess cash flows, we expect to use such excess cash flow to redeem the Series A Preferred Stock, invest additional primary capital into the insurance business and, over time, pursue the acquisition of other high-quality operating companies. The Vantage Acquisition is expected to have other long‑term implications for the Company’s liquidity profile, although the magnitude and timing of these impacts cannot yet be determined. The Company actively manages its liquidity position and capital resources to ensure that it can meet both its short-term and long-term obligations while maintaining financial flexibility.

Contractual Cash Obligations and Commitments The following table aggregates our contractual cash obligations and commitments as of June 30, 2026:

(a)Interest is based on the borrowings that are presently outstanding and current floating interest rates.

Debt As of June 30, 2026, the Company had $5.5 billion of outstanding debt, $970.3 million of undrawn lender commitment available to be drawn for property development, subject to certain restrictions, and $515.0 million of undrawn capacity on our Secured Bridgeland Notes.

Vantage has a $75.0 million revolving credit facility with the option to increase the aggregate amount by $50.0 million at the lender’s discretion. This facility matures in January 2028. As of June 30, 2026, there were no outstanding borrowings under this facility.

In February 2026, HHC, the Company’s wholly owned subsidiary, issued $500.0 million of 5.875% senior unsecured notes due 2032 and $500.0 million of 6.125% senior unsecured notes due 2034. These notes will pay interest semi-annually. HHC used the net proceeds to redeem its outstanding $750.0 million 5.375% senior unsecured notes due 2028, including the payment of premiums, accrued and unpaid interest and expenses related to such redemption, and will use the remaining proceeds for general corporate purposes.

Refer to Note 6 -Mortgages, Notes, and Loans Payable, Net in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information.

The Company has a collateral maintenance obligation for Floreo, its unconsolidated venture. See Note 12 -Commitments and Contingencies in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information.

Debt Compliance As of June 30, 2026, the Company was not in compliance with certain property-level debt covenants, which did not have a material impact on the Company’s liquidity or its ability to operate these assets. As a result, the excess net cash flow after debt service from the underlying properties became restricted. While the restricted cash can not be used for general corporate purposes, it can be used to fund operations of the underlying assets.

Net Debt The following table summarizes our Net Debt on a segment basis as of June 30, 2026. The Company revised the definition of its non-GAAP measure, Net Debt, to simplify its calculation and recast the prior period to conform to the new presentation. Under the revised definition, Net Debt excludes the impact of unamortized deferred financing costs and our ownership share of debt of our unconsolidated ventures, whereas prior periods included these amounts. In addition, under the revised definition, Net Debt is reduced only by readily available cash sources, consisting of Cash and cash equivalents. Prior periods included our ownership share of our unconsolidated ventures’ cash and certain receivable balances as liquidity sources, which are excluded under the revised definition.

Net Debt is now defined as Mortgages, notes, and loans payable, excluding the impact of unamortized deferred financing costs, reduced by Cash and cash equivalents available to satisfy such obligations. Management believes the updated definition provides a more meaningful measure of the Company’s leverage by (i) focusing on obligations for which the Company has primary responsibility and control and (ii) using a more conservative measure of liquidity that reflects only readily available cash resources. This change enhances transparency and comparability for investors. Although Net Debt is a non-GAAP financial measure, we believe that such information is useful to our investors and other users of our financial statements as Net Debt and its components are important indicators of our overall liquidity, capital structure, and financial position. However, it should not be used as an alternative to our debt calculated in accordance with GAAP.

(a)Includes $1.9 billion of cash and cash equivalents held at Vantage at June 30, 2026.

Insurance-Specific Considerations

Insurance Investment Portfolio The following table provides detail of the Vantage investment portfolio at fair value as of June 30, 2026:

(a)Represents cash, cash equivalents, and restricted cash held at the Vantage level only.

(b)The weighted-average credit rating of the Company’s AFS fixed maturity securities portfolio was AA+ as of June 30, 2026.

Insurance Claims Following the Vantage Acquisition, the Company is obligated to pay claims arising from property and casualty contracts issued by our insurance subsidiaries. The timing and amount of the payments under insurance and reinsurance contracts are contingent upon the outcome of future events and actual payments will likely vary, perhaps materially, from any forecasted payments, as well as from the liabilities recorded in our Condensed Consolidated Balance Sheets. As of June 30, 2026, the reserve for claims and claim expenses was $2.1 billion, with $0.5 billion expected to be settled in less than one year and $1.6 billion expected to be settled in future years. The estimated timing of payments was determined using Vantage’s historical claims payment experience, supplemented by industry and peer group data. Given the inherent uncertainty in projecting the timing of claim settlements, actual cash outflows in any period may differ materially from the amounts presented. The reserve amounts disclosed above exclude the impact of anticipated amounts recoverable on unpaid losses from reinsurers of $563.9 million as of June 30, 2026. Refer to Note 9 -Reserves for Claims and Claim Expenses in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information. We anticipate that these payments will be funded by operating cash flows.

Insurance-Related Statutory Capital and Dividend Restrictions The Company’s insurance subsidiaries are subject to insurance laws and regulations in the jurisdictions in which they operate and have regulatory capital and solvency requirements and restrictions on the ability of such subsidiaries to pay dividends to the parent company. The ability of the insurance and reinsurance subsidiaries to pay dividends to the parent company is also influenced by the maintenance of financial strength ratings assigned by independent rating agencies. Additionally, as a condition to the approval by the Delaware Department of Insurance (the Department) of the Vantage Acquisition, the Company has agreed that, until June 4, 2028, any dividends (whether ordinary or otherwise) by the Company’s Delaware insurance subsidiaries will require the Department’s prior approval. As of June 30, 2026, all insurance subsidiaries exceeded minimum regulatory capital requirements.

The Company’s insurance subsidiaries are required to maintain assets on deposit, which primarily consist of restricted cash and fixed maturity securities, with various regulatory authorities to support their operations. As of June 30, 2026, the assets on deposit available to settle insurance and reinsurance liabilities to third parties were $307.6 million.