Howard Hughes Holdings reports net loss of $1.09 million

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For the quarterly period ended June September 30, 2026

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The number of shares of common stock, $0.01 par value, outstanding as of July October 29, 2026, was 59,721,036 59,716,007 .

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Financial statements 254 changes

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Land 335,872 307,625

Restricted cash 717,395 628,651

Municipal Utility District (MUD) receivables, net 579,160 459,729

Intangibles, net 586,439 34,658

thousands except par values and share amounts June September 30, 2026 December 31, 2025

Master Planned Communities assets $ 2,646,774 2,948,512 $ 2,635,077

Buildings and equipment 4,031,804 4,071,990 4,028,862

Less: accumulated depreciation ( 1,117,166 1,147,577 ) ( 1,082,124 )

Land 323,754 307,625

Developments 1,072,034 1,158,230 1,477,615

Net investment in real estate 6,969,318 7,354,909 7,367,055

Investments in fixed maturity securities 246,583 11,036 —

Investments in equity securities 1,077,535 1,263,521 —

Short-term investments 27,822 27,761 —

Investments in unconsolidated ventures 186,153 121,022 170,122

Cash and cash equivalents 2,647,959 2,868,758 1,468,507

Restricted cash 873,032 628,651

Accounts receivable, net 940,400 883,267 134,122

Municipal district receivables, net 444,017 459,729

Reinsurance recoverable on paid and unpaid losses 601,602 630,049 —

Deferred expenses, net 175,243 217,467 160,966

Intangibles, net 512,475 34,658

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Total assets $ 15,910,043 $ 10,639,461

Total liabilities 10,880,306 6,797,215

Other assets, net 872,216 829,514 213,315

Total assets $ 16,319,046 $ 10,639,461

Mortgages, notes, and loans payable, net $ 5,456,403 5,703,949 $ 5,109,828

Reserves for claims and claim expenses 2,115,416 2,262,306 —

Unearned premiums 1,406,691 1,358,785 —

Deferred tax liabilities, net 223,113 225,783 164,472

Other liabilities, net 1,678,683 1,694,218 1,522,915

Total liabilities 11,245,041 6,797,215

1 unchanged paragraph

Series A non-voting exchangeable perpetual preferred stock: $ 0.01 par value; 140,000 shares issued and outstanding as of June September 30, 2026, and none issued or outstanding as of December 31, 2025

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Noncontrolling interests 73,577 66,790

Common stock: $ 0.01 par value; 150,000,000 shares authorized, 66,253,546 66,314,259 issued, and 59,657,062 59,717,775 outstanding as of June September 30, 2026, and 65,910,640 shares issued, and 59,370,353 outstanding as of December 31, 2025

Additional paid-in capital 4,478,286 4,483,276 4,458,838

Retained earnings (accumulated deficit) 104,495 103,408 ( 62,096 )

Accumulated other comprehensive income (loss) 1,544 10,057 ( 1,827 )

Treasury stock, at cost, 6,596,484 shares as of June September 30, 2026, and 6,540,287 shares as of December 31, 2025 ( 624,592 ) ( 620,118 )

Total stockholders' equity 3,960,396 3,972,812 3,775,456

Noncontrolling interests 105,540 66,790

Total equity 4,033,973 4,078,352 3,842,246

Total liabilities, mezzanine equity, and equity $ 15,910,043 16,319,046 $ 10,639,461

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Six Months Ended June 30,

Three Months Ended June September 30,

Nine Months Ended September 30,

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Condominium rights and unit sales $ 706,311 $ 193 $ 709,445 $ 535

Master Planned Communities land sales 170,936 125,041 270,509 196,683

Rental revenue 114,198 111,092 227,747 219,505

Builder price participation 6,868 14,138 15,550 23,425

Other revenues 15,779 10,416 26,758 20,060

Total revenues 1,122,327 260,880 1,358,244 460,208

Master Planned Communities cost of sales 59,057 45,178 93,799 70,392

Operating costs 54,723 50,518 107,756 101,307

Rental property real estate taxes 14,798 15,365 31,026 30,664

Insurance underwriting expenses 37,381 — 37,381 —

General and administrative 36,136 34,552 61,894 56,988

Depreciation and amortization 56,609 44,325 105,249 89,464

Other expenses 6,173 4,273 10,065 9,070

Total expenses 895,599 195,564 1,080,967 359,324

Other income (loss), net ( 660 ) 885 ( 533 ) ( 482 )

Total other 12,862 2,541 12,989 14,903

Operating income (loss) 239,590 67,857 290,266 115,787

Interest income 13,803 10,331 28,466 16,449

Interest expense ( 45,812 ) ( 43,694 ) ( 87,602 ) ( 84,788 )

Income (loss) before income taxes 206,914 ( 15,897 ) 217,597 ( 1,623 )

Income tax expense (benefit) 49,957 ( 3,821 ) 52,575 ( 385 )

Net income (loss) 156,957 ( 12,076 ) 165,022 ( 1,238 )

Net income (loss) attributable to common stockholders $ 158,365 $ ( 12,144 ) $ 166,591 $ ( 1,611 )

Basic income (loss) per share $ 2.68 $ ( 0.22 ) $ 2.82 $ ( 0.03 )

Diluted income (loss) per share $ 2.68 $ ( 0.22 ) $ 2.82 $ ( 0.03 )

Condominium rights and unit sales $ 6,189 $ 142 $ 715,634 $ 677

Master Planned Communities land sales 133,657 248,467 404,166 445,150

Rental revenue 115,852 111,377 343,599 330,882

Net earned insurance premiums 97,247 315,849 — 97,247 413,096 —

Net insurance investment income 10,988 22,678 — 10,988 33,666 —

Builder price participation 11,366 16,012 26,916 39,437

Other revenues 30,705 14,237 57,463 34,297

Total revenues 636,296 390,235 1,994,540 850,443

Condominium rights and unit cost of sales 575,389 811 578,523 1,053 5,414 59 583,937 1,112

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and 174 more changes in the filing

MD&A 80 changes

RESULTS OF OPERATIONS

LIQUIDITY AND CAPITAL RESOURCES

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.

Six Months Ended June 30,

Cash provided by (used in) operating activities $ 277,131 $ (47,651)

Cash provided by (used in) investing activities (357,454) (122,671)

Cash provided by (used in) financing activities 1,348,519 970,648

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.

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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.

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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:

thousands Remaining in 2026

2027 2028 2029 2030 Thereafter Total

Mortgages, notes, and loans payable $ 229,512 $ 596,007 $ 293,099 $ 1,048,015 $ 366,629 $ 2,967,139 $ 5,500,401

Interest payments (a) 151,985 270,915 237,601 191,764 163,720 268,505 1,284,490

Operating lease obligations 1,524 1,729 911 871 637 5,810 11,482

Total $ 383,021 $ 868,651 $ 531,611 $ 1,240,650 $ 530,986 $ 3,241,454 $ 6,796,373 (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.

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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.

thousands June 30, 2026 December 31, 2025

Operating Assets debt $ 2,686,141 $ 2,448,784

MPC debt 154,681 163,534

Strategic Developments debt 359,579 481,896

Senior unsecured notes 2,300,000 2,050,000

Unamortized deferred financing costs (43,998) (34,386)

Mortgages, notes, and loans payable, net 5,456,403 5,109,828

Less: Unamortized deferred financing costs 43,998 34,386

Less: Cash and cash equivalents (a) (2,647,959) (1,468,507)

Net Debt $ 2,852,442 $ 3,675,707

(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:

thousands Fair Value % of Total

Cash, cash equivalents, and restricted cash (a) $ 2,033,218 60 %

Investments in fixed maturity securities, AFS (b) 246,583 7 %

Investments in equity securities 1,077,535 32 %

Short-term investments 27,822 1 %

Total $ 3,385,158 100 %

(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.

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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.

CRITICAL ACCOUNTING POLICIES AND ESTIMATES

The preparation of financial statements in accordance with GAAP requires management to make informed judgments, assumptions, and estimates that affect the reported amounts of assets, liabilities, revenues, and expenses. We base our estimates on historical experience and on various other assumptions that we believe to be reasonable under the circumstances. Changes in facts and circumstances or additional information may result in revised estimates, and actual results may differ from these estimates. Other than as set forth below, there are no material changes to the critical accounting policies and estimates previously disclosed in our 2025 Annual Report.

Following the acquisition of Vantage, the Company recognized reserves for claims and claim expenses, goodwill, and other intangible assets. The preliminary purchase price allocation and the ongoing determination of the reserves for claims and claim expenses require complex or significant judgments and include estimates about matters which are inherently uncertain. These estimates are critical to the understanding of our financial condition and operating results, and as such, accounting for business combinations and reserves for claims and claim expenses represent new critical accounting estimates. A discussion of our significant accounting policies impacted by the Vantage Acquisition, including further discussion of the accounting policies described below, can be found in Note 1 - Presentation of Financial Statements and Significant Accounting Policies in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report.

Accounting for Business Combinations

Methodology The Vantage Acquisition was accounted for as a business combination under ASC 805, which requires the assets acquired and liabilities assumed to be recorded at their estimated acquisition-date fair values. The preliminary purchase price allocation includes the recognition of identifiable intangible assets and any excess of the purchase price over the estimated fair value of net tangible and identifiable intangible assets acquired as goodwill, if applicable. The Company will finalize the purchase price allocation during the measurement period as additional information becomes available, including final appraisals of certain acquired assets and assumed liabilities and final underlying tax bases. The Company engaged independent valuation specialists to assist management in determining the fair values of certain acquired assets and assumed liabilities. The most significant areas of judgment in the preliminary fair value assessment relate to broker relationships, trade name, internally developed technology, value of business acquired (VOBA), insurance licenses, and reserves for claims and claim expenses, net of reinsurance recoverable on unpaid losses. The resulting fair values and useful lives assigned to acquisition-related intangible assets will affect the amount and timing of future amortization expense.

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CRITICAL ACCOUNTING ESTIMATES

Judgments and Uncertainties Determining the fair value of the acquired assets and assumed liabilities required significant judgment and estimates and was based on information available as of the acquisition date. The valuation of broker relationships was based on the multi-period excess earnings method and incorporated significant assumptions including projected net premiums written insurance premiums, retention rates, normalized growth assumptions, contributory asset charges, discount rates, long-term tax rates, and investment yields. The trade name was valued using the relief-from-royalty method, which required assumptions regarding royalty rates, projected net premiums written insurance premiums, growth assumptions, and discount rates. Internally developed technology was valued using the replacement cost method and incorporated estimates of labor costs, development timing, developer's profit, entrepreneurial incentive, and obsolescence. VOBA was valued using a discounted cash flow model applied to the run-off of unearned premium reserves, net of reinsurance, and incorporated assumptions for loss and expense ratios, payment patterns, capital requirements, risk margin, and discount rates. Reserves for claims and claim expenses, net of reinsurance recoverable on unpaid losses, were measured using a discounted cash flow model applied to the actuarial run-off of recorded reserves and incorporated assumptions related to the time value of money, risk margin, actuarial payment patterns, capital requirements, cost of capital, and reserve payout assumptions. Changes in these assumptions or the receipt of additional information during the measurement period could result in material revisions to the preliminary purchase price allocation, including the amounts assigned to identifiable intangible assets, insurance-related liabilities, and goodwill.

1 unchanged paragraph

Nature of the Estimate As a result of our June 4, 2026 acquisition of Vantage, reserves for claims and claim expenses have become a critical accounting estimate in our Condensed Consolidated Financial Statements. These reserves represent management's estimate of the unpaid portion of the ultimate liability for claims and claim adjustment expenses for insured and reinsured events that have occurred on or before the balance sheet date. They comprise (i) case reserves for claims that have been reported to us and (ii) reserves for losses incurred but not reported (IBNR), which also reflect expected development on reported claims. The reserves were initially recorded at fair value as of the acquisition date in accordance with the acquisition method of accounting and are subsequently estimated using the actuarial methods and assumptions described below. We consider this the most significant accounting judgment associated with the acquired insurance and reinsurance operations because the ultimate cost of claims is not known at the reporting date, the estimate requires significant judgment, and a change in the estimate could have a material effect on our financial condition and results of operations.

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Because the acquisition closed on June 4, 2026, our results for the quarter ended June 30, 2026, include only approximately one month of post-acquisition activity for Vantage. Accordingly, while the reserve balance at June 30, 2026, reflects management's best estimate based on information available at that date, early post-acquisition claims activity may be less predictive of future development, and reserve estimates may be adjusted in future periods as additional post-acquisition experience becomes available.

At June 30, 2026, our reserves for claims and claim expenses related to Vantage were approximately $2.1 billion on a gross basis and $1.6 billion net of reinsurance recoverable on unpaid losses. The gross reserves represented approximately 19% of our total consolidated liabilities and 53% of our total consolidated stockholders' equity at that date. For the period from June 4, 2026 through June 30, 2026, changes in estimates of prior-period claims and claim expense reserves were not material.

Given the interrelationship of assumptions across lines of business, the limited period of post-acquisition activity, and the judgment involved in estimating reserves, management has not identified a single-assumption sensitivity that would be representative of the potential variability in the loss reserve estimate as of June 30, 2026. If a quantitative sensitivity to a reasonably likely change in a significant assumption becomes material and reasonably available, we will disclose the estimated effect of that change. While we believe that recorded loss reserves at June 30, 2026, are adequate, new information, events, or circumstances may result in ultimate losses that are materially greater or less than our recorded reserves, particularly with respect to catastrophe or large-event losses and longer-tail lines of business.

For additional information, 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.

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MARKET RISK AND CONTROLS AND PROCEDURES Table of Contents

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Market risk 7 changes

1 unchanged paragraph

The Company uses derivative instruments to manage its interest rate risk, primarily through the use of interest rate swaps caps, and collars. caps. The Company had $1.4 $1.7 billion of variable-rate debt outstanding at June September 30, 2026, of which $656.5 $656.1 million was swapped to a fixed rate through the use of interest rate swaps and $641.9 $611.6 million had interest rate cap contracts in place. Additionally, the interest rate caps and collars are on construction loans and mortgages with undrawn loan commitments of $136.2 $87.6 million as of June September 30, 2026, which will be covered by the interest rate cap and collar contracts upon drawing. Refer to Note 7 - Derivative Instruments and Hedging Activities in the Notes to Condensed Consolidated Financial Statements under Item 1 of this Quarterly Report for additional information.

As of June September 30, 2026, annual interest costs would increase approximately $1.0 $3.9 million for every 1% increase in floating interest rates. The Company is focused on prudently limiting exposure to potentially higher interest rates based upon market dynamics and general expected financing activity. Generally, a significant portion of our interest expense is capitalized due to the level of assets we currently have under development; therefore, the impact of a change in our interest rate on our Condensed Consolidated Statements of Operations would be less than the total change in interest costs, but we would incur higher cash payments and the development costs of our assets would be higher, resulting in greater depreciation or cost of sales in later years.

Investments in equity securities represent the most significant portion of our consolidated investment portfolio. The Company seeks to invest in businesses that possess excellent economics and management, and prefers to invest a meaningful amount in each company. Currently, our investments are concentrated in relatively few issuers. At June September 30, 2026, approximately 78% 53% of the aggregate fair value of our investments in equity securities was concentrated in seven five companies.

The Company expects to hold its investments for long periods and short-term price volatility is expected to occur in the future. We also maintain significant levels of shareholder capital and ample liquidity to provide a margin of safety against short-term price volatility. The following table summarizes our investments in equity securities and the estimated effects of a hypothetical 10% increase or decrease in market prices as of June September 30, 2026.

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Investments in equity securities $ 1,077,535 1,263,521 10% increase

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MARKET RISK AND CONTROLS AND PROCEDURES Table of Contents

Controls and procedures 3 changes

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As required by SEC rules, we carried out an evaluation, under the supervision and with the participation of our management, including our principal executive officer, principal financial officer, and principal accounting officer, of the effectiveness of the design and operation of our disclosure controls and procedures as of June September 30, 2026, the end of the period covered by this report. Based on the foregoing, our principal executive officer, principal financial officer, and principal accounting officer concluded that our disclosure controls and procedures were effective as of June September 30, 2026.

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On June 4, 2026, the Company completed the acquisition of Vantage Acquisition. In connection with the acquisition, the Company is in the process of integrating the acquired business into the Company's internal control over financial reporting framework. Management is evaluating the existing controls and procedures of the acquired business and implementing additional controls, policies, procedures and system changes, where appropriate. Other than the integration activities associated with the acquisition, there were no changes to our internal control over financial reporting that occurred during the period covered by this report that have materially affected, or are reasonably likely to materially affect, our internal control over financial reporting.

HHH 2026 FORM 10-Q | 70 74

Risk factors 51 changes

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.

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

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

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

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 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.

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.

There have been no material changes to the risk factors previously disclosed in our 2025 Annual Report, except as set forth below and in Part II, Item 1A of the Company's Quarterly Report on Form 10-Q for the period ended June 30, 2026. At our 2026 annual meeting of stockholders, held on September 30, 2026, we announced plans to accelerate our transformation into a diversified holding company by monetizing a substantial portion of the real estate assets of HHC, transitioning HHC into an asset-light real estate asset management platform, and redeploying the resulting proceeds primarily into Vantage, our specialty insurance and reinsurance subsidiary. The following risk factors relate to these plans and should be read in conjunction with the risk factors disclosed in our 2025 Annual Report and in our Quarterly Report on Form 10-Q for the period ended June 30, 2026.

RISKS RELATED TO OUR INSURANCE OPERATIONS REAL ESTATE MONETIZATION STRATEGY

We may be unable to monetize HHC's real estate assets at the values, on the terms, or within the time frame we anticipate, or to realize the anticipated benefits of redeploying the proceeds into Vantage.

Our plans to monetize HHC's real estate assets are in their early stages, and as of the date of this Quarterly Report, we have not entered into definitive agreements for any transactions related to our real estate monetization strategy. Our ability to sell interests in HHC's real estate assets and enter into joint ventures, and the proceeds we receive, will depend on factors beyond our control, including investor demand, real estate and capital market conditions, interest rates, and the availability of financing. If the value of any such assets is lower than we expect, we may be unable to monetize those assets on favorable terms or at all. We may also be required to reduce pricing, accept lower returns, or incur additional costs in remarketing or reconfiguring assets. The proceeds of any such transactions may be less than our estimates or the carrying values of the assets, which could result in impairment charges or losses on sale, and many of these transactions will require consents from lenders, joint venture partners, or other third parties. In addition, these proceeds will be received by HHC, and the indentures governing HHC's senior unsecured notes restrict HHC's ability to pay dividends and make other distributions to the Company, and require that net proceeds from certain asset sales be used to repay indebtedness or be reinvested in HHC's business within a specified period or, to the extent not so applied, be used to offer to repurchase such notes at par. As a result, we may be unable to redeploy proceeds into Vantage in the amounts or at the times we intend, and Vantage may be unable to deploy additional capital at attractive returns or at all. We may modify, delay, or discontinue these plans at any time, and the estimates we have presented publicly regarding the value of HHC's real estate assets and potential returns at Vantage are based on assumptions that may prove to be incorrect.

Our plans to monetize HHC's real estate assets and redeploy the proceeds into Vantage will significantly change our business, including by increasing our dependence on Vantage and transitioning HHC to an asset-light real estate asset management platform.

If implemented as planned, these plans will substantially change the composition of our assets and sources of earnings, and we expect that, following the completion of such transactions, Vantage will represent a substantial majority of our equity value. As a result, our results will depend increasingly on Vantage's insurance and reinsurance operations and investment portfolio, and our reported results may become more volatile because changes in the fair value of the equity securities in Vantage's investment portfolio are recognized in net income. In addition, risks related to Vantage's business and operations will become increasingly significant to us, including but not limited to risks related to its limited operating history, its ability to accurately assess the risks associated with the insurance and reinsurance business it writes and retains, and its ability to collect amounts due from reinsurers. Further, following the sale of interests in its assets, HHC will hold minority interests in those assets, its ability to retain operational control will depend on contractual arrangements with its partners, and its future development activities will depend on its ability to raise third-party capital. HHC has limited experience raising third-party capital or operating as a fee-based asset manager, and the fees it earns may not offset the income we forgo by selling interests in our assets. Any of these factors could adversely affect our business, financial condition, results of operations, and the trading price of our common stock.

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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.

Unregistered sales of stock 11 changes

PURCHASES OF EQUITY SECURITIES BY THE ISSUER

Common Stock Repurchases

The following sets forth information with respect to repurchases made by the Company of its shares of common stock during the second quarter of 2026:

Period Total number of shares purchased (a) Average price paid per share Total number of shares purchased as part of publicly announced plans or programs Approximate dollar value of shares that may yet be purchased under the plans or programs (b)

April 1 - 30, 2026 1,046 $ 63.05 — $ 15,009,600

May 1 - 31, 2026 — $ — — $ 15,009,600

June 1 - 30, 2026 82 $ 62.89 — $ 15,009,600

Total 1,128 $ 63.04 —

(a) During the second quarter of 2026, all 1,128 shares repurchased related to stock received by the Company for the payment of withholding taxes due on employee share issuances under share-based compensation plans.

There were no unregistered sales of equity securities or repurchases of equity securities during the third quarter of 2026.

(b) In March 2022, the Board authorized a share repurchase program pursuant to which the Company may, from time to time, purchase up to $250.0 million of its common stock through open-market transactions. The approximate dollar value of shares that may yet be purchased under this program remained at $15.0 million during the third quarter of 2026.

Other information 1 change

None of our directors or officers adopted or terminated a 10b5-1 plan or non-10b5-1 trading arrangement during the second third quarter of 2026.

1 unchanged paragraph

Exhibits 8 changes

2 unchanged paragraphs

3.4 Certificate of Designations of Series A Non-Voting Exchangeable Perpetual Preferred Stock of Howard Hughes Holding s Inc. (incorporated by reference to Exhibit 3.1 to the Company's Current Report on Form 8-K filed June 5, 2026)

4.6 Form of Warrant Agreement, by and between Howard Hughes Holdings Inc. and Marc Grandisson, dated April 20, 2026 (incorporated by reference to Exhibit 4.1 to the Company's Current Report on Form 8-K filed April 21, 2026)

4.7 Supplemental Indemnification Agreement, by and between Howard Hughes Holdings Inc. and Marc Grandisson, dated April 20, 2026 (incorporated by reference to Exhibit 4.2 to the Company's Current Report on Form 8-K filed April 21, 2026)

10.39 Subscription Agreement, dated as of June 4, 2026, by and between Howard Hughes Holdings Inc., Pershing Square Holdings, Ltd . , and Howard Hughes Insurance Holdings, LLC (incorporated by reference to Exhibit 10.1 to the Company's Current Report on Form 8-K filed June 5, 2026)

10.40 Registration Rights Agreement, dated as of June 4, 2026, by and between Howard Hughes Holdings Inc., Pershing Square Holdings, Ltd . , and Howard Hughes Insurance Holdings, LLC incorporated by reference to Annex D to the Subscription Agreement included in Exhibit 10.1 to the Company's Current Report on Form 8-K filed June 5, 2026 (incorporated by reference to Exhibit 10.2 to the Company's Current Report on Form 8-K filed June 5, 2026)

10.41*+ Form of indemnification agreement for directors and certain executive officers of Howard Hughes Holdings In c.

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* Management contract, compensatory plan, or arrangement

1 unchanged paragraph

Attached as Exhibit 101 to this report are the following documents formatted in iXBRL (Inline Extensible Business Reporting Language): (i) the Condensed Consolidated Statements of Operations for the three and six nine months ended June September 30, 2026 and 2025, (ii) Condensed Consolidated Statements of Comprehensive Income (Loss) for the three and six nine months ended June September 30, 2026 and 2025, (iii) the Condensed Consolidated Balance Sheets as of June September 30, 2026 and December 31, 2025, (iv) Condensed Consolidated Statements of Equity for the three and six nine months ended June September 30, 2026 and 2025, (v) the Condensed Consolidated Statements of Cash Flows for the six nine months ended June September 30, 2026 and 2025, and (vi) the Notes to Condensed Consolidated Financial Statements.

6 unchanged paragraphs