This summary highlights selected information from this proxy statement related to the merger of a subsidiary of DB Insurance Co., Ltd. to be incorporated in Delaware following the date of the Merger Agreement (as defined in this proxy statement) and prior to the closing of such merger in accordance with the terms of the Merger Agreement, with and into The Fortegra Group, Inc. (the “Merger”), with The Fortegra Group, Inc. surviving as a subsidiary of DB Insurance Co., Ltd., and may not contain all of the information that is important to you. We have included page references in parentheses to direct you to more complete descriptions of the topics presented in this summary. To understand the Merger more fully and for a more complete description of the legal terms of the Merger, you should read carefully this entire proxy statement, the annexes to this proxy statement, including the Merger Agreement attached as Annex A, and the documents we incorporate by reference in this proxy statement. You may obtain the documents and information incorporated by reference in this proxy statement without charge by following the instructions under “Where You Can Find More Information” beginning on page 225.

Except as otherwise specifically noted in this proxy statement or as context otherwise requires, “Tiptree,” “we,” “our,” “us” and similar words in this proxy statement refer to Tiptree Inc. including, in certain cases, our subsidiaries. Throughout this proxy statement, we refer to The Fortegra Group, Inc. as “Fortegra,” any entity in which a majority of the outstanding capital stock, voting power or other equity interests is owned by Fortegra or another Subsidiary of Fortegra as a “Subsidiary,” Fortegra and its Subsidiaries, collectively, as the “Group Companies,” DB Insurance Co., Ltd. as “Purchaser” and a subsidiary of Purchaser to be incorporated in Delaware following the date of the Merger Agreement (as defined in this proxy statement) and prior to the closing of the Merger in accordance with the terms of the Merger Agreement as “Merger Sub.” In addition, throughout this proxy statement we refer to the Agreement and Plan of Merger, dated as of September 26, 2025, as it may be amended from time to time, among Tiptree, Fortegra, Purchaser and Merger Sub, as the “Merger Agreement,” and the closing of the transactions contemplated by the Merger Agreement as the “closing.”

On September 26, 2025, Tiptree entered into the Merger Agreement with Fortegra and Purchaser. Merger Sub will, upon its formation, execute a joinder to the Merger Agreement and thereby become a party thereto. Pursuant to the Merger Agreement, on the terms and subject to the satisfaction or waiver of the conditions precedent to closing set forth in the Merger Agreement (the “Condition Satisfaction”), at the time of filing the Certificate of Merger with the Secretary of State of the State of Delaware in accordance with the General Corporation Law of the State of Delaware (the “DGCL”) (the “Effective Time”), in accordance with the Merger Agreement and the DGCL, Merger Sub will be merged with and into Fortegra, the separate corporate existence of Merger Sub will cease and Fortegra will continue as the surviving corporation. As a result of the Merger, the surviving corporation will become a wholly-owned subsidiary of Purchaser. Throughout this proxy statement, we use the term “surviving corporation” to refer to Fortegra as the surviving corporation following the Merger. If the Merger is completed, Tiptree will not own any shares of the surviving corporation.

The Merger may constitute a “transfer of assets” under Section 3-105 of the Maryland General Corporation Law (the “MGCL”), and we are therefore seeking the approval of the Merger and the other transactions contemplated by the Merger Agreement by our stockholders. The closing of the Merger is conditioned on, among other things, Tiptree obtaining the affirmative vote of the holders of shares of common stock, par value $0.001 per share, of Tiptree (“Tiptree common stock”) entitled to cast a majority of all of the votes entitled to be cast on the Merger and the other transactions contemplated by the Merger Agreement. The closing will take place on (a) the last business day of the month in which the Condition Satisfaction occurs; provided, that if the Condition Satisfaction occurs less than five business days prior to the last business day of such month, the closing will occur on the last business day of the month immediately following the month in which the Condition Satisfaction occurs, or (b) such other date or at such other time as the parties to the Merger Agreement may mutually agree.

Following the completion of the Merger, Tiptree expects to continue to own its non-insurance and non-mortgage operations, assets and other investments (the “Retained Business”). Tiptree expects to maintain the same corporate functions and the same senior executives as Tiptree had prior to the completion of the Merger and the same board of directors that is in place as of the date of this proxy statement.

Tiptree Inc., a Maryland corporation, allocates capital to select small and middle market companies with the mission of building long-term value. Established in 2007, Tiptree has a significant track record investing across a variety of industries and asset types, including the insurance, asset management, specialty finance, real estate and shipping sectors. With proprietary access and a flexible capital base, Tiptree seeks to uncover compelling investment opportunities and support management teams in unlocking the full value potential of their businesses.

Shares of Tiptree common stock are listed on the Nasdaq Capital Market (“Nasdaq”) under the symbol “TIPT.”

The Fortegra Group, Inc., a Delaware corporation, is a growing, consistently profitable, and multinational specialty insurance company focused on underwriting complex and niche risks in underserved markets. Founded in 1978, the business has a long-standing track record of disciplined and stable underwriting results while generating strong growth and attractive returns on capital. Fortegra is an underwriting-focused company, with deep expertise within the admitted and E&S insurance lines and capital light fee-based services markets. It targets moderate risk limits and utilizes a sophisticated reinsurance strategy to reduce volatility and protect its capital. The business differentiates itself through its go-to-market strategy, expertise in customized underwriting solutions and the value-added services offered to its distribution partners. Upon completion of the Merger, Fortegra will be a subsidiary of Purchaser.

DB Insurance Co., Ltd., incorporated and existing under the laws of the Republic of Korea with its registered office at DB Financial Center, 432, Teheran-ro, Gangnam-gu, Seoul, Korea, 06194. DB Insurance Co., Ltd. was established as Korea’s first automobile insurance company in 1962 and today is the second largest non-life insurer in South Korea, servicing over 11 million customers. DB Insurance offers a diversified portfolio including long-term medical, auto, and property and casualty insurance policies.

A subsidiary of Purchaser to be incorporated in Delaware following the date of the Merger Agreement and prior to the closing of the Merger in accordance with the terms of the Merger Agreement (“Merger Sub”) for the purpose of entering into the Merger Agreement and completing the transactions contemplated by the Merger Agreement. Upon completion of the Merger, Merger Sub will cease to exist.

At the Effective Time, in accordance with the Merger Agreement and the DGCL, Merger Sub will be merged with and into Fortegra, the separate existence of Merger Sub will cease and Fortegra will continue as the surviving corporation. As a result of the Merger, the surviving corporation will become a wholly-owned subsidiary of Purchaser. If the Merger is completed, Tiptree will not own any shares of the surviving corporation. Tiptree estimates that Tiptree will receive total gross proceeds of approximately $1.12 billion in cash upon consummation of the Merger, subject to adjustments for Leakage (as defined in this proxy statement) and assuming a closing date for the transactions contemplated by the Merger Agreement (the “closing date”) prior to June 1, 2026, having an estimated book value of approximately $930 million as of September 30, 2025, net of estimated transaction-related taxes and expenses.

Upon the terms and subject to the conditions of the Merger Agreement, the parties to the Merger Agreement will deliver at the closing to the Secretary of State of the State of Delaware a certificate of merger that effectuates the transactions contemplated by the Merger Agreement (the “Certificate of Merger”) and will make all other filings or recordings as may be required under the DGCL and any other applicable law in order to effect the Merger. The Merger will become effective at the time of filing the Certificate of Merger with the Secretary of State of the State of Delaware in accordance with the DGCL.

If the Merger is not approved by Tiptree stockholders, or if the Merger is not completed for any other reason, Tiptree will not receive any payment for its shares of common stock, par value $0.01 per share, of Fortegra (“Fortegra common stock”) or its warrants to purchase shares of Fortegra common stock (the “Fortegra warrants”) in connection with the Merger, and Tiptree will continue to hold its shares of Fortegra common stock and its Fortegra warrants. Under specified circumstances, Tiptree or Fortegra may be required to pay Purchaser $49,500,000 (the “termination fee”) and Tiptree may be required to pay Purchaser $8,250,000 (the “Stockholder Vote Failure Fee”) upon the termination of the Merger Agreement, as described under “The Merger Agreement—Termination of the Merger Agreement—Termination Fee.”

At the Effective Time, by virtue of the Merger and without any action on the part of the holder thereof, (i) each share of Fortegra common stock issued and outstanding immediately prior to the Effective Time (other than shares of Fortegra common stock that are held by (A) any holder of shares of Fortegra common stock who is entitled to demand and properly demands appraisal of such shares (the “Appraisal Shares”) pursuant to, and who complies in all respects with, the provisions of Section 262 of the DGCL or (B) Fortegra, any of its Subsidiaries or Merger Sub, if any, which in each case will be cancelled) will be converted into and thereafter evidence the right to receive, without interest, an amount in cash equal to (1) the Per Share Closing Merger Consideration (as defined in this proxy statement) plus (2) the applicable Pro Rata Percentage (as defined in the Merger Agreement) of the amount by which the amount that is held back from the consideration payable at closing for potential Additional Leakage (as defined in this proxy statement), or $8,000,000 (the “Leakage Reserve Holdback Amount”), exceeds the amount of Additional Leakage (if any) (the “Leakage Delayed Consideration”), which in the case of a holder of Fortegra common stock other than Tiptree and WP Falcon Aggregator, L.P. (the “WP Investor”) (such other Fortegra equityholders, the “Minority Investors,” and each a “Minority Investor”), will be reduced by such holder’s Pro Rata Percentage of an expense fund of $500,000 that is held back from the consideration payable at closing for expenses incurred by Tiptree and the WP Investor as Equityholders’ Representatives in connection with post-closing matters (such amount, the “Equityholders’ Representative Expense Amount”), and (ii) each share of preferred stock, par value $0.01 per share, of Fortegra, designated as Series A Preferred Stock under that certain Certificate of Designation of Series A Preferred Stock of Fortegra, dated June 21, 2022 (the “Certificate of Designation”) (“Fortegra preferred stock” and shares of Fortegra preferred stock together with shares of Fortegra common stock, “Fortegra shares”), issued and outstanding immediately prior to the Effective Time will be converted into and thereafter evidence the right to receive in cash the Series A Liquidation Preference (as defined in this proxy statement).

Pursuant to the terms of the Merger Agreement, in the event that the closing date occurs after June 1, 2026 (the “Profit Sharing Fee Start Date”), Purchaser will additionally be required to pay to the Fortegra equityholders the “Aggregate Delayed Closing Consideration”, which amount will be equal to (a) $1,650,000,000, multiplied by (b) 10% per annum, divided by (c) 365, multiplied by (d) the aggregate number of days from and after the Profit Sharing Fee Start Date to and including the closing date (counting each such date and the closing date, as applicable, as one full day).

The “Per Share Closing Merger Consideration” means an amount equal to the quotient obtained by dividing (a) the sum of (i) the Aggregate Closing Purchase Price (as defined in this proxy statement) plus (ii) an amount equal to the aggregate exercise price of all options (or portions thereof) to acquire shares of Fortegra common stock granted under The Fortegra Group, Inc. 2022 Equity Incentive Plan (as from time to time amended and in effect, the “Fortegra Equity Plan”) (each, a “Fortegra stock option”) (the aggregate amount contemplated by this clause (ii), the “Aggregate Option Exercise Price”) plus (iii) the Aggregate Delayed Closing Consideration, if applicable, by (b) the total number of outstanding shares of Fortegra common stock immediately prior to the Effective Time, as determined on a Fully-Diluted Basis (as defined in the Merger Agreement).

The “Series A Liquidation Preference” means an amount per share of Fortegra preferred stock equal to the greater of (a) the $15.00 per share of Fortegra preferred stock (subject to appropriate adjustment in the event of any share dividend, share split, share combination or other similar recapitalization with respect to the Fortegra preferred stock, if applicable), plus any Accruing Dividends (as defined in the Certificate of Designation) accrued but unpaid thereon, whether or not declared, together with any other dividends declared but unpaid thereon, and (b) the amount of the Aggregate Closing Purchase Price (as defined in this proxy statement) that a holder of such share of Fortegra preferred stock would have been entitled to receive if such share of Fortegra preferred stock were converted into Fortegra common stock immediately prior to the Effective Time (the amount described in this clause (b), the “As-Converted Amount”).

The “Aggregate Closing Purchase Price” means (a) $1,650,000,000 minus (b) the amount of any Leakage (as defined in this proxy statement) (including any interest accrued thereon pursuant to the terms of the Merger Agreement), minus (c) the amount equal to the product of (1) the total number of shares of Fortegra preferred stock issued and outstanding immediately prior to the Effective Time (other than any shares of Fortegra preferred stock held by Fortegra or the Subsidiaries), if any, multiplied by (2) the Series A Liquidation Preference (the product of clauses

(1) and (2), the “Series A Aggregate Liquidation Preference”) (provided, that if the holders of shares of Fortegra preferred stock are entitled to receive the As-Converted Amount then for the purposes of this definition, the Series A Aggregate Liquidation Preference will be deemed to equal zero), minus (d) the Leakage Reserve Holdback Amount.

The “Aggregate Closing Common Purchase Price” means (i) the Aggregate Closing Purchase Price (without reference to the proviso in such definition), plus (ii) the Aggregate Delayed Closing Consideration, if applicable, minus (iii) an amount equal to the sum of (a) for each vested Fortegra stock option, an amount equal to the product obtained by multiplying (1) the difference of (A) the Per Share Closing Merger Consideration minus (B) the exercise price per share of such Fortegra stock option by (2) the aggregate number of shares of Common Stock underlying such Fortegra stock option (the aggregate amount contemplated by this clause (a), the “Option Closing Merger Consideration”) payable to all holders of Fortegra stock options and (b) the aggregate Per Share Closing Merger Consideration payable to all Fortegra equity award holders (other than holders of Fortegra stock options) with respect to their restricted stock unit awards granted under the Fortegra Equity Plan (each, a “Fortegra RSU award”) pursuant to the terms of the Merger Agreement (the aggregate amount contemplated by this clause (iii), the “Equity Award Closing Merger Consideration”).

Fortegra warrants will either be exercised on a cashless basis automatically immediately prior to the Effective Time pursuant to their terms or cancelled at the Effective Time for no consideration, whether or not such cancellation happens pursuant to their terms. Fortegra warrants that are so exercised will be converted into and thereafter evidence the right to receive, without interest, an amount in cash equal to (A) the Per Share Closing Merger Consideration plus (B) the applicable Pro Rata Percentage of the Leakage Delayed Consideration (if any), which in the case of a holder of Fortegra common stock that is a Minority Investor, will be reduced by such holder’s Pro Rata Percentage of the Equityholders’ Representative Expense Amount.

Prior to the Effective Time, the board of directors of Fortegra (the “Fortegra Board”) (or, if appropriate, any committee thereof administering the Fortegra Equity Plan) will adopt resolutions or take such other actions as may be required to cause each Fortegra stock option and each Fortegra RSU award that is outstanding and unvested immediately prior to the Effective Time, whether or not then subject to any performance or other condition, to accelerate and vest at the Effective Time, with the performance conditions applicable to the Fortegra stock options deemed achieved as determined by Fortegra.

At the Effective Time, each such vested Fortegra RSU award will, by virtue of the Merger, be cancelled, and in full consideration of such cancellation, will be converted into and thereafter evidence the right to receive, without interest and less applicable tax withholding, an amount in cash equal to (i) (A) the Per Share Closing Merger Consideration multiplied by (B) the number of Fortegra shares subject to such vested Fortegra RSU award plus (ii) the Leakage Delayed Consideration attributable to such Fortegra shares (if any), and (iii) minus, in the case of each of the Minority Investors, such holder’s Pro Rata Percentage of the Equityholders’ Representative Expense Amount, attributable to such Fortegra shares.

At the Effective Time, each such vested Fortegra stock option will, by virtue of the Merger, be cancelled, and in full consideration of such cancellation, will be converted into and thereafter evidence the right to receive, without interest and less applicable tax withholding, the Option Closing Merger Consideration and the Leakage Delayed Consideration attributable to such Fortegra stock option (if any), minus, in the case of each of the Minority Investors, such holder’s Pro Rata Percentage of the Equityholders’ Representative Expense Amount, attributable to such vested Fortegra stock option.

Any Leakage (as defined in this proxy statement), including any Transaction Expenses (as defined in this proxy statement) but excluding Permitted Leakage (as defined in this proxy statement), that occurs after June 30, 2025 (the “Lockbox Date”) and at or prior to the closing will decrease the Aggregate Closing Purchase Price payable to Fortegra equityholders.

In this proxy statement, “Leakage” means, without duplication, any of the following payments, liabilities, or obligations that occur after the Lockbox Date and at or prior to the closing, in each case, excluding Permitted Leakage: (a) any Transaction Expenses of the Group Companies; (b) any dividend or other distribution declared, paid or made by any of the Group Companies to a Related Party (as defined in this proxy statement); (c) any payments made by any of the Group Companies to a Related Party in respect of any equity interests or other securities of such Group Company being returned, redeemed, purchased or repaid, or any other return of capital, or any payments made

by any of the Group Companies to a Related Party in respect of any obligations for borrowed money; (d) any gift or payment made to, liability assumed or incurred or guarantee or indemnity provided to or for the benefit of a Related Party other than to certain parties listed in the applicable disclosure schedule (each, an “Excepted Related Party”) in the ordinary course; (e) the monetary value of any lien created over any asset of the Group Companies in favor of a Related Party; (f) the monetary value of any sale of any securities of any of the Group Companies to a Related Party (other than in connection with a Fortegra compensation or benefit plan); (g) any amount waived by any of the Group Companies owed to such Group Company by a Related Party; (h) the forgiveness, release or waiver of any right, debt or claim outstanding against a Related Party for no consideration or for consideration that does not represent fair market value (with the amount of Leakage arising under this clause (h) being equal to the amount by which the consideration paid for such forgiveness, release or waiver (if any) falls short of the fair market value attributable to such forgiveness, release or waiver); (i) the amount of (1) any payment made by any of the Group Companies in excess of fair market value for any transfer by a Related Party of any asset to any of the Group Companies or (2) the fair market value of any asset transferred by any of the Group Companies to a Related Party in excess of any payment made therefor; (j) the amount of any loan by any of the Group Companies to a Related Party; (k) the amount of any reasonable and documented out-of-pocket third-party costs and expenses incurred by Purchaser or its affiliates in recovering any Leakage; and (l) any tax paid, payable or incurred by the Group Companies as a consequence of the matters referred to in clauses (a) through (k) above.

In this proxy statement, “Permitted Leakage” means the amount of any of the following payments or transactions made, or to be made, between a Group Company, on the one hand, and a Related Party, on the other hand (except to the extent constituting Transaction Expenses, which, for the avoidance of doubt, will constitute Leakage instead of Permitted Leakage): (a) payment of any amounts specifically reserved for in the applicable interim financial statements of Fortegra and its Subsidiaries set forth in the Merger Agreement, to the extent of the amounts so reserved for therein (up to such amounts); (b) payment of any amounts pursuant to a written request by, or with the prior written consent of, Purchaser to pay such amount (including, for the avoidance of doubt, any Payoff Amount (as defined in this proxy statement) paid by the Group Companies prior to closing at the written request of the Purchaser); (c) payment of any amounts (i) in settlement of accounts to the extent by and between Fortegra and a wholly owned Subsidiary or between any such wholly owned Subsidiaries of Fortegra or (ii) for bona fide services rendered in the ordinary course pursuant to any contract between a Group Company and a Related Party set forth on the applicable schedule to the Merger Agreement in connection with the terminal settlement of intercompany obligations; (d) payments of (i) bonuses or benefits to directors, managers, officers, employees or consultants of the Group Companies (including annual bonuses) made in the ordinary course of business and not arising in connection with the transactions contemplated by the Merger Agreement or (ii) compensation (A) in respect of Fortegra equity awards (1) outstanding on the date of the Merger Agreement or (2) issued to directors, managers, officers, employees or consultants in the ordinary course of business to the extent set forth in the applicable schedule of the Merger Agreement or (B) pursuant to contractual obligations existing on the date of the Merger Agreement as set forth in the applicable disclosure schedule (in the case of each of the foregoing clauses (A) through (B), including any employer taxes associated with that amount and any equity interests withheld in the satisfaction of taxes or the exercise price of any equity awards); (e) any reimbursement for premiums, and any related cost, paid to a third-party insurer in connection with the coverage of any of the Group Companies under any insurance policy of Tiptree and its affiliates provided in the ordinary course of business consistent with the allocation methodology reflected in Fortegra’s financial statements specified in the Merger Agreement; (f) any reimbursement for any audit-related expense incurred by Tiptree that is allocated to the Group Companies in the ordinary course of business consistent with the allocation methodology reflected in Fortegra’s financial statements specified in the Merger Agreement; (g) any distribution of cash (i) to pay any dividend by a Subsidiary of Fortegra to Fortegra or to a wholly owned Subsidiary of Fortegra or (ii) to the extent of Accruing Dividends, as defined in and pursuant to the Certificate of Designation, on the Fortegra preferred stock, that accrue or have accrued pursuant to their terms beginning on June 30, 2025, to the holder of such Fortegra preferred stock, in each case, in the ordinary course of business; (h) payments made to, liability assumed or incurred or guarantee or indemnity provided by or for the benefit of a Related Party, in each case, (i) pursuant to a Fortegra compensation or benefit plan or in connection with employment or compensation agreements with a Related Party employed by a Group Company, (ii) in exchange for services on arms’ length terms in the ordinary course of business performed by (A) a portfolio company of the WP Investor pursuant to and in accordance with the terms of a contract between a Group Company and such portfolio or (B) another Related Party in the ordinary course of business and pursuant to a contract set forth in the applicable disclosure schedule or (iii) pursuant to an arrangement entered into after the date of the Merger Agreement with the prior consent of Purchaser; (i) any payment,

liability, obligation or reimbursement as required under the tax sharing agreement specified in the Merger Agreement and under the investment advisory agreements specified in the Merger Agreement; and (j) any tax paid, payable or incurred by the Group Companies as a consequence of the matters referred to in clauses (a) through (h) of this definition.

In this proxy statement, “Related Party” means (a) each person that holds equity interests in a Group Company and any affiliate of such holder of equity interests in a Group Company, (b) each person that serves as a director, officer, manager, partner, executor or trustee (or in a similar capacity) of Tiptree or its subsidiaries, including the Group Companies, or of any person that holds equity interests of Fortegra or any affiliate of a person that holds equity interest in a Group Company, and (c) with respect to an individual described in the preceding clause (a) or clause (b), (i) such individual’s spouse and lineal descendants including those by adoption and (ii) any other individual who resides with such individual; provided no Group Company will be deemed to be a Related Party of the other Group Companies.

In this proxy statement, “Transaction Expenses” means, without duplication, (a) all liabilities, fees and expenses paid or payable by any Group Company directly in connection with the direct or indirect change of ownership of (i) the Group Companies, (ii) the business of the Group Companies or (iii) any material portion thereof, in each case, directly in connection with the transactions contemplated by the Merger Agreement, including any such liabilities, fees and expenses incurred in connection with the marketing process managed by Barclays and its affiliates and BofA Securities, Inc. (“BofA Securities”) and its affiliates, including the preparation of marketing materials, management presentations, evaluating indications of interest of Purchaser and other bidders, sell-side diligence and interactions and negotiations with other interested parties and the drafting, negotiation, execution and delivery of the Merger Agreement and the other transaction documents and other documents contemplated by the Merger Agreement and the consummation of the transactions contemplated by the Merger Agreement, including by the following financial advisors and legal counsel: BofA Securities, Barclays and its affiliates, Ropes & Gray LLP (“Ropes & Gray”) and Sidley Austin LLP (“Sidley”) but excluding (w) Keefe, Bruyette & Woods, Inc. (“KBW”) for aggregate payments of less than or equal to $500,000, (x) the Change of Control Waiver Fees and Expenses (as defined in this proxy statement), (y) any other liabilities, fees or expenses borne by Purchaser pursuant to the terms of the Merger Agreement and (z) any Payoff Amount; (b) the employer portion of any employment, payroll or similar taxes attributable to payment of Equity Award Closing Merger Consideration to holders of Fortegra equity awards; (c) any amounts due and payable by a Group Company to any present or former service provider for any change in control, retention or similar transaction payments or bonuses, severance, termination or other similar arrangement or payment triggered solely as a result of the consummation of the transactions contemplated by the Merger Agreement (including any termination of employment, other than a termination of employment initiated by Purchaser or any of its affiliates (including the surviving corporation) after the closing), including, for the avoidance of doubt, the transaction bonuses and payments made pursuant to the retention program, in each case, that are contemplated by the applicable section of the disclosure schedule, together with the employer portion of any employment, payroll or similar taxes attributable to such amounts; (d) the Other Change of Control Consent Fees Amount (as defined in this proxy statement); (e) 50% of any premiums, fees and expenses to procure the D&O Insurance (as defined in this proxy statement) referenced in the Merger Agreement; (f) 50% of all Transfer Taxes (as defined in this proxy statement); and (g) 50% of all antitrust, competition and foreign direct investment filing fees, including the HSR and CFIUS filing fees. For the avoidance of doubt, Transaction Expenses does not include (i) issuances and payments in respect of equity interests to directors, managers, officers, employees or consultants of Fortegra or any of its Subsidiaries or (ii) any increase in the salary, wages, bonuses or other compensation or benefits payable to any current or former director, officer, employee or consultants of Fortegra or any of its Subsidiaries, in each case in the ordinary course.

Purchaser is required to provide written notice to the Equityholders’ Representatives of the amount of any Leakage (without duplication of any Leakage included in the calculation of the Aggregate Closing Purchase Price as a reduction thereto) plus interest on such Leakage calculated at the annual rate of the prime rate, as published in The Wall Street Journal in effect on the closing date, from (and including) the closing date to (but excluding) the date of such payment to the Purchaser (the “Additional Leakage” and such notice, the “Additional Leakage Notice”). Purchaser will only be entitled to deliver an Additional Leakage Notice during the period starting on the closing date and ending at 11:59 p.m. Eastern Time on the four-month anniversary of the closing. The Purchaser and the Equityholders’ Representative will discuss in good faith any discrepancies in the calculation of the total amount of such Additional Leakage for a period of 15 days following delivery by Purchaser of the Additional Leakage Notice.

The Purchaser will, after such 15-day consultation period, deliver a written notice to SRS Acquiom (or its applicable affiliate) as paying agent, or if SRS Acquiom (or its applicable affiliate) is unwilling or unable to accept such appointment (including because it is unable to make payments within the timing called for in the Merger Agreement), such paying agent that is mutually acceptable to Fortegra and Purchaser, each acting reasonably (the “Paying Agent”), instructing the Paying Agent to pay the Purchaser or the surviving corporation an amount in cash equal to the Additional Leakage from the account established by the Paying Agent to hold the Leakage Reserve Holdback Amount (the “Leakage Reserve Holdback Account”). If no Additional Leakage Notice is received or, if following any payment of Additional Leakage to Purchaser or the surviving corporation, there are amounts remaining in the Leakage Reserve Holdback Account, the Purchaser will promptly (and in any event within two business days of determining there is no Additional Leakage or such payment of Additional Leakage, as applicable) instruct the Paying Agent to release the Leakage Delayed Consideration to each holder of Fortegra shares issued and outstanding immediately prior to the Effective Time (other than Appraisal Shares and shares of Fortegra common stock held by Fortegra, any of its Subsidiaries or Merger Sub) and each holder of Fortegra warrants that are exercised on a cashless basis in accordance with the terms of the Merger Agreement (such holders, collectively, the “Eligible Holders”) in accordance with their respective Pro Rata Percentages.

See the section of this proxy statement entitled “The Merger Agreement—Additional Leakage” beginning on page 76.

Tiptree estimates that Tiptree will receive total gross proceeds of approximately $1.12 billion in cash upon consummation of the Merger, subject to adjustments for Leakage and assuming a closing date for the transactions contemplated by the Merger Agreement prior to June 1, 2026, having an estimated book value of approximately $930 million as of September 30, 2025, net of estimated transaction-related taxes and expenses. See the section of this proxy statement entitled “The Merger—Anticipated Use of Tiptree’s Portion of the Proceeds from the Merger” beginning on page 39 and “Risk Factors—Tiptree will have broad discretion in the use of the proceeds from the Merger and may use proceeds in ways that you and other stockholders may not approve” beginning on page 29.

Tiptree intends to use proceeds from the Merger for working capital and general corporate purposes, including to pay transaction expenses, to pay taxes on the transactions contemplated by the Merger Agreement, to repay existing debt of Tiptree, to engage in opportunistic stock repurchases and/or pay dividends, to purchase additional assets or businesses and/or for any other purpose that the Tiptree Board deems appropriate.

Tiptree does not expect to distribute cash to its stockholders in connection with the Merger. The Tiptree Board has previously repurchased, and may from time to time repurchase, shares of Tiptree common stock and/or pay cash dividends. Factors that may impact our decisions regarding the method, timing and amount of a return of capital, if any, include economic and market conditions, our financial condition and operating results, cash requirements, capital requirements of our operating subsidiaries, legal requirements, regulatory constraints, investment opportunities at the time any such payment is considered, and other factors the Tiptree Board deems relevant. Furthermore, the specific timing and amount of any dividend payments are subject to declaration on future dates by the Tiptree Board in its sole discretion. There can be no assurances that we will complete any return of capital to our stockholders.

For additional information, see the section of this proxy statement entitled “Unaudited Pro Forma Condensed Consolidated Financial Statements” beginning on page 118, which assumes completion of the Merger.

On September 24, 2025, Barclays rendered its oral opinion (which was subsequently confirmed in writing) to the Fortegra Board, to the effect that, as of such date and based upon and subject to the assumptions, limitations, qualifications and other matters stated in its opinion, the aggregate consideration of $1,650,000,000 in cash in the Merger is fair, from a financial point of view, to holders of Fortegra common stock.

The full text of Barclays’ written opinion, dated as of September 26, 2025, is attached as Annex B to this proxy statement. Barclays’ written opinion sets forth, among other things, the assumptions made, procedures followed, factors considered and limitations upon the review undertaken by Barclays in rendering its opinion. You are urged to read the opinion carefully in its entirety. For a further discussion of Barclays’ opinion, see the section entitled “The Merger—Opinion of Barclays.”

Following the completion of the Merger, Tiptree will continue to be a public company operating under the name Tiptree Inc. listed on Nasdaq under the symbol “TIPT” and will continue to file periodic reports with the U.S. Securities and Exchange Commission (the “SEC”). Tiptree expects to continue to own the Retained Business. Tiptree expects to maintain the same corporate functions and the same senior executives as Tiptree had prior to the completion of the Merger and the same board of directors that is in place as of the date of this proxy statement. As of immediately following the closing of the Merger, all of Tiptree’s revenues will be generated by the Retained Business. Tiptree intends to use proceeds from the Merger for working capital and general corporate purposes, including to pay transaction expenses, to pay taxes on the transactions contemplated by the Merger Agreement, to repay existing debt of Tiptree, to engage in opportunistic stock repurchases and/or pay dividends, to purchase additional assets or businesses and/or for any other purpose that the Tiptree Board deems appropriate. For additional information, see the section of this proxy statement entitled “The Merger—Activities of Tiptree Following the Merger” beginning on page 65 and the section of this proxy statement entitled “Unaudited Pro Forma Condensed Consolidated Financial Statements” beginning on page 118, which assumes completion of the Merger.

Tiptree does not believe that any director, director nominee or executive officer of Tiptree since January 1, 2024, has any direct or indirect substantial interest in the Merger that is different from or in addition to the interests of our stockholders generally.

See the section of this proxy statement entitled “The Merger—Interests of Tiptree’s Directors and Executive Officers in the Merger” beginning on page 66.

Purchaser anticipates that the total amount of funds necessary to consummate the Merger and the other transactions contemplated by the Merger Agreement will be approximately $1.68 billion. Purchaser expects to finance the Merger through cash on hand. The obligations of Purchaser and Merger Sub under the Merger Agreement are not conditioned upon their ability to obtain financing (or upon any cooperation by Tiptree in respect of any such financing).

For U.S. federal income tax purposes, the proposed Merger will be treated as a taxable sale of Fortegra common stock by Tiptree. The proposed Merger is entirely a corporate action undertaken by Tiptree. Our stockholders will not realize any direct taxable gain or loss on their shares of Tiptree common stock for U.S. federal income tax purposes as a result of the Merger, as our stockholders will not receive any direct proceeds from the Merger. We do not anticipate that the Merger or the other transactions contemplated by the Merger Agreement will result in any U.S. federal income tax consequences to our stockholders.

See the section of this proxy statement entitled “The Merger—Material U.S. Federal Income Tax Consequences of the Merger” beginning on page 67 and the section of this proxy statement entitled “Unaudited Pro Forma Condensed Consolidated Financial Statements” beginning on page 118 for additional information.

The Tiptree Board is seeking stockholder approval of the Merger and the other transactions contemplated by the Merger Agreement because Tiptree is a Maryland corporation and the Merger may constitute a “transfer of assets” under Section 3-105 of the MGCL. Additionally, approval of the Merger Proposal by the affirmative vote of the holders of shares of Tiptree common stock entitled to cast a majority of all of the votes entitled to be cast on the Merger and the other transactions contemplated by the Merger Agreement is a closing condition under the Merger Agreement.

The special meeting of our stockholders to consider and vote on the proposal to approve the Merger and the other transactions contemplated by the Merger Agreement (the “Merger Proposal”), among other matters, will be

held virtually on December 3, 2025, at 4:00 p.m., Eastern Time. You may participate in the special meeting via Internet webcast by visiting the following website and following the registration and participation instructions contained therein: www.virtualshareholdermeeting.com/TIPT2025SM. Please have the control number located on your proxy card available.

At the special meeting, we will ask our stockholders of record as of the record date to consider and vote upon (i) the Merger Proposal and (ii) one or more adjournments of the special meeting, if necessary, to solicit additional proxies, in the event that there are insufficient votes to approve the Merger Proposal.

Only Tiptree stockholders of record at the close of business on October 30, 2025, the record date for the special meeting, are entitled to notice of, and entitled to cast votes at, the special meeting and any postponements or adjournments thereof. You will be entitled to cast one vote at the special meeting for each share of Tiptree common stock you owned as of the close of business on the record date.

A quorum must be present at the special meeting in order to transact business. A quorum will be present if the holders of at least a majority of the shares of Tiptree common stock issued and outstanding as of the record date and entitled to vote on the Merger Proposal are present or represented by proxy at the special meeting. As of the close of business on the record date of October 30, 2025, there were 37,823,734 shares of Tiptree common stock outstanding and entitled to vote on the Merger Proposal. Thus, 18,911,868 shares of Tiptree common stock must be represented at the special meeting to have a quorum.

In the event that a quorum is not present at the special meeting, it is expected that the special meeting would be adjourned to a later date to solicit additional proxies.

Approval of the Merger Proposal requires the affirmative vote of the holders of shares of Tiptree common stock entitled to cast a majority of all of the votes entitled to be cast on the Merger Proposal. As a result, the holders of at least 18,911,868 shares of Tiptree common stock entitled to vote on the Merger Proposal must cast an affirmative vote electronically or by proxy at the special meeting for the Merger Proposal to be approved. The approval of the proposal to approve one or more adjournments of the special meeting, if necessary, to solicit additional proxies if, at the time of the special meeting, there are insufficient votes to approve the Merger Proposal, requires the affirmative vote of a majority of the votes cast on the matter at the special meeting. Only Tiptree stockholders of record at the close of business on October 30, 2025, the record date for the special meeting, are entitled to notice of, and entitled to cast votes at, the special meeting and any postponements or adjournments thereof. You will be entitled to cast one vote at the special meeting for each share of Tiptree common stock you owned as of the close of business on the record date.

Abstentions will be counted toward the presence of a quorum at the special meeting. Abstentions will not be considered votes cast on any proposal brought before the special meeting. Because the affirmative vote of the holders of shares of Tiptree common stock entitled to cast a majority of all of the votes entitled to be cast on the Merger Proposal is required to approve the Merger Proposal, the failure of any stockholder of record to submit a signed proxy card, grant a proxy electronically over the Internet or by telephone or to vote electronically by ballot at the special meeting will have the same effect as a vote “AGAINST” the Merger Proposal, and any abstention with respect to such proposal will have the same effect as a vote “AGAINST” the Merger Proposal.

The approval of the proposal to approve one or more adjournments of the special meeting, if necessary, to solicit additional proxies, in the event that there are insufficient votes to approve the Merger Proposal requires the affirmative vote of a majority of the votes cast at the special meeting.

Abstentions from voting by a Tiptree stockholder and the failure of any Tiptree stockholder to submit a vote will not be considered votes cast in respect of the proposal to approve one or more adjournments of the special meeting, and so will not have the effect of a vote “FOR” or “AGAINST” the proposal, but will increase the relative influence of those stockholders voting with respect to such proposal.

Because all of the proposals to be voted on at the special meeting are “non-routine” matters, brokers, banks and other nominees will not have authority to vote on any proposals unless instructed. As a result, Tiptree does not expect there to be any broker non-votes at the special meeting.

Only Tiptree stockholders of record at the close of business on October 30, 2025, the record date for the special meeting, are entitled to notice of, and entitled to cast votes at, the special meeting and any postponements or adjournments thereof. You will be entitled to cast one vote at the special meeting for each share of Tiptree common stock you owned as of the close of business on the record date.

As of the close of business on the record date, our directors and executive officers beneficially owned and were entitled to vote, in the aggregate, 11,108,777 shares of Tiptree common stock, representing approximately 29.37% of the shares of Tiptree common stock issued and outstanding on that date. The directors and executive officers have informed Tiptree that they currently intend to vote all of their shares of Tiptree common stock (i) “FOR” the Merger Proposal and (ii) “FOR” the proposal to approve one or more adjournments of the special meeting, if necessary, to solicit additional proxies, in the event that there are insufficient votes to approve the Merger Proposal. In addition, certain of our directors and executive officers have entered into voting agreements to vote their shares in favor of the Merger Proposal, among other matters. See the section of this proxy statement entitled “The Merger Agreement—Tiptree Voting Agreements” beginning on page 112 for more information.

The Tiptree board of directors (the “Tiptree Board”), after considering various reasons described in the section of this proxy statement entitled “The Merger—Tiptree Board’s Recommendation and Reasons for the Merger” beginning on page 51, has unanimously: (a) determined that the Merger and the other transactions contemplated by the Merger Agreement are advisable and in the best interests of Tiptree and its stockholders; (b) approved the execution and delivery of the Merger Agreement by Tiptree and the consummation of the Merger and the other transactions contemplated by the Merger Agreement; (c) directed that the Merger and the other transactions contemplated by the Merger Agreement be submitted for consideration at a meeting of Tiptree’s stockholders; and (d) resolved to recommend that the stockholders of Tiptree approve the Merger and the other transactions contemplated by the Merger Agreement. Accordingly, the Tiptree Board recommends that Tiptree stockholders vote (i) “FOR” the Merger Proposal and (ii) “FOR” the proposal to approve one or more adjournments of the special meeting, if necessary, to solicit additional proxies, in the event that there are insufficient votes to approve the Merger Proposal.

For a description of factors considered by the Tiptree Board in determining to recommend approval of the Merger Proposal, see the section of this proxy statement entitled “The Merger—Tiptree Board’s Recommendation and Reasons for the Merger” beginning on page 51.

Holders of Tiptree common stock are not entitled to appraisal rights, rights of objecting stockholders or other similar rights in connection with the Merger.

See the section of this proxy statement entitled “No Appraisal Rights” beginning on page 223.

The Merger and the other transactions contemplated by the Merger Agreement, including the possibility that the Merger and such other transactions may not be completed, involve and are subject to a number of risks to Tiptree and our stockholders, including the following:

For additional information regarding the risk factors related to the Merger Agreement, the Merger and the other transactions contemplated thereby, and the operation of the Retained Business by Tiptree following the closing of the Merger, see the section of this proxy statement entitled “Risk Factors” beginning on page 28.

To consummate the Merger, Fortegra and Purchaser must obtain approvals or consents from, or make filings with, a number of regulatory authorities. We describe certain material approvals, consents and filings below.

We currently expect to consummate the Merger during mid-2026. Each party has agreed to, and to cause its affiliates and representatives to use reasonable best efforts to, take promptly any and all steps and actions necessary to avoid or eliminate each and every impediment that may be asserted by any governmental authority or any other person with respect to the transactions contemplated by the Merger Agreement so as to enable the closing to occur expeditiously, but in no case later than the Termination Date, except that the Group Companies, Purchaser or its affiliates, including Merger Sub, or its representatives, are not required to take or refrain from taking any action that would or would reasonably be expected to result in the imposition of a burdensome condition. Although we believe that we will receive the required consents and approvals to consummate the Merger, we cannot give any assurance as to the timing of these consents and approvals or as to Fortegra’s and Purchaser’s ultimate ability to obtain such consents or approvals (or any additional consents or approvals which may otherwise become necessary). We also cannot ensure that we will obtain such consents or approvals on terms and subject to conditions satisfactory to Fortegra and Purchaser.

Under the Merger Agreement, the Merger cannot be completed until the waiting period applicable to the Merger under the Hart-Scott-Rodino Antitrust Improvements Act of 1976, as amended, and the rules and regulations promulgated thereunder (the “HSR Act”), has expired or been terminated and any required approvals thereunder have been obtained.

A transaction notifiable under the HSR Act may not be completed until the expiration or termination of a 30-day waiting period following the parties’ filings of their HSR Act notification and report forms. If the Federal Trade Commission (the “FTC”) or the Antitrust Division of the Department of Justice (the “DOJ”) issues a request for additional information and documentary materials (a “Second Request”) prior to the expiration of the initial waiting period, the parties must observe a second 30-day waiting period, which would begin to run only after the parties have substantially complied with the Second Request, unless the waiting period is terminated earlier or the parties otherwise agree not to consummate the Merger and the other transactions contemplated by the Merger Agreement until a specified time has expired or the agreement has been terminated. Purchaser and Merger Sub shall not amend, revoke or refile any filing, submission, application, notification or report form or extend any applicable waiting or review periods or enter into any agreement with a governmental authority to delay or not to consummate the transactions contemplated hereby, except with the prior written consent of Fortegra, which consent shall not be unreasonably withheld.

At any time before or after consummation of the Merger, notwithstanding the termination or expiration of the waiting period under the HSR Act, the FTC or the DOJ could take such action under the antitrust laws as it deems necessary or desirable in the public interest, and at any time before or after the completion of the Merger, any U.S. state could take such action under the antitrust laws as it deems necessary or desirable in the public interest. Such action could include seeking to enjoin the completion of the Merger or seeking divestiture of assets of the parties. Private parties may also seek to take legal action under the antitrust laws under certain circumstances. We cannot be certain that a challenge to the Merger will not be made or that, if a challenge is made, we will prevail.

Under the Merger Agreement, the Merger cannot be completed until one of the following events related to the Committee on Foreign Investment in the United States (“CFIUS”) has occurred (collectively, defined as “CFIUS Approval”): (a) Fortegra and Purchaser have received written notice from CFIUS that CFIUS has determined that the transactions contemplated by the Merger Agreement are not “covered transactions” (within the meaning of the Defense Production Act of 1950, as amended, including all implementing regulations thereof (the “DPA”)) and are not subject to review under the DPA; (b) Fortegra and Purchaser have received written notice from CFIUS that it has concluded all action under the DPA with respect to the transactions contemplated by the Merger Agreement and has determined that there are no unresolved national security concerns; (c) CFIUS has determined, pursuant to 31 C.F.R. § 800.407(a)(2), that it is not able to conclude action under the DPA with respect to the transactions contemplated by the Merger Agreement pursuant to a declaration filing with respect to the transactions contemplated by the Merger Agreement submitted to CFIUS by the parties to the Merger Agreement pursuant to 31 C.F.R. Part 800 Subpart D (such declaration filing, a “CFIUS Declaration”) submitted by the parties to the Merger Agreement but has not requested the submission of a joint voluntary notice with respect to the transactions contemplated by the Merger Agreement submitted to CFIUS by Fortegra and Purchaser pursuant to 31 C.F.R. Part 800 Subpart E (such notice, a “CFIUS Notice”); or (d) if CFIUS has sent a report (the “CFIUS Report”) to the President of the United States requesting the President’s decision, then the President has (i) announced a decision not to take any action to suspend or prohibit the transactions contemplated by the Merger Agreement or (ii) not taken any action to suspend or prohibit the transactions contemplated by the Merger Agreement after 15 days from the date of receipt of the CFIUS Report.

The Merger is also conditioned on the consents, approvals, authorizations, waivers, filings or notifications having been made or obtained from, as applicable (and being in full force and effect), among others, the Financial Services Commission of South Korea in connection with Fortegra becoming Purchaser’s subsidiary through the formation of Merger Sub and the transactions contemplated by the Merger Agreement.

In addition, the parties are required to make filings with, and obtain approvals from, certain U.S. state insurance regulatory authorities and non-U.S. insurance regulators. The insurance companies and other regulated entities within Fortegra are domiciled or licensed in multiple jurisdictions, and as such, the Merger requires filings and approvals in each relevant jurisdiction as described below.

Generally, in each U.S. state where a Fortegra insurance company is domiciled, a person seeking to acquire voting securities or other interests that would result in such person controlling, directly or indirectly, the domestic insurer must file a statement requesting approval of the acquisition of control of the domestic insurer (referred to as a “Form A” or equivalent change of control application). The insurance laws of each such state require prior approval of the Form A application before the acquisition of control may be consummated. A hearing may be required with respect to certain of such approvals whether by law or by the determination of the applicable state insurance regulatory authority. If the regulatory authority intends to disapprove the Form A application, it may do so only after a hearing and the disapproval must be based on one or more prescribed statutory grounds. There is no statutorily prescribed time period in which the insurance regulatory authority must render a decision approving or disapproving the applicable Form A application, and the authority may request additional information before deeming the Form A filing complete.

The Merger is conditioned on Form A filings and other insurance regulatory submissions required in Arizona, California, Delaware, Georgia, Kentucky and Louisiana.

Additional filings, notifications, and approvals and/or non-disapprovals as required in connection with the acquisition of control of licensed insurance companies, premium finance companies, service contract providers, and third-party administrators in Alaska, Florida, Iowa, Massachusetts, Michigan, Minnesota, Nebraska, New York, North Dakota, Ohio, South Dakota, Tennessee, Texas and Wyoming. Insurance regulatory submissions are also required in Turks and Caicos, Malta, Belgium and the United Kingdom.

The Merger is also subject to clearance by the Polish Office of Competition and Consumer Protection and the Romanian Commission for the Examination of Foreign Direct Investments. In addition, the Merger is subject to foregoing consents, approvals, authorizations, waivers, filings or notifications, and all approvals from governmental authorities that are required under applicable law (including pursuant to any insurance laws) to permit the consummation of the transactions contemplated by the Merger Agreement, the failure of which to obtain would be material to the businesses of the Group Companies (the parties to the Merger Agreement are required to act reasonably and in good faith in making determinations as to whether a jurisdiction is “required” for these purposes) and that are identified one business day prior to the date on which the definitive proxy statement is filed with the SEC (such approvals, the “additional regulatory approvals”), having been made or obtained, as applicable, and being in full force and effect, and the waiting periods, clearances, approvals and/or consents (as applicable) and any other additional regulatory approvals having expired, been terminated or been obtained (as applicable), in each case, without the imposition of the applicable burdensome condition on Purchaser or its affiliates or on the surviving corporation and its affiliates from and after the closing, are conditions to the obligations of each party to the Merger Agreement to consummate the transactions contemplated by the Merger Agreement. No additional regulatory approvals were so identified prior to the date of this definitive proxy statement.

The foregoing consents, approvals, authorizations, waivers, filings or notifications, and the additional regulatory approvals are collectively referred to herein as the “Regulatory Approvals Conditions.”

Except as otherwise provided in the Merger Agreement, during the period commencing with the execution and delivery of the Merger Agreement and continuing until the closing or, if earlier, the termination of the Merger Agreement, Tiptree will not, and will cause its subsidiaries, directors and officers not to, and will use reasonable best efforts to cause its and their other respective representatives not to, directly or indirectly:

Notwithstanding anything to the contrary contained in the Merger Agreement, if at any time following the execution and delivery of the Merger Agreement and prior to the time at which the Tiptree stockholder approval is obtained, (i) Tiptree or any of its representatives has received a bona fide written acquisition proposal that did not result from a breach of Tiptree’s non-solicitation obligations under the Merger Agreement and (ii) the Tiptree Board determines in good faith, after consultation with its financial advisors and outside legal counsel, that such acquisition proposal constitutes or would reasonably be expected to lead to or result in a superior proposal (as defined in this proxy statement), then Tiptree may (A) furnish information with respect to Tiptree and its subsidiaries to the person making such acquisition proposal and its representatives and (B) engage or participate in discussions or negotiations with such person and its representatives regarding such acquisition proposal; provided, that, Tiptree is required not to, and to instruct its representatives not to, disclose any non-public information to such person and its representatives unless Tiptree has entered into, or first enters into, a confidentiality agreement with such person with terms (including governing confidentiality) that are not less favorable in the aggregate to Purchaser than those contained in the confidentiality agreement entered into between Purchaser and Fortegra; provided, further, that (A) such confidentiality agreement may contain a less restrictive or no standstill restriction and such confidentiality agreement may not contain terms that prohibit Tiptree from complying with the “Acquisition Proposals” section of the Merger Agreement, and (B) Tiptree is required to provide or make available to Purchaser as promptly as reasonably practicable (and in any event within 24 hours thereafter) any non-public information concerning Tiptree or its subsidiaries provided or made available to such other person or any of its representatives that was not previously provided or made available to Purchaser and Merger Sub.

From and after the date of the Merger Agreement, Tiptree will, within 24 hours of the receipt by Tiptree of any acquisition proposal, notify Purchaser with respect to such acquisition proposal, and will in any such notice include copies of any written materials relating to such acquisition proposal (including materials provided by Tiptree or its representatives in response thereto) and indicate the identity of the person making such acquisition proposal, and the material terms and conditions of such acquisition proposal and thereafter will promptly (within 24 hours) keep Purchaser reasonably informed on a reasonably current basis of any material change to the terms of any such acquisition proposal, including by providing a copy of all material additional written documentation relating thereto.

The Tiptree Board and each committee thereof will not, subject to the terms and conditions of the Merger Agreement, (i) cause or knowingly permit Tiptree or Fortegra to enter into any alternative acquisition agreement (as defined in this proxy statement) or (ii) make an adverse recommendation change (as defined in this proxy statement).

Notwithstanding anything to the contrary contained in the Merger Agreement, the Tiptree Board or a committee thereof may, at any time prior to the time at which the Tiptree stockholder approval is obtained, in response to a bona fide written acquisition proposal that did not result from a breach of Tiptree’s non-solicitation obligations under the Merger Agreement, (1) terminate the Merger Agreement and substantially concurrently enter into an alternative acquisition agreement in respect of the acquisition proposal described in the following clause (2)(A) or (2) make an adverse recommendation change if (A) Tiptree receives an acquisition proposal that the Tiptree Board determines, in good faith, after consultation with its outside legal counsel and financial advisors, constitutes a superior proposal and the failure to take such action would reasonably be expected to be inconsistent with the duties of the directors of Tiptree under applicable law; (B) Tiptree has notified Purchaser in writing that it intends to terminate the Merger Agreement to enter into an alternative acquisition agreement or the Tiptree Board intends to effect an adverse

recommendation change, which written notice must include the information with respect to such superior proposal that is specified in the Merger Agreement; (C) through the fifth business day following the date of such notice, Fortegra and Tiptree consider, negotiate and discuss with Purchaser in good faith (to the extent Purchaser so desires to negotiate) any amendments or modifications to the terms of the Merger Agreement proposed by Purchaser and (D) no earlier than the fifth business day following the date of such notice, the Tiptree Board determines, in good faith, after consultation with its financial advisors and outside legal counsel, taking into consideration the terms of any proposed amendment or modification to the Merger Agreement that Purchaser has committed to make during such five-business-day period, that the acquisition proposal continues to constitute a superior proposal and the failure to take such action would reasonably be expected to be inconsistent with the duties of the directors of Tiptree under applicable law; provided, that in the event of any change to any of the material terms or conditions (including the form, amount and timing of payment of consideration) of the acquisition proposal described in the foregoing clause (A), Tiptree must, in each case, deliver to Purchaser an additional notice consistent with that described in clause (B) above and a new notice period under clause (C) will commence with respect to each such change in terms or conditions of the acquisition proposal (except that the five-business-day notice period will instead be equal to three business days).

Notwithstanding anything to the contrary contained in the Merger Agreement, Tiptree may, at any time prior to the time at which the Tiptree stockholder approval is obtained, make an adverse recommendation change, pursuant to clause (a) or (b) of the definition thereof if (A) an intervening event (as defined in this proxy statement) has occurred, (B) Tiptree has notified Purchaser in writing that the Tiptree Board intends to effect an adverse recommendation change, which notice will identify and include all material information with respect to such intervening event, (C) through the fifth business day following the date of such notice, Fortegra and Tiptree consider, negotiate and discuss with Purchaser in good faith (to the extent Purchaser so desires to negotiate) any amendments or modifications to the terms of the Merger Agreement proposed by Purchaser and (D) no earlier than the fifth business day following the date of such notice, the Tiptree Board determines, in good faith, after consultation with its financial advisors and outside legal counsel, taking into consideration the terms of any proposed amendment or modification to the Merger Agreement that Purchaser has committed to make during such five-business-day period, that the failure to effect an adverse recommendation change would reasonably be expected to be inconsistent with the duties of the directors of Tiptree under applicable law.

The respective obligations of each party to the Merger Agreement to consummate the transactions contemplated by the Merger Agreement are subject to the satisfaction or waiver at or prior to the closing of each of the following conditions, any one or more of which may be waived in writing at the option of the party whose obligations to consummate the transactions contemplated by the Merger Agreement are subject thereto to the extent permitted by applicable law: (i) the affirmative vote of the holders of a majority of the issued and outstanding shares of Fortegra common stock and Fortegra preferred stock (voting as a single class on an as-converted basis) (the “Fortegra stockholder approval”) having been obtained validly under the DGCL and Fortegra’s certificate of incorporation, bylaws and stockholders’ agreement, (ii) the Tiptree stockholder approval having been obtained validly under the laws of the State of Maryland and Tiptree’s charter and bylaws, (iii) that no temporary restraining order, preliminary or permanent injunction or other judgment or order, injunction, ruling, decision, assessment, award, administrative order, judicial decision or decree entered or issued by, or in agreement with, any governmental authority to which Fortegra or any of its Subsidiaries is a party or to which it is subject, issued by a court of competent jurisdiction that prevents the consummation of the transactions contemplated by the Merger Agreement has been issued and remains in effect, and no statute, rule, regulation or other law has been enacted, enforced or promulgated by any governmental authority which would restrain, enjoin or otherwise prohibit the consummation of the transactions contemplated by the Merger Agreement (the “No Injunctions or Legal Prohibitions Conditions”), (iv) the Regulatory Approvals Conditions, (v) the accuracy of the representations and warranties contained in the Merger Agreement (subject to specified materiality qualifiers), (vi) compliance with the covenants and obligations under the Merger Agreement in all material respects, (vii) the absence of a Material Adverse Effect (as defined in this proxy statement) with respect to Fortegra and its Subsidiaries, taken as a whole, (viii) the formation of Merger Sub and the continued effectiveness of the Merger Sub Joinder (as defined in this proxy statement), (ix) (1) the delivery of an officer’s certificate by Tiptree and Fortegra certifying to the satisfaction of the conditions set forth in clauses (v), (vi) and (vii) of this paragraph, and (2) the delivery of an officer’s certificate by Purchaser and Merger Sub certifying to the satisfaction

of the conditions set forth in clauses (v) and (vi) of this paragraph, and (x) Purchaser or Merger Sub having made the payments set forth in Section 3.04 of the Merger Agreement.

The Merger Agreement may be terminated and the transactions contemplated thereby may be abandoned at any time prior to the closing:

If the Merger Agreement is validly terminated by Purchaser, in connection with an adverse recommendation change (subject to the limitations set forth in the Merger Agreement) (or pursuant to any other termination right if Purchaser was then entitled to terminate the Merger Agreement in connection with an adverse recommendation change (subject to the limitations set forth in the Merger Agreement)), then Fortegra will pay the termination fee to Purchaser in immediately available funds within two business days after such valid termination; provided, that if the intervening event resulting in such termination relates to the “Tiptree Capital” business of Tiptree as described in Tiptree’s Annual Report on Form 10-K for the fiscal year ended December 31, 2024, then Tiptree will pay the termination fee; provided, further, that Fortegra will be jointly and severally liable for the payment of such termination fee to the extent not paid by Tiptree.

If the Merger Agreement is validly terminated by Tiptree, if at any time prior to the receipt of the Tiptree stockholder approval, in order to substantially concurrently enter into an agreement to effect a superior proposal in compliance with the applicable terms of the Merger Agreement (provided that Tiptree has complied in all material respects with its non-solicitation obligations under the Merger Agreement with respect to such superior proposal) then Fortegra will pay the termination fee to Purchaser in immediately available funds substantially concurrently with and as a condition to such valid termination; provided, that if the superior proposal resulting in such termination is a sale of capital stock of Tiptree (or a similar transaction) to a third party other than WP Investor or any of its affiliates, pursuant to which the equity interests of Fortegra held by WP Investor will continue to be held by WP Investor, then Tiptree will pay the termination fee; provided, further, that Fortegra will be jointly and severally liable for the payment of such termination fee to the extent not paid by Tiptree.

If (A) after the date of the Merger Agreement, an acquisition proposal has been publicly made to Tiptree or has been publicly made directly to the stockholders of Tiptree generally (and, in any such case, whether or not such acquisition proposal has been withdrawn), (B) thereafter, the Merger Agreement is validly terminated (1) by Purchaser or Fortegra at any time after the Termination Date, by giving written notice of such termination to the other party, if the closing has not occurred on or prior to such date (unless the failure to consummate the closing by such date is due to or has resulted from any breach of the representations or warranties made by, or the failure to perform

or comply with any of the agreements or covenants of the Merger Agreement to be performed or complied with prior to the closing by, the party seeking to terminate the Merger Agreement (or Tiptree, in the event Fortegra is seeking to terminate the Merger Agreement)); provided, that, if on a date that would have been the Termination Date, the Regulatory Approvals Conditions set forth in the Merger Agreement are the only conditions (other than those conditions that by their nature are to be satisfied at the closing) that have not been satisfied or waived on or before such date, the Termination Date will be automatically extended to December 26, 2026, in which case the Termination Date will be deemed for all purposes to be such later date, or (2) by either Fortegra or Purchaser, if at the special meeting (including any postponement or adjournment thereof) at which a vote on the approval of the Merger and the other transactions contemplated by the Merger Agreement was taken, the Tiptree stockholder approval is not obtained, or (3) by Purchaser, by written notice to Fortegra, if Fortegra or Tiptree has breached or failed to perform any of its covenants or other agreements set forth in the Merger Agreement or if any representation of Fortegra or Tiptree contained in the Merger Agreement is or has become inaccurate, in either case such that both (i) any condition to Purchaser’s obligations to effect the Merger pertaining to the accuracy of representations and warranties of Fortegra and Tiptree, Fortegra and Tiptree’s performance and compliance with the covenants in the Merger Agreement or Fortegra and Tiptree’s delivery of the required closing certificate would not be satisfied as of the time of such breach or failure or as of the time such representation was or has become inaccurate, and (ii) such breach or failure to perform or inaccuracy cannot be cured by Fortegra or Tiptree or, if capable of being cured, has not been cured within 30 calendar days after receipt by Fortegra of notice in writing from Purchaser specifying the nature of such breach and requesting that it be cured, provided that Purchaser will not have the right to terminate the Merger Agreement pursuant to this paragraph if it or Merger Sub is then in breach of any of their respective covenants or other agreements set forth in the Merger Agreement that would result in the condition to Fortegra’s and Tiptree’s obligations to effect the closing pertaining to the accuracy of representations and warranties of Purchaser and Merger Sub, or Purchaser and Merger Sub’s performance and compliance with the covenants in the Merger Agreement (other than those conditions which by their terms are to be satisfied at the closing, but subject to such conditions being capable of being satisfied at the closing) not being satisfied, and (C) within 12 months after such termination, Tiptree enters into a definitive agreement for any acquisition proposal or any acquisition proposal is consummated (regardless of when made or the counterparty thereto (unless such counterparty is an affiliate of Purchaser)), then Fortegra will pay to Purchaser the termination fee by wire transfer within two business days of the earlier of the date that Fortegra enters into such definitive agreement or the date on which such acquisition proposal is consummated; provided, that, if the superior proposal resulting in such termination is in respect of a sale of capital stock of Tiptree (or a similar transaction) to a third party other than WP Investor or any of its affiliates, pursuant to which the equity interests of Fortegra held by WP Investor will continue to be held by WP Investor, then Tiptree will pay the termination fee; provided, further, that Fortegra will be jointly and severally liable for the payment of such termination fee to the extent not paid by Tiptree. For purposes of this paragraph, all references to “15%” in the definition of “acquisition proposal” will be deemed to be references to “50%”.

If the Merger Agreement is validly terminated by Purchaser due to a failure to obtain the Tiptree stockholder approval at the special meeting (including any postponement or adjournment thereof) at which a vote on the Merger and the other transactions contemplated by the Merger Agreement was taken and the termination fee is not otherwise then payable pursuant to the terms of the Merger Agreement, then Tiptree is obligated to pay Purchaser the Stockholder Vote Failure Fee in immediately available funds within two business days after such valid termination.

In connection with the Merger Agreement, each of Michael G. Barnes, Jonathan Ilany and Arif Inayatullah (collectively, the “Tiptree Signing Stockholders”) entered into a voting and support agreement with Purchaser with respect to shares of Tiptree common stock beneficially owned now or in the future by such Tiptree Signing Stockholder (collectively, the “Tiptree Voting Agreements”).

The Tiptree Signing Stockholders owned, in the aggregate, approximately 37% of the outstanding shares of Tiptree common stock as of September 26, 2025, and each has separately agreed, pursuant to his respective Tiptree Voting Agreement, among other things, to vote all shares of Tiptree common stock beneficially owned and entitled to vote in favor of approval of the Merger Agreement and the Merger and the other transactions contemplated by the Merger Agreement.

Each Tiptree Voting Agreement will terminate upon the earliest to occur of certain specified events, including the obtainment of the Tiptree stockholder approval and an adverse recommendation change by the Tiptree Board.

See the section of this proxy statement entitled “The Merger Agreement—Tiptree Voting Agreements” beginning on page 112 for more information.

In connection with the Merger Agreement, each of Tiptree Holdings LLC (“Tiptree Holdings”) and the WP Investor (collectively, the “Fortegra Signing Stockholders”) entered into a voting and support agreement with Purchaser with respect to the Fortegra shares beneficially owned now or in the future by such Fortegra Signing Stockholder (collectively, the “Fortegra Voting Agreements”).

The Fortegra Signing Stockholders owned, in the aggregate, approximately 95% of the outstanding Fortegra Shares as of September 26, 2025, and each has separately agreed, pursuant to its respective Fortegra Voting Agreement, among other things, to vote all Fortegra shares owned and entitled to vote in favor of the approval of the Merger Agreement and the Merger and the other transactions contemplated by the Merger Agreement.

Each Fortegra Voting Agreement will terminate upon the earliest to occur of certain specified events, including delivery of the Fortegra stockholder approval and an adverse recommendation change by the Tiptree Board.

See the section of this proxy statement entitled “The Merger Agreement—Fortegra Voting Agreements” beginning on page 113 for more information.

In connection with the Merger Agreement, Tiptree, Fortegra and Purchaser entered into a restrictive covenant agreement (the “Tiptree Restrictive Covenant Agreement”) pursuant to which Tiptree is subject to certain restrictive covenants relating to non-solicitation for a five-year term with respect to certain Restricted Executives (as defined in this proxy statement) and a two-year term with respect to other employees of Fortegra or its Subsidiaries, non-disparagement for a period of two years following the closing and confidentiality.

See the section of this proxy statement entitled “The Merger Agreement—Tiptree Restrictive Covenant Agreement” beginning on page 114 for more information.