GTS Triple S Management Corporation

Projected Financial Information

Triple-S does not as a matter of course make public projections as to future performance or earnings and is especially wary of making projections for extended earnings periods given, among other reasons, the unpredictability and uncertainty of the underlying assumptions and estimates. However, Triple-S management prepared certain financial projections in connection with the Triple-S board of directors’ review of potential strategic alternatives to reflect Triple-S’s management’s then-current expectations of Triple-S’s financial performance for fiscal years 2021 through 2024 and certain financial metrics for 2025 (the “Projections”). The Projections were also provided to Triple-S’s financial advisor, Goldman Sachs, in connection with Triple-S’s strategic review process, and based on Triple-S management’s assessments as to the relative likelihood of achieving the financial results reflected in the Projections and such management’s judgment that the Projections best reflected the anticipated future financial performance of Triple-S, the Triple-S board of directors directed Goldman Sachs to utilize and rely upon the Projections for purposes of its financial analyses and opinion as described under “The Merger (Proposal 1)—Opinion of Triple-S’s Financial Advisor.”

We have included a summary of the Projections to give stockholders access to certain nonpublic information prepared by Triple-S management for the Triple-S board of directors in connection with Triple-S’s strategic review process, including the merger, and provided to Triple-S’s financial advisor in connection with such process. The inclusion of the Projections should not be regarded as an indication that Triple-S, Parent, Merger Sub or any of their respective affiliates, officers, directors, advisors or other representatives or any other recipient of this information considered, or now considers, it to be an assurance of the achievement of actual future results.

The Projections and the underlying assumptions upon which the Projections were based are subjective in many respects. The Projections reflect numerous estimates and assumptions with respect to industry performance, general business, economic, market and financial conditions, changes to the business, financial condition or results of operations of Triple-S and other matters, including those described under “Caution Regarding Forward-Looking Statements,” many of which are difficult to predict, subject to significant economic and competitive uncertainties, are beyond Triple-S’s control and may cause the Projections or the underlying assumptions not to be realized. Since the Projections cover multiple years, such information by its nature becomes less predictive with each successive year. The Projections do not take into account any circumstances or events occurring after the date they were prepared. As a result, there can be no assurance that the Projections will be realized or that actual results will not be significantly higher or lower than projected. The Projections were not prepared with a view toward public disclosure or toward complying with GAAP, the published guidelines of the SEC regarding projections or the guidelines established by the American Institute of Certified Public Accountants for preparation and presentation of prospective financial information. For example, certain metrics included in the Projections are non-GAAP measures, and the Projections do not include footnote disclosures as may be required by GAAP. Neither Triple-S’s independent auditors, nor any other independent accountants, have compiled, examined, or performed any procedures with respect to the prospective financial information contained herein, nor have they expressed any opinion or any other form of assurance on such information or its achievability, and assume no responsibility for, and disclaim any association with, the prospective financial information.

Adjusted EBITDA, adjusted EBITDA margin, adjusted net income, adjusted net income margin and adjusted net earnings per share (as defined below) contained in the management projections set forth below are non-GAAP financial measures, which are financial performance measures that are not calculated in accordance with GAAP. These non-GAAP financial measures should not be viewed as substitutes for GAAP financial measures and may be different from similarly titled non-GAAP financial measures used by other companies, which limits their usefulness as a comparative measure. Furthermore, there are limitations inherent in non-GAAP financial measures because they exclude charges and credits that are required to be included in a GAAP presentation. The items excluded from net income to common stockholders to arrive at

these non-GAAP financial measures are significant components for understanding and assessing the Company’s financial performance and liquidity. Accordingly, these non-GAAP financial measures should be considered together with, and not as an alternative to, financial measures prepared in accordance with GAAP.

Financial measures used by a financial advisor are excluded from the definition of non-GAAP financial measures under SEC rules and, therefore, are not subject to SEC rules regarding disclosures of non-GAAP financial measures, which would otherwise require a reconciliation of a non-GAAP financial measure to a GAAP financial measure. A reconciliation of the non-GAAP financial measures was not relied upon by Goldman Sachs for purposes of its financial analysis as described above in “The Merger—Opinion of Triple-S’s Financial Advisor” or the Board in connection with its consideration of the Merger. Accordingly, we have not provided a reconciliation of the non-GAAP financial measure included in the management projections to the most directly comparable GAAP financial measure.

Readers of this proxy statement are cautioned not to place undue reliance on the specific portions of the Projections below. No one has made or makes any representation to any stockholder regarding the information included in the Projections.

For the foregoing reasons, as well as the basis and assumptions on which the Projections were compiled, the inclusion of specific portions of the Projections in this proxy statement should not be regarded as necessarily predictive of actual future events, and they should not be relied on as such. Except as required by applicable securities laws, Triple-S does not intend to update or otherwise revise the Projections or the specific portions presented to reflect circumstances existing after the date on which they were prepared or to reflect the occurrence of future events, even in the event that any or all of the assumptions are shown not to be appropriate.

In preparing the Projections, Triple-S management made the following material assumptions:

¹ Adjusted EBITDA includes stock-based compensation expense of $10 million in 2021E through 2024E.

For purposes of Goldman Sachs’ illustrative discounted cash flow analysis, 2025E Total Revenue is $5.06 billion, Adjusted EBITDA is $314 million, which includes stock-based compensation expense of $10 million, and Unlevered Free Cash Flow is $141 million.

Interests of Triple-S’s Directors and Executive Officers in the Merger

In considering the recommendation of the Triple-S board of directors to approve the merger proposal, you should be aware that some of Triple-S’s directors and executive officers have interests in the merger that are different from, or in addition to, those of Triple-S’s stockholders generally. The Triple-S board of directors was aware of these interests and considered them, among other matters, in evaluating the merger agreement, in reaching its decision to approve the merger agreement and in recommending to our stockholders that the merger agreement be approved. These interests are described and quantified below.

Certain Assumptions

Except as otherwise specifically noted, for purposes of quantifying the potential payments and benefits described in this section, the following assumptions were used:

As the amounts provided below are estimates based on multiple assumptions that may or may not actually occur or be accurate as of the date referenced, the actual amounts, if any, that may be paid or become payable may materially differ from the amounts set forth below.

Treatment and Quantification of Equity-Based Awards

Triple-S’s executive officers currently hold vested and unvested Triple-S restricted share awards, Triple-S restricted stock units and Triple-S performance share units. Triple-S’s directors currently hold vested and unvested Triple-S restricted stock units.

The merger agreement provides that, prior to the effective time of the merger, the Triple-S board of directors shall adopt resolutions to effect the following treatment of the equity awards of Triple-S:

Each award of (or with respect to) Triple-S common stock that is outstanding as of the date of the merger agreement and immediately prior to the effective time of the merger shall, at the effective time of the merger:

underlying the Triple-S restricted stock unit award as of immediately prior to the effective time of the merger; and

Each award of (or with respect to) Triple-S common stock with respect to any restricted stock unit or performance share unit that is granted following the date of the merger agreement and outstanding immediately prior to the effective time of the merger, at the effective time of the merger, shall be canceled and converted into the right to receive an amount in cash equal to the product of the merger consideration and the number of shares of Triple-S common stock underlying such award as of immediately prior to the effective time (determined, in the case of performance share units, based on target performance), payable on the date the award would have otherwise vested pursuant to its vesting schedule, subject to the holder’s continuing employment as of each such vesting date or as otherwise provided in the applicable award agreements.

See the section entitled “Golden Parachute Compensation” beginning on page [●] of this proxy statement for an estimate of the amounts that would become payable to each Triple-S named executive officer in respect of his or her unvested Triple-S restricted share awards, Triple-S restricted stock unit awards and Triple-S performance share unit awards. Based on the assumptions described above under “Interests of Triple-S’s Directors and Executive Officers in the Merger —Certain Assumptions,” the estimated aggregate amounts that would become payable to Triple-S’s seven (7) executive officers who are not named executive officers (Ivelisse M. Fernández-Cruz, Victor Haddock, Pedro Aponte Gil De Lamadrid, José M. Del Amo Mojica, Carlos L. Rodriguez-Ramos, Juan R. Serrano and Ilia S. Rodriguez-Torres) and the eight (8) members of Triple-S’s board of directors (David H. Chafey, Jr., Manuel Figueroa-Collazo, Cari M. Dominguez, Roberta Herman, Gail B. Marcus, Stephen L. Ondra, Luis A. Clavell-Rodriguez and Roberto Santa Maria) in respect of their unvested Triple-S restricted share awards, Triple-S restricted stock units and Triple-S performance share unit awards are $8,314,092 and $1,277,280, respectively.

Employment Agreements / Severance Arrangements / Retention Arrangements

Employment Agreements

Triple-S does not maintain employment agreements with any of its named executive officers except Roberto García-Rodríguez, its chief executive officer.

Triple-S intends to enter into an employment agreement, as amended, with Mr. García-Rodríguez (the “CEO Employment Agreement”). The CEO Employment Agreement will provide that the chief executive officer will be eligible to receive the following severance benefits upon a termination of employment by Triple-S without Cause (as defined below), or a resignation by the executive officer for Good Reason (as defined below), in either case, in connection with a change in control during the term of his contract:

For purposes of the CEO Employment Agreement:

“Cause” means any of the following: (a) a material breach of the chief executive officer’s obligations and duties as specified in the CEO Employment Agreement; (b) a conviction or allegation of nolo contendere of any felony or certain misdemeanors; (c) his insubordination; (d) his material non-compliance of the CEO Employment Agreement or the rules, regulations, guidelines, policies or code of ethics of Triple-S; (e) his improper or disorderly conduct; or (f) the existence of a conflict of interest not previously disclosed to Triple-S’s board of directors.

“Good Reason” means any of the following: (a) a change in the nature or scope of the chief executive officer’s duties or functions from those performed on the date immediately preceding a change in control of Triple-S; (b) a reduction in the chief executive officer’s base salary from that received on the date immediately preceding a change in control of Triple-S; (c) a reduction in the chief executive officer’s ability to participate in the compensation plans in which he participated on the date immediately preceding a change in control of Triple-S, as determined in comparison to the opportunities that Triple-S provides to executives with comparable duties or the opportunities of participation that the chief executive officer had under such plans immediate preceding such change in control; (d) a change in the location of the chief executive officer’s principal place of employment of more than twenty-five (25) miles from the place where he maintained his work office on the date immediately preceding a change in control of Triple-S; or (e) the reasonable determination by Triple-S’s board of directors to the effect that, because of a change in control of Triple-S and a change in the circumstances thereafter affecting the employment position of the chief executive officer, he is unable to exercise the authority, powers, functions or duties assigned to his position in Triple-S on the date immediately preceding the date of the change of control.

Severance Arrangements

In connection with the merger, Triple-S intends to establish a severance program under which any executive officer (other than Triple-S’s chief executive officer) whose employment is terminated (i) due to job elimination, corporate reorganization, reduction in force or similar reason and not for Cause (as defined below) or (ii) by the executive for Good Reason (as defined below), in each case on or after the consummation of the transaction and prior to the twenty-four (24) month anniversary of the consummation of the merger, subject to execution and non-revocation of a general release of claims, receives severance (in all cases, reduced by any statutory severance to which the employee is entitled) in an amount equal to the sum of two (2) times the executive officer’s base salary and one times his or her target short-term incentive opportunity.

Retention Arrangements

In connection with the merger, Triple-S intends to establish a cash retention program under which it will grant retention bonuses to each executive officer (other than Triple-S’s chief executive officer, president of Triple-S Vida, Inc. and executive officers who are not named executive officers) in an amount between a minimum of $200,000 and a maximum equal to the sum of two (2) times the executive officer’s base salary and one times his or her target short-term incentive opportunity, subject to the executive officer’s continued employment through the applicable payment date (unless an executive officer’s employment is terminated (i) due to job elimination, corporate reorganization, reduction in force or similar reason and not for Cause (as defined below) or (ii) by the executive officer for Good Reason (as defined below), subject to the executive officer’s execution and non-revocation of a general release of claims), in each case, payable 40% and 60% on the twelve (12) month and the twenty-four (24) month anniversaries of the consummation of the merger, respectively. Triple-S’s chief executive officer is not eligible for any retention bonus, and the president of Triple-S Vida, Inc. is eligible for a retention bonus in the amount of $200,000, subject to the continued employment terms described above.

If an executive officer experiences a termination of employment that triggers payments under both the severance arrangements and retention arrangements, then the sum of (a) their payments under the severance arrangements, (b) their payments under the retention arrangements and (c) any statutory severance they are entitled to will be capped at two (2) times the sum of their (A) base salary and (B) target short-term incentive opportunity.

For purposes of the severance arrangements and retention arrangements:

“Cause” shall mean the definition of “Cause” (or words of similar import) set forth in any individual agreement with the applicable executive or, if there is no such agreement or such term is not defined therein, the executive’s: (a) misuse of trade secrets or other confidential or proprietary information; (b) conviction of or plea of nolo contendere to fraud, embezzlement, a felony or equivalent crime, or any other crime involving moral turpitude; (c) committing an act of fraud or embezzlement against Triple-S; (d) gross negligence or willful misconduct in the performance of, or willful failure to perform, his or her duties; (e) failure to comply with Triple-S’s written policies or rules, which failure causes, or could cause, material harm to Triple-S; or (f) “just cause” as provided under Puerto Rico’s Wrongful Discharge Act (Law 80) (other than due to job elimination, corporate reorganization, reduction in force or similar reason)’ provided that, if an executive is offered a different position by Parent or its applicable affiliate in connection with the consummation of the merger, and such executive’s employment terminates due to such employee’s refusal to accept such offer, such termination shall not constitute a termination for Cause.

“Good Reason” shall mean, without the executive’s written consent: (a) a reduction in base salary or target incentive opportunity, (b) relocation outside of Puerto Rico or (c) a material and significant reduction in duties or responsibilities; provided that, Good Reason shall not be triggered solely as a result of Triple-S becoming a wholly owned subsidiary of Parent as a result of the consummation of the merger; and provided further that, in order for an executive to claim Good Reason, (i) the executive must give written notice to Parent or its applicable affiliate of Good Reason within thirty (30) days after becoming aware of the condition giving rise to Good Reason, (ii) Parent or its applicable affiliate must not cure the condition giving rise to Good Reason within 30 days after receiving written notice of such condition from the executive and (iii) the executive must resign within thirty (30) days following the end of the cure period.

See “Interests of Triple-S’s Directors and Executive Officers in the Merger —Golden Parachute Compensation” beginning on page [●] of this proxy statement for the estimated amounts that each of Triple-S’s named executive officers would receive either under an employment agreement or in connection with the severance arrangements and retention arrangements, as applicable, upon a qualifying termination of employment. Based on the assumptions described above under “Interests of Triple-S’s Directors and Executive Officers in the Merger —Certain Assumptions,” the estimated aggregate amounts of the payments (excluding amounts payable in respect of unvested Triple-S restricted share awards, unvested Triple-S restricted stock unit awards and Triple-S performance share unit awards, which are discussed and quantified above under the section entitled “Treatment and Quantification of Triple-S Equity Awards”) to be provided to Triple-S’s seven (7) executive officers who are not named executive officers under the severance arrangements and retention arrangements upon a qualifying termination of employment are $5,973,470 and $4,792,850, respectively.

Golden Parachute Compensation

In accordance with Item 402(t) of Regulation S-K under the Securities Act, the table below sets forth the compensation that is based on, or otherwise relates to, the merger that will or may become payable to each named executive officer of Triple-S in connection with the merger. For additional details regarding the terms of the payments and benefits described below, see the discussion under the heading “Interests of Triple-S Directors and Executive Officers in the Merger” above, which is incorporated herein.

The amounts shown in the table below are estimates based on multiple assumptions that may or may not actually occur or be accurate on the relevant date, including the assumptions described above under “Interests of Triple-S’s Directors and Executive Officers in the Merger —Certain Assumptions” and in the footnotes to the table below, and do not reflect certain compensation actions that may occur prior to completion of the merger that are unrelated to the merger, including any ordinary course equity award grants that may be made after the assumed effective date of February 28, 2021.

Triple-S’s stockholders are being asked to approve, on a non-binding, advisory basis, the compensation that will or may be paid by Triple-S to these named executive officers that is based on or otherwise relates to the merger (see the section entitled “Advisory Vote on Named Executive Officer Merger-Related Compensation Arrangements (Proposal 2)” beginning on page [●] of this proxy statement). Because the vote to approve such compensation is advisory only, it will not be binding on either Triple-S or Parent. Accordingly, if the merger is approved by Triple-S’s stockholders and the merger is completed, the compensation will be payable regardless of the outcome of the advisory vote to approve such compensation, subject only to the conditions applicable to the vote to approve the merger, which are described in the footnotes to the table and above under the section entitled “The Merger (Proposal 1)—Interests of Triple-S’s Directors and Executive Officers in the Merger” beginning on page [●] of this proxy statement.

Directors’ and Officers’ Indemnification and Insurance

For information regarding indemnification of Triple-S’s directors and executive officers, see the section entitled “The Merger Agreement—Directors’ and Officers’ Indemnification and Insurance” beginning on page [●] of this proxy statement.

Regulatory Approvals Required for the Merger

The completion of the merger is conditioned on, among other things, certain specified regulatory approvals having been obtained and remaining in full force and effect (or, in the case of certain specified regulatory approvals that are statutory waiting periods, having expired or been terminated), including the expiration or termination of any applicable waiting period under the HSR Act. In addition, prior to the effective time of the merger, Triple-S and Parent are required to obtain regulatory approvals from the Office of the Commissioner of Insurance of Puerto Rico, the Office of Industrial Tax Exemption of Puerto Rico, the Puerto Rico Health Insurance Administration, the BVI Financial Services Commission and the Anguilla Financial Services Commission. Under the terms of the merger agreement, each of Triple-S and Parent have agreed to use their respective reasonable best efforts to take, or cause to be taken, all actions and to do, or cause to be done, all things necessary, proper or advisable under applicable law to consummate the transactions contemplated by the merger agreement as promptly as reasonably practicable, including preparing and filing as promptly as practicable with any government authority or other third party all documentation to effect all necessary filings and obtaining certain specified regulatory approvals, subject to certain limitations set forth in the merger agreement.

See the section entitled “The Merger Agreement—Regulatory Approvals Required for the Merger” beginning on page [●] of this proxy statement for a more detailed discussion of the parties’ obligations with respect to obtaining regulatory approvals in connection with the merger.

Accounting Treatment

The merger will be accounted for as a “purchase transaction” for financial accounting purposes.

Material U.S. Federal Income Tax Consequences of the Merger

The exchange of Triple-S common stock for cash in the merger will be a taxable transaction for U.S. federal income tax purposes and may also be taxable under state and local and other tax laws. In general, a “U.S. holder” (as defined in the section entitled “Material U.S. Federal Income Tax Consequences of the Merger” beginning on page [●] of this proxy statement) whose shares of Triple-S common stock are converted into the right to receive cash in the merger will recognize capital gain or loss for U.S. federal income tax purposes in an amount equal to the difference, if any, between the amount of cash received with respect to such shares and the U.S. holder’s adjusted tax basis in such shares. With respect to a stockholder that is a “non-U.S. holder” (as defined in the section entitled “Material U.S. Federal Income Tax Consequences of the Merger” beginning on page [●] of this proxy statement), the exchange of shares of Triple-S common stock for the merger consideration pursuant to the merger generally will not result in U.S. federal income tax to such non-U.S. holder unless such non-U.S. holder has certain connections with the United States. Backup withholding may apply to the cash payment made pursuant to the merger unless the stockholder or other payee provides a valid taxpayer identification number and complies with certain certification procedures (generally, by providing a properly completed and executed U.S. Internal Revenue Service (“IRS”) Form W-9 or IRS Form W-8 or applicable successor form).

You should read the section entitled “Material U.S. Federal Income Tax Consequences of the Merger” beginning on page [●] of this proxy statement and consult your tax advisors regarding the U.S. federal income tax consequences of the merger to you in your particular circumstances, as well as tax consequences arising under the laws of any state, local or foreign taxing jurisdiction.

Material Puerto Rico Income Tax Consequences of the Merger  

The exchange of Triple-S common stock for cash in the merger will be a taxable transaction for Puerto Rico income tax purposes. Accordingly, a stockholder that is a “P.R. holder” (as defined in the section entitled “Material Puerto Rico Income Tax Consequences of the Merger” beginning on page [●] of this proxy statement) will generally recognize taxable gain or loss in an amount equal to the difference, if any, between (i) the merger consideration received by such P.R. holder in the merger and (ii) such P.R. holder’s adjusted tax basis in the shares of Triple-S common stock exchanged therefor. With respect to a stockholder that is a “non-P.R. holder” (as defined in the section entitled “Material Puerto Rico Income Tax Consequences of the Merger” beginning on page [●] of this proxy statement), the exchange of shares of Triple-S common stock for the merger consideration pursuant to the merger generally will not result in Puerto Rico income tax to such non-P.R. holder unless such non-P.R. holder has certain connections with Puerto Rico which can make the gain effectively connected income to a Puerto Rico trade or business.

You should read the section entitled “Material Puerto Rico Income Tax Consequences of the Merger” beginning on page [●] of this proxy statement and consult your tax advisors regarding the Puerto Rico income tax consequences of the merger to you in your particular circumstances, as well as tax consequences arising under the laws of any non-Puerto Rico jurisdiction.

Delisting and Deregistration of Triple-S Common Stock  

Upon completion of the merger, the Triple-S common stock currently listed on the NYSE will cease to be listed on the NYSE and will subsequently be deregistered under the Exchange Act.

Appraisal Rights

Under Puerto Rico law, any record holder of Triple-S common stock at the close of business on the record date who does not vote in favor of the merger proposal, and who exercises its appraisal rights and fully complies with all of the provisions of Article 10.13 of Puerto Rico law (but not otherwise), will be entitled to demand and receive payment of the “fair value” as determined pursuant to Article 10.13 of Puerto Rico law for all (but not less than all) of his or her shares of Triple-S common stock if the merger is completed. See the section entitled “Appraisal Rights of Stockholders” beginning on page [●] of this proxy statement. The full text of Article 10.13 of Puerto Rico law is attached to this proxy statement (in English and Spanish) as Annex C.

Litigation Related to the Merger

As of the date of this proxy statement, there are no pending lawsuits challenging the merger. However, potential plaintiffs may file lawsuits challenging the merger. The outcome of any future litigation is uncertain.

Such litigation, if not resolved, could prevent or delay consummation of the merger and result in substantial costs to Triple-S, including any costs associated with the indemnification of directors and officers. One of the conditions to the consummation of the merger is that no applicable law or order issued by a court of competent jurisdiction or other legal restraint which is then in effect renders illegal or enjoins the consummation of the merger whether on a preliminary or permanent basis. Therefore, if a plaintiff were successful in obtaining an injunction prohibiting the consummation of the merger on the agreed-upon terms, then such injunction may prevent the merger from being consummated, or from being consummated within the expected time frame.

THE MERGER AGREEMENT

The following is a summary of the material terms and conditions of the merger agreement. This summary does not purport to be complete and may not contain all of the information about the merger agreement that is important to you. This summary is qualified in its entirety by reference to the complete text of the Agreement and Plan of Merger, dated as of August 23, 2021, a copy of which is attached to this proxy statement as Annex A, and which is incorporated by reference into this proxy statement. We encourage you to read the merger agreement carefully and in its entirety because it is the legal document that governs the merger.

Explanatory Note Regarding the Merger Agreement

The following summary of the Agreement and Plan of Merger, dated as of August 23, 2021, a copy of which is attached hereto as Annex A to this proxy statement, is intended to provide information regarding the terms of the merger agreement and is not intended to modify or supplement any factual disclosures about Triple-S in its public reports filed with the SEC. In particular, the merger agreement and the related summary are not intended to be, and should not be relied upon as, disclosures regarding any facts and circumstances relating to Triple-S or any of its subsidiaries or affiliates. The merger agreement contains representations and warranties by Triple-S, Parent and Merger Sub which were made only for purposes of that agreement and as of specified dates. The representations, warranties and covenants in the merger agreement were made solely for the benefit of the parties to the merger agreement; may be subject to limitations agreed upon by the contracting parties, including being qualified by the disclosure letters to the merger agreement; were made for the purposes of allocating contractual risk between the parties to the merger agreement instead of establishing these matters as facts; and may apply contractual standards of materiality or material adverse effect that generally differ from those applicable to investors. In addition, information concerning the subject matter of the representations, warranties and covenants may change after the date of the merger agreement, which subsequent information may or may not be fully reflected in Triple-S’s public disclosures.

Additional information about Triple-S may be found elsewhere in this proxy statement and Triple-S’s other public filings. See the section entitled “Where You Can Find More Information,” beginning on page [●] of this proxy statement.

Structure of the Merger

At the effective time of the merger, Merger Sub will be merged with and into Triple-S in accordance with Puerto Rico law and Delaware law. As a result of the merger, the separate corporate existence of Merger Sub will cease and Triple-S will continue as the surviving corporation. At the effective time of the merger, the articles of incorporation of Triple-S (the “Triple-S articles”), as in effect immediately prior to the effective time, will be the articles of incorporation of the surviving corporation, until thereafter amended in accordance with applicable law. The bylaws of Triple-S (the “Triple-S bylaws”), as in effect immediately prior to the effective time, will be the bylaws of the surviving corporation, until thereafter amended in accordance with applicable law. From and after the effective time of the merger, until successors are duly elected or appointed and qualified in accordance with applicable law, the directors of Merger Sub immediately prior to the effective time of the merger will be the directors of the surviving corporation and the officers of Triple-S immediately prior to the effective time of the merger will be the officers of the surviving corporation.

Closing and Effective Time of the Merger

Unless another time, date or place is mutually agreed in writing by Triple-S and Parent, the closing of the merger will take place as soon as possible, but in any event no later than three (3) business days after the date the closing conditions set forth in the merger agreement and described in the section entitled “The Merger Agreement—Conditions to Completion of the Merger” beginning on page [●] of this proxy statement (other than conditions that by their nature are to be satisfied at the closing, but subject to the satisfaction or, to the extent permissible, waiver of those conditions) have been satisfied or, to the extent permissible, waived by the party or parties entitled to the benefit of such conditions. The merger will become effective at such time as the certificate of merger is duly filed with the Secretary of State of the Commonwealth of Puerto Rico or at such later time as Triple-S and Parent shall agree and specify in the certificate of merger. As of the date of this proxy statement, we expect to complete the merger in the first half of 2022. However, completion of the merger is subject to the satisfaction or waiver of the conditions to the completion of the merger, which are described below, and it is possible that factors outside the control of Triple-S or Parent could delay the completion of the merger, or prevent it from being completed at all. There may be a

substantial amount of time between the special meeting and the completion of the merger. We expect to complete the merger promptly following the receipt of all required approvals.

Effect of the Merger on Triple-S Common Stock

At the effective time of the merger, each share of Triple-S common stock issued and outstanding immediately prior to the effective time of the merger (other than (i) shares owned by Triple-S (as treasury stock), Parent or Merger Sub; (ii) shares owned by any stockholder who has properly demanded appraisal rights in accordance with Puerto Rico law; and (iii) restricted share awards) will be converted into the right to receive $36.00 in cash, without interest and less any applicable withholding taxes (the “merger consideration”). As of the effective time of the merger, all such shares of Triple-S common stock will no longer be outstanding and will automatically be canceled and retired and cease to exist, and will thereafter represent only the right to receive the merger consideration to be paid in accordance with the terms of the merger agreement.

At the effective time of the merger, each share of Triple-S common stock held by Triple-S (as treasury stock) or owned by Parent or Merger Sub will be canceled without payment of any consideration. In addition, shares of Triple-S common stock issued and outstanding immediately prior to effective time of the merger and held by a stockholder who has not voted in favor of the merger or consented thereto in writing and who has properly demanded appraisal for such shares in accordance with Puerto Rico law will not be converted into the right to receive the merger consideration, unless and until such holder fails to perfect, withdraws or otherwise loses the right to appraisal. If any holder of Triple-S common stock that demands appraisal rights properly perfects such rights, such holder will be entitled to the fair value of such shares as determined by the Court of First Instance of the Commonwealth of Puerto Rico, Superior Court, plus interest, if any, on the amount determined to be the fair value, as further described in the section entitled “Appraisal Rights of Stockholders” beginning on page [●] of this proxy statement.

Each share of common stock of Merger Sub outstanding immediately prior to the effective time of the merger will be converted into one share of common stock of the surviving corporation.

Procedures for Surrendering Shares for Payment

Prior to the effective time of the merger, Parent will appoint an paying agent reasonably acceptable to Triple-S for the purpose of exchanging for the merger consideration certificates representing shares of Triple-S common stock or uncertificated shares of Triple-S common stock. As promptly as practicable after the effective time of the merger, Parent will make available to the paying agent the aggregate merger consideration to be paid in respect of the certificates representing shares of Triple-S common stock or uncertificated shares of Triple-S common stock.

As promptly after the effective time of the merger (but no later than five (5) business days thereafter), the paying agent will send to each holder of shares of Triple-S common stock at the effective time of the merger a letter of transmittal and instructions (which will specify that the delivery will be effected, and risk of loss and title will pass, only upon proper delivery of certificates representing shares of Triple-S common stock or transfer of uncertificated shares of Triple-S common stock to the paying agent) for use in such exchange.

Each holder of shares of Triple-S common stock that have been converted into the right to receive the merger consideration will be entitled to receive, upon (i) surrender to the paying agent of a certificate, together with a properly completed letter of transmittal, or (ii) receipt of an “agent’s message” by the paying agent (or such other evidence, if any, of transfer as the paying agent may reasonably request) in the case of a book-entry transfer of uncertificated shares, in each case (i) or (ii), the merger consideration in respect of Triple-S common stock represented by a certificate or uncertificated share. Until so surrendered or transferred, as the case may be, each such certificate or uncertificated share will represent after the effective time of the merger for all purposes only the right to receive such merger consideration.

If any portion of the merger consideration is to be paid to a person other than the person in whose name the surrendered certificate or the transferred uncertificated share is registered, it will be a condition to such payment that (i) either such certificate be properly endorsed or otherwise be in proper form for transfer or such uncertificated share be properly transferred and (ii) the person requesting such payment must pay to the paying agent any transfer or other taxes required as a result of such payment or establish to the satisfaction of the paying agent that such tax has been paid or is not payable.

After the effective time of the merger, there will be no further registration of transfers of shares of Triple-S common stock. If, after the effective time of the merger, certificates representing shares of Triple-S common stock or uncertificated shares of Triple-S common stock are presented to the surviving corporation or the paying agent, they will be canceled and exchanged for the merger consideration.

Any portion of the merger consideration made available to the paying agent for payment to the stockholders that remains unclaimed by the holders of Triple-S common stock one year after the effective time of the merger will be returned to Parent, upon demand, and any such holder who has not exchanged shares of Triple-S common stock will thereafter look only to Parent for payment of the merger consideration in respect of such shares without any interest thereon.

If any certificate or uncertificated share has not been surrendered prior to the 24-month anniversary of the effective time of the merger (or, if earlier, immediately prior to the date on which the merger consideration in respect of such certificate or uncertificated share would otherwise escheat to or become the property of any governmental entity), any such merger consideration in respect of such certificate or uncertificated share shall, to the extent permitted by applicable law, become the property of the surviving corporation, free and clear of all claims or interest of any person previously entitled thereto.

Withholding

Each of the surviving corporation, Merger Sub, Parent and the paying agent will be entitled to deduct and withhold from the consideration otherwise payable pursuant to the merger agreement such amounts as may be required to be deducted and withheld with respect to the making of such payment under any applicable tax law. Amounts so withheld and paid over to the appropriate taxing authority will be treated for all purposes of the merger agreement as having been paid to the person in respect of which such deduction or withholding was made.

Treatment of Triple-S Equity Awards

The merger agreement provides that, prior to the effective time of the merger, the Triple-S board of directors shall adopt resolutions to effect the following treatment of the equity awards of Triple-S:

Each award of (or with respect to) Triple-S common stock that is outstanding as of the date of the merger agreement and immediately prior to the effective time of the merger shall, at the effective time of the merger:

Each award of (or with respect to) Triple-S common stock with respect to any restricted stock unit or performance share unit that is granted following the date of the merger agreement and outstanding immediately prior to the effective time of the merger, at the effective time of the merger, shall be canceled and converted into the right to receive an amount in cash equal to the product of the merger consideration and the number of shares of Triple-S common stock underlying such award as of immediately prior to the effective time (determined, in the case of performance share units, based on target performance), payable on the date the award would have otherwise vested pursuant to its vesting schedule, subject to the holder’s continuing employment as of each such vesting date or as otherwise provided in the applicable award agreements.

Representations and Warranties

Triple-S’s representations and warranties to Parent in the merger agreement relate to, among other things:

Parent’s representations and warranties to Triple-S in the merger agreement relate to, among other things:

None of the representations and warranties in the merger agreement survive the effective time of the merger.

Definition of  “Company Material Adverse Effect”

Many of Triple-S’s representations and warranties in the merger agreement are qualified by a “company material adverse effect” standard (that is, they will not be deemed to be untrue or incorrect unless their failure to be true or correct has had or would reasonably be expected to have, individually or in the aggregate, a company material adverse effect). For purposes of the merger agreement, a “company material adverse effect” means any change, event, effect, fact, circumstance, development or occurrence that, individually or in the aggregate with other changes, events, effects, facts, circumstances, developments or occurrences, has a material adverse effect on the business, properties, assets, financial condition, financial performance or results of operations of Triple-S and its subsidiaries, taken as a whole; provided, however, that none of the following, nor any change, event, effect, fact, circumstance development or occurrence to the extent or arising out of or relating to the following, shall be deemed either alone or in combination to constitute or be taken into account in determining whether a “company material adverse effect” has occurred or may, would or could occur:

The exclusions set forth in the first, second, third, fourth and fifth bullets above shall only be applicable to the extent they do not have a disproportionate impact on Triple-S and its subsidiaries, taken as a whole, relative to other similarly sized participants in the health care services or insurance industries in the geographic regions or product markets in which Triple-S and its subsidiaries operate.

Certain of Parent’s representations and warranties in the merger agreement are qualified by a “parent material adverse effect” standard (that is, they will not be deemed to be untrue or incorrect unless their failure to be true or correct has had or would reasonably be expected to have, individually or in the aggregate, a parent material adverse effect). For purposes of the merger agreement, a “parent material adverse effect” means any change, effect, event, circumstance, fact, development or occurrence that prevents or materially impairs or delays the consummation of the merger and the other transactions contemplated by the merger agreement or the ability of Parent or Merger Sub to perform its obligations under the merger agreement.

Conduct of the Business Pending the Merger

Triple-S has agreed to certain covenants in the merger agreement restricting the conduct of its business between the date of the merger agreement and the effective time of the merger. In general, except as set forth on the disclosure letters to the merger agreement, as expressly contemplated by the merger agreement, as required by applicable law (including COVID-19 measures), or with the prior written consent of Parent (which shall not be unreasonably withheld, conditioned or delayed), from the date of the merger agreement to the effective time, Triple-S will, and will cause each of its subsidiaries to, conduct its business in the ordinary course of business consistent with past practice and use reasonable best efforts to preserve its present organization, assets, employees, authorizations, contractors and relationships with customers, distributors, strategic partners, governmental entities, licensors, licensees and others that, in each case, have material business dealings with it.

In addition, without limiting the generality of the foregoing, except as set forth on the disclosure letters to the merger agreement, as expressly contemplated by the merger agreement, as required by applicable law (including COVID-19 measures), or with the prior written consent of Parent (which shall not be unreasonably withheld, conditioned or delayed), Triple-S will not, and will not permit any of its subsidiaries to:

stock to satisfy tax obligations with respect to the vesting, exercise or settlement of Triple-S restricted share awards, restricted stock unit awards or performance share unit awards outstanding as of the date of the merger agreement (or issued after the date of the merger agreement in accordance with the terms of the merger agreement) in accordance with their respective terms in effect at such time, (B) the acquisition by Triple-S of Triple-S restricted share awards, restricted stock unit awards or performance share unit awards in connection with the forfeiture of such awards in accordance with their respective terms in effect at such time or (C) redemptions, repurchases or acquisitions of the capital stock or other equity interests of a subsidiary of Triple-S, in connection with transactions exclusively among Triple-S and any of its subsidiaries or exclusively among Triple-S’s subsidiaries;

casualty insurance claims as of June 30, 2021 or (B) would obligate Triple-S or any of its subsidiaries to take any material action or impose any material restrictions on the business of the Triple-S or any of its subsidiaries or (ii) commence any comparable proceeding against a third party other than any such proceeding commenced in the ordinary course of business consistent with past practice where the total amount of damages sought does not equal or exceed $500,000;

Board Obligation to Call a Stockholders Meeting

Triple-S has agreed under the merger agreement to take all necessary actions in accordance with applicable law, the Triple-S articles and the Triple-S bylaws, and the rules and regulations of NYSE to duly call, give notice of, convene and hold a stockholders meeting for the purpose of obtaining the stockholder approval as soon as reasonably practicable after the SEC confirms that it will not review or that it has no further comments on this proxy statement, including establishing a record date for such stockholders meeting promptly after the date on which the SEC confirms that it will not review or that it has no further comments on this proxy statement and duly convening and holding the stockholders meeting no later than 45 days after the record date. Unless the Triple-S board has made an adverse recommendation change in

accordance with the merger agreement, Triple-S will use reasonable best efforts to solicit and obtain stockholder approval, including engaging a proxy solicitation firm for the purpose of assisting in the solicitation of proxies for the stockholders meeting. Triple-S may, after consultation with Parent, adjourn, recess or postpone the stockholders meeting only (i) to the extent required by applicable law to ensure that any required supplement or amendment to this proxy statement is provided to the stockholders of Triple-S within a reasonable amount of time in advance of the stockholders meeting, (ii) to the extent required by a court of competent jurisdiction in connection with any proceedings in connection with the merger agreement or the transactions contemplated by the merger agreement, (iii) if, as of the time for which the stockholders meeting is originally scheduled (as set forth in this proxy statement), there are insufficient shares of Triple-S common stock represented (either in person or by proxy) to constitute a quorum necessary to conduct the business of the stockholders meeting or Parent reasonably believes that Triple-S will not receive proxies sufficient to obtain stockholder approvals, whether or not a quorum is present, or (iv) the Triple-S board or any committee thereof determines in good faith (after consultation with its outside counsel) that the failure to adjourn, recess or postpone the stockholders meeting would violate the directors’ fiduciary duties under applicable law. Notwithstanding the foregoing, Triple-S will not adjourn, recess or postpone the stockholders meeting to a date that is (x) more than 30 days after the date on which the stockholders meeting was originally scheduled or (y) less than five business days prior to the outside date, in the case of each of (x) and (y) without the prior written consent of Parent. Unless the Triple-S board has made an adverse recommendation change in accordance with the merger agreement, Triple-S will keep Parent updated with respect to proxy solicitation results as reasonably requested by Parent.

Restrictions on Solicitation of Company Takeover Proposals

Triple-S has agreed that it will not, and will cause its subsidiaries and all of its and their respective directors, officers, employees, financial advisors, legal counsel, accountants and other agents, advisors or representatives (collectively, “representatives”) not to, directly or indirectly:

If any subsidiaries of Triple-S or any of its or their representatives violates any of these restrictions, then Triple-S will be deemed to have breached such restrictions.

Triple-S has also agreed that it will, and will cause its subsidiaries and all of its and their respective representatives to, immediately:

In addition, Triple-S has agreed that it will not, and will cause its subsidiaries and all of its and their respective representatives not to, release any person from, or waive, amend or modify any provision of, or grant any permission under any “standstill” provision or similar provision with respect to any of its capital stock in any agreement to which it or any of its subsidiaries is a party; provided that the Triple-S board or any committee thereof will be permitted to grant waivers of, and not to enforce, any “standstill” or similar provision to the extent that (x) the Triple-S board or any committee thereof determines in good faith (after

consultation with its outside counsel) that the failure to take such action would violate the directors’ fiduciary duties under applicable law and (y) any such action by the Triple-S board or any committee thereof does not violate any other provision of the merger agreement. Except to the extent otherwise permitted by the foregoing sentence, Triple-S will, and will cause its affiliates to, (i) enforce the “standstill” or similar provisions of any such agreement and (ii) immediately take all reasonable steps within their power to terminate any waiver under any such provisions that may have been heretofore granted to any person other than Parent and any of Parent’s affiliates.

Notwithstanding anything to the contrary described above, at any time prior to obtaining the approval of Triple-S stockholders, in response to a qualifying company takeover proposal, Triple-S may (A) enter into an acceptable confidentiality agreement with such person or group making the qualifying company takeover proposal and thereafter furnish information with respect to Triple-S to such person or group and its representatives pursuant to such acceptable confidentiality agreement so long as Triple-S also provides Parent promptly, and in no event later than 24 hours after the time such information is provided or made available to such person or group or any of its representatives, any information furnished to such person or group or any of its representatives which was not previously furnished to Parent and (B) participate in discussions or negotiations with such person or group and its representatives regarding such qualifying company takeover proposal. Triple-S is required to notify Parent prior to furnishing any information and/or entering into any discussions or negotiations.

Triple-S is required to promptly, and in no event later than 24 hours after receipt thereof, (i) advise Parent in writing of Triple-S’s or any of its subsidiaries’ or its or their respective representatives’ receipt of any company takeover proposal or any inquiries regarding, or the submission of any proposal or offer that constitutes, or would reasonably be expected to lead to, any company takeover proposal and (ii) provide to Parent an unredacted copy of any such company takeover proposal or such inquiry made in writing (including any financing commitments or other agreements related thereto) (or if such company takeover proposal or inquiry is not in writing, a written description of the material terms and conditions thereof) and unredacted copies of all other written materials, draft and final agreements (including all schedules and exhibits thereto) and correspondence exchanged between Triple-S or any of its affiliates or its or their representatives, on the one hand, and the person or group or its representatives, on the other hand, making such company takeover proposal or inquiry in connection with such company takeover proposal or inquiry. From and after such notification, Triple-S is required to keep Parent reasonably informed on a reasonably current basis of any material developments, discussions or negotiations regarding, or changes to the material terms and conditions of, any such company takeover proposal or inquiry, including providing to Parent promptly, and in no event later than 24 hours after receipt thereof, unredacted copies of any additional proposals, counterproposals, written materials, draft and final agreements (including all schedules and exhibits thereto) and correspondence exchanged between Triple-S or any of its affiliates or its or their representatives, and the person or group or its representatives making such company takeover proposal or inquiry in connection with such company takeover proposal or inquiry.

For purposes of the merger agreement, “company takeover proposal” means, any inquiry, proposal or offer from any person or group relating to, in a single transaction or series of related transactions, any:

direct or indirect parent of Triple-S or such surviving entity (or any equity interests representing such voting power giving effect to any right of conversion or exchange thereof); or

For purposes of the merger agreement, “superior proposal” means any bona fide binding written offer which is made by a third party or group which, if consummated, would result in such third party or group (or in the case of a direct merger, consolidation, share exchange or other similar transaction between such third party or group and Triple-S, the stockholders of such third party or group) beneficially owning, directly or indirectly, more than 50% of the outstanding Triple-S common stock or the outstanding voting power of the Triple-S (or any other equity interests representing such voting power giving effect to any right of conversion or exchange thereof) or all or substantially all the consolidated assets of Triple-S and its subsidiaries that the Triple-S board or any committee thereof determines in good faith, after consultation with its outside counsel and financial advisor, (a) is more favorable to the Triple-S’s stockholders from a financial point of view than the transactions contemplated by the merger agreement, taking into account all terms and conditions of such offer (including all legal, regulatory, financial, timing and other aspects of such offer, including the identity of the person making the proposal) as well as the merger agreement and all changes to the terms of the transactions proposed by Parent in response to such offer or otherwise and (b) is reasonably likely to be completed on the terms proposed, taking into account all terms and conditions of such offer (including all legal, regulatory, financial, timing and other aspects of such offer, including the identity of the person making the proposal) as well as the merger agreement and all changes to the terms of the transactions proposed by Parent in response to such offer or otherwise.

Changes in Board Recommendation

Under the merger agreement, prior to obtaining the Triple-S stockholder approval, the Triple-S board or any committee thereof may make an adverse recommendation change if (i) the Triple-S board or any committee thereof determines in good faith (after consultation with its outside counsel and financial advisor) that, as a result of an intervening event, failure to take such action would violate the directors’ fiduciary duties under applicable law or (ii) Triple-S receives a company takeover proposal after the date of the merger agreement that did not result from a material breach of its non-solicitation obligations and for which the Triple-S board or any committee thereof determines in good faith (after consultation with its outside counsel and financial advisor) that such company takeover proposal constitutes a superior proposal and that the failure to take such action would violate the directors’ fiduciary duties under applicable law; provided that:

outside counsel and financial advisor) (1) that it would continue to violate the directors’ fiduciary duties under applicable law not to effect the adverse recommendation change and (2) in connection with a company takeover proposal, that the company takeover proposal received by the Company would continue to constitute a superior proposal, in each case, if such changes offered by Parent were given effect.

Notwithstanding the foregoing, Triple-S is required to submit the matters to obtain approval of Triple-S stockholders at the stockholders meeting; provided, however, that (i) if the Triple-S board has made an adverse recommendation change, then in submitting such matters to the stockholders meeting, the Triple-S board may recommend against such matters or submit such matters without recommendation, in which event the Triple-S board will communicate the basis for its recommendation or lack thereof to Triple-S’s stockholders in the proxy statement or an appropriate amendment or supplement thereto to the extent it determines, after consultation with its outside legal counsel, that such action is compelled by applicable law and (ii) Triple-S shall have the right to terminate the merger agreement if the Triple-S board makes an adverse recommendation change concurrently with its entry into a definitive merger agreement concerning a superior proposal so long as it pays the termination fee.

Nothing in the merger agreement prevents Triple-S from:

provided, however, that (A) any such disclosure permitted under the first bullet above that relates to a company takeover proposal (other than a “stop, look and listen” communication) shall be deemed an adverse recommendation change unless the Triple-S board expressly publicly reaffirms the company board recommendation in connection with such disclosure and (B) any adverse recommendation change may only be made in accordance with “Merger Agreement—Changes in Board Recommendation”.

For purposes of the merger agreement, “company board recommendation” means the Triple-S board, at a meeting duly called and held, duly and unanimously adopted resolutions (i) determining that the merger agreement and the transactions contemplated by the merger agreement, including the merger, are in the best interests of Triple-S and its stockholders, (ii) approving, adopting and declaring advisable the merger agreement and the transactions contemplated by the merger agreement, including the merger, in each case on the terms and subject to the conditions set forth in the merger agreement and (iii) recommending that the holders of shares of Triple-S common stock adopt the merger agreement and directing that the merger agreement be submitted to the Triple-S’s stockholders at the stockholders meeting.

For purposes of the merger agreement, “adverse recommendation change” means the Triple-S board or any committee thereof (A)  withdraw, withhold, qualify or modify in a manner adverse to Parent or Merger Sub, or propose publicly to withdraw, withhold, qualify or modify in a manner adverse to Parent or Merger Sub, the company board recommendation, or authorize, resolve or agree to take any such action, (B) adopt, endorse, approve or recommend, or propose publicly to adopt, endorse, approve or recommend, or submit to the vote of any securityholders of Triple-S, any company takeover proposal, or authorize, resolve or agree to take any such action, (C) fail to include the company board recommendation in the proxy statement or to recommend against any company takeover proposal that is a tender offer or exchange offer within 10 business days after the commencement thereof or, (D) make any public statement inconsistent with the company board recommendation.

For purposes of the merger agreement, “intervening event” means a material development or change in circumstances relating to Triple-S or any of its subsidiaries (other than (a) a company takeover proposal, (b) changes in the price of Triple-S common stock, in and of itself (however, the underlying reasons for such changes may constitute an intervening event) or (c) the fact that, in and of itself, Triple-S exceeds any internal or published projections, estimates or expectations of its revenue, earnings or other financial performance or results of operations for any period (however, the underlying reasons for such events may constitute an intervening event)) that occurs or arises after the execution and delivery of the merger agreement and on or prior to the date of Triple-S’s stockholder approval and was not known to or reasonably

foreseeable by the Triple-S board or any committee thereof prior to the execution and delivery of the merger agreement.

Regulatory Approvals Required for the Merger

The completion of the merger is conditioned on, among other things, certain specified regulatory approvals having been obtained and remaining in full force and effect (or, in the case of certain specified regulatory approvals that are statutory waiting periods, having expired or been terminated). Under the terms of the merger agreement, each of Triple-S and Parent agrees to use their respective reasonable best efforts to take, or cause to be taken, all actions, and to do, or cause to be done, and to assist and cooperate with the other parties in doing, all things necessary, proper or advisable to cause the conditions to closing to be satisfied as promptly as reasonably practicable and to consummate and make effective, in the most expeditious manner reasonably practicable, the transactions, including (i) obtaining all necessary or advisable consents from, making all necessary registrations, declarations and filings with and taking all reasonable steps as may be necessary to obtain a consent from or avoid a proceeding by any governmental entity or other third party with respect to the merger agreement or the transactions, (ii) furnishing all information required to be furnished in connection with obtaining any consents from or making any filings with any governmental entity or other third party, and promptly cooperating with and furnishing information in connection with any such requirements imposed upon any party or any of their respective subsidiaries in connection with the merger agreement or the consummation of the transactions, (iii) executing and delivering any additional instruments necessary to consummate the transactions and to fully carry out the purposes of the merger agreement and (iv) defending or contesting in good faith any proceeding brought by a third party that could otherwise prevent or impede, interfere with, hinder or delay in any material respect the consummation of the transactions, in the case of each of clauses (i) through (iv), other than with respect to consents, registrations, declarations, filings, instruments and proceedings relating to or under applicable antitrust laws, health care laws and insurance laws.

Notwithstanding anything to the contrary, with respect to any consent, none of Parent, Merger Sub or any of their respective subsidiaries will be required to, and Triple-S and its subsidiaries will not, without the prior written consent of Parent, pay or agree to pay any amount as consideration therefor to, or grant or agree to grant any financial, contractual or other concession in favor of, the person from whom such consent is sought, other than (i) filing and processing fees and (ii) any such payment or concession that is solely applicable to Triple-S and its subsidiaries (a “company concession”) and, when taken together with all company concessions and company restrictions (as defined below), is de minimis to Triple-S and its subsidiaries, taken as a whole.

Parent will use its reasonable best efforts to take, or cause to be taken, all actions necessary to assist the Company in obtaining all consents and approvals under the license agreements with the Blue Cross and Blue Shield Association (“BCBSA”), including any other transfer or change of control consents or approvals of the BCBSA needed as a result of the merger agreement, the merger or the other transactions. Parent will use its reasonable best efforts to cooperate in all respects with the Company in connection with any filings or submissions requested or required by the BCBSA.

Each of Triple-S and Parent will (i) make an appropriate filing of a Notification and Report Form pursuant to the HSR Act within 30 days after the date of the merger agreement, unless otherwise mutually agreed to by the parties, and to make any other required filings pursuant to applicable antitrust laws, health care Laws or insurance laws with respect to the transactions as promptly as reasonably practicable and advisable, (ii) supply as promptly as practicable and advisable any additional information and documentary material that may be requested by any governmental entity with competent jurisdiction, including pursuant to the HSR Act or any other applicable antitrust laws, health care laws or insurance laws, (iii) cooperate with any investigation, review or other inquiry by or before a governmental entity of competent jurisdiction relating to the transactions and (iv) use reasonable best efforts to take or cause to be taken all other actions necessary to cause as promptly as reasonably practicable the expiration or termination of the applicable waiting periods under the HSR Act and any other applicable antitrust laws and to obtain as promptly as reasonably practicable all consents under any applicable antitrust laws, health care laws and insurance laws that may be required by the United Stated Federal Trade Commission (“FTC”), the United States Department of Justice (the “DOJ”) or any other governmental entity with competent jurisdiction. Each of Triple-S and Parent shall use reasonable best efforts to take or cause to be taken as promptly as practicable all actions necessary to resolve objections, if any, as may be asserted with respect to the transactions under any applicable antitrust law, health care laws or insurance laws; provided, however, without the prior written consent of each party, none of Parent, Merger Sub or Triple-S shall be required to defend any lawsuit brought by a governmental entity or other adjudicatory action initiated by or at the behest of a governmental entity (and not upon the filing of a claim, challenge or complaint by any person other than such

governmental entity), in each case, seeking to either (i) restrain, enjoin, prevent, prohibit, or otherwise make illegal the consummation of the Merger or the other Transactions or (ii) impose a Burdensome Condition (as defined below). Parent, Merger Sub, or any of their respective subsidiaries, and Triple-S and its subsidiaries shall not, without the prior written consent of Parent, propose, negotiate, effect or agree to, or execute any settlements, undertakings, consent decrees, stipulations or other agreements with any governmental entity (including ASES) or with any other person (including the BCBSA) obligating Parent, the Company or any of their respective subsidiaries, (i) sell, divest, license or otherwise convey or hold separate any asset or business of Parent, Triple-S or any of their respective subsidiaries, (ii) terminate or alter any existing relationship, contractual right or obligation of Parent, Triple-S or any of their respective subsidiaries, (iii) create any relationship, contractual right or obligation, including any payment obligation (other than customary filing fees), of Parent, Triple-S or any of their respective subsidiaries or (iv) implement any limitations or restrictions on the ability of Parent, Merger Sub or any of their respective subsidiaries to hold and exercise full rights of ownership of any equity interests in the surviving corporation, including the right to vote such equity interests, or to effectively control the business or operations of Triple-S or any of its subsidiaries, in each case other than any action or condition described in the immediately preceding clauses (i)-(iv) that applies solely to Triple-S and its subsidiaries (a “company restriction”) and, when taken together with all company concessions and company restrictions, is de minimis to Triple-S and its subsidiaries, taken as a whole (a “de minimis company restriction”). The term “burdensome condition” means any action or condition described in clauses (i)-(iv) of the immediately preceding sentence other than any de minimis company restriction.

Each of Parent and the Company will (i) cooperate in all respects with each other in connection with any filing or submission with a governmental entity by any person in connection with the transactions, and in connection with any investigation or other inquiry by or before a governmental entity relating to the transactions, (ii) give the other party reasonable prior notice of any such filings or submissions and, to the extent reasonably practicable, of any communication with, and any inquiries or requests for additional information from, the FTC, the DOJ, the Puerto Rico Commissioner of Insurance (the “OCI”) and any other governmental entity regarding the merger or any of the other transactions, and permit the other party to review and discuss in advance, and consider in good faith the views of, and secure the participation of, the other party in connection with, any such filings, submissions, communications, inquiries or requests, (iii) unless prohibited by applicable law or by the applicable governmental entity, and to the extent reasonably practicable, (A) not participate in or attend any meeting, or engage in any substantive conversation, with any governmental entity in respect of the Merger or any of the other transactions without the other party, (B) give the other party reasonable prior notice of any such meeting or conversation, (C) in the event one party is prohibited by applicable law or by the applicable governmental entity from participating in or attending any such meeting or engaging in any such conversation, keep such party apprised, (D) cooperate with one another in the filing of any substantive memoranda, white papers, filings, correspondence or other written communications explaining or defending the merger agreement, the merger or any of the other transactions, articulating any regulatory or competitive argument or responding to requests or objections made by any governmental entity and (E) furnish the other party with copies of all filings, submissions, correspondence and communications (and memoranda setting forth the substance) between it and its affiliates and their respective representatives, on the one hand, and any governmental entity or members of any governmental entity’s staff, on the other hand, with respect to the merger agreement, the merger and the other transactions, (iv) comply with any inquiry or request from the FTC, the DOJ, the OCI or any other governmental entity as promptly as reasonably practicable and (v) consult with one another in connection with any inquiry, hearing, investigation, proceeding or litigation by, or negotiations with, any governmental entity relating to the merger agreement, the merger or any of the other transactions. Parent shall control and lead all communications and strategy for dealing with the FTC, the DOJ, the OCI and any other governmental entity with respect to the HSR Act and any other applicable Law, including antitrust laws, health care laws or insurance laws.

In addition, Triple-S and the Triple-S board will (i) take all action necessary to ensure that no state or territorial takeover statute, “business combination”, “control share acquisition”, “fair price”, “moratorium” or similar Law is or becomes applicable to any Transaction or the merger agreement and (ii) if any state or territorial takeover statute, “business combination”, “control share acquisition”, “fair price”, “moratorium” or similar law becomes applicable to any transaction or the merger agreement, take all action necessary to ensure that the transactions may be consummated as promptly as practicable on the terms contemplated by the merger agreement and otherwise to minimize the effect of such statute or regulation on the transactions and the merger agreement.

Litigation Related to the Merger

From the date of the merger agreement and until the termination of the merger agreement, Triple-S will promptly advise Parent of any proceeding commenced or, to the knowledge of Triple-S, threatened by a stockholder or holder of any equity interests of Triple-S against Triple-S or its directors or executive officers relating to the merger or any of the other transactions, and will keep Parent reasonably informed, consult with Parent regarding and give Parent the opportunity to participate, but not control, the defense and settlement of any such proceeding. Neither Triple-S nor any of the its subsidiaries, nor any of their respective representatives, will agree to or propose any settlement of any such proceeding without Parent’s prior written consent (which consent may not be unreasonably withheld, conditioned or delayed).

Employee Matters

For a period from the closing of the merger through the first anniversary of the closing of the merger, each Triple-S employee who remains employed (the “Triple-S continuing employees”) shall receive (i) a base salary, wage or commission rate at least equal to the base salary, wage or commission rate provided to such Triple-S continuing employee by Triple-S immediately prior to the closing of the merger, (ii) incentive compensation opportunities no less favorable than the incentive compensation opportunities provided to such Triple-S continuing employee by Triple-S immediately prior to the closing of the merger (including the target value of annual equity-based compensation awards historically granted to such Triple-S continuing employee prior to the closing of the merger, but excluding any one-time, special or transaction-related incentive compensation opportunities), which incentive compensation opportunities will be subject to the terms and conditions of Parent’s incentive compensation programs and (iii) other employee benefits that are no less favorable in the aggregate to the benefits provided by Triple-S to such Triple-S continuing employee immediately prior to the closing of the merger.

On or after the closing of the merger, Parent will, or will cause its affiliates, including the surviving corporation, to recognize the service of each Triple-S continuing employee for all purposes under any employee benefit plan, other than (i) any post-employment health plan or post-employment welfare plan or defined benefit pension plan or (ii) any severance plan to the extent that a Triple-S continuing employee is covered under another severance arrangement with Triple-S, but excluding any severance payable pursuant to applicable law, to the same extent such service credit was granted under any Triple-S benefit plan or arrangement and not in the case where such service credit would result in a duplication of benefits.

In addition, following the closing of the merger, the merger agreement provides that Parent will use reasonable best efforts to cause its affiliates to (i) waive all limitations as to preexisting conditions or exclusions, actively-at-work requirements and waiting periods with respect to participation and coverage requirements applicable to each Triple-S continuing employee (and eligible dependents) to the extent such conditions and exclusions were satisfied or did not apply to such employees under the welfare plans of Triple-S prior to the closing of the merger and (ii) provide each Triple-S continuing employee (and eligible dependents) with credit for any co-payments, deductibles and similar expenses incurred by each Triple-S continuing employee during the calendar year in which the closing of the merger occurs in satisfying any analogous deductible or out-of-pocket requirements to the extent applicable under the relevant benefit plan in which each Triple-S continuing employee will be eligible to participate from and after the closing of the merger.

Directors’ and Officers’ Indemnification and Insurance

Parent has agreed to assume the obligations with respect to all rights to indemnification, advancement of expenses and exculpation from liabilities, for acts or omissions occurring at or prior to the effective time of the merger now existing in favor of the current or former directors or officers (the “indemnified persons”) of Triple-S or any of its subsidiaries as provided in the Triple-S articles and the Triple-S bylaws, the organizational documents of any Triple-S’s subsidiary or any indemnification agreement between an indemnified person and Triple-S or any of its subsidiaries as of the effective time of the merger, and such obligations will survive the merger and will continue in full force and effect in accordance with their terms.

Parent will obtain, or will cause the surviving corporation to obtain, at or prior to the effective time of the merger, a prepaid (or “tail”) directors’ and officers’ liability insurance policy in respect of acts or omissions occurring at or prior to the effective time of the merger, covering each person currently covered by the Triple-S’s or any Triple-S’s subsidiary’s directors’ and officers’ liability insurance policies, with coverage for six years following the effective time on terms with respect to such coverage and amounts no less favorable to the insureds than those of such policy in effect immediately prior to the effective time; provided, however, that in no event will Parent or the surviving corporation be required to expend an amount in excess of 300%

of the most recent annual premium paid by Triple-S or any of its subsidiaries for such insurance for its current fiscal year (such 300% threshold, the “maximum premium”); provided further that, if the amount necessary to procure such prepaid (or “tail”) insurance coverage exceeds such maximum premium, Parent or the surviving corporation, as the case may be, shall only be obligated to provide as much coverage as may be obtained for such maximum premium. Triple-S may, prior to the effective time, purchase for an aggregate amount not to exceed the maximum premium, a six-year prepaid (or “tail”) policy on terms and conditions providing at least substantially equivalent benefits as the current policies of directors’ and officers’ liability insurance maintained by Triple-S and its subsidiaries in respect of acts or omissions occurring at or prior to the effective time. If such prepaid (or “tail”) policy has been obtained by Triple-S, it will be deemed to satisfy all obligations to obtain insurance pursuant to the merger agreement and the surviving corporation will use its reasonable best efforts to cause such policy to be maintained in full force and effect, for its full term, and to honor all of its obligations thereunder.

In the event that Parent, the surviving corporation or any of their respective successors or assigns (i) consolidates with or merges into any other person and is not the continuing or surviving corporation or entity of such consolidation or merger or (ii) transfers or conveys all or substantially all of its properties and assets to any person, then, in each such case, Parent or the surviving corporation will make proper provision so that the successors and assigns of Parent or the surviving corporation, as the case may be, or at Parent’s option, Parent, assume the obligations set forth in the merger agreement.

Other Covenants

The merger agreement contains other covenants, including those relating to access to information, notices, and employee matters.

Conditions to Completion of the Merger

The obligations of Triple-S, Parent and Merger Sub to consummate the merger are subject to the satisfaction (or, to the extent permitted by applicable law, waiver by the parties entitled thereto) of the following conditions:

The obligations of Parent and Merger Sub to consummate the merger are also subject to the satisfaction (or, to the extent permitted by law, waiver by Parent and Merger Sub) at or prior to the effective time of the merger, of each of the following conditions:

The obligation of Triple-S to consummate the merger is also subject to the satisfaction (or, to the extent permitted by law, waiver by Triple-S) at or prior to the effective time of the merger of each of the following conditions:

Termination of the Merger Agreement

Reverse Termination Fee Payable by Parent” beginning on page [●] of this proxy statement.

Termination Fee Payable by Triple-S and Reverse Termination Fee Payable by Parent

Remedies; Maximum Liability

The merger agreement provides that in no event will Triple-S be required to pay the termination fee on more than one occasion, whether or not the termination fee may be payable under more than one provision of the merger agreement at the same or at different times and the occurrence of different events. If the termination fee becomes payable in accordance with the merger agreement, the payment to Parent or its designee of the termination fee will be the sole and exclusive remedy of Parent and Merger Sub for any loss suffered by Parent or Merger Sub as a result of the failure of the transactions to be consummated and, upon such payment in accordance with the merger agreement, Triple-S will not have any further liability or obligation relating to or arising out of the merger agreement or the transactions, except in the case of fraud or willful or intentional breach of the merger agreement by Triple-S.

In addition, the merger agreement provides that in no event will Parent be required to pay the reverse termination fee on more than one occasion, whether or not the reverse termination fee may be payable under more than one provision of the merger agreement at the same time or at different times and the occurrence of different events. If the reverse termination fee becomes payable in accordance with the merger agreement, the payment to Triple-S or its designee of the reverse termination fee will be the sole and exclusive remedy of Triple-S for any loss suffered by Triple-S as a result of the failure of the transactions to be consummated and, upon such payment in accordance with the merger agreement, neither Parent nor Merger Sub will have any further liability or obligation relating to or arising out of the merger agreement or the transactions, except in the case of fraud or willful or intentional breach of the merger agreement by Parent or Merger Sub, as applicable.

Specific Performance

The merger agreement provides that the parties will be entitled to an injunction or injunctions, or any other appropriate form of equitable relief, to prevent breaches of the merger agreement and to specifically enforce the performance of the terms and provisions of the merger agreement in any court, without the necessity of providing any bond or other security or proving actual damages or the inadequacy of monetary damages as a remedy. Each of the parties further agrees not to oppose a remedy of specific enforcement on the basis that the other party has an adequate alternative remedy at law.

Fees and Expenses

Except as set forth in the section “The Merger Agreement—Termination Fee Payable by Triple-S and Reverse Termination Fee Payable by Parent” beginning on page [●] of this proxy statement, all fees and expenses incurred in connection with the merger agreement will be paid by the party incurring such fees or expense.

Amendments and Waivers

The merger agreement may be amended, modified and supplemented in any and all respects only by an instrument in writing signed on behalf of each of the parties. Any agreement on the part of a party to any extension or waiver with respect to the merger agreement shall be valid only if set forth in an instrument in writing signed on behalf of such party. At any time prior to the effective time of the merger, the parties (treating Parent and Merger Sub as one party for this purpose) may (i) extend the time for the performance of any of the obligations or other acts of the other party, (ii) waive any inaccuracies in the representations and warranties of the other party contained in the merger agreement or in any document delivered pursuant to the merger agreement or (iii) waive compliance by the other party with any of the agreements or conditions contained in the merger agreement. Notwithstanding the foregoing, there will be made no amendment, modification or supplement to the merger agreement (i) after receipt of the Triple-S stockholder

approval which requires further approval by the stockholders of Triple-S without the further approval of such stockholders or (ii) after the effective time of the merger. The failure of any party to the merger agreement to assert any of its rights under the merger agreement or otherwise shall not constitute a waiver of such rights.

Governing Law and Venue, Waiver of Jury Trial

The parties agreed that the merger agreement will be governed by, and construed in accordance with, the laws of the State of Delaware, regardless of the laws that might otherwise govern under applicable principles of conflicts of laws, except to the extent that the Laws of the Commonwealth of Puerto Rico are mandatorily applicable to the merger agreement, the transactions or the certificate of merger filed in Puerto Rico.

Each of the parties irrevocably submits to the exclusive jurisdiction of the Court of Chancery of the State of Delaware (or, if such court is unavailable, any state or federal court sitting in the State of Delaware) for the purpose of any proceeding arising out of or relating to the merger agreement, the merger or any of the other transactions, and each of the parties irrevocably agrees that all claims with respect to such proceeding may be heard and determined exclusively in such court. Each of the parties (i) consents to submit itself to the personal jurisdiction of the Court of Chancery of the State of Delaware (or, if such court is unavailable, any state or federal court sitting in the State of Delaware) in the event any proceeding arises out of the merger agreement, the merger or any of the other transactions, (ii) agrees that it will not attempt to deny or defeat such personal jurisdiction by motion or other request for leave from any such court, (iii) irrevocably consents to the service of process in any Proceeding arising out of or relating to the merger agreement, the merger or any of the other transactions, on behalf of itself or its property, in accordance with the merger agreement (provided that nothing in the merger agreement will affect the right of any party to serve legal process in any other manner permitted by law) and (iv) agrees that it will not bring any proceeding relating to the merger agreement, the merger or any of the other transactions in any court other than the Court of Chancery of the State of Delaware (or, if such court is unavailable, any state or federal court sitting in the State of Delaware). The parties agree that a final trial court judgment in any such proceeding will be conclusive and may be enforced in other jurisdictions by suit on the judgment or in any other manner provided by Law. The foregoing statement will not restrict any party’s right to seek any post-judgment relief regarding, or any appeal from, such final trial court judgment, or to bring suit for the recognition or enforcement of any judgment obtained in any court sitting in the State of Delaware or in any other court of competent jurisdiction following final determination of the applicable matter.

Each party further waived, to the fullest extent permitted by applicable law, any right it may have to a trial by jury in respect of any proceeding arising out of or relating to the merger agreement, the merger or any of the other transactions. Each party (a) certifies that no representative agent or attorney of any other party has represented expressly or otherwise, that such party would not, in the event of any proceeding, seek to enforce this waiver and (b) acknowledges that it makes this waiver voluntarily and that the other parties have been induced to enter into the merger agreement by, among other things, the mutual waiver and certifications described in this paragraph.

MARKET PRICES OF TRIPLE-S COMMON STOCK

Triple-S common stock is listed on the NYSE under the symbol “GTS.” The following table sets forth on a per share basis the high and low intra-day prices of Triple-S common stock as reported in published financial sources. At the close of business on [●], 2021, there were [●] holders of record of Triple-S common stock. A number of Triple-S stockholders have their shares in street name; therefore, Triple-S believes that there are substantially more beneficial owners of Triple-S common stock.

* On August 6, 2019, all holders of class B shares at the close of business on July 26, 2019 received a share dividend of 0.051107 class B shares for every class B share they owned as of that time.

The closing price of Triple-S common stock on the NYSE on [●], 2021, the most recent practicable date prior to the date of this proxy statement, was $[●] per share. As of  [●], 2021, Triple-S had [●] shares of Triple-S common stock issued and outstanding, and Triple-S had approximately [●] holders of record. You are encouraged to obtain current market prices of Triple-S common stock in connection with voting your shares of Triple-S common stock.

Dividends

On July 16, 2019, Triple-S announced that the Triple-S board of directors authorized the conversion of Triple-S’s then remaining issued and outstanding class A common shares into class B common shares, effective August 7, 2019. In connection with the conversion, all holders of class B shares at the close of business on July 26, 2019 received a share dividend of 0.051107 class B shares for every class B share they owned as of that time, as determined by the anti-dilution formula in Triple-S’s articles of incorporation. The class B share dividend was paid on August 6, 2019; cash was paid in lieu of fractional shares. Effective upon Triple-S’s public announcement on August 7, 2019, all class A holders of record received one class B share for each class A share held. Upon the conversion of the class A common shares, all remaining outstanding Class A shares were automatically cancelled and extinguished, and Triple-S now maintains a single class of common shares.

Other than as described above, Triple-S did not declare any cash dividends during the four most recent fiscal years and does not expect to pay any cash dividends in the near future. Under the terms of the merger agreement, from the date of the merger agreement until the earlier of the effective time of the merger or the termination of the merger agreement, Triple-S may not declare, set aside or pay any dividend or other distribution (whether in cash, stock or property or any combination thereof) in respect of its capital stock or other equity interests, except for dividends or other such distributions by any of its wholly owned subsidiaries, without the prior written consent of Parent.

APPRAISAL RIGHTS OF STOCKHOLDERS

The following discussion summarizes appraisal rights under Puerto Rico law. The following discussion is not a complete statement of the law relating to appraisal rights and is qualified in its entirety by the full text of Article 10.13 of Puerto Rico law, referred to as “Article 10.13,” which is attached to this proxy statement (in English and Spanish) as Annex C. The following summary does not constitute legal or other advice, nor does it constitute a recommendation that stockholders exercise their appraisal rights under Article 10.13.

Under Article 10.13, holders of shares of Triple-S common stock who do not vote in favor of the adoption of the merger agreement and who otherwise follow the procedures set forth in Article 10.13 will be entitled to have their shares appraised by the Puerto Rico Court of First Instance, Superior Court, and to receive payment in cash of the “fair value” of the shares, exclusive of any element of value arising from the accomplishment or expectation of the merger, as determined by the Puerto Rico Court of First Instance, Superior Court, together with interest, if any, to be paid upon the amount determined to be the fair value.

Under Article 10.13, where a merger agreement is to be submitted for adoption and approval at a meeting of stockholders, the corporation, not less than 20 days prior to the meeting, must notify each of its stockholders entitled to appraisal rights that appraisal rights are available and include in the notice a copy of Article 10.13. This proxy statement shall constitute such notice, and the full text of Article 10.13. is attached to this proxy statement (in English and Spanish) as Annex C.

ANY HOLDER OF TRIPLE-S COMMON STOCK WHO WISHES TO EXERCISE APPRAISAL RIGHTS, OR WHO WISHES TO PRESERVE SUCH HOLDER’S RIGHT TO DO SO, SHOULD CAREFULLY REVIEW THE FOLLOWING DISCUSSION AND ANNEX C BECAUSE FAILURE TO TIMELY AND PROPERLY COMPLY WITH THE PROCEDURES SPECIFIED WILL RESULT IN THE LOSS OF APPRAISAL RIGHTS. MOREOVER, BECAUSE OF THE COMPLEXITY OF THE PROCEDURES FOR EXERCISING THE RIGHT TO SEEK APPRAISAL OF SHARES OF TRIPLE-S COMMON STOCK, TRIPLE-S BELIEVES THAT, IF A STOCKHOLDER CONSIDERS EXERCISING SUCH RIGHTS, SUCH STOCKHOLDER SHOULD SEEK THE ADVICE OF LEGAL COUNSEL.

Filing Written Demand

Any holder of Triple-S common stock wishing to exercise appraisal rights must, before the stockholder vote on the adoption of the merger agreement at the special meeting is taken, deliver to Triple-S a written demand for the appraisal of the stockholder’s shares, and not vote in favor of the adoption of the merger agreement. A holder of Triple-S common stock wishing to exercise appraisal rights must hold of record the shares on the date the written demand for appraisal is made and must continue to hold the shares of record through the effective date of the merger. The holder must not vote in favor of the adoption of the merger agreement. A proxy that is submitted and does not contain voting instructions will, unless revoked, be voted in favor of the adoption of the merger agreement, and it will effectively constitute a waiver of the stockholder’s right of appraisal and will effectively nullify any previously delivered written demand for appraisal. Therefore, a stockholder who submits a proxy and who wishes to exercise appraisal rights must submit a proxy containing instructions to vote against the adoption of the merger agreement or abstain from voting on the adoption of the merger agreement. Neither voting against the merger proposal, nor abstaining from voting or failing to vote on the merger proposal, will in and of itself constitute a written demand for appraisal satisfying the requirements of Article 10.13. The written demand for appraisal must be in addition to and separate from any proxy or vote on the adoption of the merger agreement. The demand must reasonably inform Triple-S of the identity of the holder as well as the intention of the holder to demand an appraisal of the “fair value” of the shares held by the holder. A stockholder’s failure to make the written demand prior to the taking of the vote on the adoption of the merger agreement at the special meeting of stockholders will constitute a waiver of appraisal rights.

Only a holder of record of shares of Triple-S common stock is entitled to demand an appraisal of the shares registered in that holder’s name. A demand for appraisal in respect of shares of Triple-S common stock should be executed by or on behalf of the holder of record. The demand should set forth the registered holder’s name as it appears on the holder’s stock certificates. A demand for appraisal will be sufficient if it reasonably informs Triple-S of the identity of the stockholder and that the stockholder intends thereby to demand the appraisal of such stockholder’s shares. If the shares are owned of record in a fiduciary capacity, such as by a trustee, guardian or custodian, execution of the demand must be made in that capacity, and if the shares are owned of record by more than one person, as in a joint tenancy and tenancy-in-common, the demand must be executed by or on behalf of all joint owners. An authorized agent, including an agent for two or more joint owners, may execute a demand for appraisal on behalf of a holder of record; however, the

agent must identify the record owner or owners and expressly disclose that, in executing the demand, the agent is acting as agent for the record owner or owners. If the shares are held in “street name” by a broker, bank or nominee, the broker, bank or nominee may exercise appraisal rights with respect to the shares held for one or more beneficial owners while not exercising the rights with respect to the shares held for other beneficial owners; in such case, however, the written demand should set forth the number of shares as to which appraisal is sought. Where no number of shares is expressly mentioned, the demand will be presumed to cover all shares of Triple-S common stock held in the name of the record owner. If a stockholder holds shares of Triple-S common stock through a broker who in turn holds the shares through a central securities depository nominee such as Cede & Co., a demand for appraisal of such shares must be made by or on behalf of the depository nominee and must identify the depository nominee as record holder. Stockholders who hold their shares in brokerage accounts or other nominee forms and who wish to exercise appraisal rights are urged to consult with their brokers or other nominees to determine the appropriate procedures for the making of a demand for appraisal by such a nominee.

All written demands for appraisal pursuant to Article 10.13 should be sent or delivered to Triple-S at:

Triple-S Management Corporation
1441 F.D. Roosevelt Avenue
San Juan, Puerto Rico 00920
Attention: General Counsel and Secretary

At any time within sixty (60) days after the effective date of the merger, any stockholder who has not commenced an appraisal proceeding or joined that proceeding as a named party may withdraw his, her or its demand for appraisal and accept the consideration offered pursuant to the merger agreement by delivering to Triple-S, as the surviving corporation, a written withdrawal of the demand for appraisal. However, any such attempt to withdraw the demand made more than sixty (60) days after the effective date of the merger will require written approval of Triple-S, as the surviving corporation. No appraisal proceeding in the Puerto Rico Court of First Instance, Superior Court, will be dismissed as to any stockholder without the approval of the Puerto Rico Court of First Instance, Superior Court, and such approval may be conditioned upon such terms as the Puerto Rico Court of First Instance, Superior Court deems just; provided, however, that any stockholder who has not commenced an appraisal proceeding or joined that proceeding as a named party may withdraw his, her or its demand for appraisal and accept the merger consideration offered pursuant to the merger agreement within sixty (60) days after the effective date of the merger. If Triple-S, as the surviving corporation, does not approve a request to withdraw a demand for appraisal when that approval is required, or, except with respect to any stockholder who withdraws such stockholder’s demand in accordance with the proviso in the immediately preceding sentence, if the Puerto Rico Court of First Instance, Superior Court, does not approve the dismissal of an appraisal proceeding with respect to a stockholder, the stockholder will be entitled to receive only the appraised value determined in any such appraisal proceeding, which value could be less than, equal to or more than the consideration being offered pursuant to the merger agreement.

Notice by the Surviving Corporation

Within ten (10) days after the effective date of the merger, Triple-S, as the surviving corporation, must notify each holder of Triple-S common stock who has complied with Article 10.13, and who has not voted in favor of the adoption of the merger agreement, of the date on which the merger became effective.

Filing a Petition for Appraisal

Within one hundred twenty (120) days after the effective date of the merger, but not thereafter, Triple-S, as the surviving corporation, or any holder of Triple-S common stock who has complied with Article 10.13 and is entitled to appraisal rights under Article 10.13, may commence an appraisal proceeding by filing a petition in the Puerto Rico Court of First Instance, Superior Court, with a copy served upon the surviving corporation in the case of a petition filed by a stockholder, demanding a determination of the fair value of the shares held by all such holders. Triple-S, as the surviving corporation, is under no obligation to and has no present intention to file a petition and holders should not assume that Triple-S as the surviving corporation will file a petition. Accordingly, any holders of Triple-S common stock who desire to have their shares appraised should initiate all necessary action to perfect their appraisal rights in respect of shares of Triple-S common stock within the time prescribed in Article 10.13. Within one hundred twenty (120) days after the effective date of the merger, any holder of common stock who has complied with the requirements of Article 10.13 will be entitled, upon written request, to receive from Triple-S as the surviving corporation a statement setting forth the aggregate number of shares not voted in favor of the adoption of the merger agreement and with respect to which demands for appraisal have been received and the aggregate number of holders of

such shares. The statement must be mailed within ten (10) days after a written request therefor has been received by Triple-S as the surviving corporation or within ten (10) days after the expiration of the period for delivery of demands for appraisal, whichever is later. The foregoing notwithstanding, a person who is the beneficial owner of shares of Triple-S common stock held either in a voting trust or by a nominee on behalf of such person may, in such person’s own name, file a petition or request from Triple-S as the surviving corporation the statement described in this paragraph. If a petition for appraisal is not timely filed, then the right to appraisal will cease.

If a petition for an appraisal is timely filed by a holder of shares of Triple-S common stock and a copy thereof is served upon Triple-S as the surviving corporation, Triple-S as the surviving corporation will then be obligated within twenty (20) days to file with the Puerto Rico Department of State a duly verified list containing the names and addresses of all stockholders who have demanded an appraisal of their shares and with whom agreements as to the value of their shares have not been reached. After notice to the stockholders, the Puerto Rico Court of First Instance, Superior Court, will conduct a hearing on the petition to determine those stockholders who have complied with Article 10.13 and who have become entitled to appraisal rights thereunder. The Puerto Rico Court of First Instance, Superior Court, may require the stockholders who demanded payment for their shares to submit their stock certificates to the Puerto Rico Department of State for notation thereon of the pendency of the appraisal proceeding; and if any stockholder fails to comply with the direction, the Puerto Rico Court of First Instance, Superior Court, may dismiss the proceedings as to such stockholder.

Determination of Fair Value

After the Puerto Rico Court of First Instance, Superior Court, determination of the stockholders entitled to appraisal of their shares of Triple-S common stock, an appraisal proceeding shall be conducted in accordance with the rules of the Puerto Rico Court of First Instance, Superior Court, including any rules specifically governing appraisal proceedings. Through this proceeding, the Puerto Rico Court of First Instance, Superior Court, will determine the fair value of the shares of Triple-S common stock as of the effective time of the merger exclusive of any element of value arising from the accomplishment or expectation of the merger, together with interest, if any, to be paid upon the amount determined to be the fair value. When the value is determined, the Puerto Rico Court of First Instance, Superior Court, will direct the payment of such fair value, with interest, if any, by the surviving corporation to the stockholders entitled thereto. Upon application by the surviving corporation or by any stockholder entitled to participate in the appraisal proceeding, the Puerto Rico Court of First Instance, Superior Court, may, in its discretion, proceed to trial upon the appraisal prior to the final determination of the stockholders entitled to an appraisal. Any stockholder whose name appears on the list filed by the surviving corporation pursuant to Article 10.13 of Puerto Rico law and who has submitted such stockholder’s stock certificates to the Puerto Rico Department of State, if such is required, may participate fully in all proceedings until it is finally determined that such stockholder is not entitled to appraisal rights under Article 10.13 of Puerto Rico law.

No representation is made as to the outcome of the appraisal of fair value as determined by the Puerto Rico Court of First Instance, Superior Court. In addition, Puerto Rico courts have not decided whether the statutory appraisal remedy would be a dissenter’s exclusive remedy. You should be aware that the fair value of your shares as determined under Article 10.13 of Puerto Rico law could be greater than, the same as, or less than the merger consideration that you would otherwise be entitled to receive under the terms of the merger agreement. Triple-S does not anticipate offering an amount greater than the merger consideration to any stockholder who exercises appraisal rights and reserves the right to assert, in any appraisal proceeding, that, for purposes of Article 10.13 of Puerto Rico law, the fair value of the Triple-S common stock shares is less than the merger consideration.

Costs of the appraisal proceeding may be imposed upon the surviving corporation and the stockholders participating in the appraisal proceeding by the Puerto Rico Court of First Instance, Superior Court, as the Puerto Rico Court of First Instance, Superior Court, deems equitable in the circumstances. Upon the application of a stockholder, the Puerto Rico Court of First Instance, Superior Court, may order all or a portion of the expenses incurred by any stockholder in connection with the appraisal proceeding, including, without limitation, reasonable attorneys’ fees and the fees and expenses of experts, to be charged pro rata against the value of all shares entitled to appraisal. Any stockholder who has demanded appraisal rights will not, after the effective date of the merger, be entitled to vote such shares for any purpose or to receive payments of dividends or any other distribution with respect to those shares, other than dividends or other distributions payable to stockholders of record at a date prior to the effective date of the merger; however, if no petition for appraisal is filed within one hundred twenty (120) days after the effective date of the merger, or if the stockholder delivers a written withdrawal of his, her or its demand for appraisal and an acceptance of the terms of the merger, either within 60 days after the effective date of the merger or thereafter with the

written approval of the corporation, then the right of that stockholder to appraisal will cease and that stockholder will be entitled to receive the merger consideration for shares of his, her or its common stock pursuant to the merger agreement.

In view of the complexity of Article 10.13 of Puerto Rico law, our stockholders who may wish to dissent from the merger and pursue appraisal rights should consult their legal advisor. To the extent there are any inconsistencies between the foregoing summary and Article 10.13 of Puerto Rico law, Puerto Rico law shall govern.

ADVISORY VOTE ON NAMED EXECUTIVE OFFICER MERGER-RELATED
COMPENSATION ARRANGEMENTS (PROPOSAL 2)

As required by Section 14A of the Exchange Act and the applicable SEC rules issued thereunder, Triple-S is required to submit a proposal to Triple-S stockholders for a non-binding, advisory vote to approve the payment by Triple-S of certain compensation that will or may be paid by Triple-S to its named executive officers that is based on or otherwise relates to the merger. This proposal, commonly known as “say-on-golden parachutes,” and which we refer to as the named executive officer merger-related compensation proposal, gives Triple-S stockholders the opportunity to vote, on a non-binding, advisory basis, on the named executive officer merger-related compensation proposal. This compensation is summarized in the table under “The Merger (Proposal 1)—Interests of Triple-S’s Directors and Executive Officers in the Merger —Golden Parachute Compensation” beginning on page [●] of this proxy statement, including the footnotes to the table.

The board of Triple-S encourages you to review carefully the named executive officer merger-related compensation information disclosed in this proxy statement.

The board of Triple-S unanimously recommends that the stockholders of Triple-S approve the following resolution:

“RESOLVED, that the stockholders of Triple-S hereby approve, on a non-binding, advisory basis, the agreements or understandings with and compensation to be paid or become payable by Triple-S to its named executive officers that are based on or otherwise relate to the merger as disclosed pursuant to Item 402(t) of Regulation S-K in the Golden Parachute Compensation table, the footnotes to that table and the accompanying narrative disclosure.”

The vote on the proposal to approve, on a non-binding, advisory basis, the named executive officer merger-related compensation is a vote separate and apart from the vote on the merger proposal. Accordingly, you may vote to approve and adopt the merger agreement and vote not to approve the named executive officer merger-related compensation proposal and vice versa. Because the vote on the named executive officer merger-related compensation proposal is advisory only, it will not be binding on either Triple-S or Parent. Accordingly, if the merger agreement is approved and adopted and the merger is completed, the compensation will be payable, subject only to the conditions applicable thereto, regardless of the outcome of the non-binding, advisory vote of Triple-S stockholders.

The above resolution approving the named executive officer merger-related compensation on an advisory basis will require the affirmative vote of at least a majority of the outstanding shares of Triple-S common stock present via the virtual meeting website or represented by proxy and entitled to vote and voting on the proposal at the special meeting (provided a quorum is present or represented by proxy).

The Triple-S board of directors unanimously recommends a vote “FOR” the proposal to approve, on a non-binding, advisory basis, certain compensation that will or may be paid by Triple-S to its named executive officers that is based on or otherwise relates to the merger.