1044-00004 · Client 1044 · Diligence

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FORM OF OFFICERS' CERTIFICATE

Officers' Certificate Pursuant to Section [●] of the Purchase Agreement

Delivered in connection with the offering of $400,000,000 aggregate principal amount of 8.750% Senior Secured Notes due 2029 (the "Notes")

Co-Issuers:

Thalassa Shipping & Logistics SA ("TSL") and Thalassa Finance Pte. Ltd. ("TFPL," and together with TSL, the "Co-Issuers")

[FORM — UNEXECUTED]

Dated: [●], 2022

RECITALS

The undersigned, Spyros Andreou, in his capacity as Chief Executive Officer of Thalassa Shipping & Logistics SA, a Société Anonyme organized and existing under the laws of the Hellenic Republic ("TSL"), and Marina Demetriou, in her capacity as Chief Financial Officer of TSL and Sole Director of Thalassa Finance Pte. Ltd., a private company limited by shares organized and existing under the laws of the Republic of Singapore ("TFPL," and together with TSL, the "Co-Issuers"), hereby certify as follows in connection with the offering of $400,000,000 aggregate principal amount of 8.750% Senior Secured Notes due 2029 (the "Notes") by the Co-Issuers:

WHEREAS, the Co-Issuers, the Guarantor Subsidiaries identified below, Kallistratos Maritime Holdings Ltd. (as limited parent guarantor), and the Initial Purchasers identified below have entered into, or are contemporaneously entering into, a purchase agreement (the "Purchase Agreement," near-final draft), among:

(a) the Co-Issuers, being TSL and TFPL;

(b) Thalassa Dry Bulk Operations Ltd. (a company organized under the laws of the Republic of Malta), Thalassa Container Feeder Ltd. (a corporation organized under the laws of the Republic of the marshall Islands), Thalassa Port Services FZCO (a free zone company organized under the laws of the Emirate of Dubai, United Arab Emirates), and Thalassa Freight Solutions Pte. Ltd. (a private company limited by shares organized under the laws of the Republic of Singapore) (collectively, the "Guarantor Subsidiaries");

(d) Anchor Bay Securities LLC ("ABS," acting as lead bookrunner) and Halcyon Partners International Ltd. ("HPI," acting as co-manager) (together, the "Initial Purchasers");

WHEREAS, the Notes will be issued pursuant to an indenture (the "Indenture," near-final, 5th draft, dated September 6, 2022) among the Co-Issuers, the Guarantor Subsidiaries, Marlowe Asset Management Trust Company of Singapore Pte. Ltd. (as trustee, the "Trustee"), and Atlas Collateral Agency Pte. Ltd. (as security agent, the "Security Agent"), governing the Notes;

WHEREAS, in connection with the offering and sale of the Notes, the Co-Issuers have prepared or caused to be prepared an offering memorandum (the "Offering Memorandum," near-final, 4th draft, dated September 12, 2022), containing information concerning the Co-Issuers, the Guarantor Subsidiaries, the Notes, and the transactions contemplated by the Transaction Documents;

WHEREAS, this Officers' Certificate (this "Certificate") is being delivered pursuant to Section [●] of the Purchase Agreement as a condition precedent to the obligations of the Initial Purchasers to purchase the Notes on the Closing Date (as defined in the Purchase Agreement); and

WHEREAS, capitalized terms used but not otherwise defined herein shall have the meanings assigned to them in the Purchase Agreement or, if not defined therein, in the Indenture.

NOW, THEREFORE, the undersigned hereby certify as follows:

SECTION 1 — CAPACITY AND AUTHORITY

1.1 Each of the undersigned officers hereby certifies that he or she is a duly elected or appointed officer of TSL (and, in the case of Marina Demetriou, the Sole Director of TFPL) and is duly authorized to execute and deliver this Certificate on behalf of TSL and, where applicable, TFPL. Each of the undersigned has been so authorized by all requisite corporate action, including the resolutions of the board of directors of TSL adopted on [●], 2022, and the sole director resolution of TFPL dated [●], 2022, copies of which have been delivered to the Initial Purchasers and their counsel.

1.2 Each of the undersigned certifies that he or she has made, or has caused to be made, such investigations and inquiries as he or she deemed necessary and appropriate in order to enable him or her to make the certifications and deliver the confirmations set forth in this Certificate. In making such investigations and inquiries, the undersigned have, among other things, reviewed the Transaction Documents, consulted with legal counsel (including Calderwood & Harkness LLP, Delphi & Karidis LLP, and Rajendra & Osman LLP), discussed relevant matters with the independent auditors of TSL (Kestrel & White Chartered Accountants), reviewed internal financial records and reports, and conferred with the management teams of the Co-Issuers and the Guarantor Subsidiaries.

1.3 Each of the undersigned confirms that he or she is familiar with the terms and provisions of the Purchase Agreement, the Indenture, the Security Documents (including the Deeds of Ship Mortgage, the Deeds of Assignment of Earnings and Insurances, the Share Pledge Agreements, and the Assignment of Intercompany Loan Receivables), the Intercreditor Agreement, the Registration Rights Agreement, and all other Transaction Documents (as such term is defined in the Purchase Agreement), and has reviewed the Offering Memorandum in its entirety.

SECTION 2 — ACCURACY OF REPRESENTATIONS AND WARRANTIES

2.1 Purchase Agreement Representations

Each of the undersigned hereby certifies that each of the representations and warranties of the Co-Issuers and the Guarantor Subsidiaries set forth in Section [●] of the Purchase Agreement is true and correct in all material respects as of the date hereof (the Closing Date), with the same force and effect as though such representations and warranties had been made on and as of the Closing Date, except to the extent that any such representation or warranty expressly relates to an earlier specified date, in which case such representation or warranty was true and correct in all material respects as of such earlier specified date.

Without limiting the generality of the foregoing, the undersigned confirm that the following representations and warranties, among others, contained in the Purchase Agreement are true and correct in all material respects as of the Closing Date:

(a) Due Organization, Valid Existence, and Good Standing of TSL. TSL is duly organized, validly existing, and in good standing as a Société Anonyme under the laws of the Hellenic Republic, with registration number GEMI No. 148276201000, and with its registered office located at 42 Akti Miaouli, Piraeus 185 35, Greece. TSL has all requisite corporate power and authority to own, lease, and operate its properties and assets and to conduct its business as presently conducted and as described in the Offering Memorandum.

(b) Due Organization, Valid Existence, and Good Standing of TFPL. TFPL is duly organized, validly existing, and in good standing as a private company limited by shares under the laws of the Republic of Singapore, with Unique Entity Number (UEN) 202209345K, and with its registered office located at 8 Marina Boulevard, #36-02, Marina Bay Financial Centre Tower 1, Singapore 018981. TFPL has all requisite corporate power and authority to own, lease, and operate its properties and assets and to conduct its business as presently conducted and as described in the Offering Memorandum.

(c) Due Organization of Guarantor Subsidiaries. Each of the Guarantor Subsidiaries is duly organized, validly existing, and in good standing (to the extent that the concept of good standing is recognized) under the laws of its respective jurisdiction of organization, specifically: (i) Thalassa Dry Bulk Operations Ltd. under the laws of the Republic of Malta; (ii) Thalassa Container Feeder Ltd. under the laws of the Republic of the marshall Islands; (iii) Thalassa Port Services FZCO under the laws of the Emirate of Dubai, United Arab Emirates; and (iv) Thalassa Freight Solutions Pte. Ltd. under the laws of the Republic of Singapore. Each Guarantor Subsidiary has all requisite corporate or similar power and authority to own, lease, and operate its properties and assets, to conduct its business as presently conducted, and to execute, deliver, and perform its obligations under the Transaction Documents to which it is a party.

(d) Corporate Power and Authority. Each of the Co-Issuers and each Guarantor Subsidiary has full corporate power and authority to execute, deliver, and perform its obligations under each Transaction Document to which it is a party, and to consummate the transactions contemplated thereby, including without limitation the issuance of the Notes by the Co-Issuers, the grant of the Guarantees by the Guarantor Subsidiaries, and the execution, delivery, and performance of the Security Documents.

(e) Due Authorization. The execution, delivery, and performance by each of the Co-Issuers and each Guarantor Subsidiary of each Transaction Document to which it is a party, and the consummation of the transactions contemplated thereby, have been duly authorized by all necessary corporate action, including, without limitation, the resolutions of the board of directors of TSL and the sole director resolutions of TFPL, copies of which have been delivered to the Initial Purchasers and their counsel. No further corporate action on the part of any of the Co-Issuers or any Guarantor Subsidiary is required in connection therewith.

(f) No Conflicts. The execution, delivery, and performance by each of the Co-Issuers and each Guarantor Subsidiary of each Transaction Document to which it is a party, and the consummation of the transactions contemplated thereby, do not and will not (i) conflict with or violate any provision of the organizational documents (including the articles of association, memorandum of association, certificate of incorporation, or equivalent documents) of such entity, (ii) conflict with, violate, result in a breach of, or constitute a default (or an event that, with the giving of notice or the lapse of time or both, would constitute a default) under any material agreement, instrument, contract, or obligation to which such entity is a party or by which any of its properties or assets are bound, or (iii) conflict with or violate any applicable law, rule, regulation, order, judgment, decree, or governmental requirement applicable to such entity or any of its properties or assets.

(g) Capitalization and Ownership Structure. The capitalization and ownership structure of TSL is as described in the Offering Memorandum. As of the date hereof, the issued and outstanding share capital of TSL is owned as follows: (i) 72.5% by Kallistratos Maritime Holdings Ltd.; (ii) 18.0% by Pelagos Capital Partners Fund III LP; and (iii) 9.5% by the management employee stock ownership plan trust (the "ESOP Trust"). All issued and outstanding shares of TSL have been duly authorized and validly issued, are fully paid and non-assessable, and were issued in compliance with all applicable securities laws.

(h) Valid Issuance; Enforceability. The Notes, when issued and delivered in accordance with the terms of the Indenture and the Purchase Agreement and paid for by the Initial Purchasers, will be validly issued, fully paid, and non-assessable obligations of the Co-Issuers, enforceable against the Co-Issuers in accordance with their terms, subject to applicable bankruptcy, insolvency, reorganization, moratorium, and similar laws affecting creditors' rights generally and to general principles of equity. The Indenture, the Guarantees, and the Security Documents constitute, or upon execution and delivery will constitute, valid and legally binding obligations of the parties thereto, enforceable in accordance with their respective terms, subject to the same qualifications.

(i) No Required Governmental or Regulatory Consents. No consent, approval, authorization, order, registration, filing, or qualification of or with any governmental or regulatory authority is required for the execution, delivery, and performance by any of the Co-Issuers or any Guarantor Subsidiary of any Transaction Document to which it is a party, or for the consummation of the transactions contemplated thereby, other than (i) those that have been obtained on or prior to the date hereof, (ii) the filing of the application with Singapore Exchange Securities Trading Limited ("SGX-ST") for the listing of the Notes, and (iii) such as may be required under state securities or "blue sky" laws in connection with the purchase and distribution of the Notes by the Initial Purchasers.

(j) Compliance with Laws. Each of the Co-Issuers and each Guarantor Subsidiary is in compliance in all material respects with all applicable laws, rules, regulations, orders, judgments, and decrees, including without limitation the securities laws of the Republic of Singapore (including the Securities and Futures Act 2001 of Singapore, as amended), the laws of the Hellenic Republic, the securities laws of the United States of America (including the Securities Act of 1933, as amended (the "Securities Act"), and the Securities Exchange Act of 1934, as amended (the "Exchange Act")), and the laws of all other relevant jurisdictions in which the Co-Issuers and the Guarantor Subsidiaries conduct their respective businesses.

(k) Accuracy of Financial Information. The financial information included or incorporated by reference in the Offering Memorandum has been prepared in accordance with the accounting principles described therein, has been accurately extracted from the books and records of the Co-Issuers and the Guarantor Subsidiaries, and presents fairly in all material respects the financial condition and results of operations of TSL, TFPL, and the Guarantor Subsidiaries as of the dates and for the periods specified therein.

2.2 Offering Memorandum Representations

Each of the undersigned hereby certifies that the Offering Memorandum (comprising approximately 280 pages, near-final, 4th draft, dated September 12, 2022), as of its date and as of the Closing Date, does not contain any untrue statement of a material fact or omit to state a material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading.

This certification extends to all sections of the Offering Memorandum, including without limitation the following:

(a) the summary and cover pages, which describe the offering of $400,000,000 aggregate principal amount of 8.750% Senior Secured Notes due 2029 by the Co-Issuers;

(b) the section entitled "Risk Factors," setting forth material risks relating to the business and financial condition of the Co-Issuers and the Guarantor Subsidiaries, the industry in which they operate, and the terms of the Notes;

(c) the section entitled "Use of Proceeds," which describes the intended application of the proceeds of the offering as follows: approximately $190,000,000 to refinance the bilateral ship-finance facility of Meridian Maritime Bank AG; approximately $120,000,000 to refinance the bilateral ship-finance facility of Clearwater Shipping Finance Ltd.; approximately $72,000,000 for general corporate purposes and fleet capital expenditures; and approximately $18,000,000 for estimated fees and expenses of the offering, including original issue discount;

(d) the capitalization table, reflecting the pro forma capitalization of TSL and its consolidated subsidiaries after giving effect to the issuance of the Notes and the application of the proceeds therefrom;

(e) the section entitled "Business," describing the operations, fleet, and competitive position of TSL and the Guarantor Subsidiaries, including the 50-vessel fleet consisting of 38 dry-bulk carriers (spanning Supramax, Ultramax, and Kamsarmax classes) and 12 container feeder vessels, with a total fleet appraised value of approximately $1.82 billion and operations conducted across the Eastern Mediterranean, Black Sea, and Southeast Asia trade lanes;

(f) the sections entitled "Selected Financial Data" and "Management's Discussion and Analysis of Financial Condition and Results of Operations";

(g) the section entitled "Description of the Notes," setting forth the material terms of the Notes, including the coupon rate (8.750% per annum), maturity date (2029), security package, financial and restrictive covenants, optional and mandatory redemption provisions, and events of default;

(h) the section entitled "Taxation," describing certain material tax considerations for holders of the Notes;

(i) the section entitled "Plan of Distribution," describing the offer and sale of the Notes pursuant to Rule 144A under the Securities Act and Regulation S under the Securities Act; and

(j) the section entitled "Transfer Restrictions," setting forth the restrictions on the offer, sale, and transfer of the Notes.

Provided, however, that the certifying officers make no representation or warranty with respect to (i) information provided in writing by the Initial Purchasers specifically for inclusion in the Offering Memorandum (the "Initial Purchaser Information"), as identified in Section [●] of the Purchase Agreement, which the undersigned understand to consist solely of the information described in the [●] paragraph[s] under the caption "Plan of Distribution" in the Offering Memorandum, and (ii) statements in the Offering Memorandum made in reliance upon and in conformity with information furnished in writing by Polaris Ratings Group Ltd. or Oceanic Credit Assessments Inc., including credit rating designations, rating agency methodologies, and rating definitions.

SECTION 3 — FINANCIAL CERTIFICATIONS

3.1 Each of the undersigned hereby certifies that the financial data included in the Offering Memorandum, including the key financial metrics set forth below, was accurately presented as of the dates specified therein, was prepared in accordance with the accounting principles described in the Offering Memorandum, and has not become materially misleading as of the Closing Date:

3.2 The undersigned further certify that the methodologies and assumptions used to calculate the financial metrics set forth above, including the definitions of "Adjusted EBITDA," "LTM Revenue," "Pro Forma Total Debt," "Pro Forma Net Debt," "Pro Forma Net Leverage Ratio," and "Pro Forma Interest Coverage Ratio," are consistent with the definitions and methodologies described in the Offering Memorandum and the Indenture. The pro forma adjustments reflected in the foregoing financial data give effect to (i) the issuance of the Notes and the receipt of the gross proceeds therefrom, (ii) the application of such proceeds to refinance the existing indebtedness of TSL owing to Meridian Maritime Bank AG and Clearwater Shipping Finance Ltd., and (iii) the payment of estimated fees and expenses of the offering.

3.3 To the knowledge of the undersigned, the financial statements and financial data audited or reviewed by Kestrel & White Chartered Accountants, as referenced in the comfort letter delivered pursuant to Section [●] of the Purchase Agreement, are fairly presented in all material respects in accordance with the applicable accounting standards identified therein and are consistent with the financial information included in the Offering Memorandum. The undersigned have no reason to believe that the comfort letter delivered by Kestrel & White Chartered Accountants contains any material inaccuracy or is no longer accurate in any material respect as of the Closing Date.

SECTION 4 — NO MATERIAL ADVERSE CHANGE

4.1 Each of the undersigned hereby certifies that, since the date of the most recent financial statements included in the Offering Memorandum, there has been no Material Adverse Change (as such term is defined in the Purchase Agreement), nor any development or event involving a prospective Material Adverse Change, in or affecting:

(a) the business, properties, financial condition, or results of operations of TSL, TFPL, and the Guarantor Subsidiaries, taken as a whole;

(b) the ability of the Co-Issuers to perform their respective obligations under the Indenture, the Notes, the Purchase Agreement, or any other Transaction Document to which either of the Co-Issuers is a party; or

(c) the validity or enforceability of any Transaction Document or the rights and remedies of the Initial Purchasers, the Trustee, or the Security Agent under any Transaction Document.

4.2 The undersigned further certify that the fleet of 50 vessels (comprising 38 dry-bulk carriers and 12 container feeder vessels, with a total deadweight tonnage of approximately 2,850,000 DWT and a weighted average age of approximately 9.2 years as of the date hereof) continues to be operated in substantially the same manner as described in the Offering Memorandum. There has been no material change in the condition, classification, or operating status of any vessel in the fleet since the date of the most recent financial statements included in the Offering Memorandum. All vessels continue to maintain their respective class certifications with the relevant classification societies, and all required statutory and regulatory certifications remain in full force and effect.

4.3 The undersigned further certify that the appraised value of the 28 Collateral Vessels (as set forth in the fleet appraisal delivered by Compass Marine Valuations Ltd. dated June 2022) has not declined below the minimum collateral coverage ratio of 2.00x required under the Indenture as of the Closing Date. As of the date of the fleet appraisal, the 28 Collateral Vessels were appraised at an aggregate value of $1,175,000,000, resulting in a collateral coverage ratio at issuance of 2.94x (calculated as $1,175,000,000 divided by $400,000,000 aggregate principal amount of the Notes). To the knowledge of the undersigned, no events or circumstances have occurred since the date of such appraisal that would reasonably be expected to result in a decline in the aggregate appraised value of the 28 Collateral Vessels below $800,000,000 (which amount would represent the minimum collateral coverage ratio of 2.00x).

SECTION 5 — COMPLIANCE WITH CONDITIONS PRECEDENT

Each of the undersigned hereby certifies that, to the knowledge of the undersigned, all conditions precedent to the obligations of the Initial Purchasers to consummate the purchase of the Notes as set forth in Section [●] of the Purchase Agreement have been satisfied or, where applicable, validly waived in writing by the Initial Purchasers, as of the Closing Date. Without limiting the generality of the foregoing, the undersigned confirm that the following conditions precedent have been satisfied:

(a) Delivery of Executed Transaction Documents. The Co-Issuers and the Guarantor Subsidiaries have duly executed and delivered, or will duly execute and deliver simultaneously with the closing, each of the following Transaction Documents: the Indenture, the Purchase Agreement, the Registration Rights Agreement, the Intercreditor Agreement, the Security Documents (including the Deeds of Ship Mortgage, the Deeds of Assignment of Earnings and Insurances, the Share Pledge Agreements, and the Assignment of Intercompany Loan Receivables), and the Paying Agent and Transfer Agent Agreement.

(b) Delivery of Legal Opinions. The following legal opinions have been delivered or will be delivered on the Closing Date:

(i) an opinion of Calderwood & Harkness LLP, Singapore counsel to the Co-Issuers, as to matters of Singapore law, including the due authorization of the Transaction Documents, the valid issuance of the Notes, and the enforceability of the Notes, the Indenture, and the other Transaction Documents governed by Singapore law;

(ii) an opinion of Delphi & Karidis LLP, Greek counsel to TSL, as to matters of the laws of the Hellenic Republic, including the corporate capacity of TSL, the due authorization and valid adoption of the board resolutions of TSL, and the enforceability of obligations of TSL under Greek law;

(iii) an opinion of Rajendra & Osman LLP, Singapore counsel to TFPL, as to matters of Singapore law, including the corporate capacity of TFPL, the due authorization and valid adoption of the sole director resolutions of TFPL, and compliance with the requirements of the Accounting and Corporate Regulatory Authority of Singapore ("ACRA");

(iv) a negative assurance letter of Whitfield & Crane LLP, counsel to the Initial Purchasers, in accordance with customary practice under Rule 10b-5 of the Exchange Act; and

(v) an opinion of Thornton Ashworth LLP, counsel to the Trustee, as to the authorization and capacity of the Trustee to act in such capacity and customary trustee protection matters.

(c) Delivery of Comfort Letter. The comfort letter of Kestrel & White Chartered Accountants, in form and substance satisfactory to the Initial Purchasers, has been delivered pursuant to Section [●] of the Purchase Agreement, together with any bring-down letter required to be delivered on the Closing Date, and such comfort letter and any bring-down letter confirm the matters described therein as of the respective dates thereof.

(d) Receipt of Ratings. The Co-Issuers have received preliminary ratings of B+ (stable outlook) from Polaris Ratings Group Ltd. and B1 (stable outlook) from Oceanic Credit Assessments Inc. with respect to the Notes, and no such rating has been withdrawn, qualified, or downgraded, and no proceedings or announcements by either rating agency to withdraw, qualify, or downgrade any such rating have been made or are pending.

(e) Fleet Appraisal. The fleet appraisal from Compass Marine Valuations Ltd., dated June 2022, confirming the aggregate appraised value of the 28 Collateral Vessels and the resulting collateral coverage ratio, has been delivered to the Initial Purchasers and the Trustee.

(f) Perfection and Registration of Security Documents. The perfection and registration (or arrangements for the perfection and registration) of all Security Documents have been completed or will be completed promptly following the Closing Date, in each case in accordance with applicable law and the terms of the Indenture and the Security Documents. Such perfection and registration includes, without limitation:

(i) first-priority ship mortgages over each of the 28 Collateral Vessels, to be registered in the relevant ship registries;

(ii) share pledges over the shares of the fleet-owning Guarantor Subsidiaries and TFPL;

(iii) assignments of earnings and insurances with respect to the Collateral Vessels, in favor of the Security Agent; and

(iv) assignment of intercompany loan receivables in the aggregate amount of $365,000,000 owing from TFPL and the Guarantor Subsidiaries to TSL.

(g) Payoff Letters. Payoff letters have been received from each of (i) Meridian Maritime Bank AG, confirming the payoff amount of $190,000,000 (together with any accrued and unpaid interest as of the Closing Date, per diem interest calculations, wire transfer instructions, and the mechanics for the release of all existing security interests held by Meridian Maritime Bank AG over the relevant vessels and other assets), and (ii) Clearwater Shipping Finance Ltd., confirming the payoff amount of $120,000,000 (together with any accrued and unpaid interest as of the Closing Date, per diem interest calculations, wire transfer instructions, and the mechanics for the release of all existing security interests held by Clearwater Shipping Finance Ltd. over the relevant vessels and other assets).

(h) Corporate Resolutions. Duly certified copies of the resolutions of the board of directors of TSL and the sole director resolutions of TFPL, in each case authorizing the execution, delivery, and performance of the Transaction Documents and the consummation of the transactions contemplated thereby, have been delivered to the Initial Purchasers and their counsel.

(i) SGX-ST Listing Application. An application for the listing of the Notes on the SGX-ST has been duly filed, and the Co-Issuers are not aware of any reason why such listing should not be granted in due course.

(j) No Stop Order, Injunction, or Legal Restraint. No stop order, injunction, restraining order, or other legal or regulatory restraint or prohibition preventing the consummation of the offering, the issuance or delivery of the Notes, or any of the other transactions contemplated by the Transaction Documents has been issued, entered, or threatened by any court, governmental authority, or regulatory body, and no proceedings seeking any such stop order, injunction, restraining order, or other legal or regulatory restraint or prohibition are pending or, to the knowledge of the undersigned, threatened.

SECTION 6 — NO PROCEEDINGS

Each of the undersigned hereby certifies that, as of the Closing Date, there are no legal, governmental, or regulatory investigations, actions, suits, claims, arbitrations, or proceedings (collectively, "Proceedings") pending, or, to the knowledge of the undersigned after due inquiry, threatened in writing against any of the Co-Issuers, the Guarantor Subsidiaries, or the Parent Guarantor, which:

(a) seek to restrain, enjoin, or otherwise prevent the consummation of any of the transactions contemplated by the Purchase Agreement, the Indenture, or any other Transaction Document;

(b) challenge the validity, binding effect, or enforceability of the Notes, the Indenture, the Purchase Agreement, any Guarantee, any Security Document, or any other Transaction Document;

(c) would, individually or in the aggregate, reasonably be expected to result in a Material Adverse Change (as defined in the Purchase Agreement); or

(d) are required to be described or disclosed in the Offering Memorandum pursuant to applicable law, regulation, or the requirements of the Purchase Agreement and are not so described or disclosed therein.

The undersigned further confirm that, to their knowledge after due inquiry, there are no Proceedings pending or threatened against any director, officer, or key employee of any of the Co-Issuers or the Guarantor Subsidiaries in their capacity as such that would, individually or in the aggregate, reasonably be expected to have a material impact on the ability of the Co-Issuers or the Guarantor Subsidiaries to consummate the transactions contemplated by the Transaction Documents or to perform their respective obligations thereunder.

SECTION 7 — ORGANIZATIONAL AND CORPORATE MATTERS

7.1 The undersigned hereby confirm that TSL remains duly organized and validly existing as a Société Anonyme under the laws of the Hellenic Republic, with registration number GEMI No. 148276201000, and with its registered office located at 42 Akti Miaouli, Piraeus 185 35, Greece. TSL has not been dissolved, wound up, merged, consolidated, or otherwise reorganized, and no proceedings for the dissolution, winding up, merger, consolidation, or other reorganization of TSL have been commenced or are pending or, to the knowledge of the undersigned, threatened.

7.2 The undersigned hereby confirm that TFPL remains duly organized and validly existing as a private company limited by shares under the laws of the Republic of Singapore, with Unique Entity Number (UEN) 202209345K, and with its registered office located at 8 Marina Boulevard, #36-02, Marina Bay Financial Centre Tower 1, Singapore 018981. TFPL has not been dissolved, wound up, merged, consolidated, or otherwise reorganized, and no proceedings for the dissolution, winding up, merger, consolidation, or other reorganization of TFPL have been commenced or are pending or, to the knowledge of the undersigned, threatened. TFPL remains in good standing with the Accounting and Corporate Regulatory Authority of Singapore ("ACRA"), and all required annual filings and returns with ACRA are current.

7.3 The undersigned hereby confirm that each of the Guarantor Subsidiaries is duly organized and validly existing under the laws of its respective jurisdiction of organization, as set forth in Section 2.1 above, and that each Guarantor Subsidiary has all requisite corporate or similar power and authority to own, lease, and operate its properties and assets, to conduct its business as presently conducted, and to perform its obligations under the Transaction Documents to which it is a party. No Guarantor Subsidiary has been dissolved, wound up, merged, consolidated, or otherwise reorganized, and no proceedings for any such event have been commenced or are pending or, to the knowledge of the undersigned, threatened.

7.4 The undersigned hereby confirm that no event of bankruptcy, insolvency, receivership, reorganization, administration, winding up, liquidation, or similar proceeding has been commenced by or against any of the Co-Issuers, any Guarantor Subsidiary, or the Parent Guarantor. No petition or application for the commencement of any such proceeding has been filed or presented, and to the knowledge of the undersigned, no such petition or application is contemplated or threatened. Neither of the Co-Issuers nor any Guarantor Subsidiary is unable to pay its debts as they fall due, and neither of the Co-Issuers nor any Guarantor Subsidiary has made a general assignment for the benefit of its creditors.

SECTION 8 — USE OF PROCEEDS CONFIRMATION

Each of the undersigned hereby certifies that the proceeds of the offering of the Notes will be applied substantially as described in the Offering Memorandum under the caption "Use of Proceeds." Specifically, the net proceeds of the offering, together with cash on hand, will be applied as follows:

The Notes will be issued at an issue price of 98.00% of par, yielding gross proceeds of $392,000,000 and resulting in an original issue discount of $8,000,000. In addition, the Initial Purchaser discount payable by the Co-Issuers to the Initial Purchasers shall be $8,000,000 (representing 2.00% of the aggregate principal amount of the Notes). After accounting for the original issue discount and the remaining estimated fees and expenses of the offering (including legal fees, accounting fees, trustee and security agent fees, rating agency fees, printing and distribution costs, and other transaction expenses), the total estimated fees, expenses, and original issue discount amount to approximately $18,000,000.

The total uses of proceeds of $400,000,000 will be funded from the gross proceeds of the offering of $392,000,000, supplemented by approximately $8,000,000 from TSL cash on hand. After absorbing the original issue discount, the net additional cash contribution from TSL is approximately $10,000,000. The Co-Issuers confirm that all amounts will be applied in a manner consistent with the terms of the Indenture and the Purchase Agreement, and that no portion of the proceeds will be used in violation of any applicable law or any restrictive covenant set forth in the Indenture.

SECTION 9 — NO DEFAULT

9.1 Each of the undersigned hereby certifies that, as of the Closing Date, no Default or Event of Default (each as defined in the Indenture) has occurred and is continuing, and no Default or Event of Default would result from, or arise in connection with, the issuance of the Notes, the execution and delivery of the Indenture and the other Transaction Documents, or the application of the proceeds of the offering as described in Section 8 above and in the Offering Memorandum under "Use of Proceeds."

9.2 The undersigned further certify that, upon giving effect to the issuance of the Notes and the application of the proceeds therefrom (including the refinancing of the existing bilateral ship-finance facilities of Meridian Maritime Bank AG and Clearwater Shipping Finance Ltd.), TSL and its consolidated subsidiaries are in compliance with all incurrence-based financial tests and covenants set forth in the Indenture, including without limitation:

(a) Total Net Leverage Ratio. The Total Net Leverage Ratio (as defined in the Indenture) does not exceed 3.50x. On a pro forma basis after giving effect to the issuance and the refinancing, the Total Net Leverage Ratio is 1.59x, calculated as follows: Pro Forma Net Debt of $341,700,000 divided by LTM Adjusted EBITDA of $214,600,000.

(b) Collateral Coverage Ratio. The Collateral Coverage Ratio (as defined in the Indenture) is at or above 2.00x. At issuance, the Collateral Coverage Ratio is 2.94x, calculated as follows: aggregate appraised value of the 28 Collateral Vessels of $1,175,000,000 divided by the aggregate principal amount of the Notes of $400,000,000.

9.3 To the knowledge of the undersigned, no event has occurred or condition exists that, with the giving of notice or the lapse of time or both, would constitute a Default or Event of Default under the Indenture.

SECTION 10 — INSURANCE AND COLLATERAL MATTERS

10.1 Each of the undersigned hereby certifies that all insurance policies covering the 28 Collateral Vessels (including hull and machinery insurance, protection and indemnity insurance, war risk insurance, and loss of hire insurance) are in full force and effect as of the Closing Date, all premiums due and payable thereunder have been paid or are current, and the coverage levels and terms of such insurance policies are consistent with the requirements of the Indenture and the Security Documents. The insurances are placed with reputable insurers and/or mutual protection and indemnity associations, and the coverage amounts are consistent with customary practice in the international shipping industry for vessels of similar type, size, age, and trade.

10.2 Assignments of insurance proceeds in favor of Atlas Collateral Agency Pte. Ltd. (UEN 200115678R), in its capacity as Security Agent under the Indenture, have been or will be duly made in accordance with the Deeds of Assignment of Earnings and Insurances and the other Security Documents, and the relevant insurers and/or protection and indemnity associations have been or will be duly notified of such assignments, with acknowledgment of such assignments to be obtained in accordance with customary practice.

10.3 The undersigned further certify that no Collateral Vessel has suffered a total loss or constructive total loss since the date of the fleet appraisal delivered by Compass Marine Valuations Ltd. (June 2022). No Collateral Vessel has been arrested, detained, seized, or confiscated by any governmental or regulatory authority, and no Collateral Vessel is subject to any requisition for use or title by any governmental authority. To the knowledge of the undersigned, no event has occurred that would give rise to a claim for a total loss or constructive total loss with respect to any Collateral Vessel.

SECTION 11 — ADDITIONAL CERTIFICATIONS

11.1 Each of the undersigned hereby certifies that the certificates of incorporation, articles of association, memoranda of association, and other organizational documents of TSL and TFPL that have been delivered to the Initial Purchasers and their counsel (Whitfield & Crane LLP) are true, complete, and correct copies of such documents as in effect on and as of the Closing Date. No amendments or modifications to any such organizational documents have been adopted, approved, or proposed since the date on which such copies were delivered to the Initial Purchasers and their counsel.

11.2 Each of the undersigned hereby certifies that the incumbency and specimen signatures of the officers and directors of TSL and TFPL who are authorized to execute and deliver the Transaction Documents and any certificates, instruments, or other documents on behalf of TSL and TFPL, as set forth in the incumbency certificates delivered to the Initial Purchasers and their counsel, are true, correct, and genuine as of the Closing Date.

11.3 As of the Closing Date, the following persons are the duly elected or appointed officers and/or directors authorized to execute Transaction Documents and any related certificates, instruments, or documents on behalf of TSL and/or TFPL:

Each of the foregoing persons remains duly qualified and authorized to act in the capacity indicated above, and no revocation, suspension, or limitation of such authority has occurred or is contemplated.

SECTION 12 — RELIANCE

12.1 This Certificate is delivered to the Initial Purchasers, Anchor Bay Securities LLC and Halcyon Partners International Ltd., and to the Trustee, Marlowe Asset Management Trust Company of Singapore Pte. Ltd., in satisfaction of the conditions precedent set forth in Section [●] of the Purchase Agreement, as a condition to the obligations of the Initial Purchasers to consummate the purchase of the Notes on the Closing Date.

12.2 Each of the Initial Purchasers and their counsel (Whitfield & Crane LLP), the Trustee and its counsel (Thornton Ashworth LLP), and the Co-Issuers' counsel (Calderwood & Harkness LLP) are entitled to rely on the certifications, representations, and confirmations contained in this Certificate as though such certifications, representations, and confirmations were made directly to each such person. The delivery of this Certificate shall not, however, confer any rights upon any other person or entity, except as expressly provided in the Purchase Agreement.

12.3 The certifications, representations, and confirmations set forth in this Certificate are made as of the Closing Date and speak only as of the Closing Date. Nothing in this Certificate shall be deemed to create any obligation on the part of the undersigned or the Co-Issuers to update or supplement the certifications contained herein after the Closing Date, except as may otherwise be required under the Purchase Agreement, the Indenture, or applicable law.

SECTION 13 — GOVERNING LAW

This Certificate shall be governed by and construed in accordance with the laws of the Republic of Singapore, without regard to conflicts of law principles thereof that would result in the application of the laws of any other jurisdiction. The choice of Singapore law as the governing law of this Certificate is consistent with the governing law of the Indenture, the Purchase Agreement, and the other Transaction Documents.

[Signature Page Follows]

IN WITNESS WHEREOF, the undersigned have executed this Officers' Certificate as of the date first written above.

THALASSA SHIPPING & LOGISTICS SA

By: ________

Name: Spyros Andreou

Title: Chief Executive Officer

Date: [●], 2022

THALASSA SHIPPING & LOGISTICS SA and THALASSA FINANCE PTE. LTD.

By: ________

Name: Marina Demetriou

Title: Chief Financial Officer, Thalassa Shipping & Logistics SA;

Sole Director, Thalassa Finance Pte. Ltd.

Date: [●], 2022

[UNEXECUTED — FORM ONLY]

SCHEDULE A — DEFINED TERMS CROSS-REFERENCE

The following table sets forth a cross-reference of certain key defined terms used in this Certificate to the provisions of the Purchase Agreement or the Indenture in which such terms are defined:

SCHEDULE B — LIST OF TRANSACTION DOCUMENTS

The following is a list of the Transaction Documents referenced in this Certificate:

1. Indenture (near-final, 5th draft, dated September 6, 2022), among the Co-Issuers, the Guarantor Subsidiaries, Marlowe Asset Management Trust Company of Singapore Pte. Ltd. (as Trustee), and Atlas Collateral Agency Pte. Ltd. (as Security Agent).

2. Purchase Agreement (near-final draft), among the Co-Issuers, the Guarantor Subsidiaries, Kallistratos Maritime Holdings Ltd. (as limited parent guarantor), and the Initial Purchasers.

3. Registration Rights Agreement (near-final draft), among the Co-Issuers, the Guarantor Subsidiaries, and the Initial Purchasers.

4. Intercreditor Agreement (near-final, 3rd draft), among the Co-Issuers, the Guarantor Subsidiaries, the Trustee, the Security Agent, and such other parties as may be party thereto.

5. Deed of Ship Mortgage (form), covering the 28 Collateral Vessels, to be entered into by the relevant fleet-owning Guarantor Subsidiaries in favor of the Security Agent.

6. Deed of Assignment of Earnings and Insurances (form), to be entered into by the relevant fleet-owning Guarantor Subsidiaries in favor of the Security Agent, with respect to the earnings and insurances relating to the Collateral Vessels.

7. Share Pledge Agreement — Thalassa Finance Pte. Ltd., pursuant to which TSL will pledge its shares in TFPL in favor of the Security Agent.

8. Share Pledge Agreement — Fleet-Owning Guarantor Subsidiaries (form), pursuant to which the relevant parent entities will pledge their shares in each fleet-owning Guarantor Subsidiary in favor of the Security Agent.

9. Assignment of Intercompany Loan Receivables ($365,000,000), pursuant to which the relevant intercompany loan receivables will be assigned to the Security Agent as additional collateral for the benefit of the holders of the Notes.

10. Paying Agent and Transfer Agent Agreement (near-final draft), among the Co-Issuers and the Trustee (acting in its capacity as paying agent, transfer agent, and registrar with respect to the Notes).

11. Form of Global Note — Rule 144A, representing Notes sold pursuant to Rule 144A under the Securities Act (proposed CUSIP: 87265T AA1; proposed ISIN: US87265TAA10).

12. Form of Global Note — Regulation S, representing Notes sold pursuant to Regulation S under the Securities Act (proposed ISIN: XS2498731056; proposed Common Code: 249873105).

Calderwood & Harkness LLP — Matter No. 1044-00004 — Client No. 80214-TSL

FORM — PREPARED FOR EXECUTION AT CLOSING — UNEXECUTED

Financial Metric	Amount / Value
LTM Revenue (Q1 2022 annualized)	$687,400,000
LTM Adjusted EBITDA (Q1 2022 annualized)	$214,600,000
EBITDA Margin	31.2%
Pro Forma Total Debt (post-offering)	$400,000,000
Cash on Balance Sheet	$58,300,000
Pro Forma Net Debt	$341,700,000
Pro Forma Net Leverage Ratio	1.59x
Pro Forma Interest Coverage Ratio	6.13x
Annual Interest Expense on the Notes	$35,000,000
Application of Proceeds	Amount
Refinancing of Meridian Maritime Bank AG bilateral ship-finance facility	$190,000,000
Refinancing of Clearwater Shipping Finance Ltd. bilateral ship-finance facility	$120,000,000
General corporate purposes and fleet capital expenditures	$72,000,000
Estimated fees, expenses, and original issue discount	Approximately $18,000,000
Total	$400,000,000
Name	Title	Entity
Spyros Andreou	Chief Executive Officer	Thalassa Shipping & Logistics SA
Marina Demetriou	Chief Financial Officer / Sole Director	Thalassa Shipping & Logistics SA / Thalassa Finance Pte. Ltd.
Alexandros Theodorakis	General Counsel	Thalassa Shipping & Logistics SA
Defined Term	Defined in	Section / Article
Material Adverse Change	Purchase Agreement	Section [●]
Default	Indenture	Section 1.01
Event of Default	Indenture	Article VI
Collateral Vessels	Indenture	Section 1.01

Guarantor Subsidiaries	Purchase Agreement	Preamble
Transaction Documents	Purchase Agreement	Section [●]
Net Proceeds	Indenture	Section 1.01
Total Net Leverage Ratio	Indenture	Section 1.01
Collateral Coverage Ratio	Indenture	Section 1.01
Consolidated Net Tangible Assets	Indenture	Section 1.01
Closing Date	Purchase Agreement	Section [●]
Co-Issuers	Purchase Agreement	Preamble
Initial Purchasers	Purchase Agreement	Preamble
Offering Memorandum	Purchase Agreement	Section [●]
Security Documents	Indenture	Section 1.01
Intercreditor Agreement	Indenture	Section 1.01
Registration Rights Agreement	Purchase Agreement	Section [●]
Adjusted EBITDA	Indenture	Section 1.01
Permitted Indebtedness	Indenture	Section 4.[●]
Permitted Liens	Indenture	Section 4.[●]

FORM OF OFFICERS' CERTIFICATE
Officers' Certificate Pursuant to Section [●] of the Purchase Agreement
Delivered in connection with the offering of $400,000,000 aggregate principal amount of 8.750% Senior Secured Notes due 2029 (the "Notes")
Co-Issuers:
Thalassa Shipping & Logistics SA ("TSL") and Thalassa Finance Pte. Ltd. ("TFPL," and together with TSL, the "Co-Issuers")
[FORM — UNEXECUTED]
Dated: [●], 2022
RECITALS
The undersigned, Spyros Andreou, in his capacity as Chief Executive Officer of Thalassa Shipping & Logistics SA, a Société Anonyme organized and existing under the laws of the Hellenic Republic ("TSL"), and Marina Demetriou, in her capacity as Chief Financial Officer of TSL and Sole Director of Thalassa Finance Pte. Ltd., a private company limited by shares organized and existing under the laws of the Republic of Singapore ("TFPL," and together with TSL, the "Co-Issuers"), hereby certify as follows in connection with the offering of $400,000,000 aggregate principal amount of 8.750% Senior Secured Notes due 2029 (the "Notes") by the Co-Issuers:
WHEREAS, the Co-Issuers, the Guarantor Subsidiaries identified below, Kallistratos Maritime Holdings Ltd. (as limited parent guarantor), and the Initial Purchasers identified below have entered into, or are contemporaneously entering into, a purchase agreement (the "Purchase Agreement," near-final draft), among:
(a) the Co-Issuers, being TSL and TFPL;
(b) Thalassa Dry Bulk Operations Ltd. (a company organized under the laws of the Republic of Malta), Thalassa Container Feeder Ltd. (a corporation organized under the laws of the Republic of the marshall Islands), Thalassa Port Services FZCO (a free zone company organized under the laws of the Emirate of Dubai, United Arab Emirates), and Thalassa Freight Solutions Pte. Ltd. (a private company limited by shares organized under the laws of the Republic of Singapore) (collectively, the "Guarantor Subsidiaries");
(c) Kallistratos Maritime Holdings Ltd. (the "Parent Guarantor"); and
(d) Anchor Bay Securities LLC ("ABS," acting as lead bookrunner) and Halcyon Partners International Ltd. ("HPI," acting as co-manager) (together, the "Initial Purchasers");
WHEREAS, the Notes will be issued pursuant to an indenture (the "Indenture," near-final, 5th draft, dated September 6, 2022) among the Co-Issuers, the Guarantor Subsidiaries, Marlowe Asset Management Trust Company of Singapore Pte. Ltd. (as trustee, the "Trustee"), and Atlas Collateral Agency Pte. Ltd. (as security agent, the "Security Agent"), governing the Notes;
WHEREAS, in connection with the offering and sale of the Notes, the Co-Issuers have prepared or caused to be prepared an offering memorandum (the "Offering Memorandum," near-final, 4th draft, dated September 12, 2022), containing information concerning the Co-Issuers, the Guarantor Subsidiaries, the Notes, and the transactions contemplated by the Transaction Documents;
WHEREAS, this Officers' Certificate (this "Certificate") is being delivered pursuant to Section [●] of the Purchase Agreement as a condition precedent to the obligations of the Initial Purchasers to purchase the Notes on the Closing Date (as defined in the Purchase Agreement); and
WHEREAS, capitalized terms used but not otherwise defined herein shall have the meanings assigned to them in the Purchase Agreement or, if not defined therein, in the Indenture.
NOW, THEREFORE, the undersigned hereby certify as follows:
SECTION 1 — CAPACITY AND AUTHORITY
1.1 Each of the undersigned officers hereby certifies that he or she is a duly elected or appointed officer of TSL (and, in the case of Marina Demetriou, the Sole Director of TFPL) and is duly authorized to execute and deliver this Certificate on behalf of TSL and, where applicable, TFPL. Each of the undersigned has been so authorized by all requisite corporate action, including the resolutions of the board of directors of TSL adopted on [●], 2022, and the sole director resolution of TFPL dated [●], 2022, copies of which have been delivered to the Initial Purchasers and their counsel.
1.2 Each of the undersigned certifies that he or she has made, or has caused to be made, such investigations and inquiries as he or she deemed necessary and appropriate in order to enable him or her to make the certifications and deliver the confirmations set forth in this Certificate. In making such investigations and inquiries, the undersigned have, among other things, reviewed the Transaction Documents, consulted with legal counsel (including Calderwood & Harkness LLP, Delphi & Karidis LLP, and Rajendra & Osman LLP), discussed relevant matters with the independent auditors of TSL (Kestrel & White Chartered Accountants), reviewed internal financial records and reports, and conferred with the management teams of the Co-Issuers and the Guarantor Subsidiaries.
1.3 Each of the undersigned confirms that he or she is familiar with the terms and provisions of the Purchase Agreement, the Indenture, the Security Documents (including the Deeds of Ship Mortgage, the Deeds of Assignment of Earnings and Insurances, the Share Pledge Agreements, and the Assignment of Intercompany Loan Receivables), the Intercreditor Agreement, the Registration Rights Agreement, and all other Transaction Documents (as such term is defined in the Purchase Agreement), and has reviewed the Offering Memorandum in its entirety.
SECTION 2 — ACCURACY OF REPRESENTATIONS AND WARRANTIES
2.1 Purchase Agreement Representations
Each of the undersigned hereby certifies that each of the representations and warranties of the Co-Issuers and the Guarantor Subsidiaries set forth in Section [●] of the Purchase Agreement is true and correct in all material respects as of the date hereof (the Closing Date), with the same force and effect as though such representations and warranties had been made on and as of the Closing Date, except to the extent that any such representation or warranty expressly relates to an earlier specified date, in which case such representation or warranty was true and correct in all material respects as of such earlier specified date.
Without limiting the generality of the foregoing, the undersigned confirm that the following representations and warranties, among others, contained in the Purchase Agreement are true and correct in all material respects as of the Closing Date:
(a) Due Organization, Valid Existence, and Good Standing of TSL. TSL is duly organized, validly existing, and in good standing as a Société Anonyme under the laws of the Hellenic Republic, with registration number GEMI No. 148276201000, and with its registered office located at 42 Akti Miaouli, Piraeus 185 35, Greece. TSL has all requisite corporate power and authority to own, lease, and operate its properties and assets and to conduct its business as presently conducted and as described in the Offering Memorandum.
(b) Due Organization, Valid Existence, and Good Standing of TFPL. TFPL is duly organized, validly existing, and in good standing as a private company limited by shares under the laws of the Republic of Singapore, with Unique Entity Number (UEN) 202209345K, and with its registered office located at 8 Marina Boulevard, #36-02, Marina Bay Financial Centre Tower 1, Singapore 018981. TFPL has all requisite corporate power and authority to own, lease, and operate its properties and assets and to conduct its business as presently conducted and as described in the Offering Memorandum.
(c) Due Organization of Guarantor Subsidiaries. Each of the Guarantor Subsidiaries is duly organized, validly existing, and in good standing (to the extent that the concept of good standing is recognized) under the laws of its respective jurisdiction of organization, specifically: (i) Thalassa Dry Bulk Operations Ltd. under the laws of the Republic of Malta; (ii) Thalassa Container Feeder Ltd. under the laws of the Republic of the marshall Islands; (iii) Thalassa Port Services FZCO under the laws of the Emirate of Dubai, United Arab Emirates; and (iv) Thalassa Freight Solutions Pte. Ltd. under the laws of the Republic of Singapore. Each Guarantor Subsidiary has all requisite corporate or similar power and authority to own, lease, and operate its properties and assets, to conduct its business as presently conducted, and to execute, deliver, and perform its obligations under the Transaction Documents to which it is a party.
(d) Corporate Power and Authority. Each of the Co-Issuers and each Guarantor Subsidiary has full corporate power and authority to execute, deliver, and perform its obligations under each Transaction Document to which it is a party, and to consummate the transactions contemplated thereby, including without limitation the issuance of the Notes by the Co-Issuers, the grant of the Guarantees by the Guarantor Subsidiaries, and the execution, delivery, and performance of the Security Documents.
(e) Due Authorization. The execution, delivery, and performance by each of the Co-Issuers and each Guarantor Subsidiary of each Transaction Document to which it is a party, and the consummation of the transactions contemplated thereby, have been duly authorized by all necessary corporate action, including, without limitation, the resolutions of the board of directors of TSL and the sole director resolutions of TFPL, copies of which have been delivered to the Initial Purchasers and their counsel. No further corporate action on the part of any of the Co-Issuers or any Guarantor Subsidiary is required in connection therewith.
(f) No Conflicts. The execution, delivery, and performance by each of the Co-Issuers and each Guarantor Subsidiary of each Transaction Document to which it is a party, and the consummation of the transactions contemplated thereby, do not and will not (i) conflict with or violate any provision of the organizational documents (including the articles of association, memorandum of association, certificate of incorporation, or equivalent documents) of such entity, (ii) conflict with, violate, result in a breach of, or constitute a default (or an event that, with the giving of notice or the lapse of time or both, would constitute a default) under any material agreement, instrument, contract, or obligation to which such entity is a party or by which any of its properties or assets are bound, or (iii) conflict with or violate any applicable law, rule, regulation, order, judgment, decree, or governmental requirement applicable to such entity or any of its properties or assets.
(g) Capitalization and Ownership Structure. The capitalization and ownership structure of TSL is as described in the Offering Memorandum. As of the date hereof, the issued and outstanding share capital of TSL is owned as follows: (i) 72.5% by Kallistratos Maritime Holdings Ltd.; (ii) 18.0% by Pelagos Capital Partners Fund III LP; and (iii) 9.5% by the management employee stock ownership plan trust (the "ESOP Trust"). All issued and outstanding shares of TSL have been duly authorized and validly issued, are fully paid and non-assessable, and were issued in compliance with all applicable securities laws.
(h) Valid Issuance; Enforceability. The Notes, when issued and delivered in accordance with the terms of the Indenture and the Purchase Agreement and paid for by the Initial Purchasers, will be validly issued, fully paid, and non-assessable obligations of the Co-Issuers, enforceable against the Co-Issuers in accordance with their terms, subject to applicable bankruptcy, insolvency, reorganization, moratorium, and similar laws affecting creditors' rights generally and to general principles of equity. The Indenture, the Guarantees, and the Security Documents constitute, or upon execution and delivery will constitute, valid and legally binding obligations of the parties thereto, enforceable in accordance with their respective terms, subject to the same qualifications.
(i) No Required Governmental or Regulatory Consents. No consent, approval, authorization, order, registration, filing, or qualification of or with any governmental or regulatory authority is required for the execution, delivery, and performance by any of the Co-Issuers or any Guarantor Subsidiary of any Transaction Document to which it is a party, or for the consummation of the transactions contemplated thereby, other than (i) those that have been obtained on or prior to the date hereof, (ii) the filing of the application with Singapore Exchange Securities Trading Limited ("SGX-ST") for the listing of the Notes, and (iii) such as may be required under state securities or "blue sky" laws in connection with the purchase and distribution of the Notes by the Initial Purchasers.
(j) Compliance with Laws. Each of the Co-Issuers and each Guarantor Subsidiary is in compliance in all material respects with all applicable laws, rules, regulations, orders, judgments, and decrees, including without limitation the securities laws of the Republic of Singapore (including the Securities and Futures Act 2001 of Singapore, as amended), the laws of the Hellenic Republic, the securities laws of the United States of America (including the Securities Act of 1933, as amended (the "Securities Act"), and the Securities Exchange Act of 1934, as amended (the "Exchange Act")), and the laws of all other relevant jurisdictions in which the Co-Issuers and the Guarantor Subsidiaries conduct their respective businesses.
(k) Accuracy of Financial Information. The financial information included or incorporated by reference in the Offering Memorandum has been prepared in accordance with the accounting principles described therein, has been accurately extracted from the books and records of the Co-Issuers and the Guarantor Subsidiaries, and presents fairly in all material respects the financial condition and results of operations of TSL, TFPL, and the Guarantor Subsidiaries as of the dates and for the periods specified therein.
2.2 Offering Memorandum Representations
Each of the undersigned hereby certifies that the Offering Memorandum (comprising approximately 280 pages, near-final, 4th draft, dated September 12, 2022), as of its date and as of the Closing Date, does not contain any untrue statement of a material fact or omit to state a material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading.
This certification extends to all sections of the Offering Memorandum, including without limitation the following:
(a) the summary and cover pages, which describe the offering of $400,000,000 aggregate principal amount of 8.750% Senior Secured Notes due 2029 by the Co-Issuers;
(b) the section entitled "Risk Factors," setting forth material risks relating to the business and financial condition of the Co-Issuers and the Guarantor Subsidiaries, the industry in which they operate, and the terms of the Notes;
(c) the section entitled "Use of Proceeds," which describes the intended application of the proceeds of the offering as follows: approximately $190,000,000 to refinance the bilateral ship-finance facility of Meridian Maritime Bank AG; approximately $120,000,000 to refinance the bilateral ship-finance facility of Clearwater Shipping Finance Ltd.; approximately $72,000,000 for general corporate purposes and fleet capital expenditures; and approximately $18,000,000 for estimated fees and expenses of the offering, including original issue discount;
(d) the capitalization table, reflecting the pro forma capitalization of TSL and its consolidated subsidiaries after giving effect to the issuance of the Notes and the application of the proceeds therefrom;
(e) the section entitled "Business," describing the operations, fleet, and competitive position of TSL and the Guarantor Subsidiaries, including the 50-vessel fleet consisting of 38 dry-bulk carriers (spanning Supramax, Ultramax, and Kamsarmax classes) and 12 container feeder vessels, with a total fleet appraised value of approximately $1.82 billion and operations conducted across the Eastern Mediterranean, Black Sea, and Southeast Asia trade lanes;
(f) the sections entitled "Selected Financial Data" and "Management's Discussion and Analysis of Financial Condition and Results of Operations";
(g) the section entitled "Description of the Notes," setting forth the material terms of the Notes, including the coupon rate (8.750% per annum), maturity date (2029), security package, financial and restrictive covenants, optional and mandatory redemption provisions, and events of default;
(h) the section entitled "Taxation," describing certain material tax considerations for holders of the Notes;
(i) the section entitled "Plan of Distribution," describing the offer and sale of the Notes pursuant to Rule 144A under the Securities Act and Regulation S under the Securities Act; and
(j) the section entitled "Transfer Restrictions," setting forth the restrictions on the offer, sale, and transfer of the Notes.
Provided, however, that the certifying officers make no representation or warranty with respect to (i) information provided in writing by the Initial Purchasers specifically for inclusion in the Offering Memorandum (the "Initial Purchaser Information"), as identified in Section [●] of the Purchase Agreement, which the undersigned understand to consist solely of the information described in the [●] paragraph[s] under the caption "Plan of Distribution" in the Offering Memorandum, and (ii) statements in the Offering Memorandum made in reliance upon and in conformity with information furnished in writing by Polaris Ratings Group Ltd. or Oceanic Credit Assessments Inc., including credit rating designations, rating agency methodologies, and rating definitions.
SECTION 3 — FINANCIAL CERTIFICATIONS
3.1 Each of the undersigned hereby certifies that the financial data included in the Offering Memorandum, including the key financial metrics set forth below, was accurately presented as of the dates specified therein, was prepared in accordance with the accounting principles described in the Offering Memorandum, and has not become materially misleading as of the Closing Date:
3.2 The undersigned further certify that the methodologies and assumptions used to calculate the financial metrics set forth above, including the definitions of "Adjusted EBITDA," "LTM Revenue," "Pro Forma Total Debt," "Pro Forma Net Debt," "Pro Forma Net Leverage Ratio," and "Pro Forma Interest Coverage Ratio," are consistent with the definitions and methodologies described in the Offering Memorandum and the Indenture. The pro forma adjustments reflected in the foregoing financial data give effect to (i) the issuance of the Notes and the receipt of the gross proceeds therefrom, (ii) the application of such proceeds to refinance the existing indebtedness of TSL owing to Meridian Maritime Bank AG and Clearwater Shipping Finance Ltd., and (iii) the payment of estimated fees and expenses of the offering.
3.3 To the knowledge of the undersigned, the financial statements and financial data audited or reviewed by Kestrel & White Chartered Accountants, as referenced in the comfort letter delivered pursuant to Section [●] of the Purchase Agreement, are fairly presented in all material respects in accordance with the applicable accounting standards identified therein and are consistent with the financial information included in the Offering Memorandum. The undersigned have no reason to believe that the comfort letter delivered by Kestrel & White Chartered Accountants contains any material inaccuracy or is no longer accurate in any material respect as of the Closing Date.
SECTION 4 — NO MATERIAL ADVERSE CHANGE
4.1 Each of the undersigned hereby certifies that, since the date of the most recent financial statements included in the Offering Memorandum, there has been no Material Adverse Change (as such term is defined in the Purchase Agreement), nor any development or event involving a prospective Material Adverse Change, in or affecting:
(a) the business, properties, financial condition, or results of operations of TSL, TFPL, and the Guarantor Subsidiaries, taken as a whole;
(b) the ability of the Co-Issuers to perform their respective obligations under the Indenture, the Notes, the Purchase Agreement, or any other Transaction Document to which either of the Co-Issuers is a party; or
(c) the validity or enforceability of any Transaction Document or the rights and remedies of the Initial Purchasers, the Trustee, or the Security Agent under any Transaction Document.
4.2 The undersigned further certify that the fleet of 50 vessels (comprising 38 dry-bulk carriers and 12 container feeder vessels, with a total deadweight tonnage of approximately 2,850,000 DWT and a weighted average age of approximately 9.2 years as of the date hereof) continues to be operated in substantially the same manner as described in the Offering Memorandum. There has been no material change in the condition, classification, or operating status of any vessel in the fleet since the date of the most recent financial statements included in the Offering Memorandum. All vessels continue to maintain their respective class certifications with the relevant classification societies, and all required statutory and regulatory certifications remain in full force and effect.
4.3 The undersigned further certify that the appraised value of the 28 Collateral Vessels (as set forth in the fleet appraisal delivered by Compass Marine Valuations Ltd. dated June 2022) has not declined below the minimum collateral coverage ratio of 2.00x required under the Indenture as of the Closing Date. As of the date of the fleet appraisal, the 28 Collateral Vessels were appraised at an aggregate value of $1,175,000,000, resulting in a collateral coverage ratio at issuance of 2.94x (calculated as $1,175,000,000 divided by $400,000,000 aggregate principal amount of the Notes). To the knowledge of the undersigned, no events or circumstances have occurred since the date of such appraisal that would reasonably be expected to result in a decline in the aggregate appraised value of the 28 Collateral Vessels below $800,000,000 (which amount would represent the minimum collateral coverage ratio of 2.00x).
SECTION 5 — COMPLIANCE WITH CONDITIONS PRECEDENT
Each of the undersigned hereby certifies that, to the knowledge of the undersigned, all conditions precedent to the obligations of the Initial Purchasers to consummate the purchase of the Notes as set forth in Section [●] of the Purchase Agreement have been satisfied or, where applicable, validly waived in writing by the Initial Purchasers, as of the Closing Date. Without limiting the generality of the foregoing, the undersigned confirm that the following conditions precedent have been satisfied:
(a) Delivery of Executed Transaction Documents. The Co-Issuers and the Guarantor Subsidiaries have duly executed and delivered, or will duly execute and deliver simultaneously with the closing, each of the following Transaction Documents: the Indenture, the Purchase Agreement, the Registration Rights Agreement, the Intercreditor Agreement, the Security Documents (including the Deeds of Ship Mortgage, the Deeds of Assignment of Earnings and Insurances, the Share Pledge Agreements, and the Assignment of Intercompany Loan Receivables), and the Paying Agent and Transfer Agent Agreement.
(b) Delivery of Legal Opinions. The following legal opinions have been delivered or will be delivered on the Closing Date:
(i) an opinion of Calderwood & Harkness LLP, Singapore counsel to the Co-Issuers, as to matters of Singapore law, including the due authorization of the Transaction Documents, the valid issuance of the Notes, and the enforceability of the Notes, the Indenture, and the other Transaction Documents governed by Singapore law;
(ii) an opinion of Delphi & Karidis LLP, Greek counsel to TSL, as to matters of the laws of the Hellenic Republic, including the corporate capacity of TSL, the due authorization and valid adoption of the board resolutions of TSL, and the enforceability of obligations of TSL under Greek law;
(iii) an opinion of Rajendra & Osman LLP, Singapore counsel to TFPL, as to matters of Singapore law, including the corporate capacity of TFPL, the due authorization and valid adoption of the sole director resolutions of TFPL, and compliance with the requirements of the Accounting and Corporate Regulatory Authority of Singapore ("ACRA");
(iv) a negative assurance letter of Whitfield & Crane LLP, counsel to the Initial Purchasers, in accordance with customary practice under Rule 10b-5 of the Exchange Act; and
(v) an opinion of Thornton Ashworth LLP, counsel to the Trustee, as to the authorization and capacity of the Trustee to act in such capacity and customary trustee protection matters.
(c) Delivery of Comfort Letter. The comfort letter of Kestrel & White Chartered Accountants, in form and substance satisfactory to the Initial Purchasers, has been delivered pursuant to Section [●] of the Purchase Agreement, together with any bring-down letter required to be delivered on the Closing Date, and such comfort letter and any bring-down letter confirm the matters described therein as of the respective dates thereof.
(d) Receipt of Ratings. The Co-Issuers have received preliminary ratings of B+ (stable outlook) from Polaris Ratings Group Ltd. and B1 (stable outlook) from Oceanic Credit Assessments Inc. with respect to the Notes, and no such rating has been withdrawn, qualified, or downgraded, and no proceedings or announcements by either rating agency to withdraw, qualify, or downgrade any such rating have been made or are pending.
(e) Fleet Appraisal. The fleet appraisal from Compass Marine Valuations Ltd., dated June 2022, confirming the aggregate appraised value of the 28 Collateral Vessels and the resulting collateral coverage ratio, has been delivered to the Initial Purchasers and the Trustee.
(f) Perfection and Registration of Security Documents. The perfection and registration (or arrangements for the perfection and registration) of all Security Documents have been completed or will be completed promptly following the Closing Date, in each case in accordance with applicable law and the terms of the Indenture and the Security Documents. Such perfection and registration includes, without limitation:
(i) first-priority ship mortgages over each of the 28 Collateral Vessels, to be registered in the relevant ship registries;
(ii) share pledges over the shares of the fleet-owning Guarantor Subsidiaries and TFPL;
(iii) assignments of earnings and insurances with respect to the Collateral Vessels, in favor of the Security Agent; and
(iv) assignment of intercompany loan receivables in the aggregate amount of $365,000,000 owing from TFPL and the Guarantor Subsidiaries to TSL.
(g) Payoff Letters. Payoff letters have been received from each of (i) Meridian Maritime Bank AG, confirming the payoff amount of $190,000,000 (together with any accrued and unpaid interest as of the Closing Date, per diem interest calculations, wire transfer instructions, and the mechanics for the release of all existing security interests held by Meridian Maritime Bank AG over the relevant vessels and other assets), and (ii) Clearwater Shipping Finance Ltd., confirming the payoff amount of $120,000,000 (together with any accrued and unpaid interest as of the Closing Date, per diem interest calculations, wire transfer instructions, and the mechanics for the release of all existing security interests held by Clearwater Shipping Finance Ltd. over the relevant vessels and other assets).
(h) Corporate Resolutions. Duly certified copies of the resolutions of the board of directors of TSL and the sole director resolutions of TFPL, in each case authorizing the execution, delivery, and performance of the Transaction Documents and the consummation of the transactions contemplated thereby, have been delivered to the Initial Purchasers and their counsel.
(i) SGX-ST Listing Application. An application for the listing of the Notes on the SGX-ST has been duly filed, and the Co-Issuers are not aware of any reason why such listing should not be granted in due course.
(j) No Stop Order, Injunction, or Legal Restraint. No stop order, injunction, restraining order, or other legal or regulatory restraint or prohibition preventing the consummation of the offering, the issuance or delivery of the Notes, or any of the other transactions contemplated by the Transaction Documents has been issued, entered, or threatened by any court, governmental authority, or regulatory body, and no proceedings seeking any such stop order, injunction, restraining order, or other legal or regulatory restraint or prohibition are pending or, to the knowledge of the undersigned, threatened.
SECTION 6 — NO PROCEEDINGS
Each of the undersigned hereby certifies that, as of the Closing Date, there are no legal, governmental, or regulatory investigations, actions, suits, claims, arbitrations, or proceedings (collectively, "Proceedings") pending, or, to the knowledge of the undersigned after due inquiry, threatened in writing against any of the Co-Issuers, the Guarantor Subsidiaries, or the Parent Guarantor, which:
(a) seek to restrain, enjoin, or otherwise prevent the consummation of any of the transactions contemplated by the Purchase Agreement, the Indenture, or any other Transaction Document;
(b) challenge the validity, binding effect, or enforceability of the Notes, the Indenture, the Purchase Agreement, any Guarantee, any Security Document, or any other Transaction Document;
(c) would, individually or in the aggregate, reasonably be expected to result in a Material Adverse Change (as defined in the Purchase Agreement); or
(d) are required to be described or disclosed in the Offering Memorandum pursuant to applicable law, regulation, or the requirements of the Purchase Agreement and are not so described or disclosed therein.
The undersigned further confirm that, to their knowledge after due inquiry, there are no Proceedings pending or threatened against any director, officer, or key employee of any of the Co-Issuers or the Guarantor Subsidiaries in their capacity as such that would, individually or in the aggregate, reasonably be expected to have a material impact on the ability of the Co-Issuers or the Guarantor Subsidiaries to consummate the transactions contemplated by the Transaction Documents or to perform their respective obligations thereunder.
SECTION 7 — ORGANIZATIONAL AND CORPORATE MATTERS
7.1 The undersigned hereby confirm that TSL remains duly organized and validly existing as a Société Anonyme under the laws of the Hellenic Republic, with registration number GEMI No. 148276201000, and with its registered office located at 42 Akti Miaouli, Piraeus 185 35, Greece. TSL has not been dissolved, wound up, merged, consolidated, or otherwise reorganized, and no proceedings for the dissolution, winding up, merger, consolidation, or other reorganization of TSL have been commenced or are pending or, to the knowledge of the undersigned, threatened.
7.2 The undersigned hereby confirm that TFPL remains duly organized and validly existing as a private company limited by shares under the laws of the Republic of Singapore, with Unique Entity Number (UEN) 202209345K, and with its registered office located at 8 Marina Boulevard, #36-02, Marina Bay Financial Centre Tower 1, Singapore 018981. TFPL has not been dissolved, wound up, merged, consolidated, or otherwise reorganized, and no proceedings for the dissolution, winding up, merger, consolidation, or other reorganization of TFPL have been commenced or are pending or, to the knowledge of the undersigned, threatened. TFPL remains in good standing with the Accounting and Corporate Regulatory Authority of Singapore ("ACRA"), and all required annual filings and returns with ACRA are current.
7.3 The undersigned hereby confirm that each of the Guarantor Subsidiaries is duly organized and validly existing under the laws of its respective jurisdiction of organization, as set forth in Section 2.1 above, and that each Guarantor Subsidiary has all requisite corporate or similar power and authority to own, lease, and operate its properties and assets, to conduct its business as presently conducted, and to perform its obligations under the Transaction Documents to which it is a party. No Guarantor Subsidiary has been dissolved, wound up, merged, consolidated, or otherwise reorganized, and no proceedings for any such event have been commenced or are pending or, to the knowledge of the undersigned, threatened.
7.4 The undersigned hereby confirm that no event of bankruptcy, insolvency, receivership, reorganization, administration, winding up, liquidation, or similar proceeding has been commenced by or against any of the Co-Issuers, any Guarantor Subsidiary, or the Parent Guarantor. No petition or application for the commencement of any such proceeding has been filed or presented, and to the knowledge of the undersigned, no such petition or application is contemplated or threatened. Neither of the Co-Issuers nor any Guarantor Subsidiary is unable to pay its debts as they fall due, and neither of the Co-Issuers nor any Guarantor Subsidiary has made a general assignment for the benefit of its creditors.
SECTION 8 — USE OF PROCEEDS CONFIRMATION
Each of the undersigned hereby certifies that the proceeds of the offering of the Notes will be applied substantially as described in the Offering Memorandum under the caption "Use of Proceeds." Specifically, the net proceeds of the offering, together with cash on hand, will be applied as follows:
The Notes will be issued at an issue price of 98.00% of par, yielding gross proceeds of $392,000,000 and resulting in an original issue discount of $8,000,000. In addition, the Initial Purchaser discount payable by the Co-Issuers to the Initial Purchasers shall be $8,000,000 (representing 2.00% of the aggregate principal amount of the Notes). After accounting for the original issue discount and the remaining estimated fees and expenses of the offering (including legal fees, accounting fees, trustee and security agent fees, rating agency fees, printing and distribution costs, and other transaction expenses), the total estimated fees, expenses, and original issue discount amount to approximately $18,000,000.
The total uses of proceeds of $400,000,000 will be funded from the gross proceeds of the offering of $392,000,000, supplemented by approximately $8,000,000 from TSL cash on hand. After absorbing the original issue discount, the net additional cash contribution from TSL is approximately $10,000,000. The Co-Issuers confirm that all amounts will be applied in a manner consistent with the terms of the Indenture and the Purchase Agreement, and that no portion of the proceeds will be used in violation of any applicable law or any restrictive covenant set forth in the Indenture.
SECTION 9 — NO DEFAULT
9.1 Each of the undersigned hereby certifies that, as of the Closing Date, no Default or Event of Default (each as defined in the Indenture) has occurred and is continuing, and no Default or Event of Default would result from, or arise in connection with, the issuance of the Notes, the execution and delivery of the Indenture and the other Transaction Documents, or the application of the proceeds of the offering as described in Section 8 above and in the Offering Memorandum under "Use of Proceeds."
9.2 The undersigned further certify that, upon giving effect to the issuance of the Notes and the application of the proceeds therefrom (including the refinancing of the existing bilateral ship-finance facilities of Meridian Maritime Bank AG and Clearwater Shipping Finance Ltd.), TSL and its consolidated subsidiaries are in compliance with all incurrence-based financial tests and covenants set forth in the Indenture, including without limitation:
(a) Total Net Leverage Ratio. The Total Net Leverage Ratio (as defined in the Indenture) does not exceed 3.50x. On a pro forma basis after giving effect to the issuance and the refinancing, the Total Net Leverage Ratio is 1.59x, calculated as follows: Pro Forma Net Debt of $341,700,000 divided by LTM Adjusted EBITDA of $214,600,000.
(b) Collateral Coverage Ratio. The Collateral Coverage Ratio (as defined in the Indenture) is at or above 2.00x. At issuance, the Collateral Coverage Ratio is 2.94x, calculated as follows: aggregate appraised value of the 28 Collateral Vessels of $1,175,000,000 divided by the aggregate principal amount of the Notes of $400,000,000.
9.3 To the knowledge of the undersigned, no event has occurred or condition exists that, with the giving of notice or the lapse of time or both, would constitute a Default or Event of Default under the Indenture.
SECTION 10 — INSURANCE AND COLLATERAL MATTERS
10.1 Each of the undersigned hereby certifies that all insurance policies covering the 28 Collateral Vessels (including hull and machinery insurance, protection and indemnity insurance, war risk insurance, and loss of hire insurance) are in full force and effect as of the Closing Date, all premiums due and payable thereunder have been paid or are current, and the coverage levels and terms of such insurance policies are consistent with the requirements of the Indenture and the Security Documents. The insurances are placed with reputable insurers and/or mutual protection and indemnity associations, and the coverage amounts are consistent with customary practice in the international shipping industry for vessels of similar type, size, age, and trade.
10.2 Assignments of insurance proceeds in favor of Atlas Collateral Agency Pte. Ltd. (UEN 200115678R), in its capacity as Security Agent under the Indenture, have been or will be duly made in accordance with the Deeds of Assignment of Earnings and Insurances and the other Security Documents, and the relevant insurers and/or protection and indemnity associations have been or will be duly notified of such assignments, with acknowledgment of such assignments to be obtained in accordance with customary practice.
10.3 The undersigned further certify that no Collateral Vessel has suffered a total loss or constructive total loss since the date of the fleet appraisal delivered by Compass Marine Valuations Ltd. (June 2022). No Collateral Vessel has been arrested, detained, seized, or confiscated by any governmental or regulatory authority, and no Collateral Vessel is subject to any requisition for use or title by any governmental authority. To the knowledge of the undersigned, no event has occurred that would give rise to a claim for a total loss or constructive total loss with respect to any Collateral Vessel.
SECTION 11 — ADDITIONAL CERTIFICATIONS
11.1 Each of the undersigned hereby certifies that the certificates of incorporation, articles of association, memoranda of association, and other organizational documents of TSL and TFPL that have been delivered to the Initial Purchasers and their counsel (Whitfield & Crane LLP) are true, complete, and correct copies of such documents as in effect on and as of the Closing Date. No amendments or modifications to any such organizational documents have been adopted, approved, or proposed since the date on which such copies were delivered to the Initial Purchasers and their counsel.
11.2 Each of the undersigned hereby certifies that the incumbency and specimen signatures of the officers and directors of TSL and TFPL who are authorized to execute and deliver the Transaction Documents and any certificates, instruments, or other documents on behalf of TSL and TFPL, as set forth in the incumbency certificates delivered to the Initial Purchasers and their counsel, are true, correct, and genuine as of the Closing Date.
11.3 As of the Closing Date, the following persons are the duly elected or appointed officers and/or directors authorized to execute Transaction Documents and any related certificates, instruments, or documents on behalf of TSL and/or TFPL:
Each of the foregoing persons remains duly qualified and authorized to act in the capacity indicated above, and no revocation, suspension, or limitation of such authority has occurred or is contemplated.
SECTION 12 — RELIANCE
12.1 This Certificate is delivered to the Initial Purchasers, Anchor Bay Securities LLC and Halcyon Partners International Ltd., and to the Trustee, Marlowe Asset Management Trust Company of Singapore Pte. Ltd., in satisfaction of the conditions precedent set forth in Section [●] of the Purchase Agreement, as a condition to the obligations of the Initial Purchasers to consummate the purchase of the Notes on the Closing Date.
12.2 Each of the Initial Purchasers and their counsel (Whitfield & Crane LLP), the Trustee and its counsel (Thornton Ashworth LLP), and the Co-Issuers' counsel (Calderwood & Harkness LLP) are entitled to rely on the certifications, representations, and confirmations contained in this Certificate as though such certifications, representations, and confirmations were made directly to each such person. The delivery of this Certificate shall not, however, confer any rights upon any other person or entity, except as expressly provided in the Purchase Agreement.
12.3 The certifications, representations, and confirmations set forth in this Certificate are made as of the Closing Date and speak only as of the Closing Date. Nothing in this Certificate shall be deemed to create any obligation on the part of the undersigned or the Co-Issuers to update or supplement the certifications contained herein after the Closing Date, except as may otherwise be required under the Purchase Agreement, the Indenture, or applicable law.
SECTION 13 — GOVERNING LAW
This Certificate shall be governed by and construed in accordance with the laws of the Republic of Singapore, without regard to conflicts of law principles thereof that would result in the application of the laws of any other jurisdiction. The choice of Singapore law as the governing law of this Certificate is consistent with the governing law of the Indenture, the Purchase Agreement, and the other Transaction Documents.
[Signature Page Follows]
IN WITNESS WHEREOF, the undersigned have executed this Officers' Certificate as of the date first written above.
THALASSA SHIPPING & LOGISTICS SA
By: ________
Name: Spyros Andreou
Title: Chief Executive Officer
Date: [●], 2022
THALASSA SHIPPING & LOGISTICS SA and THALASSA FINANCE PTE. LTD.
By: ________
Name: Marina Demetriou
Title: Chief Financial Officer, Thalassa Shipping & Logistics SA;
Sole Director, Thalassa Finance Pte. Ltd.
Date: [●], 2022
[UNEXECUTED — FORM ONLY]
SCHEDULE A — DEFINED TERMS CROSS-REFERENCE
The following table sets forth a cross-reference of certain key defined terms used in this Certificate to the provisions of the Purchase Agreement or the Indenture in which such terms are defined:
SCHEDULE B — LIST OF TRANSACTION DOCUMENTS
The following is a list of the Transaction Documents referenced in this Certificate:
1.  Indenture (near-final, 5th draft, dated September 6, 2022), among the Co-Issuers, the Guarantor Subsidiaries, Marlowe Asset Management Trust Company of Singapore Pte. Ltd. (as Trustee), and Atlas Collateral Agency Pte. Ltd. (as Security Agent).
2.  Purchase Agreement (near-final draft), among the Co-Issuers, the Guarantor Subsidiaries, Kallistratos Maritime Holdings Ltd. (as limited parent guarantor), and the Initial Purchasers.
3.  Registration Rights Agreement (near-final draft), among the Co-Issuers, the Guarantor Subsidiaries, and the Initial Purchasers.
4.  Intercreditor Agreement (near-final, 3rd draft), among the Co-Issuers, the Guarantor Subsidiaries, the Trustee, the Security Agent, and such other parties as may be party thereto.
5.  Deed of Ship Mortgage (form), covering the 28 Collateral Vessels, to be entered into by the relevant fleet-owning Guarantor Subsidiaries in favor of the Security Agent.
6.  Deed of Assignment of Earnings and Insurances (form), to be entered into by the relevant fleet-owning Guarantor Subsidiaries in favor of the Security Agent, with respect to the earnings and insurances relating to the Collateral Vessels.
7.  Share Pledge Agreement — Thalassa Finance Pte. Ltd., pursuant to which TSL will pledge its shares in TFPL in favor of the Security Agent.
8.  Share Pledge Agreement — Fleet-Owning Guarantor Subsidiaries (form), pursuant to which the relevant parent entities will pledge their shares in each fleet-owning Guarantor Subsidiary in favor of the Security Agent.
9.  Assignment of Intercompany Loan Receivables ($365,000,000), pursuant to which the relevant intercompany loan receivables will be assigned to the Security Agent as additional collateral for the benefit of the holders of the Notes.
10.  Paying Agent and Transfer Agent Agreement (near-final draft), among the Co-Issuers and the Trustee (acting in its capacity as paying agent, transfer agent, and registrar with respect to the Notes).
11.  Form of Global Note — Rule 144A, representing Notes sold pursuant to Rule 144A under the Securities Act (proposed CUSIP: 87265T AA1; proposed ISIN: US87265TAA10).
12.  Form of Global Note — Regulation S, representing Notes sold pursuant to Regulation S under the Securities Act (proposed ISIN: XS2498731056; proposed Common Code: 249873105).
Calderwood & Harkness LLP — Matter No. 1044-00004 — Client No. 80214-TSL
FORM — PREPARED FOR EXECUTION AT CLOSING — UNEXECUTED
Financial Metric | Amount / Value
LTM Revenue (Q1 2022 annualized) | $687,400,000
LTM Adjusted EBITDA (Q1 2022 annualized) | $214,600,000
EBITDA Margin | 31.2%
Pro Forma Total Debt (post-offering) | $400,000,000
Cash on Balance Sheet | $58,300,000
Pro Forma Net Debt | $341,700,000
Pro Forma Net Leverage Ratio | 1.59x
Pro Forma Interest Coverage Ratio | 6.13x
Annual Interest Expense on the Notes | $35,000,000
Application of Proceeds | Amount
Refinancing of Meridian Maritime Bank AG bilateral ship-finance facility | $190,000,000
Refinancing of Clearwater Shipping Finance Ltd. bilateral ship-finance facility | $120,000,000
General corporate purposes and fleet capital expenditures | $72,000,000
Estimated fees, expenses, and original issue discount | Approximately $18,000,000
Total | $400,000,000
Name | Title | Entity
Spyros Andreou | Chief Executive Officer | Thalassa Shipping & Logistics SA
Marina Demetriou | Chief Financial Officer / Sole Director | Thalassa Shipping & Logistics SA / Thalassa Finance Pte. Ltd.
Alexandros Theodorakis | General Counsel | Thalassa Shipping & Logistics SA
Defined Term | Defined in | Section / Article
Material Adverse Change | Purchase Agreement | Section [●]
Default | Indenture | Section 1.01
Event of Default | Indenture | Article VI
Collateral Vessels | Indenture | Section 1.01
Guarantor Subsidiaries | Purchase Agreement | Preamble
Transaction Documents | Purchase Agreement | Section [●]
Net Proceeds | Indenture | Section 1.01
Total Net Leverage Ratio | Indenture | Section 1.01
Collateral Coverage Ratio | Indenture | Section 1.01
Consolidated Net Tangible Assets | Indenture | Section 1.01
Closing Date | Purchase Agreement | Section [●]
Co-Issuers | Purchase Agreement | Preamble
Initial Purchasers | Purchase Agreement | Preamble
Offering Memorandum | Purchase Agreement | Section [●]
Security Documents | Indenture | Section 1.01
Intercreditor Agreement | Indenture | Section 1.01
Registration Rights Agreement | Purchase Agreement | Section [●]
Adjusted EBITDA | Indenture | Section 1.01
Permitted Indebtedness | Indenture | Section 4.[●]
Permitted Liens | Indenture | Section 4.[●]

FORM OF OFFICERS' CERTIFICATE

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THALASSA SHIPPING & LOGISTICS SA

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