Contract analysis

I. TRANSMITTAL MEMORANDUM / INTRODUCTORY NOTE TO PAVLOPOULOS & DRAKOS June 30, 2023 Theodoros Pavlopoulos, Esq. Senior Partner Pavlopoulos & Drakos Law Firm 22 Filellinon Street Athens 105 57, Greece Dear Mr. Pavlopoulos: This draft outline has been prepared by Calderwood & Harkness LLP ("C&H"), counsel to Thalassa Shipping & Logistics SA ("TSL" or the "Company"), in connection with the proposed $150,000,000 senior s

II. PROPOSED FORM OF OPINION LETTER The following sets forth the proposed form, structure, and substance of the Greek-law legal opinion to be prepared by P&D and delivered at closing. Each section includes both the proposed language and, where appropriate, internal annotations for P&D's consideration. P&D should treat the form below as a starting point and adapt it as necessary to conform with Greek legal practice an

1. Credit Agreement dated as of [Closing Date] among Thalassa Shipping & Logistics SA, as Borrower, the Guarantors party thereto, Meridian Atlantic Bank, National Association, as Administrative Agent, and the Lenders party thereto (the "Credit Agreement"), providing for a $150,000,000 senior secured revolving credit facility — governed by New York law;

2. Guaranty Agreement executed by each of the Guarantors, including: (a) Thalassa Dry Bulk Holdings Ltd., a company organized under the laws of the Republic of Cyprus; (b) Thalassa Tanker Operations Ltd., a company organized under the laws of the Republic of the marshall Islands; and (c) Thalassa Logistics International Ltd., a company organized under the laws of the Republic of Cyprus; Note: This Greek-law opinion a

3. First Preferred Ship Mortgages on the Mortgaged Vessels (18 vessels), to the extent any such vessels are registered under the Greek flag and are therefore subject to Greek maritime law and Greek Ship Registry (Νηολόγιο) requirements;

4. Share Pledge Agreement(s) with respect to the shares of certain subsidiaries of TSL, as specified in the Credit Agreement and the related security documents;

5. Assignment of Earnings, pursuant to which TSL assigns to the Collateral Agent, for the benefit of the Secured Parties, TSL's rights to receive earnings and freight revenues from the Mortgaged Vessels;

6. Assignment of Insurances, pursuant to which TSL assigns to the Collateral Agent, for the benefit of the Secured Parties, TSL's rights under the hull and machinery, protection and indemnity, and other insurance policies covering the Mortgaged Vessels; and

7. Such other ancillary documents as may be specified upon finalization of the closing checklist (including any fee letters, notices, or subordination agreements required under the Transaction Documents). The scope of this opinion is limited exclusively to matters of Greek law applicable to TSL as a société anonyme organized under the laws of the Hellenic Republic. This opinion does not address the laws of the State

1. A certified copy of the articles of association (Καταστατικό) of TSL, as currently in effect, together with all amendments thereto through the date hereof, as filed with the General Electronic Commercial Registry (GEMI) of the Hellenic Republic;

2. A certified extract from the General Electronic Commercial Registry (GEMI) of the Hellenic Republic for TSL, GEMI Registration No. 143209501000, dated no earlier than [●] business days before the closing date, reflecting TSL's current registered status, registered office, corporate purpose, authorized share capital, members of the Board of Directors, and other particulars recorded with GEMI;

3. Certified copies of the minutes of the meeting of the Board of Directors (Διοικητικό Συμβούλιο) of TSL held on [●], 2023, at which a quorum was present and acting throughout, authorizing (a) the execution, delivery, and performance by TSL of each of the Transaction Documents to which TSL is a party, (b) the borrowing by TSL of up to $150,000,000 under the Credit Agreement, (c) the grant by TSL of the security inte

4. Certified copies of the minutes of any general meeting of shareholders of TSL (to the extent that shareholder approval is required under TSL's articles of association or under applicable provisions of Law 4548/2018 on sociétés anonymes) approving or ratifying the transactions contemplated by the Transaction Documents, including the borrowing under the Facility, the grant of security over vessels and subsidiary sha

5. An incumbency certificate issued by TSL, together with specimen signatures of the authorized officers designated to execute the Transaction Documents on behalf of TSL, including Elena Vassiliou (CEO) and Dimitrios Pantazis (CFO), and such other officers as may be designated from time to time;

6. A tax clearance certificate (φορολογική ενημερότητα) issued by the competent Greek tax authority with respect to TSL, dated no earlier than [●] business days before the closing date, confirming that TSL is current with respect to its Greek tax obligations;

7. A social security clearance certificate (ασφαλιστική ενημερότητα) issued by the competent Greek social security authority with respect to TSL, dated no earlier than [●] business days before the closing date, confirming that TSL is current with respect to its Greek social security contribution obligations;

8. Copies of the Transaction Documents (as defined above) in substantially final form, as circulated to the parties and their respective counsel on or about the date hereof;

9. Such other documents, records, certificates, instruments, and evidence of matters of law or fact as we have deemed necessary or appropriate in order to render the opinions expressed herein. In our examination of the foregoing documents, we have assumed the accuracy and completeness of all factual representations and statements contained therein. We have not undertaken any independent investigation of the factual m

1. Authenticity and Conformity. All documents submitted to us as originals are authentic and complete, and all documents submitted to us as copies conform to the originals thereof. All documents submitted to us have been duly and properly executed by the parties thereto (to the extent not addressed by the express opinions set forth below with respect to TSL).

2. Genuineness of Signatures. All signatures on all documents reviewed by us are genuine and have been affixed by the persons whose signatures they purport to be.

3. Due Organization of Other Parties. Each party to the Transaction Documents (other than TSL) is duly organized, validly existing, and in good standing (or the equivalent thereof) under the laws of its respective jurisdiction of organization, and has the legal capacity and standing to enter into and perform its obligations under the Transaction Documents.

4. Corporate Power and Authority of Other Parties. Each party to the Transaction Documents (other than TSL) has the requisite corporate or other organizational power and authority to execute, deliver, and perform its obligations under the Transaction Documents, and has taken all necessary corporate or other organizational action to authorize such execution, delivery, and performance.

5. Due Authorization, Execution, and Delivery by Other Parties. The Transaction Documents have been duly authorized, executed, and delivered by each party thereto other than TSL. With respect to TSL, express opinions on authorization, execution, and delivery are given below in Section E of this opinion.

6. Enforceability Under Governing Law. The Transaction Documents constitute legal, valid, binding, and enforceable obligations of each party thereto under the laws governing such documents (other than as to TSL under Greek law, as to which express opinions are given below). In particular, we have assumed, without independent investigation, that the Credit Agreement and related Transaction Documents constitute valid a

7. Validity of Choice of Law. The choice of New York law as the governing law of the Credit Agreement is valid and effective under the laws of the State of New York and under any other applicable law (other than Greek law, as to which we express an opinion below regarding the recognition of such choice of law by Greek courts). We have not undertaken any investigation of New York law in connection with this opinion.

8. No Usury Violation. The financial terms of the Transaction Documents, including without limitation the rate of interest, fees, and other charges payable thereunder, do not violate any applicable usury or similar laws of any jurisdiction (including the laws of the State of New York). We express no opinion on usury or similar laws.

9. Accuracy of Officer's Certificates. All factual matters stated in certificates of officers of TSL reviewed by us in connection with this opinion are true, correct, and complete as of the date hereof and as of the closing date. We have relied upon such certificates without independent verification and have assumed that no information has been withheld from us that would affect the opinions expressed herein.

10. No Subsequent Changes in GEMI Records. No event has occurred since the date of the GEMI extract reviewed by us that would alter, amend, or otherwise affect TSL's registered status, registered office, corporate purpose, authorized share capital, membership of the Board of Directors, or any other particulars recorded with GEMI. We have assumed that the GEMI extract accurately reflects TSL's registered status as of

III. ANNEXES TO THE OUTLINE Annex A: Open Questions for Pavlopoulos & Drakos The following questions remain open and require P&D's prompt review and response. C&H requests that P&D address each of the following items and revert with its responses at the earliest practicable opportunity, in order to facilitate timely preparation of the opinion and to avoid delay in the closing process.

1. Shareholder Approval. Please confirm whether shareholder approval (in addition to board of directors approval) is required under TSL's articles of association or under the applicable provisions of Law 4548/2018 (Greek law on sociétés anonymes) for (a) borrowings of the magnitude contemplated by the Facility ($150,000,000), (b) the grant of first preferred ship mortgages over the Mortgaged Vessels, and/or (c) the p

2. Greek-Flagged Vessels. Please confirm whether any of the eighteen (18) Mortgaged Vessels identified in the Credit Agreement are registered under the Greek flag. If any Mortgaged Vessels are Greek-flagged, please describe in detail the requirements applicable to the recording of first preferred ship mortgages with the Greek Ship Registry (Νηολόγιο), including (a) the form and content of the mortgage instrument, (b)

3. Stamp Duty, Notarial Fees, and Registration Taxes. Please confirm whether any stamp duty (τέλος χαρτοσήμου), notarial fees, registration taxes, or other documentary taxes or duties are payable in Greece in connection with the execution, delivery, recording, or enforcement of any of the Transaction Documents. If so, please provide estimated amounts and identify the party responsible for payment of such taxes or dut

4. Ability to Give Proposed Opinions. Please confirm P&D's ability to give each of the opinions proposed in Section E above (Opinions 1 through 8) in the form set forth herein. If P&D is unable to give any of the proposed opinions, or if any opinion would require material modification, additional qualification, or limitation, please identify such opinion and describe the nature of the modification, qualification, or

5. Additional Qualifications or Limitations. Please identify any additional qualifications, limitations, or assumptions that P&D considers necessary or appropriate under current Greek law and practice that have not been included in the proposed form of opinion set forth herein. In particular, please advise whether any qualifications are required in connection with (a) Greek foreign exchange controls or capital contro

6. Officer's Certificates. Please confirm the form and substance of any officer's certificates that P&D will require from TSL in connection with the preparation and delivery of the opinion. C&H is prepared to assist in preparing such certificates in coordination with TSL's General Counsel, Aris Komnenidis.

7. Turnaround Time. Please confirm P&D's expected turnaround time for preparation of the final opinion once (a) final execution versions of the Transaction Documents have been made available, (b) all supporting corporate documents (board minutes, shareholder minutes, GEMI extract, incumbency certificates, clearance certificates) have been delivered, and (c) all open questions set forth in this Annex A have been resol

1. Credit Agreement (Item 1 of the Closing Checklist)

2. Guaranty Agreement (Item 3 of the Closing Checklist) — to the extent relevant to TSL as Borrower only

3. First Preferred Ship Mortgages (Items 12–29 of the Closing Checklist) — to the extent any Mortgaged Vessels are Greek-flagged

4. Share Pledge Agreement(s) (Items 30–33 of the Closing Checklist)

5. Assignment of Earnings (Items 34–51 of the Closing Checklist)

6. Assignment of Insurances (Items 52–69 of the Closing Checklist)

7. Any additional ancillary documents identified upon finalization of the closing checklist Status of Document Circulation: For reference, we note the following: • The near-final Credit Agreement was circulated to all parties on July 3, 2023. • Draft security documents (first preferred ship mortgages, share pledge agreements, assignment of earnings, and assignment of insurances) were circulated by Whitmore, Jennings

IV. DISTRIBUTION AND NEXT STEPS This draft outline is being distributed as follows:

1. Pavlopoulos & Drakos Law Firm. This outline is being transmitted by Calderwood & Harkness LLP to Theodoros Pavlopoulos, Senior Partner, Pavlopoulos & Drakos Law Firm, 22 Filellinon Street, Athens 105 57, Greece, for review and comment. P&D is requested to review this outline, respond to the open questions set forth in Annex A, and revert to C&H with its comments, proposed revisions, and any questions at the earlie

2. Thalassa Shipping & Logistics SA. A copy of this outline is being provided to Aris Komnenidis, General Counsel, Thalassa Shipping & Logistics SA, 14 Akti Miaouli, Piraeus 185 35, Greece, for information purposes and to facilitate coordination between TSL's in-house legal team and P&D with respect to the corporate documents and officer's certificates required in connection with the opinion.

3. Calderwood & Harkness LLP (Internal). An internal copy of this outline is being retained in the C&H matter file for this transaction, Matter No. 1044-00002, in accordance with C&H's document retention policies. Note Regarding Status of this Outline. This outline was prepared by Calderwood & Harkness LLP in anticipation of the closing of the Facility and for the purpose of facilitating coordination with Pavlopoulos