Contract analysis

I. Introduction Calderwood & Harkness LLP ("Calderwood & Harkness" or "we") acts as international counsel to Thalassa Shipping & Logistics SA ("TSL"), a Société Anonyme organized and existing under the laws of the Hellenic Republic (GEMI No. 148276201000), with its registered office and principal place of business at 42 Akti Miaouli, Piraeus 185 35, Greece, and to Thalassa Finance Pte. Ltd. ("TFPL," UEN 202209345K),

II. Purpose of the Request This letter constitutes a formal request on behalf of the Co-Issuers and, with the knowledge and consent of the Initial Purchasers, for K&W to provide the Comfort Letter substantially in accordance with Statement on Auditing Standards No. 72 ("SAS 72"), as issued by the Auditing Standards Board of the American Institute of Certified Public Accountants ("AICPA"), or, to the extent K&W determ

III. Scope of the Comfort Letter The Comfort Letter should address each of the following matters, which together comprise the customary scope for comfort letters delivered in connection with Rule 144A/Regulation S high-yield offerings.

III.A. Independence. K&W is requested to confirm in the Comfort Letter that it is independent with respect to TSL and all of TSL's subsidiaries, including without limitation: (i) Thalassa Finance Pte. Ltd. (Singapore); (ii) Thalassa Dry Bulk Operations Ltd. (Malta); (iii) Thalassa Container Feeder Ltd. (Marshall Islands); (iv) Thalassa Port Services FZCO (Dubai, United Arab Emirates); and (v) Thalassa Freight Solutio

III.B. Audited Financial Statements K&W is requested to state in the Comfort Letter that it has audited the consolidated financial statements of TSL and its subsidiaries for each of the fiscal years ended December 31, 2021, December 31, 2020, and December 31, 2019, as included in the OM, and that such audits were conducted in accordance with International Standards on Auditing ("ISA") as issued by the IAASB. K&W is f

III.C. Unaudited Interim Financial Statements K&W is requested to state in the Comfort Letter that it has performed a review (or, if applicable, a limited review) of the unaudited condensed consolidated interim financial statements of TSL and its subsidiaries for the three-month period ended March 31, 2022, as included in the OM, and that such review was conducted in accordance with International Standard on Review E

III.D. Financial Data and Statistical Information — Agreed-Upon Procedures / Specified Procedures K&W is requested to perform specified procedures (commonly referred to as "read and compare" procedures) with respect to certain financial data, financial amounts, percentages, ratios, and statistical information appearing in the OM, including but not limited to the specific items identified in Section IV of this letter

III.E. Subsequent Events (Change Period) K&W is requested to perform specified procedures relating to events subsequent to the date of the most recent audited financial statements (December 31, 2021) and the most recent unaudited condensed consolidated interim financial statements (March 31, 2022) through a "cut-off date" that is no more than five (5) business days prior to the date of the Comfort Letter (the period

IV. Circle-Up Items — Financial Data and Statistical Information to Be Covered Set forth below is a description of the specific financial data and statistical information appearing in the OM that K&W is requested to cover through the specified procedures described in Section III.D above. All page references set forth below are to the 4th Draft OM dated September 12, 2022, and will be updated to reflect the final OM p

IV.A. Revenue and Profitability Data K&W is requested to perform specified procedures with respect to the following revenue and profitability data as presented in the OM: (1) LTM Revenue (Q1 2022 annualized): $687,400,000 (stated as "$687.4 million" in the OM). K&W should compare this figure to the underlying quarterly revenue data for the last twelve months ended March 31, 2022, as derived from the audited financial

IV.B. Capitalization and Indebtedness K&W is requested to perform specified procedures with respect to the following capitalization and indebtedness data as presented in the OM: (1) Cash on balance sheet: $58,300,000 (stated as "$58.3 million" in the OM). K&W should compare this figure to the unaudited condensed consolidated balance sheet of TSL as of March 31, 2022, or, if more recent data is available, to the most

IV.C. Use of Proceeds K&W is requested to perform specified procedures with respect to the following use of proceeds data as presented in the OM: (1) Total offering size: $400,000,000 aggregate principal amount. (2) Issue price: 98.00% of par, resulting in gross proceeds to the Co-Issuers of $392,000,000. (3) Original issue discount ("OID"): $8,000,000, representing the difference between the aggregate principal amou

IV.D. Fleet and Operational Data K&W is requested to perform specified procedures with respect to the following fleet and operational data as presented in the OM: (1) Total fleet: 50 vessels (consisting of 38 dry-bulk carriers and 12 container feeder vessels). (2) Fleet appraised value (as of June 2022, per Compass Marine Valuations Ltd.): $1,820,000,000 (stated as "approximately $1.82 billion" in the OM). (3) Number

IV.E. Ownership and Equity Structure K&W is requested to perform specified procedures with respect to the following ownership and equity structure data as presented in the OM: (1) Kallistratos Maritime Holdings Ltd. (British Virgin Islands): 72.5% equity interest in TSL. (2) Pelagos Capital Partners Fund III LP (Cayman Islands): 18.0% equity interest in TSL. (3) Management (ESOP trust): 9.5% equity interest in TSL. (

IV.F. Semi-Annual Interest Payment Data K&W is requested to perform specified procedures with respect to the following semi-annual interest payment data as presented in the OM: (1) Semi-annual coupon payments: $17,500,000 each, calculated as $400,000,000 multiplied by 8.750% divided by 2. K&W should verify the mathematical accuracy of this calculation. (2) Payment dates: April 15 and October 15 of each year, commenci

IV.G. Other Financial Ratios and Metrics K&W is requested to perform specified procedures with respect to the following financial ratios and metrics as presented in the OM, to the extent that such ratios and metrics are derived from or relate to financial data within the scope of K&W's audit or review: (1) Maximum Total Net Leverage Ratio for incurrence: 3.50x (a covenant test under the Indenture). K&W should compare

V. Form and Delivery of the Comfort Letter

V.A. Addressees. The Comfort Letter shall be addressed to the following parties: (i) Thalassa Shipping & Logistics SA, 42 Akti Miaouli, Piraeus 185 35, Greece; (ii) Thalassa Finance Pte. Ltd., c/o Thalassa Shipping & Logistics SA, 42 Akti Miaouli, Piraeus 185 35, Greece; (iii) Anchor Bay Securities LLC, attention: Marcus Reinhardt, Managing Director, 599 Lexington Avenue, 28th Floor, New York, NY 10022, United States

V.B. Timing. The Comfort Letter is requested to be delivered on or about the pricing date of the Notes. The pricing date is currently anticipated to be on or about September 26, 2022, subject to market conditions and further adjustment by the Co-Issuers and the Initial Purchasers. We will advise K&W promptly of any changes to the anticipated pricing date. The cut-off date for the Change Period procedures described in

V.C. Form. The Comfort Letter should be substantially in the form customarily used for Rule 144A and Regulation S offerings of debt securities, consistent with SAS 72 or the applicable ISAE equivalent. We expect the Comfort Letter to follow the general structure and conventions of comfort letters delivered in comparable high-yield offerings, with such modifications as may be appropriate to reflect the specific facts

VI. Bring-Down Letter In addition to the Comfort Letter, K&W is requested to deliver a bring-down comfort letter (the "Bring-Down Letter") dated as of the closing date of the Offering, which is currently anticipated to be October 15, 2022. The Bring-Down Letter should update the Comfort Letter through a cut-off date that is no more than three (3) business days prior to the closing date. By way of illustration, if the

VII. Access to Information and Management Cooperation Calderwood & Harkness confirms that it has coordinated with TSL management to ensure that K&W will have full and timely access to the books, records, accounting workpapers, management schedules, internal reports, and all other supporting documentation necessary to perform the procedures described in this letter and to prepare and deliver the Comfort Letter and the

VIII. Fees and Expenses TSL has authorized Calderwood & Harkness to confirm that K&W's professional fees for the preparation and delivery of the Comfort Letter and the Bring-Down Letter, together with any reasonable out-of-pocket expenses incurred by K&W in connection therewith, estimated at approximately €85,000 (approximately $89,250 at the prevailing exchange rate of approximately 1.05 EUR/USD as of the date of th

IX. Confidentiality This letter and the matters described herein are strictly confidential. Neither this letter nor its contents should be disclosed to any third party without the prior written consent of TSL, except as may be required by applicable law, regulation, or professional standards applicable to K&W. K&W acknowledges that the information contained in this letter relates to a proposed securities offering tha

X. Contact Information and Closing The primary contact at Calderwood & Harkness for all matters relating to the Comfort Letter, the Bring-Down Letter, and the Offering generally is: Mr. Brendan Walsh Lead Associate, Capital Markets Calderwood & Harkness LLP 125 Broad Street New York, NY 10004 Telephone: (212) 555-7824 Email: brendan.walsh@calderwoodharkness.com The responsible partner for this matter is: Mr. Robert A

XI. Signature Very truly yours, CALDERWOOD & HARKNESS LLP By: ________ Name: Brendan Walsh Title: Lead Associate, Capital Markets Approved by: ________________________________________ Robert Adeyemi Partner, Capital Markets

XII. Distribution List cc: (by email and hard copy) Mr. Spyros Andreou, Chief Executive Officer, Thalassa Shipping & Logistics SA Ms. Marina Demetriou, Chief Financial Officer, Thalassa Shipping & Logistics SA Mr. Alexandros Theodorakis, General Counsel, Thalassa Shipping & Logistics SA Mr. Robert Adeyemi, Partner, Calderwood & Harkness LLP Ms. Jennifer Kwon, Billing Partner, Calderwood & Harkness LLP Mr. Thomas Whit

XIII. Enclosures Enclosure 1: Near-final (4th draft) Offering Memorandum dated September 12, 2022, relating to the proposed offering of $400,000,000 aggregate principal amount of Senior Secured Notes due 2029 by Thalassa Shipping & Logistics SA and Thalassa Finance Pte. Ltd. (marked "DRAFT — SUBJECT TO CHANGE"). Note: The final OM has not yet been completed. The 4th Draft OM, circulated on September 12, 2022, is subs