1044-00004 · Client 1044 · Diligence

comfort-letter-request-kestrel-white.docx DOCUMENT Capital Markets

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PRIVILEGED & CONFIDENTIAL

CALDERWOOD & HARKNESS LLP 125 Broad Street New York, NY 10004 Telephone: (212) 555-7800 Facsimile: (212) 555-7801 www.calderwoodharkness.com

Matter No.: 1044-00004 Client No.: 80214-TSL

August 1, 2022

Kestrel & White Chartered Accountants 22 Kifisias Avenue Marousi 151 25 Athens, Greece

Attention: Georgios Papadimitriou, Audit Partner

Re: Comfort Letter Request — Proposed $400,000,000 Aggregate Principal Amount of Senior Secured Notes Due 2029 Offering by Thalassa Shipping & Logistics SA and Thalassa Finance Pte. Ltd.

Dear Mr. Papadimitriou:

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), a Singapore private company limited by shares and a wholly-owned subsidiary of TSL, acting in its capacity as co-issuer. TSL and TFPL are referred to herein collectively as the "Co-Issuers."

This letter relates to the proposed offering (the "Offering") by the Co-Issuers of $400,000,000 aggregate principal amount of Senior Secured Notes due 2029 (the "Notes"). The Notes will be offered and sold pursuant to Rule 144A under the U.S. Securities Act of 1933, as amended (the "Securities Act"), and Regulation S thereunder, to qualified institutional buyers and to persons outside the United States in reliance on Regulation S. The Notes have not been, and will not be, registered under the Securities Act.

Anchor Bay Securities LLC ("ABS") is acting as lead bookrunner and lead initial purchaser of the Notes, and Halcyon Partners International Ltd. ("HPI") is acting as co-manager and co-initial purchaser of the Notes (ABS and HPI, together, the "Initial Purchasers"). Whitfield & Crane LLP ("Whitfield & Crane") serves as counsel to the Initial Purchasers in connection with the Offering.

The Notes will be governed by the laws of the Republic of Singapore and are expected to be listed on the Singapore Exchange Securities Trading Limited (SGX-ST). The anticipated closing and settlement date for the Offering is October 15, 2022, subject to customary conditions and market conditions prevailing at the time of pricing.

In connection with the Offering, the Co-Issuers and the Initial Purchasers are preparing an Offering Memorandum (the "OM"). The current near-final draft of the OM is the fourth draft (the "4th Draft OM"), dated September 12, 2022, a copy of which is enclosed herewith as Enclosure 1, marked "DRAFT — SUBJECT TO CHANGE." The first draft of the OM was circulated on July 11, 2022, and the 4th Draft OM is substantially agreed among the parties. The final OM is expected to be finalized prior to the pricing of the Notes.

We understand that Kestrel & White Chartered Accountants ("K&W") serves as the independent auditor of TSL and its consolidated subsidiaries. We are writing to formally request that K&W deliver a comfort letter (the "Comfort Letter") and a subsequent bring-down comfort letter (the "Bring-Down Letter") in connection with the Offering, as more fully described below.

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 determines appropriate given its status as a non-U.S. audit firm, the equivalent international standards, including in particular International Standard on Assurance Engagements 3000 (Revised) ("ISAE 3000") and International Standard on Assurance Engagements 3400 ("ISAE 3400"), as applicable and as issued by the International Auditing and Assurance Standards Board ("IAASB"). We understand that K&W may tailor certain aspects of the Comfort Letter to conform with the conventions applicable to audit firms operating under the regulatory framework of the Hellenic Republic, and we are amenable to discussing any such adjustments, provided that the substance and scope of the Comfort Letter remain consistent with market practice for transactions of this type.

The Comfort Letter is a customary and market-standard deliverable in Rule 144A and Regulation S high-yield note offerings. The delivery of the Comfort Letter will constitute a condition precedent to the closing of the Offering under the terms of the purchase agreement (the "Purchase Agreement") to be entered into among the Co-Issuers, certain subsidiary guarantors of TSL (the "Guarantor Subsidiaries"), and the Initial Purchasers. The form and substance of the Comfort Letter will be subject to the reasonable satisfaction of the Initial Purchasers and their counsel.

The Comfort Letter will be addressed to TSL, TFPL, ABS, and HPI. The Comfort Letter will also be made available for reliance by Calderwood & Harkness LLP and Whitfield & Crane LLP (attention: Thomas Whitfield III, Partner) in connection with the discharge of their respective due diligence and disclosure obligations in relation to the Offering. In particular, the Comfort Letter is required to support the negative assurance letter (commonly referred to as a "10b-5 letter" or "negative assurance disclosure letter") to be delivered by Whitfield & Crane LLP on behalf of the Initial Purchasers in connection with the closing of the Offering. It is market practice for counsel to the initial purchasers in a Rule 144A/Regulation S offering to deliver such a negative assurance letter, and the availability and adequacy of the Comfort Letter is a material element of the due diligence inquiry underpinning that letter.

We would be grateful if K&W would confirm, at its earliest convenience, that it is willing and able to deliver the Comfort Letter and the Bring-Down Letter on the timeline and in the scope described in this letter. We turn now to a detailed description of the scope of the Comfort Letter.

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 Solutions Pte. Ltd. (Singapore),

throughout the entire audit period covered by the audited financial statements included in the OM (i.e., the fiscal years ended December 31, 2019, December 31, 2020, and December 31, 2021) and continuously through and including the date of the Comfort Letter. The independence confirmation should be made in accordance with the applicable independence requirements of the International Ethics Standards Board for Accountants ("IESBA") Code of Ethics for Professional Accountants and, to the extent applicable given the nature of the Offering and the involvement of U.S. capital markets participants, the independence rules of the U.S. Securities and Exchange Commission ("SEC") as set forth in Rule 2-01 of Regulation S-X under the Securities Act.

If K&W has identified any matters that could bear on its independence with respect to TSL or any of its subsidiaries, we request that K&W bring such matters to our attention promptly so that they may be evaluated and, if necessary, addressed prior to the delivery of the Comfort Letter.

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 further requested to confirm in the Comfort Letter that its audit reports on the foregoing consolidated financial statements were issued without qualification (i.e., that K&W issued an unqualified or "clean" audit opinion with respect to each set of financial statements). In the event that any qualification, emphasis of matter paragraph, or other modification was included in any of K&W's audit reports, we request that K&W identify such qualification or modification and provide a description thereof in the Comfort Letter.

K&W is also requested to confirm that the audited consolidated financial statements of TSL for the fiscal years ended December 31, 2021, December 31, 2020, and December 31, 2019, as presented in the OM, have been prepared and presented in accordance with International Financial Reporting Standards ("IFRS") as adopted by the European Union, and that such financial statements are presented in the OM in a form that is consistent with the financial statements included in K&W's audit reports.

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 Engagements 2410, "Review of Interim Financial Information Performed by the Independent Auditor of the Entity" ("ISRE 2410"), as issued by the IAASB.

K&W is further requested to confirm in the Comfort Letter that, on the basis of its review, nothing came to K&W's attention that caused it to believe that the unaudited condensed consolidated interim financial statements for the three-month period ended March 31, 2022, are not presented fairly, in all material respects, in accordance with International Accounting Standard 34, "Interim Financial Reporting" ("IAS 34").

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 (collectively, the "Circle-Up Items"). A detailed table of Circle-Up Items, with specific page references to the 4th Draft OM, is enclosed herewith as Enclosure 2 and will be updated to reflect the final pagination and content of the final OM prior to delivery of the Comfort Letter.

With respect to each Circle-Up Item, K&W is requested to report in the Comfort Letter that it has read the relevant financial data and statistical information as set forth in the OM and has compared such data to the underlying accounting records of TSL and its subsidiaries, the audited consolidated financial statements, the unaudited condensed consolidated interim financial statements, management-prepared schedules and analyses, and such other documents and records as identified by management in support of the data presented. K&W is requested to report in the Comfort Letter whether the amounts, percentages, ratios, and other data points so compared are in agreement with, or can be recalculated or derived from, such underlying records and documents, or, where applicable, whether such amounts fall within agreed-upon tolerances (to be discussed and agreed between K&W and the parties in advance of the delivery of the Comfort Letter).

For the avoidance of doubt, the specified procedures to be performed by K&W are limited in nature and do not constitute an audit or a review of the OM or any portion thereof, and K&W is not being asked to express an opinion on any financial data or statistical information other than as specifically set forth in the Comfort 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 from March 31, 2022 through such cut-off date, the "Change Period").

The procedures to be performed by K&W with respect to the Change Period should include, at a minimum, the following:

(i) reading the minutes of all meetings of the board of directors (and any committees thereof) and the shareholders of TSL held during the Change Period, as well as any written resolutions adopted during the Change Period, insofar as such minutes and resolutions relate to matters that could have a material effect on the financial condition or results of operations of TSL and its subsidiaries;

(ii) reading the latest available unaudited interim consolidated financial data of TSL and its subsidiaries as of a date and for a period subsequent to March 31, 2022 (including, to the extent available, any monthly or quarterly management accounts, trial balances, or other financial data prepared by management for internal purposes); and

(iii) making inquiries of certain officers of TSL — specifically, Mr. Spyros Andreou, Chief Executive Officer, and Ms. Marina Demetriou, Chief Financial Officer — regarding (a) whether there have been any material changes in the share capital, long-term debt, or short-term debt of TSL and its subsidiaries since March 31, 2022, (b) whether there have been any decreases in consolidated net assets, revenue, or net income (or increases in net loss) as compared to the corresponding period of the prior fiscal year or as compared to the amounts reflected in the most recent interim financial statements, and (c) whether there are any other matters that, in the judgment of such officers, could have a material adverse effect on the financial condition, results of operations, or business of TSL and its subsidiaries.

On the basis of the foregoing procedures (which do not constitute an audit and would not necessarily reveal matters of significance), K&W is requested to provide in the Comfort Letter a "negative assurance" statement to the effect that nothing came to K&W's attention that caused it to believe that there were any material adverse changes in the financial condition or results of operations of TSL and its subsidiaries during the Change Period, subject to customary limitations and qualifications, including the inherent limitations of the procedures performed and the fact that such procedures do not provide the same level of assurance as an audit conducted in accordance with ISA.

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 prior to delivery of the Comfort Letter. A separate table of Circle-Up Items, in a format suitable for use as a working document, is enclosed as Enclosure 2.

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 statements for the fiscal year ended December 31, 2021, and the unaudited condensed consolidated interim financial statements for the three-month period ended March 31, 2022, and confirm that the annualized figure presented in the OM is in agreement with such data, or identify any variances.

(2) LTM Adjusted EBITDA (Q1 2022 annualized): $214,600,000 (stated as "$214.6 million" in the OM). K&W should compare this figure to the underlying quarterly Adjusted EBITDA data, including a reconciliation from net income (loss) to Adjusted EBITDA, and confirm that the figure presented in the OM is in agreement with the underlying data. K&W should also verify that the adjustments made in arriving at Adjusted EBITDA are consistent with the definition of "Adjusted EBITDA" as set forth in the OM and in the Indenture.

(3) EBITDA margin: 31.2%, calculated as $214.6 million divided by $687.4 million. K&W should verify the mathematical accuracy of this calculation.

(4) Revenue breakdown by segment: Revenue attributable to (a) the dry-bulk segment, (b) the container feeder segment, and (c) the port logistics and freight forwarding segment, as presented in the business description section of the OM. K&W should compare such segment revenue data to the underlying segment reporting data in the audited financial statements and/or management-prepared segment schedules.

(5) Revenue and EBITDA for FY2021, FY2020, and FY2019: As presented in the "Selected Consolidated Financial Data" section of the OM. K&W should compare such data to the corresponding figures in the audited consolidated financial statements for each fiscal year.

(6) Quarterly revenue and EBITDA for Q1 2022 and Q1 2021: As presented in the interim financial data section of the OM. K&W should compare such data to the unaudited condensed consolidated interim financial statements and, for Q1 2021, to the underlying quarterly data derived from the audited financial statements for the fiscal year ended December 31, 2021.

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 recent management accounts.

(2) Existing bilateral ship-finance facility with Meridian Maritime Bank AG: $190,000,000 outstanding. K&W should compare this figure to the notes to the audited or unaudited financial statements or to the relevant loan agreement and outstanding balance confirmations provided by management.

(3) Existing bilateral ship-finance facility with Clearwater Shipping Finance Ltd.: $120,000,000 outstanding. K&W should compare this figure in the same manner as described in clause (2) above.

(4) Total existing debt: $310,000,000, calculated as the sum of $190,000,000 and $120,000,000. K&W should verify the mathematical accuracy of this calculation and confirm consistency with the debt schedule in the audited or unaudited financial statements.

(5) Pro forma total debt (post-offering, post-refinancing): $400,000,000 (representing the Notes only, with the bilateral facilities fully refinanced and retired from the proceeds of the Offering). K&W should compare this figure to the pro forma capitalization table and pro forma adjustments as presented in the OM and as supported by management-prepared schedules.

(6) Pro forma net debt: $341,700,000, calculated as $400,000,000 minus $58,300,000 in cash on balance sheet. K&W should verify the mathematical accuracy of this calculation.

(7) Pro forma net leverage: 1.59x, calculated as $341,700,000 divided by $214,600,000 (LTM Adjusted EBITDA). K&W should verify the mathematical accuracy of this calculation.

(8) Pro forma interest coverage: 6.13x, calculated as $214,600,000 (LTM Adjusted EBITDA) divided by $35,000,000 (annual interest expense on the Notes at an 8.750% coupon on $400,000,000 aggregate principal amount). K&W should verify the mathematical accuracy of this calculation.

(9) Annual interest expense on the Notes: $35,000,000, calculated as $400,000,000 multiplied by 8.750%. K&W should verify the mathematical accuracy of this calculation.

(10) Capitalization table: Both the "actual" and "pro forma as adjusted" columns of the capitalization table as presented in the OM. K&W should compare the "actual" column to the audited or unaudited financial statements and the "pro forma as adjusted" column to the pro forma adjustments and management-prepared schedules supporting the pro forma presentation.

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 amount of $400,000,000 and the gross proceeds of $392,000,000.

(4) Application of proceeds — refinancing of Meridian Maritime Bank AG facility: $190,000,000.

(5) Application of proceeds — refinancing of Clearwater Shipping Finance Ltd. facility: $120,000,000.

(6) Application of proceeds — general corporate purposes and fleet capital expenditures: $72,000,000.

(7) Estimated fees, expenses, and OID: $18,000,000, representing the aggregate of the OID ($8,000,000), Initial Purchaser discounts, and estimated transaction costs, including legal fees, accounting fees, trustee fees, printing, and other customary offering expenses.

(8) Reconciliation: K&W should verify that the sum of the foregoing application amounts ($190,000,000 + $120,000,000 + $72,000,000 + $18,000,000) equals the total aggregate principal amount of $400,000,000.

K&W should compare each of the foregoing figures to the management-prepared use of proceeds schedule and to such supporting documentation as management may provide, including pay-off letters or estimated pay-off amounts from the existing bilateral lenders, fee letters from the Initial Purchasers, and estimates of transaction expenses prepared by TSL or its advisors.

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 of Collateral Vessels: 28 vessels.

(4) Collateral Vessel appraised value: $1,175,000,000.

(5) Collateral coverage ratio: 2.94x, calculated as $1,175,000,000 divided by $400,000,000. K&W should verify the mathematical accuracy of this calculation.

(6) Average vessel age: 9.2 years.

(7) Total deadweight tonnage (DWT): Approximately 2,850,000 DWT.

(8) Intercompany loan receivables pledged (TFPL to fleet-owning subsidiaries): $365,000,000.

Important note regarding fleet valuation data: We acknowledge that the fleet valuation data described above is sourced from the independent appraisal report prepared by Compass Marine Valuations Ltd. (Robert Hargreaves, Head of Valuations) and that such valuation data is outside the scope of K&W's audit or review engagement. K&W is not being asked to audit, review, or express any opinion on the fleet valuations or the methodology employed by Compass Marine Valuations Ltd. K&W is asked only to confirm that the fleet valuation amounts cited in the OM are consistent with the corresponding figures set forth in the appraisal report provided to K&W by TSL management. With respect to the fleet composition data (number of vessels, vessel types, average age, total DWT), K&W should compare such data to TSL's fixed asset register, vessel schedules maintained by management, and/or classification society records, as applicable.

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.

(4) Kallistratos limited parent guarantee cap: $50,000,000.

K&W is requested to confirm that the foregoing equity ownership percentages are consistent with TSL's statutory share register and corporate records as reviewed by K&W in connection with its audit of TSL's consolidated financial statements. With respect to the Kallistratos limited parent guarantee cap, K&W should compare the stated amount to the relevant guarantee agreement or corporate resolution provided by management.

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, commencing April 15, 2023. K&W should confirm that the payment dates stated in the OM are consistent with the terms of the Notes as described in the draft Indenture or the description of the Notes in the OM.

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 the pro forma Total Net Leverage Ratio calculation as presented in the OM to the underlying financial data and confirm that the mathematical presentation of the incurrence test is accurate and consistent with the applicable definition in the draft Indenture.

(2) Minimum collateral coverage ratio (maintenance covenant): 2.00x. K&W should verify the mathematical presentation of this covenant test in the OM, including the components of the numerator (aggregate appraised value of Collateral Vessels) and denominator (aggregate principal amount of the Notes outstanding), and confirm that the calculation as presented is mathematically accurate.

(3) Restricted payments basket: The greater of $30,000,000 and 10% of Consolidated Net Tangible Assets. To the extent that the OM presents or references a specific Consolidated Net Tangible Assets figure in connection with the description of this covenant, K&W should compare such figure to the underlying financial data in the audited or unaudited financial statements and confirm its consistency.

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; and

(iv) Halcyon Partners International Ltd., attention: James Ogilvie, Managing Director, 25 Old Broad Street, London EC2N 1HQ, United Kingdom.

In addition, copies of the Comfort Letter should be delivered concurrently to the following parties:

(v) Calderwood & Harkness LLP, attention: Robert Adeyemi, Partner, 125 Broad Street, New York, NY 10004, United States; and

(vi) Whitfield & Crane LLP, attention: Thomas Whitfield III, Partner, One Liberty Plaza, 165 Broadway, New York, NY 10006, 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 Section III.E above should be no more than five (5) business days prior to the date of the Comfort Letter. By way of illustration, if the Comfort Letter is dated September 26, 2022, the cut-off date should be no earlier than September 19, 2022.

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 and circumstances of the Offering and the nature of K&W's engagement.

We request that K&W provide a draft of the Comfort Letter to Calderwood & Harkness LLP and Whitfield & Crane LLP for review and comment no later than two (2) weeks prior to the anticipated pricing date (i.e., on or about September 12, 2022, or such other date as may be agreed among the parties in light of any changes to the anticipated pricing timeline). It is customary for the draft Comfort Letter to be the subject of a comment and negotiation process among K&W, counsel to the Co-Issuers, and counsel to the Initial Purchasers, and we anticipate that at least one round of comments will be exchanged prior to finalization.

If K&W would find it helpful, Calderwood & Harkness is prepared to circulate to K&W a draft form of Comfort Letter based on a precedent from a prior Calderwood & Harkness Rule 144A transaction, which K&W may use as a starting point for the preparation of its draft. A copy of such a precedent form is enclosed herewith as Enclosure 3 for K&W's reference. We emphasize that the precedent form is provided for convenience only and that K&W should prepare its Comfort Letter in accordance with its own professional standards and judgment.

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 closing date is October 15, 2022 (a Saturday — to be confirmed; if the closing date falls on a non-business day, the closing will occur on the next succeeding business day), the cut-off date for the Bring-Down Letter should be no earlier than October 12, 2022 (assuming October 12, 2022 is a business day).

The Bring-Down Letter should confirm that, as of the date of the Bring-Down Letter and taking into account any events or developments occurring after the date of the Comfort Letter through the cut-off date, nothing has come to K&W's attention that would require any modification of the statements, conclusions, or negative assurance provided in the Comfort Letter. If any modifications are required — for example, if K&W becomes aware of any material changes in the financial condition or results of operations of TSL and its subsidiaries during the period between the cut-off date for the Comfort Letter and the cut-off date for the Bring-Down Letter — K&W should describe such modifications in the Bring-Down Letter.

The Bring-Down Letter should be addressed to the same parties as the Comfort Letter, as identified in Section V.A above, and copies should be delivered to the same parties identified therein.

The delivery of the Bring-Down Letter in form and substance satisfactory to the Initial Purchasers and their counsel will constitute a condition precedent to the closing of the Offering under the Purchase Agreement.

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 Bring-Down Letter. In particular, we have discussed this matter with Ms. Marina Demetriou, Chief Financial Officer of TSL, and Mr. Alexandros Theodorakis, General Counsel of TSL, each of whom has confirmed TSL's commitment to providing K&W with all reasonably requested information and cooperation.

K&W should direct any requests for additional documentation, information, or management representations to:

Ms. Marina Demetriou Chief Financial Officer Thalassa Shipping & Logistics SA 42 Akti Miaouli Piraeus 185 35, Greece

K&W is requested to copy the undersigned on all such requests so that Calderwood & Harkness may assist in facilitating the timely provision of any requested materials:

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

K&W is further requested to advise Calderwood & Harkness and TSL management promptly if, in the course of performing the procedures described in this letter, K&W identifies any matters — whether relating to the scope, timing, or substance of the Comfort Letter — that could affect the delivery of the Comfort Letter or the Bring-Down Letter on the timeline described herein, or that could require modifications to the scope of the procedures to be performed. Early identification of any such matters will enable the parties to address them efficiently and minimize the risk of delays to the Offering timeline.

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 this letter), will be borne by TSL. These fees will form part of the total estimated transaction costs of the Offering, which are currently estimated at approximately $18,000,000 in the aggregate (inclusive of Initial Purchaser discounts, OID, legal fees, accounting fees, trustee fees, listing fees, printing and distribution costs, and other customary offering expenses).

K&W should submit invoices for its fees and expenses directly to:

Ms. Marina Demetriou Chief Financial Officer Thalassa Shipping & Logistics SA 42 Akti Miaouli Piraeus 185 35, Greece

K&W is requested to provide a copy of each invoice to Calderwood & Harkness for its records, attention:

Ms. Jennifer Kwon Billing Partner Calderwood & Harkness LLP 125 Broad Street New York, NY 10004

Email: jennifer.kwon@calderwoodharkness.com

If K&W's estimated fees are expected to differ materially from the amount set forth above, we request that K&W advise us of the revised estimate as promptly as practicable so that the use of proceeds and transaction expense disclosures in the OM may be updated accordingly, if necessary.

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 that has not yet been publicly announced and that premature disclosure could be materially prejudicial to the interests of the Co-Issuers and the Initial Purchasers.

The Comfort Letter and Bring-Down Letter, once delivered, may be shared with the addressees listed in Section V.A above and with their respective legal counsel (Calderwood & Harkness LLP and Whitfield & Crane LLP). The existence of the Comfort Letter and the Bring-Down Letter may be referenced in the Purchase Agreement and in the closing deliverables for the Offering, and the Comfort Letter and Bring-Down Letter may be made available to the trustee under the Indenture and to the relevant clearing systems (Thackeray Partners LLC and Ashgrove Enterprises) to the extent required in connection with the listing of the Notes on SGX-ST. Except as described in this paragraph, neither the Comfort Letter nor the Bring-Down Letter may be reproduced, distributed, or otherwise made available to any other party without the prior written consent of K&W.

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 Adeyemi Partner, Capital Markets Calderwood & Harkness LLP 125 Broad Street New York, NY 10004 Telephone: (212) 555-7810

Email: robert.adeyemi@calderwoodharkness.com

We respectfully request that K&W confirm its receipt of this letter and its willingness to deliver the Comfort Letter and the Bring-Down Letter on the timeline and in the scope described herein, by responding in writing (by letter or email) to Brendan Walsh no later than August 8, 2022. If K&W has any questions, concerns, or preliminary comments regarding the scope or timing of the Comfort Letter request, we would welcome the opportunity to discuss them by telephone or videoconference at K&W's earliest convenience.

We appreciate K&W's continued cooperation and professionalism in connection with this Offering, and we look forward to working with you and your team to ensure the timely and successful completion of the Comfort Letter and Bring-Down Letter deliverables. Please do not hesitate to contact us if you require any additional information or clarification regarding this request.

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 Whitfield III, Partner, Whitfield & Crane LLP

Mr. Marcus Reinhardt, Managing Director, Anchor Bay Securities LLC

Mr. James Ogilvie, Managing Director, Halcyon Partners International Ltd.

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 substantially agreed among the parties. The 1st Draft OM was initially circulated on July 11, 2022. The final OM will be circulated to K&W promptly upon its completion, and the Circle-Up Items and page references will be updated accordingly.

Enclosure 2: Table of Circle-Up Items with specific OM page references (corresponding to the 4th Draft OM dated September 12, 2022). Note: This table will be updated to reflect the final OM pagination and content once the final OM is completed and distributed.

Enclosure 3: Precedent form of Comfort Letter (from a prior Calderwood & Harkness Rule 144A transaction), provided for reference purposes only.

This letter is confidential and is intended solely for the use of the addressee and the parties identified in the distribution list above. Any unauthorized use, disclosure, or distribution of this letter or its contents is strictly prohibited. This letter does not constitute legal advice to K&W. Calderwood & Harkness LLP acts solely as counsel to TSL and TFPL in connection with the Offering.

PRIVILEGED & CONFIDENTIAL
CALDERWOOD & HARKNESS LLP 125 Broad Street New York, NY 10004 Telephone: (212) 555-7800 Facsimile: (212) 555-7801 www.calderwoodharkness.com
Matter No.: 1044-00004 Client No.: 80214-TSL
August 1, 2022
Kestrel & White Chartered Accountants 22 Kifisias Avenue Marousi 151 25 Athens, Greece
Attention: Georgios Papadimitriou, Audit Partner
Re: Comfort Letter Request — Proposed $400,000,000 Aggregate Principal Amount of Senior Secured Notes Due 2029 Offering by Thalassa Shipping & Logistics SA and Thalassa Finance Pte. Ltd.
Dear Mr. Papadimitriou:
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), a Singapore private company limited by shares and a wholly-owned subsidiary of TSL, acting in its capacity as co-issuer. TSL and TFPL are referred to herein collectively as the "Co-Issuers."
This letter relates to the proposed offering (the "Offering") by the Co-Issuers of $400,000,000 aggregate principal amount of Senior Secured Notes due 2029 (the "Notes"). The Notes will be offered and sold pursuant to Rule 144A under the U.S. Securities Act of 1933, as amended (the "Securities Act"), and Regulation S thereunder, to qualified institutional buyers and to persons outside the United States in reliance on Regulation S. The Notes have not been, and will not be, registered under the Securities Act.
Anchor Bay Securities LLC ("ABS") is acting as lead bookrunner and lead initial purchaser of the Notes, and Halcyon Partners International Ltd. ("HPI") is acting as co-manager and co-initial purchaser of the Notes (ABS and HPI, together, the "Initial Purchasers"). Whitfield & Crane LLP ("Whitfield & Crane") serves as counsel to the Initial Purchasers in connection with the Offering.
The Notes will be governed by the laws of the Republic of Singapore and are expected to be listed on the Singapore Exchange Securities Trading Limited (SGX-ST). The anticipated closing and settlement date for the Offering is October 15, 2022, subject to customary conditions and market conditions prevailing at the time of pricing.
In connection with the Offering, the Co-Issuers and the Initial Purchasers are preparing an Offering Memorandum (the "OM"). The current near-final draft of the OM is the fourth draft (the "4th Draft OM"), dated September 12, 2022, a copy of which is enclosed herewith as Enclosure 1, marked "DRAFT — SUBJECT TO CHANGE." The first draft of the OM was circulated on July 11, 2022, and the 4th Draft OM is substantially agreed among the parties. The final OM is expected to be finalized prior to the pricing of the Notes.
We understand that Kestrel & White Chartered Accountants ("K&W") serves as the independent auditor of TSL and its consolidated subsidiaries. We are writing to formally request that K&W deliver a comfort letter (the "Comfort Letter") and a subsequent bring-down comfort letter (the "Bring-Down Letter") in connection with the Offering, as more fully described below.
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 determines appropriate given its status as a non-U.S. audit firm, the equivalent international standards, including in particular International Standard on Assurance Engagements 3000 (Revised) ("ISAE 3000") and International Standard on Assurance Engagements 3400 ("ISAE 3400"), as applicable and as issued by the International Auditing and Assurance Standards Board ("IAASB"). We understand that K&W may tailor certain aspects of the Comfort Letter to conform with the conventions applicable to audit firms operating under the regulatory framework of the Hellenic Republic, and we are amenable to discussing any such adjustments, provided that the substance and scope of the Comfort Letter remain consistent with market practice for transactions of this type.
The Comfort Letter is a customary and market-standard deliverable in Rule 144A and Regulation S high-yield note offerings. The delivery of the Comfort Letter will constitute a condition precedent to the closing of the Offering under the terms of the purchase agreement (the "Purchase Agreement") to be entered into among the Co-Issuers, certain subsidiary guarantors of TSL (the "Guarantor Subsidiaries"), and the Initial Purchasers. The form and substance of the Comfort Letter will be subject to the reasonable satisfaction of the Initial Purchasers and their counsel.
The Comfort Letter will be addressed to TSL, TFPL, ABS, and HPI. The Comfort Letter will also be made available for reliance by Calderwood & Harkness LLP and Whitfield & Crane LLP (attention: Thomas Whitfield III, Partner) in connection with the discharge of their respective due diligence and disclosure obligations in relation to the Offering. In particular, the Comfort Letter is required to support the negative assurance letter (commonly referred to as a "10b-5 letter" or "negative assurance disclosure letter") to be delivered by Whitfield & Crane LLP on behalf of the Initial Purchasers in connection with the closing of the Offering. It is market practice for counsel to the initial purchasers in a Rule 144A/Regulation S offering to deliver such a negative assurance letter, and the availability and adequacy of the Comfort Letter is a material element of the due diligence inquiry underpinning that letter.
We would be grateful if K&W would confirm, at its earliest convenience, that it is willing and able to deliver the Comfort Letter and the Bring-Down Letter on the timeline and in the scope described in this letter. We turn now to a detailed description of the scope of the Comfort Letter.
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 Solutions Pte. Ltd. (Singapore),
throughout the entire audit period covered by the audited financial statements included in the OM (i.e., the fiscal years ended December 31, 2019, December 31, 2020, and December 31, 2021) and continuously through and including the date of the Comfort Letter. The independence confirmation should be made in accordance with the applicable independence requirements of the International Ethics Standards Board for Accountants ("IESBA") Code of Ethics for Professional Accountants and, to the extent applicable given the nature of the Offering and the involvement of U.S. capital markets participants, the independence rules of the U.S. Securities and Exchange Commission ("SEC") as set forth in Rule 2-01 of Regulation S-X under the Securities Act.
If K&W has identified any matters that could bear on its independence with respect to TSL or any of its subsidiaries, we request that K&W bring such matters to our attention promptly so that they may be evaluated and, if necessary, addressed prior to the delivery of the Comfort Letter.
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 further requested to confirm in the Comfort Letter that its audit reports on the foregoing consolidated financial statements were issued without qualification (i.e., that K&W issued an unqualified or "clean" audit opinion with respect to each set of financial statements). In the event that any qualification, emphasis of matter paragraph, or other modification was included in any of K&W's audit reports, we request that K&W identify such qualification or modification and provide a description thereof in the Comfort Letter.
K&W is also requested to confirm that the audited consolidated financial statements of TSL for the fiscal years ended December 31, 2021, December 31, 2020, and December 31, 2019, as presented in the OM, have been prepared and presented in accordance with International Financial Reporting Standards ("IFRS") as adopted by the European Union, and that such financial statements are presented in the OM in a form that is consistent with the financial statements included in K&W's audit reports.
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 Engagements 2410, "Review of Interim Financial Information Performed by the Independent Auditor of the Entity" ("ISRE 2410"), as issued by the IAASB.
K&W is further requested to confirm in the Comfort Letter that, on the basis of its review, nothing came to K&W's attention that caused it to believe that the unaudited condensed consolidated interim financial statements for the three-month period ended March 31, 2022, are not presented fairly, in all material respects, in accordance with International Accounting Standard 34, "Interim Financial Reporting" ("IAS 34").
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 (collectively, the "Circle-Up Items"). A detailed table of Circle-Up Items, with specific page references to the 4th Draft OM, is enclosed herewith as Enclosure 2 and will be updated to reflect the final pagination and content of the final OM prior to delivery of the Comfort Letter.
With respect to each Circle-Up Item, K&W is requested to report in the Comfort Letter that it has read the relevant financial data and statistical information as set forth in the OM and has compared such data to the underlying accounting records of TSL and its subsidiaries, the audited consolidated financial statements, the unaudited condensed consolidated interim financial statements, management-prepared schedules and analyses, and such other documents and records as identified by management in support of the data presented. K&W is requested to report in the Comfort Letter whether the amounts, percentages, ratios, and other data points so compared are in agreement with, or can be recalculated or derived from, such underlying records and documents, or, where applicable, whether such amounts fall within agreed-upon tolerances (to be discussed and agreed between K&W and the parties in advance of the delivery of the Comfort Letter).
For the avoidance of doubt, the specified procedures to be performed by K&W are limited in nature and do not constitute an audit or a review of the OM or any portion thereof, and K&W is not being asked to express an opinion on any financial data or statistical information other than as specifically set forth in the Comfort 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 from March 31, 2022 through such cut-off date, the "Change Period").
The procedures to be performed by K&W with respect to the Change Period should include, at a minimum, the following:
(i) reading the minutes of all meetings of the board of directors (and any committees thereof) and the shareholders of TSL held during the Change Period, as well as any written resolutions adopted during the Change Period, insofar as such minutes and resolutions relate to matters that could have a material effect on the financial condition or results of operations of TSL and its subsidiaries;
(ii) reading the latest available unaudited interim consolidated financial data of TSL and its subsidiaries as of a date and for a period subsequent to March 31, 2022 (including, to the extent available, any monthly or quarterly management accounts, trial balances, or other financial data prepared by management for internal purposes); and
(iii) making inquiries of certain officers of TSL — specifically, Mr. Spyros Andreou, Chief Executive Officer, and Ms. Marina Demetriou, Chief Financial Officer — regarding (a) whether there have been any material changes in the share capital, long-term debt, or short-term debt of TSL and its subsidiaries since March 31, 2022, (b) whether there have been any decreases in consolidated net assets, revenue, or net income (or increases in net loss) as compared to the corresponding period of the prior fiscal year or as compared to the amounts reflected in the most recent interim financial statements, and (c) whether there are any other matters that, in the judgment of such officers, could have a material adverse effect on the financial condition, results of operations, or business of TSL and its subsidiaries.
On the basis of the foregoing procedures (which do not constitute an audit and would not necessarily reveal matters of significance), K&W is requested to provide in the Comfort Letter a "negative assurance" statement to the effect that nothing came to K&W's attention that caused it to believe that there were any material adverse changes in the financial condition or results of operations of TSL and its subsidiaries during the Change Period, subject to customary limitations and qualifications, including the inherent limitations of the procedures performed and the fact that such procedures do not provide the same level of assurance as an audit conducted in accordance with ISA.
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 prior to delivery of the Comfort Letter. A separate table of Circle-Up Items, in a format suitable for use as a working document, is enclosed as Enclosure 2.
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 statements for the fiscal year ended December 31, 2021, and the unaudited condensed consolidated interim financial statements for the three-month period ended March 31, 2022, and confirm that the annualized figure presented in the OM is in agreement with such data, or identify any variances.
(2) LTM Adjusted EBITDA (Q1 2022 annualized): $214,600,000 (stated as "$214.6 million" in the OM). K&W should compare this figure to the underlying quarterly Adjusted EBITDA data, including a reconciliation from net income (loss) to Adjusted EBITDA, and confirm that the figure presented in the OM is in agreement with the underlying data. K&W should also verify that the adjustments made in arriving at Adjusted EBITDA are consistent with the definition of "Adjusted EBITDA" as set forth in the OM and in the Indenture.
(3) EBITDA margin: 31.2%, calculated as $214.6 million divided by $687.4 million. K&W should verify the mathematical accuracy of this calculation.
(4) Revenue breakdown by segment: Revenue attributable to (a) the dry-bulk segment, (b) the container feeder segment, and (c) the port logistics and freight forwarding segment, as presented in the business description section of the OM. K&W should compare such segment revenue data to the underlying segment reporting data in the audited financial statements and/or management-prepared segment schedules.
(5) Revenue and EBITDA for FY2021, FY2020, and FY2019: As presented in the "Selected Consolidated Financial Data" section of the OM. K&W should compare such data to the corresponding figures in the audited consolidated financial statements for each fiscal year.
(6) Quarterly revenue and EBITDA for Q1 2022 and Q1 2021: As presented in the interim financial data section of the OM. K&W should compare such data to the unaudited condensed consolidated interim financial statements and, for Q1 2021, to the underlying quarterly data derived from the audited financial statements for the fiscal year ended December 31, 2021.
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 recent management accounts.
(2) Existing bilateral ship-finance facility with Meridian Maritime Bank AG: $190,000,000 outstanding. K&W should compare this figure to the notes to the audited or unaudited financial statements or to the relevant loan agreement and outstanding balance confirmations provided by management.
(3) Existing bilateral ship-finance facility with Clearwater Shipping Finance Ltd.: $120,000,000 outstanding. K&W should compare this figure in the same manner as described in clause (2) above.
(4) Total existing debt: $310,000,000, calculated as the sum of $190,000,000 and $120,000,000. K&W should verify the mathematical accuracy of this calculation and confirm consistency with the debt schedule in the audited or unaudited financial statements.
(5) Pro forma total debt (post-offering, post-refinancing): $400,000,000 (representing the Notes only, with the bilateral facilities fully refinanced and retired from the proceeds of the Offering). K&W should compare this figure to the pro forma capitalization table and pro forma adjustments as presented in the OM and as supported by management-prepared schedules.
(6) Pro forma net debt: $341,700,000, calculated as $400,000,000 minus $58,300,000 in cash on balance sheet. K&W should verify the mathematical accuracy of this calculation.
(7) Pro forma net leverage: 1.59x, calculated as $341,700,000 divided by $214,600,000 (LTM Adjusted EBITDA). K&W should verify the mathematical accuracy of this calculation.
(8) Pro forma interest coverage: 6.13x, calculated as $214,600,000 (LTM Adjusted EBITDA) divided by $35,000,000 (annual interest expense on the Notes at an 8.750% coupon on $400,000,000 aggregate principal amount). K&W should verify the mathematical accuracy of this calculation.
(9) Annual interest expense on the Notes: $35,000,000, calculated as $400,000,000 multiplied by 8.750%. K&W should verify the mathematical accuracy of this calculation.
(10) Capitalization table: Both the "actual" and "pro forma as adjusted" columns of the capitalization table as presented in the OM. K&W should compare the "actual" column to the audited or unaudited financial statements and the "pro forma as adjusted" column to the pro forma adjustments and management-prepared schedules supporting the pro forma presentation.
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 amount of $400,000,000 and the gross proceeds of $392,000,000.
(4) Application of proceeds — refinancing of Meridian Maritime Bank AG facility: $190,000,000.
(5) Application of proceeds — refinancing of Clearwater Shipping Finance Ltd. facility: $120,000,000.
(6) Application of proceeds — general corporate purposes and fleet capital expenditures: $72,000,000.
(7) Estimated fees, expenses, and OID: $18,000,000, representing the aggregate of the OID ($8,000,000), Initial Purchaser discounts, and estimated transaction costs, including legal fees, accounting fees, trustee fees, printing, and other customary offering expenses.
(8) Reconciliation: K&W should verify that the sum of the foregoing application amounts ($190,000,000 + $120,000,000 + $72,000,000 + $18,000,000) equals the total aggregate principal amount of $400,000,000.
K&W should compare each of the foregoing figures to the management-prepared use of proceeds schedule and to such supporting documentation as management may provide, including pay-off letters or estimated pay-off amounts from the existing bilateral lenders, fee letters from the Initial Purchasers, and estimates of transaction expenses prepared by TSL or its advisors.
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 of Collateral Vessels: 28 vessels.
(4) Collateral Vessel appraised value: $1,175,000,000.
(5) Collateral coverage ratio: 2.94x, calculated as $1,175,000,000 divided by $400,000,000. K&W should verify the mathematical accuracy of this calculation.
(6) Average vessel age: 9.2 years.
(7) Total deadweight tonnage (DWT): Approximately 2,850,000 DWT.
(8) Intercompany loan receivables pledged (TFPL to fleet-owning subsidiaries): $365,000,000.
Important note regarding fleet valuation data: We acknowledge that the fleet valuation data described above is sourced from the independent appraisal report prepared by Compass Marine Valuations Ltd. (Robert Hargreaves, Head of Valuations) and that such valuation data is outside the scope of K&W's audit or review engagement. K&W is not being asked to audit, review, or express any opinion on the fleet valuations or the methodology employed by Compass Marine Valuations Ltd. K&W is asked only to confirm that the fleet valuation amounts cited in the OM are consistent with the corresponding figures set forth in the appraisal report provided to K&W by TSL management. With respect to the fleet composition data (number of vessels, vessel types, average age, total DWT), K&W should compare such data to TSL's fixed asset register, vessel schedules maintained by management, and/or classification society records, as applicable.
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.
(4) Kallistratos limited parent guarantee cap: $50,000,000.
K&W is requested to confirm that the foregoing equity ownership percentages are consistent with TSL's statutory share register and corporate records as reviewed by K&W in connection with its audit of TSL's consolidated financial statements. With respect to the Kallistratos limited parent guarantee cap, K&W should compare the stated amount to the relevant guarantee agreement or corporate resolution provided by management.
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, commencing April 15, 2023. K&W should confirm that the payment dates stated in the OM are consistent with the terms of the Notes as described in the draft Indenture or the description of the Notes in the OM.
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 the pro forma Total Net Leverage Ratio calculation as presented in the OM to the underlying financial data and confirm that the mathematical presentation of the incurrence test is accurate and consistent with the applicable definition in the draft Indenture.
(2) Minimum collateral coverage ratio (maintenance covenant): 2.00x. K&W should verify the mathematical presentation of this covenant test in the OM, including the components of the numerator (aggregate appraised value of Collateral Vessels) and denominator (aggregate principal amount of the Notes outstanding), and confirm that the calculation as presented is mathematically accurate.
(3) Restricted payments basket: The greater of $30,000,000 and 10% of Consolidated Net Tangible Assets. To the extent that the OM presents or references a specific Consolidated Net Tangible Assets figure in connection with the description of this covenant, K&W should compare such figure to the underlying financial data in the audited or unaudited financial statements and confirm its consistency.
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; and
(iv) Halcyon Partners International Ltd., attention: James Ogilvie, Managing Director, 25 Old Broad Street, London EC2N 1HQ, United Kingdom.
In addition, copies of the Comfort Letter should be delivered concurrently to the following parties:
(v) Calderwood & Harkness LLP, attention: Robert Adeyemi, Partner, 125 Broad Street, New York, NY 10004, United States; and
(vi) Whitfield & Crane LLP, attention: Thomas Whitfield III, Partner, One Liberty Plaza, 165 Broadway, New York, NY 10006, 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 Section III.E above should be no more than five (5) business days prior to the date of the Comfort Letter. By way of illustration, if the Comfort Letter is dated September 26, 2022, the cut-off date should be no earlier than September 19, 2022.
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 and circumstances of the Offering and the nature of K&W's engagement.
We request that K&W provide a draft of the Comfort Letter to Calderwood & Harkness LLP and Whitfield & Crane LLP for review and comment no later than two (2) weeks prior to the anticipated pricing date (i.e., on or about September 12, 2022, or such other date as may be agreed among the parties in light of any changes to the anticipated pricing timeline). It is customary for the draft Comfort Letter to be the subject of a comment and negotiation process among K&W, counsel to the Co-Issuers, and counsel to the Initial Purchasers, and we anticipate that at least one round of comments will be exchanged prior to finalization.
If K&W would find it helpful, Calderwood & Harkness is prepared to circulate to K&W a draft form of Comfort Letter based on a precedent from a prior Calderwood & Harkness Rule 144A transaction, which K&W may use as a starting point for the preparation of its draft. A copy of such a precedent form is enclosed herewith as Enclosure 3 for K&W's reference. We emphasize that the precedent form is provided for convenience only and that K&W should prepare its Comfort Letter in accordance with its own professional standards and judgment.
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 closing date is October 15, 2022 (a Saturday — to be confirmed; if the closing date falls on a non-business day, the closing will occur on the next succeeding business day), the cut-off date for the Bring-Down Letter should be no earlier than October 12, 2022 (assuming October 12, 2022 is a business day).
The Bring-Down Letter should confirm that, as of the date of the Bring-Down Letter and taking into account any events or developments occurring after the date of the Comfort Letter through the cut-off date, nothing has come to K&W's attention that would require any modification of the statements, conclusions, or negative assurance provided in the Comfort Letter. If any modifications are required — for example, if K&W becomes aware of any material changes in the financial condition or results of operations of TSL and its subsidiaries during the period between the cut-off date for the Comfort Letter and the cut-off date for the Bring-Down Letter — K&W should describe such modifications in the Bring-Down Letter.
The Bring-Down Letter should be addressed to the same parties as the Comfort Letter, as identified in Section V.A above, and copies should be delivered to the same parties identified therein.
The delivery of the Bring-Down Letter in form and substance satisfactory to the Initial Purchasers and their counsel will constitute a condition precedent to the closing of the Offering under the Purchase Agreement.
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 Bring-Down Letter. In particular, we have discussed this matter with Ms. Marina Demetriou, Chief Financial Officer of TSL, and Mr. Alexandros Theodorakis, General Counsel of TSL, each of whom has confirmed TSL's commitment to providing K&W with all reasonably requested information and cooperation.
K&W should direct any requests for additional documentation, information, or management representations to:
Ms. Marina Demetriou Chief Financial Officer Thalassa Shipping & Logistics SA 42 Akti Miaouli Piraeus 185 35, Greece
K&W is requested to copy the undersigned on all such requests so that Calderwood & Harkness may assist in facilitating the timely provision of any requested materials:
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
K&W is further requested to advise Calderwood & Harkness and TSL management promptly if, in the course of performing the procedures described in this letter, K&W identifies any matters — whether relating to the scope, timing, or substance of the Comfort Letter — that could affect the delivery of the Comfort Letter or the Bring-Down Letter on the timeline described herein, or that could require modifications to the scope of the procedures to be performed. Early identification of any such matters will enable the parties to address them efficiently and minimize the risk of delays to the Offering timeline.
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 this letter), will be borne by TSL. These fees will form part of the total estimated transaction costs of the Offering, which are currently estimated at approximately $18,000,000 in the aggregate (inclusive of Initial Purchaser discounts, OID, legal fees, accounting fees, trustee fees, listing fees, printing and distribution costs, and other customary offering expenses).
K&W should submit invoices for its fees and expenses directly to:
Ms. Marina Demetriou Chief Financial Officer Thalassa Shipping & Logistics SA 42 Akti Miaouli Piraeus 185 35, Greece
K&W is requested to provide a copy of each invoice to Calderwood & Harkness for its records, attention:
Ms. Jennifer Kwon Billing Partner Calderwood & Harkness LLP 125 Broad Street New York, NY 10004
Email: jennifer.kwon@calderwoodharkness.com
If K&W's estimated fees are expected to differ materially from the amount set forth above, we request that K&W advise us of the revised estimate as promptly as practicable so that the use of proceeds and transaction expense disclosures in the OM may be updated accordingly, if necessary.
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 that has not yet been publicly announced and that premature disclosure could be materially prejudicial to the interests of the Co-Issuers and the Initial Purchasers.
The Comfort Letter and Bring-Down Letter, once delivered, may be shared with the addressees listed in Section V.A above and with their respective legal counsel (Calderwood & Harkness LLP and Whitfield & Crane LLP). The existence of the Comfort Letter and the Bring-Down Letter may be referenced in the Purchase Agreement and in the closing deliverables for the Offering, and the Comfort Letter and Bring-Down Letter may be made available to the trustee under the Indenture and to the relevant clearing systems (Thackeray Partners LLC and Ashgrove Enterprises) to the extent required in connection with the listing of the Notes on SGX-ST. Except as described in this paragraph, neither the Comfort Letter nor the Bring-Down Letter may be reproduced, distributed, or otherwise made available to any other party without the prior written consent of K&W.
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 Adeyemi Partner, Capital Markets Calderwood & Harkness LLP 125 Broad Street New York, NY 10004 Telephone: (212) 555-7810
Email: robert.adeyemi@calderwoodharkness.com
We respectfully request that K&W confirm its receipt of this letter and its willingness to deliver the Comfort Letter and the Bring-Down Letter on the timeline and in the scope described herein, by responding in writing (by letter or email) to Brendan Walsh no later than August 8, 2022. If K&W has any questions, concerns, or preliminary comments regarding the scope or timing of the Comfort Letter request, we would welcome the opportunity to discuss them by telephone or videoconference at K&W's earliest convenience.
We appreciate K&W's continued cooperation and professionalism in connection with this Offering, and we look forward to working with you and your team to ensure the timely and successful completion of the Comfort Letter and Bring-Down Letter deliverables. Please do not hesitate to contact us if you require any additional information or clarification regarding this request.
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 Whitfield III, Partner, Whitfield & Crane LLP
Mr. Marcus Reinhardt, Managing Director, Anchor Bay Securities LLC
Mr. James Ogilvie, Managing Director, Halcyon Partners International Ltd.
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 substantially agreed among the parties. The 1st Draft OM was initially circulated on July 11, 2022. The final OM will be circulated to K&W promptly upon its completion, and the Circle-Up Items and page references will be updated accordingly.
Enclosure 2: Table of Circle-Up Items with specific OM page references (corresponding to the 4th Draft OM dated September 12, 2022). Note: This table will be updated to reflect the final OM pagination and content once the final OM is completed and distributed.
Enclosure 3: Precedent form of Comfort Letter (from a prior Calderwood & Harkness Rule 144A transaction), provided for reference purposes only.
This letter is confidential and is intended solely for the use of the addressee and the parties identified in the distribution list above. Any unauthorized use, disclosure, or distribution of this letter or its contents is strictly prohibited. This letter does not constitute legal advice to K&W. Calderwood & Harkness LLP acts solely as counsel to TSL and TFPL in connection with the Offering.

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CALDERWOOD & HARKNESS LLP

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