Contract analysis

1. Purpose This memorandum establishes the new matter file for Calderwood & Harkness LLP's representation of Thalassa Shipping & Logistics SA ("TSL" or the "Issuer") as issuer's counsel in connection with a proposed offering of $400,000,000 aggregate principal amount of Senior Secured Notes due 2029 (the "Notes" or the "Offering"). Calderwood & Harkness LLP ("C&H" or the "Firm") has been retained as lead internationa

2. Client Information 2.1 Client Identity Full Legal Name: Thalassa Shipping & Logistics SA Short Name / Nickname: TSL / Thalassa Entity Type: Société Anonyme (SA) organized and existing under the laws of the Hellenic Republic Greek General Commercial Registry (GEMI) No.: 148276201000 Registered Office and Headquarters: 42 Akti Miaouli, Piraeus 185 35, Greece TSL is a privately held Greek shipping company with a well

3. Transaction Summary 3.1 Overview. The proposed transaction involves the offering of $400,000,000 aggregate principal amount of Senior Secured Notes due 2029. The Notes will be co-issued by Thalassa Shipping & Logistics SA (as primary issuer) and Thalassa Finance Pte. Ltd. ("TFPL"), a wholly-owned Singapore subsidiary established as the co-issuer vehicle for purposes of this transaction. The key terms of the propos

4. Scope of Calderwood & Harkness Engagement Calderwood & Harkness LLP has been retained as issuer's counsel (lead international counsel) for the proposed Notes offering. The scope of the Firm's engagement encompasses the following workstreams: (a) Indenture. Drafting and negotiation of the Indenture governing the Notes, which will be governed by the laws of the Republic of Singapore. The Indenture will contain custo

5. Engagement Team 5.1 Calderwood & Harkness Staffing The following attorneys have been staffed on this matter: Additional staffing may be required as the transaction progresses, particularly in connection with the intensive drafting and negotiation period anticipated during August and September 2022. Any additional staffing will be approved by the Responsible Partner and communicated to the Billing Partner for fee e

6. Other Transaction Parties and Advisors 6.1 Initial Purchasers The total Initial Purchaser discount is 2.00% of the aggregate principal amount of the Notes, or $8,000,000 in the aggregate. The allocation of economics between Anchor Bay Securities LLC ("ABS") and Halcyon Partners International Ltd. ("Halcyon") reflects ABS's role as lead-left bookrunner and its assumption of the primary underwriting risk and distrib

7. Proposed ISINs and Identifiers The following securities identifiers have been proposed for the Notes and will be confirmed prior to closing: These identifiers are proposed only and remain subject to confirmation by the relevant numbering agencies (CUSIP Global Services, ANNA, and the relevant local numbering agency). Final identifiers should be confirmed with the Trustee and the Initial Purchasers no later than tw

8. Anticipated Timeline and Key Milestones The following timeline sets forth the currently anticipated schedule for the transaction. All dates are approximate and subject to change based on market conditions, the progress of due diligence and document negotiations, and the receipt of preliminary ratings. The engagement team should track progress against these milestones and report any material delays to the Responsib

9. Conflicts Clearance Reference is made to the Conflict Check Memorandum dated June 10, 2022, prepared by Natasha Forbes (Working Associate) and approved by Robert Adeyemi (Responsible Partner). The conflict check was conducted in accordance with the Firm's standard conflicts clearance procedures and covered all identified transaction parties and their respective affiliates, as well as the principals, beneficial own

10. Administrative and Billing Instructions The following administrative and billing instructions apply to all time entries, expenses, and disbursements incurred in connection with this matter: Matter Number: 1044-00004 Client Number: 80214-TSL Practice Area Code: Capital Markets Time Entry Coding: All time entries by attorneys and other timekeepers working on this matter must be coded to matter number 1044-00004. Ti

11. Document Workstream Overview The following is a summary enumeration of the principal documents that Calderwood & Harkness will be responsible for drafting, reviewing, or coordinating in connection with this engagement. This list is intended to provide a high-level overview of the document production workload and is not exhaustive; additional ancillary documents, correspondence, and deliverables may be required as

1. Indenture (Singapore law governed) — the primary governing instrument for the Notes, containing covenants, events of default, redemption provisions, collateral provisions, and related terms

2. Purchase Agreement — the agreement among the Issuers, the Guarantors, and the Initial Purchasers governing the purchase and sale of the Notes

3. Registration Rights Agreement — the agreement providing for the exchange offer and/or shelf registration of the Notes

4. Intercreditor Agreement — the agreement governing the relative priorities, enforcement rights, and remedies of the secured parties with respect to the shared collateral

5. Security Documents: (a) Ship mortgages over the 28 Collateral Vessels (multiple flag-state jurisdictions) (b) Assignments of earnings and insurances for the Collateral Vessels (c) Share pledge agreements over the equity of TFPL and each Guarantor Subsidiary (d) Assignment of intercompany loan receivables from TFPL to fleet-owning subsidiaries

6. Offering Memorandum — anticipated to be approximately 280 pages in length, including business description, risk factors, capitalization and indebtedness, selected financial data, management's discussion and analysis, description of the Notes, description of the security, and financial statements

7. Forms of Global Notes — Rule 144A Global Note and Regulation S Global Note

8. Supplemental Indenture (Form — Guarantor Joinder) — form of supplemental indenture for the joinder of additional guarantors

9. Paying Agent and Transfer Agent Agreement — agreement appointing the paying agent and transfer agent for the Notes

10. Board Resolutions — resolutions of the board of directors of TSL and sole director resolutions of TFPL authorizing the Offering and the execution and delivery of the transaction documents

11. Officers' Certificate (Form) — form of officers' certificate to be delivered at closing

12. Legal Opinions: (a) Calderwood & Harkness LLP opinion (Singapore law, to the extent the Firm is qualified to deliver) (b) Delphi & Karidis LLP opinion (Greek law) — coordination and review (c) Rajendra & Osman LLP opinion (Singapore law — co-issuer capacity and enforceability) — coordination and review

13. Comfort Letter Request — letter to Kestrel & White Chartered Accountants specifying the financial data items and procedures to be covered

14. Closing Checklist and Closing Memorandum — comprehensive checklist of all closing deliverables and post-closing memorandum

15. Payoff Letter Requests — requests to Meridian Maritime Bank AG and Clearwater Shipping Finance Ltd. for payoff letters setting forth the amounts required to discharge the existing facilities

16. Investor Presentation Review — review of the roadshow deck and investor presentation for consistency with the Offering Memorandum

17. Risk Factors Drafting Memorandum — internal memorandum identifying key risk areas for disclosure in the Offering Memorandum 18. 10b-5 Disclosure Letter Framework — coordination memorandum with Whitfield & Crane LLP regarding the negative assurance letter process

19. Supplemental Correspondence — any additional correspondence, notices, or filings as may be required during the course of the transaction

12. Distribution This memorandum is being distributed to the following individuals for their respective records and administrative processing: • Robert Adeyemi, Responsible Partner • Jennifer Kwon, Billing Partner • Brendan Walsh, Lead Associate • Natasha Forbes, Working Associate • Capital Markets Practice Group Leader • Conflicts Committee (for records) • Finance / Billing Department This memorandum and its content