FR EA
1044-00004 · Client 1044 · Transaction Documents
form-of-global-note-reg-s.docx DOCUMENT Capital Markets
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EXHIBIT A-2 TO THE INDENTURE

FORM OF REGULATION S GLOBAL NOTE

THALASSA SHIPPING & LOGISTICS SA a société anonyme organized under the laws of the Hellenic Republic

and

THALASSA FINANCE PTE. LTD. a private company limited by shares incorporated under the laws of the Republic of Singapore

as Co-Issuers

8.750% SENIOR SECURED NOTES DUE 2029

REGULATION S GLOBAL NOTE

THIS NOTE HAS NOT BEEN AND WILL NOT BE REGISTERED UNDER THE UNITED STATES SECURITIES ACT OF 1933, AS AMENDED (THE "SECURITIES ACT"), OR THE SECURITIES LAWS OF ANY STATE OR OTHER JURISDICTION. NEITHER THIS NOTE NOR ANY INTEREST OR PARTICIPATION HEREIN MAY BE OFFERED, SOLD, ASSIGNED, TRANSFERRED, PLEDGED, ENCUMBERED, OR OTHERWISE DISPOSED OF IN THE ABSENCE OF SUCH REGISTRATION OR UNLESS SUCH TRANSACTION IS EXEMPT FROM, OR NOT SUBJECT TO, THE REGISTRATION REQUIREMENTS OF THE SECURITIES ACT AND ANY APPLICABLE STATE SECURITIES LAWS. SEE SECTIONS 8 AND 15 HEREOF AND THE INDENTURE FOR ADDITIONAL TRANSFER RESTRICTIONS APPLICABLE TO THIS NOTE.

Section 1 — Promise to Pay

Thalassa Shipping & Logistics SA, a société anonyme organized and existing under the laws of the Hellenic Republic ("TSL"), having its registered office at 42 Akti Miaouli, Piraeus 185 35, Greece, Greek General Commercial Registry (Geniko Emporiko Mitroo or "GEMI") No. 148276201000, and Thalassa Finance Pte. Ltd., a private company limited by shares incorporated under the laws of the Republic of Singapore ("TFPL"), having its registered office at 8 Marina Boulevard, #36-02, Marina Bay Financial Centre Tower 1, Singapore 018981, Unique Entity Number ("UEN") 202209345K (TSL and TFPL together, the "Co-Issuers" and each a "Co-Issuer"), for value received, hereby jointly and severally promise to pay to Stonefield Industries or Harborview Industries, as nominee, or registered assigns, the principal sum indicated on Schedule A hereto (as such amount may be increased or decreased from time to time by endorsement on Schedule A in accordance with the Indenture referred to herein), on the Maturity Date of October 15, 2029, unless earlier redeemed or repurchased in accordance with the terms of the Indenture and this Note.

The Co-Issuers further jointly and severally promise to pay interest on the unpaid principal amount hereof from the Original Issue Date set forth above, or from the most recent Interest Payment Date to which interest has been paid or duly provided for, at the rate of 8.750% per annum. Interest on this Note shall be payable semi-annually in arrears on each April 15 and October 15, commencing on April 15, 2023 (each, an "Interest Payment Date"), to the Person in whose name this Note (or any predecessor Note) is registered at the close of business on the Regular Record Date immediately preceding such Interest Payment Date. The Regular Record Dates for the purpose of determining the Holders entitled to receive payment of interest on this Note shall be April 1 and October 1, respectively (whether or not such date is a Business Day).

Interest on this Note shall be computed on the basis of a 360-day year consisting of twelve 30-day months (30/360 day count convention). If any Interest Payment Date, Maturity Date, or Redemption Date falls on a day that is not a Business Day (as defined in the Indenture), the required payment of principal, premium (if any), or interest shall be made on the next succeeding Business Day with the same force and effect as if made on the date such payment was due, and no additional interest shall accrue by reason of such delay in payment for the period from and after such Interest Payment Date, Maturity Date, or Redemption Date, as the case may be, to the date of such payment.

All payments of principal, premium (if any), and interest on this Note shall be made in lawful money of the United States of America in immediately available funds.

Section 2 — Method of Payment

Payments of principal of, premium (if any) on, and interest on this Global Note shall be made by wire transfer of immediately available funds in United States dollars to the account of the Depositary or its nominee, as the registered Holder of this Global Note, in accordance with the Applicable Procedures of the Depositary and the provisions of the Indenture. So long as this Note remains a Global Note registered in the name of the Depositary or its nominee, the Depositary shall be considered the sole Holder of this Note for all purposes under the Indenture, and payments to the Depositary shall satisfy the Co-Issuers' obligation to make corresponding payments to beneficial owners of interests in this Global Note.

The initial Paying Agent for the Notes is Marlowe Asset Management Trust Company of Singapore Pte. Ltd., having its principal office at 80 Robinson Road, #02-00, Singapore 068898, UEN 199804782D (the "Paying Agent"). The Paying Agent shall act in accordance with the provisions of the Paying Agent and Transfer Agent Agreement dated as of the Original Issue Date, by and among the Co-Issuers, the Trustee, and the Paying Agent, and the applicable provisions of the Indenture. The Co-Issuers may change the Paying Agent without prior notice to the Holders; provided that the Co-Issuers shall at all times maintain a Paying Agent that is a participant in, or has access to, the facilities of the Depositary.

Section 3 — Indenture; Defined Terms

This Note is one of a duly authorized issue of notes of the Co-Issuers designated as the "8.750% Senior Secured Notes due 2029" (the "Notes"), limited in aggregate principal amount to U.S.$400,000,000 (except as otherwise provided in the Indenture with respect to the issuance of Additional Notes), issued under and pursuant to an Indenture dated as of October 15, 2022 (as it may from time to time be supplemented, modified, or amended in accordance with its terms, the "Indenture"), among TSL, TFPL, the Guarantors party thereto from time to time, Marlowe Asset Management Trust Company of Singapore Pte. Ltd., as trustee (in such capacity, the "Trustee"), and Atlas Collateral Agency Pte. Ltd., as security agent (in such capacity, the "Security Agent").

The total aggregate principal amount of Notes authorized for issuance under the Indenture is U.S.$400,000,000 (Four Hundred Million United States Dollars); provided that the Co-Issuers may, subject to compliance with the covenants contained in the Indenture (including Section 4.09 thereof), issue Additional Notes from time to time under the Indenture in an unlimited aggregate principal amount, so long as such Additional Notes are treated as part of the same series as the Notes initially issued hereunder for all purposes under the Indenture and have the same terms as the Notes (other than the issue date, issue price, and, if applicable, the first interest payment date and initial interest accrual date).

This Note shall be governed by, and construed in accordance with, the laws of the Republic of Singapore, without regard to conflicts of law principles thereof that would require the application of the laws of any other jurisdiction.

Capitalized terms used but not otherwise defined in this Note shall have the respective meanings ascribed to such terms in the Indenture. The terms of the Indenture are hereby incorporated by reference into this Note and shall, for all purposes, have the same effect as if set forth at length herein. Reference is hereby made to the Indenture for a statement of the respective rights, limitations of rights, duties, obligations, and immunities thereunder of the Co-Issuers, the Guarantors, the Trustee, the Security Agent, and the Holders of the Notes and of the terms upon which the Notes are, and are to be, authenticated and delivered. In the event of any inconsistency or conflict between the provisions of this Note and the provisions of the Indenture, the provisions of the Indenture shall control and govern.

Section 4 — Guarantees

The obligations of the Co-Issuers under the Notes and the Indenture, including the obligations to pay the principal of, premium (if any) on, and interest on this Note, are jointly and severally guaranteed on a senior secured basis by each of the following entities (collectively, the "Guarantor Subsidiaries"):

(a) Thalassa Dry Bulk Operations Ltd., a limited liability company organized under the laws of Malta, company registration number C 98421;

(b) Thalassa Container Feeder Ltd., a limited liability company organized under the laws of the Republic of the marshall Islands, registration number 107429;

(c) Thalassa Port Services FZCO, a free zone company organized under the laws of the Dubai Multi Commodities Centre Free Zone, Dubai, United Arab Emirates, license number DMCC-847921; and

(d) Thalassa Freight Solutions Pte. Ltd., a private company limited by shares incorporated under the laws of the Republic of Singapore, UEN 201814567G.

In addition, the obligations of the Co-Issuers under the Notes and the Indenture are guaranteed on a limited basis by Kallistratos Maritime Holdings Ltd., a company incorporated under the laws of the British Virgin Islands, company number 2051433 (the "Parent Guarantor"). The guarantee provided by the Parent Guarantor (the "Parent Guarantee") is capped at an aggregate amount of U.S.$50,000,000 (Fifty Million United States Dollars) and is subject in all respects to the terms and conditions set forth in the Indenture and the Notation of Guarantee attached hereto as Schedule B.

Each guarantee provided by a Guarantor Subsidiary and the Parent Guarantee (each, a "Guarantee" and collectively, the "Guarantees") constitutes a senior secured obligation of the applicable Guarantor, ranking as described in Section 9 hereof and in the Indenture. The terms and conditions of each Guarantee, including limitations required by applicable fraudulent conveyance, fraudulent transfer, corporate benefit, financial assistance, capital maintenance, or similar laws, are set forth in full in Article XI of the Indenture.

Future Subsidiaries of TSL or TFPL may be required to accede as Guarantors under the Indenture by executing and delivering a Supplemental Indenture substantially in the form of the Guarantor Joinder attached as Exhibit C to the Indenture, in each case in accordance with the provisions of Section 4.15 of the Indenture.

Section 5 — Security

The Notes and the Guarantees are secured by a first-priority security interest (subject to Permitted Liens) in the Collateral, as defined in the Indenture and the Security Documents. The Collateral includes, without limitation, the following:

(a) Ship Mortgages. First-priority ship mortgages (statutory or preferred, as applicable under the laws of the relevant flag state) over twenty-eight (28) designated Collateral Vessels (the "Collateral Vessels"), being part of a total fleet of fifty (50) vessels owned or bareboat chartered by TSL and its Subsidiaries. The Collateral Vessels had an aggregate appraised fair market value of U.S.$1,175,000,000 (One Billion One Hundred Seventy-Five Million United States Dollars) as of June 30, 2022, as determined by Compass Marine Valuations Ltd. (London), an independent, internationally recognized ship valuation firm, reflecting a collateral coverage ratio of approximately 2.94x relative to the initial aggregate principal amount of the Notes of U.S.$400,000,000. A list of the Collateral Vessels, their respective flag states, and individual appraised values is set forth in Schedule 1 to the Indenture.

(b) Assignment of Earnings, Insurances, and Requisition Compensation. First-priority assignment of all earnings (including freight, hire, and demurrage), insurances (including hull and machinery, protection and indemnity, and loss of hire), and requisition compensation in respect of each Collateral Vessel.

(c) Share Pledges. First-priority pledge over 100% of the issued and outstanding equity interests (including shares, membership interests, partnership interests, and equivalent ownership interests) in TFPL and each Guarantor Subsidiary, in each case as held directly or indirectly by TSL or TFPL, as applicable.

(d) Assignment of Intercompany Receivables. First-priority assignment of intercompany loan receivables from TFPL to fleet-owning Subsidiaries of TSL, in the aggregate amount of U.S.$365,000,000 (Three Hundred Sixty-Five Million United States Dollars) as of the Original Issue Date, as evidenced by intercompany loan agreements on arm's-length terms.

The Security Agent for the Notes is Atlas Collateral Agency Pte. Ltd., having its principal office at 80 Robinson Road, #02-00, Singapore 068898, UEN 200115678R. All security interests constituting the Collateral are held by the Security Agent for the benefit of the Trustee and the Holders of the Notes, in each case pursuant to and in accordance with the terms of the Security Documents (as defined in the Indenture) and the Intercreditor Agreement dated as of October 15, 2022, among TSL, TFPL, the Guarantors, the Trustee, the Security Agent, and the other parties thereto (the "Intercreditor Agreement"). The rights of the Holders in respect of the Collateral are subject to the terms of the Intercreditor Agreement.

Section 6 — Optional Redemption

The Notes are subject to optional redemption by the Co-Issuers as follows:

Make-Whole Redemption (Prior to October 15, 2025). At any time and from time to time prior to October 15, 2025, the Co-Issuers may redeem all or any part of the Notes at a redemption price equal to 100% of the principal amount of the Notes to be redeemed, plus the Applicable Premium (as defined below), plus accrued and unpaid interest thereon, if any, to, but excluding, the Redemption Date (subject to the right of Holders of record on the relevant Regular Record Date to receive interest due on an Interest Payment Date that is on or prior to the Redemption Date).

For purposes of this Section 6, "Applicable Premium" means, with respect to any Note on any Redemption Date, the greater of:

(i) 1.00% of the principal amount of such Note; and

(ii) the excess, if any, of (A) the present value at such Redemption Date of (1) the redemption price of such Note at October 15, 2025 (as set forth in the table below) plus (2) all remaining required interest payments due on such Note through October 15, 2025 (excluding accrued but unpaid interest to the Redemption Date), computed using a discount rate equal to the Treasury Rate (as defined in the Indenture) as of such Redemption Date plus 50 basis points, over (B) the then outstanding principal amount of such Note.

Fixed-Price Optional Redemption (On or After October 15, 2025). On or after October 15, 2025, the Co-Issuers may redeem all or any part of the Notes at the following redemption prices (expressed as percentages of the principal amount of the Notes to be redeemed), plus accrued and unpaid interest thereon, if any, to, but excluding, the applicable Redemption Date (subject to the right of Holders of record on the relevant Regular Record Date to receive interest due on an Interest Payment Date that is on or prior to the Redemption Date), if redeemed during the twelve-month period beginning on the dates indicated below:

Equity Clawback. At any time prior to the date that is 180 days following the closing of an Equity Offering (as defined in the Indenture) that constitutes an initial public offering of the common equity of TSL or any direct or indirect parent entity thereof, the Co-Issuers may, on one or more occasions, redeem up to 40% of the original aggregate principal amount of the Notes (calculated after giving effect to the issuance of any Additional Notes) at a redemption price equal to 108.750% of the principal amount of the Notes to be redeemed, plus accrued and unpaid interest thereon, if any, to, but excluding, the Redemption Date (subject to the right of Holders of record on the relevant Regular Record Date to receive interest due on an Interest Payment Date that is on or prior to the Redemption Date), with the net cash proceeds received by the Co-Issuers (or any direct or indirect parent of TSL) from such Equity Offering; provided that:

(a) at least 60% of the original aggregate principal amount of the Notes (calculated after giving effect to the issuance of any Additional Notes) remains outstanding immediately after giving effect to such redemption; and

(b) such redemption occurs within 180 days of the closing of such Equity Offering.

Partial Redemption. In the event of any partial redemption of the Notes, the minimum aggregate principal amount of Notes to be redeemed shall be U.S.$5,000,000. Selection of Notes for partial redemption shall be made by the Trustee on a pro rata basis or by such other method as the Trustee shall deem fair and appropriate (or, in the case of Global Notes, in accordance with the Applicable Procedures of the Depositary), unless otherwise required by law.

Notice of Redemption. Notice of any redemption shall be given by the Co-Issuers (or the Trustee, at the Co-Issuers' request and expense) to each Holder of Notes to be redeemed at its registered address not less than 15 nor more than 60 days prior to the applicable Redemption Date, in accordance with Section 12.02 of the Indenture. Any such notice may, at the Co-Issuers' discretion, be subject to the satisfaction of one or more conditions precedent (including, without limitation, the completion of a related financing transaction), and the Co-Issuers may rescind any such notice of redemption if any such condition precedent is not satisfied.

Section 7 — Mandatory Redemption; Offers to Purchase

Change of Control Offer. Upon the occurrence of a Change of Control (as defined in the Indenture), the Co-Issuers shall be required to make an offer (a "Change of Control Offer") to repurchase all outstanding Notes at a purchase price in cash equal to 101% of the aggregate principal amount thereof, plus accrued and unpaid interest thereon, if any, to, but excluding, the date of repurchase (the "Change of Control Payment Date"), in each case in accordance with the procedures set forth in Section 4.10 of the Indenture. If the Change of Control Payment Date falls on a date that is after a Regular Record Date but on or prior to the corresponding Interest Payment Date, accrued and unpaid interest, if any, shall be paid to the Person in whose name the Note is registered at the close of business on such Regular Record Date.

Asset Sale Offer. If, on any date, the aggregate amount of Net Proceeds (as defined in the Indenture) from Asset Sales (as defined in the Indenture) that have not been applied or invested in accordance with Section 4.07 of the Indenture within 365 days of the consummation of each respective Asset Sale exceeds U.S.$15,000,000 (Fifteen Million United States Dollars), the Co-Issuers shall be required to make an offer (an "Asset Sale Offer") to all Holders to repurchase the maximum aggregate principal amount of Notes (in minimum denominations of U.S.$200,000 and integral multiples of U.S.$1,000 in excess thereof) that may be repurchased with the amount of such Excess Proceeds (as defined in the Indenture), at a purchase price in cash equal to 100% of the principal amount thereof, plus accrued and unpaid interest thereon, if any, to, but excluding, the date of repurchase, in accordance with the procedures set forth in Section 4.07 of the Indenture.

No Sinking Fund. The Notes are not entitled to the benefit of any sinking fund obligation.

Section 8 — Denominations; Transfer; Exchange

This Note is issuable only in registered form, without coupons, in minimum denominations of U.S.$200,000 (Two Hundred Thousand United States Dollars) and integral multiples of U.S.$1,000 (One Thousand United States Dollars) in excess thereof. No service charge shall be made for any registration of transfer or exchange of this Note, but the Co-Issuers or the Trustee may require payment of a sum sufficient to cover any transfer tax or similar governmental charge payable in connection therewith.

This Note is a Regulation S Global Note. Beneficial interests in this Global Note are transferable only in accordance with the transfer restrictions set forth in Section 2.06 of the Indenture and applicable securities laws of all relevant jurisdictions. During the Distribution Compliance Period (which shall be the period of 40 consecutive days following the later of (x) the commencement of the offering of the Notes and (y) the Original Issue Date), beneficial interests in this Regulation S Global Note may not be offered, sold, pledged, or otherwise transferred to a U.S. person (as defined in Regulation S under the Securities Act) or for the account or benefit of a U.S. person, unless such transfer is made pursuant to Rule 144A under the Securities Act, in which case the beneficial interest so transferred shall be transferred to a beneficial interest in the Rule 144A Global Note (ISIN US87265TAA10, CUSIP 87265T AA1) in accordance with the Applicable Procedures of the Depositary and the certification requirements set forth in Section 2.06(b) of the Indenture.

After the expiration of the Distribution Compliance Period, transfers of beneficial interests between this Regulation S Global Note and the Rule 144A Global Note may be effected in accordance with the Indenture, including the applicable certification procedures set forth in Section 2.06 of the Indenture and the forms of certification attached as exhibits thereto, and the Applicable Procedures of the Depositary.

Beneficial interests in this Global Note are exchangeable for definitive certificated Notes in registered form only in the limited circumstances described in Section 2.06(e) of the Indenture, including (i) if the Depositary notifies the Co-Issuers that it is unwilling or unable to continue as Depositary for this Global Note or ceases to be a "clearing agency" registered under applicable law, and a successor Depositary is not appointed within 90 days after such notice or cessation, (ii) if an Event of Default has occurred and is continuing and the Trustee has received a written request from a beneficial owner of an interest in this Global Note for the issuance of definitive certificated Notes, or (iii) if the Co-Issuers, in their sole discretion, notify the Trustee in writing that they elect to cause the issuance of definitive certificated Notes. Any definitive certificated Notes issued upon exchange of beneficial interests in this Global Note shall be registered in such names and in such authorized denominations as the Depositary shall instruct the Trustee, and shall bear the applicable restrictive legends set forth in Section 2.06 of the Indenture.

Section 9 — Ranking

The Notes constitute senior secured obligations of each Co-Issuer. The Notes rank:

(a) senior in right of payment to all existing and future Indebtedness of the Co-Issuers that is expressly subordinated in right of payment to the Notes;

(b) pari passu in right of payment with all existing and future senior Indebtedness of the Co-Issuers (including, without limitation, any obligations of the Co-Issuers under any Senior Credit Facility);

(c) effectively senior, to the extent of the value of the Collateral securing the Notes (after giving effect to any Permitted Liens on such Collateral that have priority over the Liens securing the Notes), to all existing and future unsecured Indebtedness of the Co-Issuers; and

(d) structurally subordinated to all existing and future Indebtedness and other liabilities (including trade payables) of any Subsidiary of TSL that is not a Guarantor, to the extent of the assets of such non-Guarantor Subsidiary.

Each Guarantee ranks, with respect to the applicable Guarantor, in the same manner as set forth in clauses (a) through (d) above, mutatis mutandis, in respect of the Indebtedness and other obligations of such Guarantor.

Section 10 — Covenants (Summary Reference)

Reference is hereby made to the Indenture for the full and complete text of all covenants applicable to the Co-Issuers, the Guarantors, and the Holders. The following is a summary description of certain covenants contained in the Indenture and is qualified in its entirety by reference to the Indenture:

(a) Incurrence of Indebtedness. The Co-Issuers shall not, and shall not permit any Restricted Subsidiary to, directly or indirectly, create, incur, issue, assume, guarantee, or otherwise become directly or indirectly liable, contingently or otherwise, with respect to any Indebtedness, unless, after giving pro forma effect to such incurrence and the application of the net proceeds thereof, the Total Net Leverage Ratio (as defined in the Indenture) would not exceed 3.50 to 1.00, subject to certain exceptions and carve-outs set forth in Section 4.09 of the Indenture.

(b) Restricted Payments. The Co-Issuers shall not, and shall not permit any Restricted Subsidiary to, directly or indirectly, make any Restricted Payment (as defined in the Indenture), except pursuant to a general basket equal to the greater of (x) U.S.$30,000,000 and (y) 10% of Consolidated Net Tangible Assets (as defined in the Indenture), and subject to additional permitted baskets and builder basket capacity as set forth in Section 4.06 of the Indenture.

(c) Collateral Coverage Ratio. The Co-Issuers shall maintain at all times a minimum collateral coverage ratio of 2.00 to 1.00, calculated as the aggregate appraised fair market value of the Collateral Vessels (determined on the basis of independent valuations by an Approved Valuation Firm) divided by the aggregate outstanding principal amount of the Notes (including any Additional Notes). The collateral coverage ratio shall be tested semi-annually (as of June 30 and December 31 of each year), with certificates delivered to the Trustee within 30 days after each testing date.

(d) Asset Sales. The Co-Issuers shall not, and shall not permit any Restricted Subsidiary to, consummate an Asset Sale unless the consideration received is not less than the fair market value of the assets sold and at least 75% of such consideration consists of cash or Cash Equivalents. Net Proceeds in excess of U.S.$15,000,000 not applied within 365 days shall trigger an Asset Sale Offer as described in Section 7 hereof and Section 4.07 of the Indenture.

(e) Mergers, Consolidations, and Sales of Substantially All Assets. The Co-Issuers shall not, directly or indirectly, consolidate or merge with or into another Person, or sell, assign, transfer, convey, or otherwise dispose of all or substantially all of the properties or assets of the Co-Issuers and their Restricted Subsidiaries, taken as a whole, except in compliance with the conditions set forth in Section 5.01 of the Indenture.

(f) Reporting. The Co-Issuers shall furnish to the Trustee and the Holders annual audited financial statements within 120 days of fiscal year end, semi-annual unaudited financial statements within 60 days of each semi-annual period end, and such other reports and certificates as are required by the Indenture.

(g) Transactions with Affiliates. The Co-Issuers shall not, and shall not permit any Restricted Subsidiary to, directly or indirectly, enter into any transaction or series of related transactions with any Affiliate unless such transaction is on terms no less favorable to the Co-Issuers or the relevant Restricted Subsidiary than those that could reasonably be obtained in a comparable arm's-length transaction with an unrelated third party, subject to the exceptions and thresholds set forth in Section 4.11 of the Indenture.

The foregoing summaries do not purport to be complete and are subject to, and are qualified in their entirety by reference to, the full and complete text of the Indenture. The rights and obligations of each Holder in respect of such covenants are governed entirely by the Indenture, and no Holder shall have any rights or claims hereunder except as provided in the Indenture.

Section 11 — Events of Default and Remedies

Reference is hereby made to Article VI of the Indenture for the full and complete list of Events of Default and the rights, remedies, and obligations of the Trustee, the Security Agent, and the Holders upon the occurrence and during the continuance of an Event of Default. Events of Default under the Indenture include, among others: (a) failure to pay principal of or premium on any Note when due; (b) failure to pay interest on any Note within 30 days after the date when due; (c) failure to comply with certain covenants in the Indenture; (d) default under other Indebtedness in excess of a specified threshold; (e) certain events of bankruptcy or insolvency; and (f) invalidity or unenforceability of any Guarantee or Security Document.

Upon the occurrence and during the continuance of an Event of Default, the Trustee or the Holders of not less than 25% in aggregate principal amount of the then outstanding Notes may declare the principal of, premium (if any) on, and accrued and unpaid interest on all Notes to be due and payable immediately. The Security Agent may, at the direction of the Trustee (acting upon the instructions of the requisite Holders), enforce the security interests in the Collateral and exercise all remedies available under the Security Documents, the Indenture, and applicable law.

The Trustee for the Notes is Marlowe Asset Management Trust Company of Singapore Pte. Ltd. The Security Agent for the Notes is Atlas Collateral Agency Pte. Ltd. The respective duties, rights, and immunities of the Trustee and the Security Agent are set forth in the Indenture and the Security Documents.

Section 12 — Trustee Dealings with the Co-Issuers

Marlowe Asset Management Trust Company of Singapore Pte. Ltd., the Trustee under the Indenture, in its individual capacity or in any other capacity, may become the owner or pledgee of Notes and may otherwise deal with the Co-Issuers, the Guarantors, or any Affiliate of the Co-Issuers or the Guarantors with the same rights as it would have if it were not Trustee. Any Agent may do the same with like rights. The Trustee is also permitted to act as paying agent, registrar, transfer agent, and custodian under the Indenture, and any related agreements, without conflict with its duties as Trustee.

Section 13 — No Recourse Against Others

No past, present, or future director, officer, employee, incorporator, member, partner, stockholder, or controlling person of either Co-Issuer or any Guarantor, in his or her capacity as such, shall have any liability for any obligations of the Co-Issuers or the Guarantors under the Notes, the Indenture, or the Guarantees, or for any claim based on, in respect of, or by reason of such obligations or their creation. Each Holder of a Note, by accepting such Note, waives and releases all such liability. The waiver and release contained in this Section 13 are part of the consideration for the issuance of the Notes. This waiver may not be effective to waive liabilities under the United States federal securities laws, and it is the view of the U.S. Securities and Exchange Commission that such a waiver is against public policy.

Section 14 — Authentication

This Note shall not be valid or obligatory for any purpose until the certificate of authentication hereon has been manually executed (or executed by facsimile) by an authorized signatory of the Trustee, Marlowe Asset Management Trust Company of Singapore Pte. Ltd., or an authenticating agent appointed by the Trustee in accordance with Section 2.02 of the Indenture. The authentication by the Trustee shall be conclusive evidence that this Note has been duly authenticated and delivered under the Indenture.

Section 15 — Global Note Legend

The following legend shall appear on the face of this Global Note:

"THIS NOTE IS A GLOBAL NOTE WITHIN THE MEANING OF THE INDENTURE HEREINAFTER REFERRED TO AND IS REGISTERED IN THE NAME OF A DEPOSITARY OR A NOMINEE THEREOF. THIS NOTE MAY NOT BE EXCHANGED IN WHOLE OR IN PART FOR A NOTE REGISTERED, AND NO TRANSFER OF THIS NOTE IN WHOLE OR IN PART MAY BE REGISTERED, IN THE NAME OF ANY PERSON OTHER THAN SUCH DEPOSITARY OR A NOMINEE THEREOF, EXCEPT IN THE LIMITED CIRCUMSTANCES DESCRIBED IN THE INDENTURE."

The following additional legend shall appear on the face of this Global Note:

"THIS NOTE IS BEING OFFERED AND SOLD OUTSIDE THE UNITED STATES IN RELIANCE ON REGULATION S UNDER THE SECURITIES ACT. THIS NOTE MAY NOT BE OFFERED, SOLD, OR DELIVERED IN THE UNITED STATES OR TO, OR FOR THE ACCOUNT OR BENEFIT OF, ANY U.S. PERSON (AS DEFINED IN REGULATION S) UNLESS REGISTERED UNDER THE SECURITIES ACT OR AN EXEMPTION FROM SUCH REGISTRATION IS AVAILABLE."

The following additional legends shall also appear on the face of this Global Note, as applicable:

"BY ITS ACQUISITION HEREOF OR OF A BENEFICIAL INTEREST HEREIN, THE ACQUIRER (1) REPRESENTS THAT IT IS NOT ACQUIRING THIS NOTE OR AN INTEREST HEREIN WITH THE ASSETS OF (A) AN 'EMPLOYEE BENEFIT PLAN' AS DEFINED IN SECTION 3(3) OF THE EMPLOYEE RETIREMENT INCOME SECURITY ACT OF 1974, AS AMENDED ('ERISA'), THAT IS SUBJECT TO THE PROVISIONS OF TITLE I OF ERISA, (B) A 'PLAN' AS DEFINED IN AND SUBJECT TO SECTION 4975 OF THE INTERNAL REVENUE CODE OF 1986, AS AMENDED (THE 'CODE'), (C) AN ENTITY WHOSE UNDERLYING ASSETS INCLUDE 'PLAN ASSETS' BY REASON OF SUCH EMPLOYEE BENEFIT PLAN'S OR PLAN'S INVESTMENT IN SUCH ENTITY, OR (D) ANY OTHER PLAN OR ARRANGEMENT THAT IS SUBJECT TO ANY LAW, REGULATION, OR RULE THAT IS SUBSTANTIALLY SIMILAR TO TITLE I OF ERISA OR SECTION 4975 OF THE CODE ('SIMILAR LAW'), UNLESS ITS ACQUISITION AND HOLDING HEREOF OR OF A BENEFICIAL INTEREST HEREIN DOES NOT AND WILL NOT CONSTITUTE OR RESULT IN A NON-EXEMPT PROHIBITED TRANSACTION UNDER ERISA, THE CODE, OR APPLICABLE SIMILAR LAW AND (2) WILL NOT SELL OR OTHERWISE TRANSFER THIS NOTE OR AN INTEREST HEREIN OTHERWISE THAN IN COMPLIANCE WITH THE FOREGOING."

"BY ITS ACQUISITION HEREOF OR OF A BENEFICIAL INTEREST HEREIN, THE ACQUIRER ACKNOWLEDGES THAT THIS NOTE HAS NOT BEEN REGISTERED UNDER THE SECURITIES AND FUTURES ACT 2001 OF SINGAPORE (THE 'SFA'). THIS NOTE MAY NOT BE OFFERED OR SOLD, NOR MAY THIS NOTE OR ANY OTHER DOCUMENT OR MATERIAL IN CONNECTION WITH THE OFFER OR SALE, OR INVITATION FOR SUBSCRIPTION OR PURCHASE, OF THIS NOTE BE CIRCULATED OR DISTRIBUTED, WHETHER DIRECTLY OR INDIRECTLY, TO PERSONS IN SINGAPORE OTHER THAN (I) TO AN INSTITUTIONAL INVESTOR (AS DEFINED IN SECTION 4A OF THE SFA) UNDER SECTION 274 OF THE SFA, (II) TO A RELEVANT PERSON (AS DEFINED IN SECTION 275(2) OF THE SFA) PURSUANT TO SECTION 275(1) OF THE SFA, OR ANY PERSON PURSUANT TO SECTION 275(1A) OF THE SFA, AND IN ACCORDANCE WITH THE CONDITIONS SPECIFIED IN SECTION 275 OF THE SFA, OR (III) OTHERWISE PURSUANT TO, AND IN ACCORDANCE WITH THE CONDITIONS OF, ANY OTHER APPLICABLE PROVISION OF THE SFA."

"THIS NOTE CONSTITUTES AN 'ASSET-BACKED SECURITY' FOR PURPOSES OF THE EU AND UK RISK RETENTION AND DUE DILIGENCE REQUIREMENTS ONLY IF AND TO THE EXTENT EXPRESSLY STATED IN THE OFFERING MEMORANDUM DATED ON OR ABOUT THE ORIGINAL ISSUE DATE. EACH ACQUIRER OF A BENEFICIAL INTEREST IN THIS NOTE IS SOLELY RESPONSIBLE FOR DETERMINING ITS OWN COMPLIANCE WITH REGULATION (EU) 2017/2402 (THE 'EU SECURITISATION REGULATION') AND REGULATION (EU) 2017/2402 AS IT FORMS PART OF UK DOMESTIC LAW BY VIRTUE OF THE EUROPEAN UNION (WITHDRAWAL) ACT 2018 (THE 'UK SECURITISATION REGULATION'), IN EACH CASE AS APPLICABLE."

Section 16 — Governing Law

This Note and any non-contractual obligations arising out of or in connection with this Note shall be governed by, and construed in accordance with, the laws of the Republic of Singapore, without regard to conflicts of law principles thereof that would require the application of the laws of any other jurisdiction.

Each of the Co-Issuers and, by its acceptance of this Note, each Holder irrevocably and unconditionally submits to the non-exclusive jurisdiction of the courts of the Republic of Singapore for the purpose of any suit, action, or proceeding arising out of or relating to this Note or the Indenture, and each party irrevocably and unconditionally waives, to the fullest extent it may legally and effectively do so, any objection that it may now or hereafter have to the laying of venue of any such suit, action, or proceeding in any such court and any claim that any such suit, action, or proceeding brought in any such court has been brought in an inconvenient forum. Each of the Co-Issuers irrevocably appoints Thalassa Freight Solutions Pte. Ltd., 8 Marina Boulevard, #36-02, Marina Bay Financial Centre Tower 1, Singapore 018981, as its agent to receive service of process in any such suit, action, or proceeding. Nothing in this Section 16 shall affect the right of any Holder to serve legal process in any other manner permitted by law or to bring any suit, action, or proceeding in any other court of competent jurisdiction.

Section 17 — Agents

The initial Paying Agent and Transfer Agent for the Notes is:

Marlowe Asset Management Trust Company of Singapore Pte. Ltd. 80 Robinson Road, #02-00 Singapore 068898 UEN 199804782D

The Co-Issuers may from time to time appoint one or more additional Paying Agents or Transfer Agents, or substitute any Paying Agent or Transfer Agent, in accordance with the provisions of the Indenture; provided that the Co-Issuers shall at all times maintain at least one Paying Agent and one Transfer Agent, each of which shall be a participant in, or have access to, the facilities of the Depositary. Notice of any change in the identity or address of any Paying Agent or Transfer Agent shall be given to the Holders in accordance with Section 12.02 of the Indenture.

[SIGNATURE PAGE TO REGULATION S GLOBAL NOTE]

IN WITNESS WHEREOF, the Co-Issuers have caused this Note to be duly executed as of the Original Issue Date set forth above.

THALASSA SHIPPING & LOGISTICS SA

By: ________

Name: Spyros Andreou

Title: Chief Executive Officer

THALASSA SHIPPING & LOGISTICS SA

By: ________

Name: Marina Demetriou

Title: Chief Financial Officer

THALASSA FINANCE PTE. LTD.

By: ________

Name: Marina Demetriou

Title: Sole Director

TRUSTEE'S CERTIFICATE OF AUTHENTICATION

This is one of the Notes referred to in the within-mentioned Indenture.

Marlowe Asset Management TRUST COMPANY OF SINGAPORE PTE. LTD. as Trustee

By: ________

Name: ________

Title: Authorized Signatory

Date of Authentication: ________

SCHEDULE A

SCHEDULE OF INCREASES AND DECREASES IN GLOBAL NOTE

The initial aggregate principal amount of this Global Note is U.S.$280,000,000. The following increases and decreases in the principal amount of this Global Note have been made as a result of exchanges between this Regulation S Global Note (ISIN XS2498731056, Common Code 249873105) and the Rule 144A Global Note (ISIN US87265TAA10, CUSIP 87265T AA1) in accordance with the provisions of the Indenture:

Note: All increases and decreases in the principal amount of this Global Note result from exchanges between this Regulation S Global Note and the Rule 144A Global Note in accordance with Section 2.06 of the Indenture. No increase or decrease shall be made unless the Trustee has received written instructions from the Depositary or its nominee and, where applicable, the required certifications and opinions of counsel in accordance with the Indenture.

SCHEDULE B

FORM OF NOTATION OF GUARANTEE

Each of the undersigned Guarantors hereby jointly and severally, unconditionally and irrevocably, guarantees, on a senior secured basis, to each Holder of Notes authenticated and delivered by the Trustee under the Indenture and to the Trustee and its successors and assigns, the full and punctual payment of principal of, premium (if any) on, and interest on the Notes when due, whether at stated maturity, by acceleration, by redemption, or otherwise, and all other monetary obligations of the Co-Issuers under the Indenture and the Notes (including obligations to the Trustee), whether for payment of principal, premium, interest, fees, expenses, indemnities, or otherwise, in each case in accordance with the terms of the Indenture and the Notes.

Each Guarantor agrees that its obligations hereunder are primary, absolute, and unconditional, irrespective of, and shall be unaffected by, any invalidity, irregularity, or unenforceability of any Note or the Indenture, any failure to enforce the provisions of any Note or the Indenture, or any waiver, modification, consent, or indulgence granted to either Co-Issuer or any other Guarantor with respect to any provision of any Note or the Indenture, or any other circumstance that might otherwise constitute a legal or equitable discharge of a surety or guarantor.

Each Guarantor waives diligence, presentment, demand of payment, filing of claims with a court in the event of insolvency or bankruptcy of either Co-Issuer, any right to require a proceeding first against either Co-Issuer, protest, notice, and all demands whatsoever, and covenants that its Guarantee shall not be discharged except by the complete performance of the obligations contained in the Notes and the Indenture.

Notwithstanding the foregoing, the liability of each Guarantor under its Guarantee shall be limited to the maximum amount that would not render such Guarantee voidable or unenforceable under applicable fraudulent conveyance, fraudulent transfer, corporate benefit, financial assistance, capital maintenance, or similar laws of the jurisdiction of organization or incorporation of such Guarantor, after giving effect to all other contingent and fixed liabilities of such Guarantor.

The Guarantee of the Parent Guarantor (Kallistratos Maritime Holdings Ltd.) is further limited to an aggregate amount not exceeding U.S.$50,000,000 (Fifty Million United States Dollars), as described in the Indenture.

Each Guarantee shall be released and discharged automatically in the circumstances described in Section 11.06 of the Indenture.

This Notation of Guarantee shall be governed by, and construed in accordance with, the laws of the Republic of Singapore.

IN WITNESS WHEREOF, each of the undersigned Guarantors has caused this Notation of Guarantee to be duly executed as of the Original Issue Date.

GUARANTOR SUBSIDIARIES:

THALASSA DRY BULK OPERATIONS LTD. (Malta, company registration number C 98421)

By: ________

Name: ________

Title: ________

THALASSA CONTAINER FEEDER LTD. (Marshall Islands, registration number 107429)

By: ________

Name: ________

Title: ________

THALASSA PORT SERVICES FZCO (Dubai, UAE, DMCC license number DMCC-847921)

By: ________

Name: ________

Title: ________

THALASSA FREIGHT SOLUTIONS PTE. LTD. (Singapore, UEN 201814567G)

By: ________

Name: ________

Title: ________

PARENT GUARANTOR (LIMITED GUARANTEE — CAPPED AT U.S.$50,000,000):

KALLISTRATOS MARITIME HOLDINGS LTD. (British Virgin Islands, company number 2051433)

The Guarantee of this Parent Guarantor is limited to a maximum aggregate amount of U.S.$50,000,000 (Fifty Million United States Dollars) as described in the Indenture.

By: ________

Name: ________

Title: ________

[Remainder of Page Intentionally Left Blank]

ISIN:XS2498731056
Common Code:249873105
CUSIP:Not applicable (Regulation S tranche)
Certificate Number:RS-1
Principal Amount:Up to U.S.$280,000,000 (Two Hundred Eighty Million United States Dollars) (aggregate principal amount of the Regulation S tranche, forming part of the total U.S.$400,000,000 issuance, subject to adjustment as provided on Schedule A hereto)
Original Issue Date:October 15, 2022
Issue Price:98.00% of par (original issue discount of 2.00%)
Maturity Date:October 15, 2029
Interest Rate:8.750% per annum
Interest Payment Dates:April 15 and October 15 of each year, commencing April 15, 2023
Regular Record Dates:April 1 and October 1
Redemption PeriodRedemption Price
On or after October 15, 2025 and prior to October 15, 2026104.375%
On or after October 15, 2026 and prior to October 15, 2027102.188%
On or after October 15, 2027 and thereafter100.000%
Date of ExchangeAmount of Increase in Principal Amount of this Global Note (U.S.$)Amount of Decrease in Principal Amount of this Global Note (U.S.$)Principal Amount of this Global Note Following Such Increase or Decrease (U.S.$)Signature of Authorized Signatory of Trustee
October 15, 2022 (Original Issue Date)——280,000,000