EX-4.2



 Exhibit 4.2 

This FIRST SUPPLEMENTAL INDENTURE (the “First Supplemental Indenture”), dated as of August 8, 2014, is entered into
between PARAGON SHIPPING INC., a corporation duly organized and existing under the laws of the Republic of The Marshall Islands (the “Company”), and DEUTSCHE BANK TRUST COMPANY AMERICAS, a New York banking corporation, as trustee
(the “Trustee”). 
 RECITALS 

WHEREAS, the Company and the Trustee have heretofore executed and delivered an indenture, dated as of August 8, 2014 (the
“Indenture”), providing for the issuance by the Company from time to time of its Securities to be issued in one or more series; 

WHEREAS, Sections 2.01, 2.02 and 9.01 of the Indenture provide, among other things, that the Company and the Trustee may enter into indentures
supplemental to the Indenture to provide for the issuance of, and to establish the form, terms and conditions applicable to any series of Securities; 

WHEREAS, the Company intends by this First Supplemental Indenture to create and provide for the issuance of a new series of Securities to be
designated as the “8.375% Senior Notes due 2021” (the “Notes”); 
 WHEREAS, pursuant to Section 9.01(e) of
the Indenture, the Trustee and the Company are authorized to execute and deliver this First Supplemental Indenture to supplement the Indenture; and 

WHEREAS, all things necessary to make the Notes, when executed by the Company and authenticated and delivered by the Trustee, issued upon the
terms and subject to the conditions set forth hereinafter and in the Indenture and delivered as provided in the Indenture against payment therefor, valid, binding and legal obligations of the Company according to their terms, and all actions
required to be taken by the Company under the Indenture to make this First Supplemental Indenture a valid, binding and legal agreement of the Company, have been done. 

NOW, THEREFORE, in consideration of the premises and for other good and valuable consideration, the sufficiency and adequacy of which are
hereby acknowledged, the parties hereto hereby agree as follows: 
 ARTICLE I 

DEFINITIONS AND INCORPORATION BY REFERENCE 

Section 1.01. Definitions.

(a) All capitalized terms used herein and not otherwise defined below shall have the meanings ascribed thereto in the Indenture. 

(b) The following are definitions used in this First Supplemental Indenture, and to the extent that a term is defined both herein and in the
Indenture, the definition in this First Supplemental Indenture shall govern with respect to the Notes. 
 “Cash and Cash
Equivalents” means, as of a given date, the Company’s cash and cash equivalents as determined in accordance with GAAP. 

“Continuing Director” means a director who either was a member of the Board of Directors on the Issue Date or who becomes a
member of the Board of Directors subsequent to the Issue Date and whose election, appointment or nomination for election by the Company’s stockholders is duly approved by a majority of the continuing directors on the Board of Directors at the
time of such approval by such election or appointment. 
 “Credit Facility” means, with respect to the Company or any
Subsidiary of the Company, any debt or commercial paper facilities with banks or other lenders providing for revolving credit, term loans or letters of credit or any agreement treated as a finance or capital lease if and to the extent any of the
preceding items would appear as a liability upon a balance sheet of the specified Person prepared in accordance with GAAP. 







 “Cross Default” means the occurrence, with respect to any debt of the Company or
any Subsidiary having an aggregate principal amount of $10.0 million or more in the aggregate for all such debt of all such Persons, of (i) an event of default that results in such debt being due and payable prior to its scheduled maturity or
(ii) a failure to make a principal payment when due and such defaulted payment is not made, waived or extended within any applicable grace period. 

“GAAP” means generally accepted accounting principles in the United States of America as in effect as of the Issue Date,
including those set forth in the opinions and pronouncements of the Accounting Principles Board of the American Institute of Certified Public Accountants and statements and pronouncements of the Financial Accounting Standards Board or in such other
statements by such other entity as approved by a significant segment of the accounting profession. All ratios and computations based on GAAP contained in the Indenture will be computed in conformity with GAAP, except that in the event the Company is
acquired in a transaction that is accounted for using purchase accounting, the effects of the application of purchase accounting shall be disregarded in the calculation of such ratios and other computations contained in the Indenture. 

“Immaterial Subsidiary” means any Subsidiary of the Company whose net book value of its assets or revenues is not in excess
of 10% of the net book value of the consolidated Total Assets or consolidated vessel revenue of the Company as set out in the annual audited consolidated financial statements of the Company for the immediately preceding fiscal year, provided,
that, at no time shall (a) the total assets of all Immaterial Subsidiaries exceed 10% of the consolidated Total Assets of the Company or (b) the total vessel revenues calculated with respect to all Immaterial Subsidiaries (calculated on a
stand-alone basis), in the aggregate, exceed 10% of the consolidated vessel revenue of the Company, in each case as set out in the annual audited consolidated financial statements of the Company for the immediately preceding fiscal year. 

“Immediate Family Member” means any of an individual’s spouse, parents, children and siblings. 

“Issue Date” means August 8, 2014, the original issue date of the Notes. 

“Issue Date Specified Holdings” means the shares of common stock, or any securities convertible into or exchangeable for
shares of common stock, of Box Ships Inc. and Korea Lines Corporation beneficially owned, directly or indirectly, by the Company as of August 5, 2014. 

“Limited Permitted Asset Sale” means any sale, transfer, lease or other disposition of any of the Company’s or its
Subsidiaries’ assets (in the ordinary course of business or otherwise) during a single fiscal year, in a single transaction or series of transactions, (i) the Net Proceeds of which have not been applied pursuant to clauses 6.06(a) through
6.06(e) of this First Supplemental Indenture in accordance with the requirements of Section 6.06 of this First Supplemental Indenture and (ii) that results in Net Proceeds in excess of the amount provided for in clause (b)(A) of the
definition of Permitted Asset Sale, provided, that the Net Proceeds of such Limited Permitted Asset Sale represent consideration at the time of such sale, transfer, lease or other disposition at least equal to the fair market value (including
as to the value of all non-cash consideration), as determined in good faith by the Board of Directors of the Company, of the assets subject to such sale, transfer, lease or other disposition. Any Net Proceeds that are not applied or invested as
provided in (i) above and are in excess of the amount provided for in clause (b)(A) of the definition of Permitted Asset Sale will constitute “Excess Proceeds.” For the avoidance of doubt, a Limited Permitted Asset Sale
may occur only once. Following the first occurrence of a Limited Permitted Asset Sale, no further Limited Permitted Asset Sale shall be permitted. 

“Net Borrowings” means, in respect of the Company, on a consolidated basis, as of a given date, the difference of the
following, without duplication: 
 (a) Total Borrowings; minus 

(b) Cash and Cash Equivalents; 

  
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 provided that, for purposes of such calculation only, Cash and Cash Equivalents shall also include any
cash and cash equivalents that are classified as restricted cash on the Company’s balance sheet maintained in accordance with GAAP, which restricted cash shall be composed of pledged cash deposits or minimum liquidity required to be maintained
under the Company’s borrowing arrangements or in relation to bank guarantees issued on behalf of the Company. 
 “Net
Proceeds” means the aggregate cash proceeds received by the Company or any Subsidiary of the Company in respect of any Asset Sale (including, without limitation, any cash received upon the sale or other disposition of any non-cash
consideration received in any Asset Sale, but excluding any other consideration received in the form of assumption by the purchaser of indebtedness or other obligations relating to the property or assets that are the subject of such Asset Sale or
received in any other non-cash form and not disposed of for cash), net of fees, commissions, expenses and other direct costs relating to such Asset Sale, including, without limitation, (a) fees and expenses related to such Asset Sale (including
legal, accounting and investment banking fees, title and recording tax fees and sales and brokerage commissions, and any relocation expenses and severance or shutdown costs incurred as a result of such Asset Sale), (b) all federal, state,
provincial, foreign and local taxes paid or payable as a result of the Asset Sale, (c) any escrow or reserve for adjustment in respect of the sale price of such assets established in accordance with GAAP and any reserve in accordance with GAAP
against any liabilities associated with such Asset Sale and retained by the seller after such Asset Sale, including liabilities related to environmental matters and liabilities under any indemnification obligations associated with such Asset Sale,
except to the extent that such proceeds are released from any such escrow or to the extent such reserve is reduced or eliminated, and (d) any indebtedness required by its terms to be repaid, repurchased, redeemed or otherwise retired upon the
applicable Asset Sale. 
 “Net Worth” means, as of a given date, the result of, without duplication: 

(a) Total Assets, minus 
 (b)
Total Borrowings (without giving effect to any fair value adjustments pursuant to the Financial Accounting Standards Board Accounting Standards Codification 820). 

“Permitted Asset Sale” means: 

(a) any sale, assignment, conveyance, transfer or other disposition of (i) Issue Date Specified Holdings or (ii) common stock, or
securities convertible into or exchangeable for common stock, of Box Ships Inc. or Korea Lines Corporation that are received by the Company or any Subsidiary as dividends or distributions in respect of the Issue Date Specified Holdings after
August 5, 2014; 
 (b) any sale, transfer, lease or other disposition of any of the Company’s or its Subsidiaries’ assets (in
the ordinary course of business or otherwise) in any transaction or series of transactions, such that (A) the aggregate market value of all assets so sold, transferred, leased or otherwise disposed of during any fiscal year may be up to (and
including) 20% of the aggregate market value of all of the Company’s and the Company’s Subsidiaries’ assets (on a consolidated basis) on the last day of the immediately preceding fiscal year and (B) the Company receives, or the
relevant Subsidiary receives, consideration at the time of such sale, transfer, lease or other disposition at least equal to the fair market value (including as to the value of all non-cash consideration), as determined in good faith by the Board of
Directors of the Company, of the assets subject to such sale, transfer, lease or other disposition; and 
 (c) (i) the actual or
constructive total loss of a Vessel or the agreed or compromised total loss of a Vessel, (ii) the destruction of a Vessel, (iii) damage to a Vessel to an extent as shall make repair thereof uneconomical or shall render such Vessel
permanently unfit for normal use (other than obsolescence) or (iv) the condemnation, confiscation, requisition for title, seizure, forfeiture or other taking of title to or use of a Vessel that shall not be revoked within 30 days, in each case
as determined in good faith by the Board of Directors of the Company, provided, that the aggregate market value of all assets included as a Permitted Asset Sale pursuant to this paragraph (c) during any fiscal year may not exceed 10% of
the aggregate market value of all of the Company’s and the Company’s Subsidiaries’ assets (on a consolidated basis) on the last day of the immediately preceding fiscal year. 

  
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 “Permitted Business” means any business conducted by the Company or any of its
Subsidiaries as described in the Company’s annual report on Form 20-F for the year ended December 31, 2013 and any businesses that, in the good faith judgment of the Board of Directors of the Company, are reasonably related, ancillary,
supplemental or complementary thereto, or reasonable extensions thereof, including without limitation, the direct or indirect ownership, management, operation and chartering of Vessels and any business incidental thereto. 

“Permitted Holder” means (a) Michael Bodouroglou, (b) any Immediate Family Member of Michael Bodouroglou, or
(c) one or more Affiliates of any person listed in (a) or (b). 
 “Redemption Date” means, with respect to any
Notes or portion thereof to be redeemed, the date fixed for such redemption pursuant to this First Supplemental Indenture or such Notes. 

“Related Assets” means (a) any insurance policies and contracts from time to time in force with respect to a Vessel,
(b) the Capital Stock of any Subsidiary of the Company owning one or more Vessels and related assets, (c) any requisition compensation payable in respect of any compulsory acquisition of a Vessel, (d) any earnings derived from the use
or operation of a Vessel and/or any earnings account with respect to such earnings, (e) any charters, operating leases, contracts of affreightment, Vessel purchase options and related agreements entered and any security or guarantee in respect
of the charterer’s or lessee’s obligations under such charter, lease, Vessel purchase option or agreement, (f) any cash collateral account established with respect to a Vessel pursuant to the financing arrangement with respect
thereto, (g) any building, conversion or repair contracts relating to a Vessel and any security or guarantee in respect of the builder’s obligations under such contract and (h) any security interest in, or agreement or assignment
relating to, any of the foregoing or any mortgage in respect of a Vessel and any asset reasonably related, ancillary or complementary thereto. 

“Replacement Assets” means (1) all or substantially all of the assets of, or any Capital Stock of, a person primarily
engaged in a Permitted Business; provided, that in the case of the acquisition of Capital Stock of any person, such person is or becomes a subsidiary of the Company and will be subject to all restrictions described in this “Description of
Notes” as applying to subsidiaries of the Company existing on August 5, 2013; and (2) other assets that are not classified as current assets under GAAP and that are used or useful in a Permitted Business (including, without
limitation, Vessels and Related Assets). 
 “Significant Subsidiary” means (i) any direct or indirect Subsidiary of
the Company that would be a “significant subsidiary” as defined in Article 1, Rule 1-02 of Regulation S-X promulgated pursuant to the Securities Act of 1933, as amended, as such regulation is in effect on the date hereof, or (ii) any
group of direct or indirect Subsidiaries of the Company that, taken together as a group, would be a “significant subsidiary” as defined in Article 1, Rule 1-02 of Regulation S-X, promulgated pursuant to the Securities Act of 1933, as
amended, as such regulation is in effect on the date hereof. 
 “Total Assets” means, in respect of the Company on a
consolidated basis, as of a given date, all of the assets of the Company of the types presented on its consolidated balance sheet calculated in accordance with GAAP. 

“Total Borrowings” means, in respect of the Company on a consolidated basis, as of a given date, the aggregate of the
following, without duplication: 
 (a) the outstanding principal amount of any moneys borrowed; plus 

(b) the outstanding principal amount of any acceptance under any acceptance credit; plus 

(c) the outstanding principal amount of any bond, note, debenture or other similar instrument; plus 

(d) the book values of indebtedness under a lease, charter, hire purchase agreement or other similar arrangement which obligation is required
to be classified and accounted for as a capital lease obligation under GAAP (the amount of such obligation at any date will be the capitalized amount thereof at such date, determined in accordance with GAAP); plus 

  
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 (e) the outstanding principal amount of all moneys owing in connection with the sale or
discounting of receivables (otherwise than on a non-recourse basis or which otherwise meet any requirements for de-recognition under GAAP); plus 

(f) the outstanding principal amount of any indebtedness arising from any deferred payment agreements arranged primarily as a method of
raising finance or financing the acquisition of an asset (except trade payables); plus 
 (g) any fixed or minimum premium payable on the
repayment or redemption of any instrument referred to in clause (c) above; plus 
 (h) the outstanding principal amount of any
indebtedness of any Person of a type referred to in the above clauses of this definition which is the subject of a guarantee given by the Company to the extent that such guaranteed indebtedness is determined and given a value in respect of the
Company on a consolidated basis in accordance with GAAP. 
 Notwithstanding the foregoing, “Total Borrowings” shall not include
any indebtedness or obligations arising from derivative transactions entered into solely for purposes of protecting against interest rate or currency fluctuations. 

“Vessels” means one or more shipping vessels primarily designed and utilized for the transport of cargo, including, without
limitation, bulk carriers, freighters, general cargo carriers, containerships and tankers, but excluding passenger vessels, or which are otherwise engaged, used or useful in any business activities of the Company, in each case together with all
related spares, equipment and any additions or improvements. 
 “Voting Stock” of any specified Person as of any date means
the Capital Stock of such Person that is at the time entitled to vote generally in the election of the Board of Directors of such Person. 

For purposes of the foregoing definitions and the covenants set forth in Article VI of this First Supplemental Indenture, any accounting term,
phrase, calculation, determination or treatment used, required or referred to is to be construed in accordance with GAAP. 

Section 1.02. Other Definitions. 
  

			
	 Term
	  	 Defined in Section of this

First Supplemental Indenture

		
	“Additional Amounts”	  	8.01(a)
		
	“Additional Interest”	  	7.03
		
	“Additional Notes”	  	2.04(f)
		
	“Asset Sale”	  	6.06
		
	“Beneficial Owner” and “Beneficial Ownership”	  	4.01(a)
		
	“Change of Control”	  	4.01(a)
		
	“Change of Control Purchase Date”	  	4.01(a)
		
	“Change of Control Purchase Price”	  	4.01(a)


  
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	“covenant defeasance”	  	9.06
		
	“DTC”	  	2.03
		
	“Event of Default”	  	7.01
		
	“Interest Payment Date”	  	2.04(c)
		
	“legal defeasance”	  	9.05
		
	“Limited Permitted Asset Sale Purchase Date”	  	6.06
		
	“Limited Permitted Asset Sale Purchase Price”	  	6.06
		
	“Maturity Date”	  	2.04(b)
		
	“Person”	  	4.01(a)
		
	“Record Date”	  	2.04(c)
		
	“Reporting Default”	  	7.03
		
	“Restricted Payments”	  	6.04
		
	“Specified Tax Jurisdiction”	  	8.01(a)
		
	“Taxes”	  	8.01(a)

 ARTICLE II 

APPLICATION OF SUPPLEMENTAL INDENTURE AND CREATION,
FORMS, TERMS AND CONDITIONS OF NOTES 

Section 2.01. Application of this First Supplemental Indenture. Notwithstanding any other provision of this First
Supplemental Indenture, the provisions of this First Supplemental Indenture, including the covenants set forth herein, are expressly and solely for the benefit of the Holders of the Notes established by this First Supplemental Indenture. The
Notes constitute a separate series of Securities as provided in Section 2.01 of the Indenture. 
 Section 2.02. Creation
of the Notes. In accordance with Section 2.01 of the Indenture, the Company hereby creates the Notes as a separate series of its Securities issued pursuant to the Indenture, as supplemented by this First Supplemental
Indenture. The Notes shall be issued initially in an aggregate principal amount of $25,000,000.00. 
 Section 2.03. Global
Notes. The Notes shall be issued in the form of Global Securities, duly executed by the Company and authenticated by the Trustee, which shall be deposited with the Trustee as custodian for the Depository and registered in the name of
“Cede & Co.,” as the nominee of the Depository. The Depository Trust Company (“DTC”) initially shall serve as Depository for the Notes. So long as the Depository, or its nominee, is the registered owner
of a Global Security, the Depository or its nominee, as the case may be, shall be considered the sole owner or Holder of the Notes represented by such Global Security for all purposes under the Indenture, this First Supplemental Indenture and under
such Notes. Ownership of beneficial interests in such Global Security shall be shown on, and transfers thereof will be effective only through, records maintained by the Depository or its nominee (with respect to beneficial interests of
participants) or by participants or Persons that hold interests through participants (with respect to beneficial interests of beneficial owners). 

  
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 Section 2.04. Terms and Conditions of the Notes. The Notes shall be
governed by all the terms and conditions of the Indenture, as supplemented by this First Supplemental Indenture. The following provisions shall be terms of the Notes: 

(a) Designation; Aggregate Principal Amount. The title of the Notes shall be as specified in the Recitals; and the aggregate
principal amount of the Notes shall be unlimited. 
 (b) Stated Maturity. The Notes shall mature, and the principal of the
Notes shall be due and payable in Dollars to the Holders thereof, together with all accrued and unpaid interest thereon, on August 15, 2021 (the “Maturity Date”). 

(c) Payment of Principal and Interest; Additional Amounts. The Notes shall bear interest at the rate of 8.375% per
annum, from and including August 8, 2014, or from the most recent Interest Payment Date (as defined hereafter) on which interest has been paid or duly provided for to, but excluding, the next succeeding Interest Payment Date, the Maturity Date
or the Redemption Date, as the case may be. Interest shall also be paid on overdue principal, and, to the extent lawful, overdue installments of interest at the applicable interest rate for the Notes. Interest shall be calculated on the
basis of a 360-day year comprised of twelve 30-day months. Interest on the Notes shall be payable quarterly in arrears in Dollars on February 15, May 15, August 15 and November 15 of each year, commencing on
November 15, 2014 (each such date, an “Interest Payment Date” for the purposes of the Notes issued under this First Supplemental Indenture). Payments of interest shall be made to the Person in whose name a Note (or
predecessor Note) is registered at the close of business on February 1, May 1, August 1 or November 1 (whether or not that date is a Business Day), as the case may be, immediately preceding such Interest Payment Date
(each such date, a “Record Date” for the purposes of the Notes issued under this First Supplemental Indenture). All payments in respect of the Notes shall include Additional Amounts as and to the extent set forth in Article
VIII of this First Supplemental Indenture. If any Interest Payment Date or the Maturity Date of the Notes falls on a day that is not a Business Day, the payment of interest and/or principal, as the case may be, to be paid on such date shall be
made on the next succeeding Business Day as if it were made on the date such payment was due, and no interest shall accrue on the amounts so payable for the period from and after such Interest Payment Date or Maturity Date of the Notes, as the case
may be, to such next succeeding Business Day. 
 (d) Registration and Form; Denomination. The Notes shall be issuable as
registered securities without coupons, as provided in Section 2.03 of this Article II. The form of the Notes shall be as set forth in Exhibit A attached hereto, which is incorporated herein by reference. The Notes shall be
issued and may be transferred only in minimum denomination of $25.00 and integral multiples of $25.00 in excess thereof. 

(e) Discharge; Legal Defeasance and Covenant Defeasance. The provisions for satisfaction and discharge, excluding clause
8.01(a)(ii)(4) in Section 8.01 of the Indenture, shall apply with respect to the Notes. Section 8.03 of the Indenture, relating to legal defeasance, shall not apply to the Notes, and shall be superseded by the provisions of
Section 9.05 of this First Supplemental Indenture. Section 8.04 of the Indenture, relating to covenant defeasance, shall not apply to the Notes, and shall be superseded by the provisions of Section 9.06 of this First Supplemental
Indenture. 
 (f) Further Issuance. Notwithstanding anything to the contrary contained herein or in the Indenture, the
Company may, from time to time, without the consent of or notice to the Holders, create and issue further debt securities having the same interest rate, maturity and other terms (except for the issue date, the public offering price and the first
Interest Payment Date) as, ranking equally and ratably with, the Notes (the “Additional Notes”). Such additional Notes shall be consolidated with and shall form a single series with the previously outstanding Notes, including
for purposes of voting and redemptions, and shall be fungible with the Notes for United States federal income tax purposes or will have a separate CUSIP number than the Notes. No Additional Notes may be issued if an Event of Default has
occurred and is continuing with respect to the Notes. 
 (g) Redemption. Except as set forth in Section 3.01 and
Section 3.02 of this First Supplemental Indenture, the Notes will not be redeemable by the Company at its option prior to August 15, 2017. 

  
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 (h) Sinking Fund. The Notes are not entitled to any sinking fund. 

(i) Registrar and Paying Agent. Section 2.04 of the Indenture shall be applicable to the Notes. With respect to the Notes,
the office or agency maintained by the Company for purposes of Section 2.04 of the Indenture shall be in the City of New York and shall initially be designated to be the Corporate Trust Office of the Trustee, as such office of the
Company. Deutsche Bank Trust Company Americas, the Trustee, initially shall be the Paying Agent and Registrar for the Notes. 

(j) Currency. The Notes shall be issued in U.S. Dollars and all amounts payable in respect of principal or interest shall be
paid in U.S. Dollars. 
 (k) Other Terms and Conditions. The Notes shall have such other terms and conditions as provided
in the form thereof attached as Exhibit A hereto. 
 ARTICLE III 

REDEMPTION 

Section 3.01. Optional Redemption On or After August 15, 2017. The Company may redeem the Notes, at its option, in
whole or in part, at any time on or after August 15, 2017 upon providing not less than 30 nor more than 60 days’ prior written notice to the Holders, at a redemption price equal to 100% of the principal amount to be redeemed, plus accrued
and unpaid interest to, but excluding, the date fixed for redemption, subject to the right of Holders of record on the relevant Record Date to receive interest due on the relevant Interest Payment Date. If money sufficient to pay the redemption
price of all of the Notes, or portions thereof, to be redeemed on the applicable Redemption Date is irrevocably deposited with the Trustee or Paying Agent on or before the applicable Redemption Date are satisfied, then on and after such Redemption
Date, interest will cease to accrue on such Notes, or such portion thereof, called for redemption, and such Notes will be deemed to be no longer outstanding. 

(a) Selection for Redemption. In accordance with Section 3.02 of the Indenture, if fewer than all of the Notes are to be
redeemed at any time, the Registrar will select the Notes, or portions thereof, to be redeemed, in compliance with the requirements of the Depository, or if the Depository prescribes no method of selection, on a pro rata basis, by lot or by any
other method the Registrar deems fair and reasonable; provided, however, that Notes, and portions thereof, selected for redemption shall only be in amounts of $25.00 or whole multiples of $25.00. 

(b) Notice of Redemption. In addition to the information provided for in Section 3.03 of the Indenture, a notice of
redemption shall also state: the provision of the Indenture pursuant to which the Notes are being redeemed; the portion of the redemption price constituting accrued and unpaid interest; the amount of Additional Amounts (as defined below), if any,
payable on the date fixed for redemption; that unless the Company defaults in making the redemption payment on the Notes called for redemption, interest on such Notes will cease to accrue on and after the Redemption Date; if any Note is being
redeemed in part, the portion of the principal amount of such Note to be redeemed; if less than all of the Notes are to be redeemed, the aggregate principal amount of Notes to be outstanding after such redemption; and that the Notes called for
redemption will become due on the date fixed for redemption. 
 Except to the extent inconsistent with the foregoing, all provisions of
Article III of the Indenture shall apply to any redemption pursuant to this Section 3.01. 
 Section 3.02. Optional
Redemption for Changes in Withholding Taxes. The Company may redeem the Notes, at its option, at any time in whole but not in part, upon not less than 30 nor more than 60 days’ prior written notice to the Holders (which notice shall be
irrevocable), at a redemption price equal to 100% of the outstanding principal amount of Notes, plus accrued and unpaid interest to, but excluding, the applicable date fixed for redemption, and all Additional Amounts (if any) then due and which will
become due on the applicable Redemption Date (subject to the right of Holders of record on the relevant Record Date to receive interest due on the relevant Interest Payment Date and Additional Amounts (if any) in respect thereof), in the event that
the Company determines in good faith that the Company has become or would become obligated to pay, on the next date on which 

  
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any amount would be payable with respect to the Notes, Additional Amounts and such obligation cannot be avoided by taking reasonable measures available to the Company (including making payment
through a paying agent located in another jurisdiction), as a result of: 
 (a) a change in or an amendment to the laws (including any
regulations or rulings promulgated thereunder) of any Specified Tax Jurisdiction affecting taxation, which change or amendment is announced or becomes effective on or after the date of this First Supplemental Indenture; or 

(b) any change in or amendment to any official position of a taxing authority in any Specified Tax Jurisdiction regarding the
application, administration or interpretation of such laws, regulations or rulings (including a holding, judgment or order by a court of competent jurisdiction), which change or amendment is announced or becomes effective on or after the date of
this First Supplemental Indenture. 
 Notwithstanding the foregoing, no notice of redemption for changes in withholding taxes may be given
earlier than 60 days prior to the earliest date on which the Company would be obligated to pay Additional Amounts if a payment in respect of the Notes were then due. At least five calendar days before the Company provides notice of redemption
of the Notes as set forth in Section 3.03 of the Indenture and Section 3.01(b) of this First Supplemental Indenture, the Company will deliver to the Trustee and Paying Agent (i) an Officers’ Certificate stating that the Company
is entitled to effect such redemption and setting forth a statement of facts showing that the conditions precedent to the right of the Company to so redeem have occurred and (ii) an opinion of a nationally recognized independent legal counsel
that the Company has or will become obligated to pay Additional Amounts as a result of the circumstances referred to in clause (a) or (b) of the preceding paragraph. 

The Trustee and Paying Agent will accept and will be entitled to conclusively rely upon the Officers’ Certificate and Opinion of Counsel
as sufficient evidence of the satisfaction of the conditions precedent described above, in which case they will be conclusive and binding on the Holders. 

Except to the extent inconsistent with the foregoing, all provisions of Article III of the Indenture shall apply to any redemption pursuant to
this Section 3.02. 
 Section 3.03. Open Market Repurchases. Notwithstanding any provision hereunder or in the
Indenture to the contrary, the Company and its Affiliates may purchase Notes from investors who are willing to sell from time to time, either in the open market at prevailing prices or in private transactions at negotiated prices. Notes that
the Company or any of its Affiliates purchase may, at the Company’s discretion, be held, resold or canceled. 
 ARTICLE IV 

CHANGE OF CONTROL 

Section 4.01. Change of Control. (a) If a Change of Control occurs at any time, Holders will have the right, at their
option, to require the Company to purchase for cash any or all of such Holder’s Notes, or any portion of the principal amount thereof, that is equal to $25.00 or an integral multiple of $25.00. The price the Company is required to pay (the
“Change of Control Purchase Price”) is equal to 101% of the principal amount of the Notes to be purchased, plus accrued and unpaid interest to, but excluding, the Change of Control Purchase Date, subject to the right of Holders of
record on the relevant Record Date to receive interest due on the relevant Interest Payment Date. The “Change of Control Purchase Date” will be a date specified by the Company that is not less than 20 or more than 35 calendar
days following the date of the Change of Control notice as described below. Any Notes purchased by the Company will be paid for in cash. A “Change of Control” will be deemed to have occurred at the time after the Notes are
originally issued if 
 (i) any “Person” (defined, for purposes of this Article IV, as such term is used in Sections
13(d) and 14(d) of the Exchange Act), other than the Permitted Holder, is or becomes the “Beneficial Owner” (as defined in Rules 13d-3 and 13d-5 under the Exchange Act, except that for purposes of this clause (i) such Person
shall be deemed to have “Beneficial Ownership” of all shares that any such Person has the right to acquire, whether such right is exercisable immediately or only after the passage of time), directly or indirectly, of more than 50% of the
total voting power of the Voting Stock of the Company; 

  
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 (ii) the merger or consolidation of the Company with or into another Person or the merger of
another Person with or into the Company, or the sale of all or substantially all the assets of the Company (determined on a consolidated basis) to another Person other than (i) a transaction in which the survivor or transferee is a Person that
is controlled by the Permitted Holder or (ii) a transaction following which, in the case of a merger or consolidation transaction, holders of securities that represented 100% of the Voting Stock of the Company immediately prior to such
transaction (or other securities into which such securities are converted as part of such merger or consolidation transaction) own directly or indirectly at least a majority of the voting power of the Voting Stock of the surviving Person in such
merger or consolidation transaction immediately after such transaction and in substantially the same proportion as before the transaction; or 

(iii) Continuing Directors cease to constitute at least a majority of the Board of Directors; or 

(iv) if after the Notes are initially listed on the New York Stock Exchange or another national securities exchange, the Notes fail, or
at any point cease, to be listed on the New York Stock Exchange or such other national securities exchange. For the avoidance of doubt, it shall not be a Change of Control if after the Notes are initially listed on the New York Stock Exchange or
another national securities exchange, such Notes are subsequently listed on a different national securities exchange and the prior listing is terminated. 

ARTICLE V 
 OFFER
TO PURCHASE 
 Section 5.01. 

(a) On or before the 30th day after the occurrence of a Change of Control or a Limited Permitted Asset Sale, as the case may be, the
Company will provide to all Holders and the Trustee and Paying Agent a written notice of the occurrence of the Change of Control or Limited Permitted Asset Sale and of the resulting purchase right. Such notice shall state, among other things:
(i) the events causing a Change of Control or Limited Permitted Asset Sale, as the case may be; (ii) the date of the Change of Control or Limited Permitted Asset Sale, as the case may be; (iii) the last date on which a Holder may
exercise repurchase right; (iv) the Change of Control Purchase Price or Limited Permitted Asset Sale Purchase Price, as applicable; (v) the Change of Control Purchase Date or Limited Permitted Asset Sale, as applicable; (vi) the name
and address of the Paying Agent; and (vii) the procedures that Holders must follow to require the Company to purchase their Notes. 

(b) Simultaneously with providing such notice, the Company will publish a notice containing this information in a newspaper of general
circulation in The City of New York or publish the information on the Company’s website or through such other public medium as the Company may use at that time to achieve a broad dissemination of such notice. 

(c) To exercise the Change of Control purchase right or Limited Permitted Asset Sale purchase right, a Holder must deliver, on or before
the third Business Day (or as otherwise provided in the notice provided for in Section 5.01(a) of this First Supplemental Indenture), immediately preceding the Change of Control Purchase Date or Limited Permitted Asset Sale Purchase Date, as
applicable, the Notes to be purchased, duly endorsed for transfer, together with a written purchase notice and the form entitled “Form of Purchase Notice” on the reverse side of the Notes duly completed, to the Paying Agent. Such
notice must: 
 (i) if the applicable Notes are not issued in global form, state the certificate numbers of the Notes to be delivered
for purchase; 
 (ii) if the applicable Notes are issued in global form, comply with requisite DTC procedures; 

  
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 (iii) state the principal amount of Notes to be purchased, which must be $25.00 or a
multiple thereof; and 
 (iv) state that the Notes are to be purchased by the Company pursuant to the applicable provisions of the
Notes and the Indenture. 
 (d) Holders may withdraw any purchase notice (in whole or in part) by a written notice of withdrawal
delivered to the Paying Agent prior to the close of business on the Business Day immediately preceding the Change of Control Purchase Date or Limited Permitted Asset Sale Purchase Date, as applicable. The notice of withdrawal shall: 

(i) if the applicable Notes are not issued in global form, state the certificate numbers of the withdrawn Notes; 

(ii) if the applicable Notes are issued in global form, comply with requisite DTC procedures; 

(iii) state the principal amount of the withdrawn Notes; and 

(iv) state the principal amount, if any, which remains subject to the purchase notice, which must be $25.00 or a multiple thereof. 

(e) On each Change of Control Purchase Date or Limited Permitted Asset Sale Purchase Date, as applicable, the Company will, to the extent
lawful, (i) accept for payment all Notes or portions of Notes properly tendered pursuant to the applicable Change of Control offer or Limited Permitted Asset Sale offer made by the Company, (ii) deposit with the Paying Agent at least one
Business Day prior to the Change of Control Purchase Date or Limited Permitted Asset Sale Purchase Date, as applicable, an amount equal to the Change of Control Purchase Price or the Limited Permitted Asset Sale Purchase Price, as applicable, in
each case, in respect of all Notes or portions of Notes properly tendered pursuant to the applicable Change of Control offer or Permitted Limited Asset Sale offer made by the Company and (iii) deliver or cause to be delivered to the Trustee the
Notes properly accepted, together with an Officers’ Certificate stating the aggregate principal amount of Notes or portions of Notes being repurchased. If the Paying Agent holds money or securities sufficient to pay the Change of Control
Purchase Price or the Limited Permitted Asset Sale Purchase Price, as applicable, of the Notes on the Change of Control Purchase Date or the Limited Permitted Asset Sale Purchase Date, as applicable, then: 

(i) the Notes will cease to be outstanding and interest will cease to accrue (whether or not book-entry transfer of the Notes is made or
whether or not the Notes are delivered to the Paying Agent); and 
 (ii) all other rights of the Holder will terminate (other than the
right to receive the Change of Control Purchase Price or the Limited Permitted Asset Sale, as applicable). 
 (f) In connection with
any offer to purchase Notes pursuant to a Change of Control purchase notice or Limited Permitted Asset Sale purchase notice, as applicable, the Company will, to the extent applicable, comply with the requirements of Rule 14e-1 under the Exchange Act
and any other applicable securities laws and regulations to the extent those laws and regulations are applicable in connection with the repurchase of the Notes as a result of a Change of Control or Limited Permitted Asset Sale. To the extent that
the provisions of any securities laws or regulations conflict with the Change of Control provisions of this First Supplemental Indenture, the Company will comply with any applicable securities laws and regulations and will not be deemed to have
breached its obligations under this First Supplemental Indenture by virtue of such compliance. 
 (g) No Notes may be purchased at the
option of Holders thereof upon a Change of Control or Limited Permitted Asset Sale if the principal amount of the Notes has been accelerated, and such acceleration has not been rescinded, on or prior to such date. 

  
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 ARTICLE VI 

Covenants 
 The covenants set
forth in this Article VI shall be applicable to the Company in addition to the covenants in Article 4 of the Indenture, which shall in all respects be applicable in respect of the Notes. 

Section 6.01. Limitation on Borrowings. The Company shall not permit Net Borrowings to equal or exceed 70% of Total
Assets. 
 Section 6.02. Limitation on Minimum Net Worth. The Company shall ensure that its Net Worth always exceeds
one hundred million dollars ($100,000,000). 
 Section 6.03. Reports. Following any Cross Default, the Company shall
promptly notify the Holders of the occurrence of such Cross Default. 
 Section 6.04. Restricted Payments. If
(a) an Event of Default or an event or circumstance which, with the giving of any notice or the lapse of time, would constitute an Event of Default has occurred and is continuing, (b) an Event of Default or an event or circumstance which,
with the giving of any notice or the lapse of time, would constitute an Event of Default would result therefrom, (c) the Company is not in compliance with the covenant described under Section 6.01 or Section 6.02 of this First
Supplemental Indenture, or (d) any payment of dividends or any form of distribution or return of capital would result in the Company not being in compliance with the covenant described under Section 6.01 of Section 6.02 of this First
Supplemental Indenture, then none of the Company or any Subsidiary will declare or pay any dividends or return any capital to its equity holders (other than the Company or a wholly-owned Subsidiary of the Company) or authorize or make any other
distribution, payment or delivery of property or cash to its equity holders (other than the Company or a wholly-owned Subsidiary of the Company), or redeem, retire, purchase or otherwise acquire, directly or indirectly, for value, any interest of
any class or series of its equity interests (or acquire any rights, options or warrants relating thereto but not including convertible debt) now or hereafter outstanding and held by Persons other than the Company or any wholly-owned Subsidiary, or
repay any subordinated loans to equity holders (other than the Company or a wholly-owned Subsidiary of the Company) or set aside any funds for any of the foregoing purposes (“Restricted Payments”). 

Section 6.05. Line of Business. The Company will not, nor will the Company permit any of its Subsidiaries (other than an
Immaterial Subsidiary) to, engage primarily in any business other than a Permitted Business. 
 Section 6.06. Limitation on
Asset Sales. The Company shall not, and shall not permit any Subsidiary to, in the ordinary course of business or otherwise, sell, lease, convey, transfer or otherwise dispose of any of the Company’s, or of any such Subsidiary’s,
assets (including Capital Stock and warrants, options or other rights to acquire Capital Stock) (an “Asset Sale”), other than pursuant to a Permitted Asset Sale or a Limited Permitted Asset Sale, unless (i) the Company
receives, or the relevant Subsidiary receives, consideration at the time of such Asset Sale at least equal to the fair market value (including as to the value of all non-cash consideration), as determined in good faith by the Board of Directors of
the Company, of the assets subject to such Asset Sale (ii) at least 75% of the consideration therefor received by the Company is in the form of (x) Cash or Cash Equivalents, provided that, the outstanding principal amount of any
indebtedness which is secured by the Asset that is the subject of the Asset Sale, which ranks senior in right of payment to the Notes, and which is assumed by the transferee, shall be deemed Cash and Cash Equivalents for purposes of this provision,
or (y) Replacement Assets, or (z) any combination of the considerations described in (x) or (y); and (iii) within 365 days after the receipt of any Net Proceeds from an Asset Sale, the Company or the relevant Subsidiary, as the
case may be, shall apply all such Net Proceeds to: 
 (a) repay or prepay indebtedness under any Credit Facility secured by a lien on
assets of the Company or any Subsidiary; 
 (b) acquire any Replacement Assets; 

  
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 (c) make a capital expenditure; 

(d) repay unsecured senior indebtedness of the Company or any Subsidiary (including any redemption, repurchase, retirement or other
acquisition of the Notes); or 
 (e) any combination of the transactions permitted by the foregoing clauses (a) through (d), 

provided, that any sale, assignment, conveyance, transfer or lease of all or substantially all of the Company’s properties and assets to any
Person or Persons (whether in a single transaction or a series of related transactions) will be governed by the provisions described under Section 4.01 of this First Supplemental Indenture and Article 5 of the Indenture and not by the
provisions of this Section 5.06. 
 A binding contract to apply the Net Proceeds in accordance with clauses (b) or (c) above shall toll the
365-day period in respect of such Net Proceeds, or a determination by the Company to apply all or a portion of such Net Proceeds toward the exercise of an outstanding purchase option contract for a transaction described in clauses (b) or
(c) above, shall toll the 365-day period in respect of such Net Proceeds or portion thereof, in each case, for a period not to exceed 365 days or, in the case of a binding contract to acquire one or more Vessels, until the end of the
construction or delivery period specified in such binding contract, as the same may be extended, from the expiration of the aforementioned 365-day period, provided, that such binding contract and such determination by the Company, in each
case, shall be treated as a permitted application of Net Proceeds from the date of such binding contract or determination until and only until the earlier of (x) the date on which such acquisition or expenditure is consummated and
(y) (i) in the case of a construction contract or any exercised purchase option contract, the date of expiration or termination of such construction contract or exercised purchase option contract and (ii) in all other cases, the 365th
day following the expiration of the aforementioned 365-day period. 
 Pending the final application of any Net Proceeds, the Company or any of its
Subsidiaries may apply Net Proceeds to the repayment or reduction of outstanding indebtedness or otherwise invest the Net Proceeds in any manner that is not prohibited by the Indenture. 

If a Limited Permitted Asset Sale occurs at any time, the Company must, within 30 days of such Limited Permitted Asset Sale, make pursuant to Article V of
this First Supplemental Indenture an offer to purchase Notes having a principal amount equal to the Excess Proceeds of such Limited Permitted Asset Sale. The price that the Company will be required to pay (the “Limited Permitted Asset Sale
Purchase Price”) is equal to 101% of the principal amount of the Notes to be purchased, plus accrued and unpaid interest to, but excluding, the Limited Permitted Asset Sale Purchase Date, subject to the right of Holders of record on the
relevant Record Date to receive interest due on the relevant Interest Payment Date. If the offer to purchase is for less than all of the outstanding Notes and Notes in an aggregate principal amount in excess of the purchase amount are tendered
and not withdrawn pursuant to the offer, the Company will purchase Notes having an aggregate principal amount equal to the purchase amount on a pro rata basis, with adjustments so that only notes in multiples of $25.00 principal amount will
be purchased. The “Limited Permitted Asset Sale Purchase Date” will be a date specified by the Company that is not less than 20 or more than 35 calendar days following the date of the Limited Permitted Asset Sale notice as
described in Article V of this First Supplemental Indenture. Any Notes purchased by the Company pursuant to such offer to purchase will be paid for in cash. 

Section 6.07. Compliance Certificate. Section 4.03 of the Indenture shall be superseded in its entirety by the
following: 
 The Company shall deliver to the Trustee, within 120 days after the end of each fiscal year, an Officers’ Certificate stating that a
review of the activities of the Company and its Subsidiaries during the preceding fiscal year has been made under the supervision of the signing Officers with a view to determining whether the Company has kept, observed, performed and fulfilled its
obligations under the Indenture, and further stating, as to such Officer signing such certificate, that to the best of his or her knowledge the Company is not in default in the performance or observance of any of the terms, provisions and
conditions of the Indenture or this First Supplemental Indenture (or, if a Default or Event of Default shall have occurred, describing all such Defaults or Events of Default of which he or she may have knowledge and what action the Company is taking
or proposes to take with respect thereto). The Company shall deliver to the Trustee, within 30 days after the occurrence thereof, written notice in the form of an 

  
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Officers’ Certificate of any Event of Default described Section 7.01 of this First Supplemental Indenture and any event of which it becomes aware that with the giving of notice or the
lapse of time would become such an Event of Default, its status and what action the Company is taking or proposes to take with respect thereto. 

ARTICLE VII 
 Events of Default

 Section 7.01. Modifications of Certain Events of Default. The Events of Default set forth in Section 6.01 of
the Indenture shall be superseded in their entirety by the following Events of Default in this Section 7.01 (each an “Event of Default”): 

(a) default in the payment of the principal of or any premium on any Notes, or any Additional Amounts payable with respect thereto, when
such principal or premium becomes or such Additional Amounts become due and payable at Maturity; or 
 (b) default in the payment of
any interest on any Security of such series, or any Additional Amounts payable with respect thereto, when such interest becomes or such Additional Amounts become due and payable, and continuance of such default for a period of 30 days; or 

(c) failure by the Company to perform or comply with the provisions of Article V of the Indenture (as amended by this First Supplemental
Indenture) relating to mergers and similar events; or 
 (d) failure by the Company to provide notice of a Change of Control or a
Limited Permitted Asset Sale or to repurchase Notes tendered for repurchase following the occurrence of a Change of Control or a Limited Permitted Asset Sale in conformity with the covenants set forth in Article IV of this First Supplemental
Indenture; or 
 (e) default in the performance, or breach, of any covenant of the Company in this First Supplemental Indenture or the
Indenture, and continuance of such default or breach for a period of 60 days after there has been given, by registered or certified mail, to the Company by the Trustee or to the Company and the Trustee by the Holders of at least 25% in
principal amount of the outstanding Notes, a written notice; or 
 (f) any debt of the Company or any Subsidiary having an aggregate
principal amount of $10 million or more in the aggregate for all such debt of all such Persons (i) is the subject of a written notice of an event of default received by such person that results in such debt being due and payable prior to its
scheduled maturity or (ii) is subject to a failure to make a principal payment when due and such defaulted payment is not made, waived or extended within the applicable grace period; or 

(g) the entry against the Company of one or more final judgments or decrees for the payment of money in an aggregate amount in excess of
$10 million, by a court or courts of competent jurisdiction, which final judgment or decree remains undischarged, unstayed or unwaived for a period of 90 consecutive days; or 

(h) the entry by a court having competent jurisdiction of: 

(i) a decree or order for relief in respect of the Company or any Significant Subsidiary in an involuntary proceeding
under any applicable bankruptcy, insolvency, reorganization or other similar law and such decree or order shall remain unstayed and in effect for a period of 60 consecutive days; or 

(ii) a decree or order adjudging the Company or any Significant Subsidiary to be insolvent, or approving a petition
seeking reorganization, arrangement, adjustment or composition of the Company or any Significant Subsidiary and such decree or order shall remain unstayed and in effect for a period of 60 consecutive days; or 

(iii) a final and non-appealable order appointing a custodian, receiver, liquidator, assignee, trustee or other similar
official of the Company or any Significant Subsidiary of any substantial part of the property of the Company or any Significant Subsidiary or ordering the winding up or liquidation of the affairs of the Company or any Significant Subsidiary; or 


  
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 (i) the commencement by the Company or any Significant Subsidiary of a voluntary proceeding
under any applicable bankruptcy, insolvency, reorganization or other similar law or of a voluntary proceeding seeking to be adjudicated insolvent or the consent by the Company or any Significant Subsidiary to the entry of a decree or order for
relief in an involuntary proceeding under any applicable bankruptcy, insolvency, reorganization or other similar law or to the commencement of any insolvency proceedings against it, or the filing by the Company or any Significant Subsidiary of a
petition or answer or consent seeking reorganization, arrangement, adjustment or composition of the Company or any Significant Subsidiary or relief under any applicable law, or the consent by the Company or any Significant Subsidiary to the filing
of such petition or to the appointment of or taking possession by a custodian, receiver, liquidator, assignee, trustee or similar official of the Company or any Significant Subsidiary or any substantial part of the property of the Company or any
Significant Subsidiary or the making by the Company or any Significant Subsidiary of an assignment for the benefit of creditors, or the taking of corporate action by the Company or any Significant Subsidiary in furtherance of any such action. 

Section 7.02. Acceleration of Maturity; Rescission and Annulment. Section 6.02(a) of the Indenture shall be applicable
to the Notes, except that the reference therein to “clauses (g) or (h) of Section 6.01” shall be replaced by a reference to “clauses (h) or (i) of Section 7.01 of the First Supplemental Indenture.”

 Section 7.03. Section 6.02(b) of the Indenture shall be superseded in its entirety by the following: 

Notwithstanding the foregoing, at the election of the Company, the sole remedy with respect to an Event of Default resulting from a failure by the Company to
comply with the requirements of Section 314(a)(1) of the Trust Indenture Act or the requirements of Section 4.02 of the Indenture (any such Event of Default, a “Reporting Default”), shall, after the occurrence of such
Reporting Default consist exclusively of the right to receive additional interest (the “Additional Interest”) on the Notes at an annual rate equal to (i) 0.25% of the principal amount of the Notes for each day during the 90
calendar day period beginning on, and including, the date on which such Reporting Default first occurs and on which such Reporting Default is continuing and (ii) 0.50% of the principal amount of the Notes for each day during the 90 calendar day
period beginning on, and including, the 91st day following the date on which such Reporting Default first occurs and on which such Reporting Default is continuing. If the Company so elects, the Additional Interest shall accrue on all
outstanding Notes from and including the date on which such Reporting Default first occurs until such violation is cured or waived and shall be payable in arrears on regular Interest Payment Dates. On the 181st day after such Reporting Default
(if such violation is not cured or waived prior to such 181st calendar day), then the Trustee or the Holders of not less than 25% in principal amount of the outstanding Notes may declare the principal of all the Notes to be due and payable
immediately, by a notice in writing to the Company (and to the Trustee if given by the Holders), and upon any such declaration such principal or such lesser amount shall become immediately due and payable. 

If the Company elects to pay the Additional Interest as the sole remedy during the first 180 days following the occurrence of a Reporting Default, the Company
shall notify in writing the Holders, the Paying Agent and the Trustee of such election at any time on or before the close of business on the fifth Business Day prior to the date on which such Reporting Default would otherwise occur. Unless and
until a Responsible Officer of the Trustee receives at the Corporate Trust Office such written notice, the Trustee may assume without inquiry that Additional Interest is not payable. 

ARTICLE VIII 

ADDITIONAL AMOUNTS 

Section 8.01. Additional Amounts. (a) All payments made by or on behalf of the Company under or with respect to the
Notes will be made free and clear of and without withholding or deduction for, or on account of, any present or future tax, duty, levy, impost, assessment or other governmental charge (including penalties, interest and other liabilities related
thereto) (hereinafter “Taxes”) unless the withholding or deduction of such Taxes is then required by law. If any deduction or withholding for, or on account of, any Taxes imposed or levied by or on behalf of the government of
the Republic of Marshall Islands or any political subdivision or any authority or agency therein 

  
 15 








 
or thereof having power to tax, or any other jurisdiction in which the Company (including any successor entity) is organized or is otherwise resident for tax purposes, or any jurisdiction from or
through which payment is made (including, without limitation, the jurisdiction of each paying agent) (each a “Specified Tax Jurisdiction”), will at any time be required to be made from any payments made under or with respect to the
Notes. the Company will pay such additional amounts (the “Additional Amounts”) as may be necessary so that the net amount received in respect of such payments by a Holder (including Additional Amounts) after such withholding or
deduction will not be less than the amount such Holder would have received if such Taxes had not been withheld or deducted; provided, however, that the foregoing obligation to pay Additional Amounts does not apply to: 

(i) any Taxes that would not have been so imposed but for the Holder or beneficial owner of the Notes having any present or former
connection with the Specified Tax Jurisdiction (other than the mere acquisition, ownership, holding, enforcement or receipt of payment in respect of the Notes); 

(ii) any estate, inheritance, gift, sales, excise, transfer, personal property tax or similar tax, assessment or governmental charge;

 (iii) any Taxes payable other than by deduction or withholding from payments under, or with respect to, the Notes; 

(iv) any Taxes imposed as a result of the failure of the Holder or beneficial owner of the Notes to complete, execute and deliver to the
Company any form or document to the extent applicable to such Holder or beneficial owner that may be required by law or by reason of administration of such law and which is reasonably requested in writing to be delivered to the Company in order to
enable the Company to make payments on the Notes without deduction or withholding for Taxes, or with deduction or withholding of a lesser amount, which form or document will be delivered within 60 days of a written request therefor by the Company;

 (v) any Taxes that would not have been so imposed but for the beneficiary of the payment having presented a Note for payment (in
cases in which presentation is required) more than 30 days after the date on which such payment or such Note became due and payable or the date on which payment thereof is duly provided for, whichever is later (except to the extent that the Holder
would have been entitled to Additional Amounts had the Note been presented on the last day of such 30-day period); 
 (vi) any Taxes
imposed on or with respect to any payment by the Company to the Holder if such Holder is a fiduciary or partnership or Person other than the sole beneficial owner of such payment, to the extent that a beneficiary or settlor with respect to such
fiduciary, a member of such partnership or the beneficial owner of such payment would not have been entitled to Additional Amounts had such beneficiary, settlor, member or beneficial owner been the actual Holder of such Note; 

(vii) any Taxes that are required to be deducted or withheld on a payment pursuant to European Council Directive 2003/48/EC or any law
implementing, or introduced in order to conform to, such directive; or 
 (viii) any combination of items (i) through
(vii) above. 
 (b) If the Company becomes aware that it will be obligated to pay Additional Amounts with respect to any payment
under or with respect to the Notes, the Company will deliver to the Trustee and Paying Agent at least 30 days prior to the date of that payment (unless the obligation to pay Additional Amounts arises after the 30th day prior to that payment date, in
which case the Company will notify the Trustee and Paying Agent in writing promptly thereafter but in no event later than five calendar days prior to the date of payment) an Officers’ Certificate stating the fact that Additional Amounts will be
payable and the amount so payable. The Officers’ Certificate shall also set forth any other information necessary to enable the Paying Agent to pay Additional Amounts to Holders on the relevant payment date. The Trustee and Paying
Agent will be entitled to rely solely on such Officers’ Certificate as conclusive proof that such payments are necessary. The Company will provide the Trustee and Paying Agent with documentation evidencing the payment of Additional
Amounts. 

  
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 (c) The Company will make all withholdings and deductions required by law and will remit the
full amount deducted or withheld to the relevant governmental authority on a timely basis in accordance with applicable law. As soon as practicable, the Company will provide the Trustee and Paying Agent with an official receipt or, if official
receipts are not obtainable, other documentation evidencing the payment of the Taxes so withheld or deducted. Upon written request, copies of those receipts or other documentation, as the case may be, will be made available by the Trustee and
Paying Agent to the Holders of the Notes. 
 (d) Whenever in the Indenture or this First Supplemental Indenture there is referenced, in
any context, the payment of amounts based upon the principal amount of the Notes or of principal, interest or any other amount payable under, or with respect to, the Notes, such reference will be deemed to include payment of Additional Amounts as
described under this heading to the extent that, in such context, Additional Amounts are, were or would be payable in respect thereof. 

(e) The Company will indemnify a Holder, within 10 Business Days after written demand therefor, for the full amount of any Taxes paid by
such Holder to a governmental authority of a Specified Tax Jurisdiction, on or with respect to any payment by on or account of any obligation of the Company to withhold or deduct an amount on account of Taxes for which the Company would have been
obligated to pay Additional Amounts hereunder and any penalties, interest and reasonable expenses arising therefrom or with respect thereto, whether or not such Taxes were correctly or legally imposed or asserted by the relevant governmental
authority. A certificate as to the amount of such payment or liability delivered to the Company by a Holder will be conclusive absent manifest error. 

(f) The Company will pay any present or future stamp, court or documentary taxes or any other excise or property taxes, charges or
similar levies that arise in any Specified Tax Jurisdiction from the execution, delivery, enforcement or registration of the Notes, the Indenture or any other document or instrument in relation thereof, or the receipt of any payments with respect to
the Notes, and the Company will indemnify the Holders for any such taxes paid by such Holders. 
 Section 8.02. Obligations to
Survive. The obligations described in Section 8.01 of this First Supplemental Indenture will survive any termination, defeasance or discharge of the Indenture and will apply mutatis mutandis to any jurisdiction in which any
successor person to the Company is organized or any political subdivision or authority or agency thereof or therein. 
 ARTICLE IX 

FURTHER MODIFICATIONS TO INDENTURE 

Section 9.01. Outstanding Securities. Section 2.09 of the Indenture shall be applicable to the Notes, except that the
third paragraph shall be superseded in its entirety by the following: 
 If, on or after the Maturity of the Securities or any redemption
date or date for purchase of the Notes pursuant to an Offer to Purchase, the Trustee (or Paying Agent, other than the Company or an Affiliate of the Company) holds money sufficient to pay all amounts then due, those Notes payable or to be redeemed
or purchased on that date cease to be outstanding and interest on them ceases to accrue. 
 Section 9.02. Successors.
Section 5.01 and Section 5.02 of the Indenture shall be superseded in their entirety by the following: 
 (a) The Company
will not 
 (i) consolidate with or merge with or into any Person or permit any Person to merge with or into the Company, or 

(ii) sell, assign, convey, transfer, or otherwise dispose of all or substantially all of its properties and assets, in one transaction or
a series of related transactions, to any Person or 

  
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 (iii) lease all or substantially all of its assets, whether in one transaction or a series
of transactions, to one or more other Persons, unless 
 (A) the successor Person, if any, is a corporation, partnership, trust or
other entity organized and validly existing under the laws of the Republic of the Marshall Islands, the United States of America, any State of the United States of America or the District of Columbia, the Commonwealth of the Bahamas, the Republic of
Liberia, the Republic of Panama, the Commonwealth of Bermuda, the British Virgin Islands, the Cayman Islands, the Isle of Man, Cyprus, Norway, Greece, Hong Kong, the United Kingdom, Malta, any Member State of the European Union and any other
jurisdiction generally acceptable, as determined in good faith by the Board of Directors of the Company, to institutional lenders in the shipping industries; 

(B) immediately after giving effect to the transaction, no Default or Event of Default has occurred and is continuing; 

(C) such Person or Persons shall expressly assume by supplemental indenture executed and delivered to the Trustee, in form satisfactory to
the Trustee, the due and punctual payment of the principal of, and any interest on, all Notes and the performance or observance of every covenant of the Indenture and the First Supplemental Indenture on the part of the Company to be performed or
observed; and 
 (D) the Company delivers to the Trustee, prior to the consummation of the transaction, an Officers’ Certificate and
an Opinion of Counsel, each stating that the consolidation, merger or transfer and the supplemental indenture (if any) comply with the Indenture, as supplemented by the First Supplemental Indenture. 

(b) Upon the consummation of any transaction effected in accordance with these provisions, the successor Person will succeed to, and be
substituted for, and may exercise every right and power of, the Company under the Indenture, the First Supplemental Indenture and the Notes with the same effect as if such successor Person had been named as the Company in the Indenture. Upon
such substitution, except in the case of (i) a lease or (ii) the sale, conveyance, transfer or disposition of less than all its assets, the Company will be released from its obligations under the Indenture, the First Supplemental Indenture
and the Notes. 
 Section 9.03. Principal and Interest Inclusive. With respect to the Notes, all provisions of this First
Supplemental Indenture and the Indenture relating to principal and interest, shall be understood to include, to the extent applicable, the Change of Control Purchase Price, the Limited Permitted Asset Sale Purchase Price, any redemption price, any
Additional Amounts, any Additional Interest, and any other amounts then payable upon the Notes. 
 Section 9.04. Satisfaction
and Discharge. Section 8.01 of the Indenture shall be applicable to the Notes, except that in Section 8.01(a)(ii) the phrase “have become due and payable, or” shall be deleted. 

Section 9.05. Legal Defeasance. Section 8.03 of the Indenture shall not apply to the Notes, and shall be superseded by
the provisions of this Section 9.05 of this First Supplemental Indenture. After the 123rd day following the deposit referred to in clause (a) below, the Company will be deemed to have paid and will be discharged from its obligations
in respect of the Notes and the Indenture, other than its obligations in Article 2 of the Indenture, and Sections 4.01 of the Indenture, Section 7.07 of the Indenture, Section 7.08 of the Indenture, Section 8.05 of the Indenture and
Section 9.07 of this First Supplemental Indenture (“legal defeasance”), provided the following conditions have been satisfied: 

(a) The Company has irrevocably deposited in trust with the Trustee, as trust funds solely for the benefit of the Holders, money or U.S.
Government Obligations or a combination thereof sufficient, in the opinion of a nationally recognized firm of independent public accountants expressed in a written certificate thereof delivered to the Trustee, without consideration of any
reinvestment, to pay principal of and interest on the Notes to maturity or redemption, as the case may be, provided that any redemption before maturity has been irrevocably provided for under arrangements satisfactory to the Trustee. 

  
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 (b) No default has occurred and is continuing on the date of the deposit or occurs at any
time during the 123-day period following the deposit. 
 (c) The deposit will not result in a breach or violation of, or constitute a
default under, the Indenture, this First Supplemental Indenture or any other agreement or instrument to which the Company is a party or by which it is bound. 

(d) The Company has delivered to the Trustee 

(i) either (x) a ruling received from the Internal Revenue Service to the effect that the beneficial owners of the Notes to be
defeased will not recognize income, gain or loss for federal income tax purposes as a result of the defeasance and will be subject to federal income tax on the same amount and in the same manner and at the same times as would otherwise have been the
case or (y) an Opinion of Counsel, based on a change in law after the date of this First Supplemental Indenture, to the same effect as the ruling described in clause (x), and 

(ii) an Opinion of Counsel to the effect that (i) the creation of the defeasance trust does not violate the Investment Company Act
of 1940, (ii) the Holders have a valid first priority Note interest in the trust funds (subject to customary exceptions), and (iii) after the passage of 123 days following the deposit, the trust funds will not be subject to the effect of
Section 547 of the United States Bankruptcy Code or Section 15 of the New York Debtor and Creditor Law. 
 (e) If the Notes
are listed on a national securities exchange, the Company has delivered to the Trustee an Opinion of Counsel to the effect that the deposit and defeasance will not cause the Notes to be delisted. 

(f) The Company has delivered to the Trustee an Officers’ Certificate and an Opinion of Counsel, in each case stating that all
conditions precedent provided for herein relating to the defeasance have been complied with. 
 Prior to the end of the 123-day period, none
of the Company’s obligations under the Indenture or the First Supplemental Indenture will be discharged. Thereafter, the Trustee upon written request will acknowledge in writing the discharge of the Company’s obligations under the
Notes, the Indenture and the First Supplemental Indenture except for the surviving obligations specified above. 

Section 9.06. Covenant Defeasance. Section 8.04 of the Indenture shall not apply to the Notes, and shall be superseded
by the provisions of this Section 9.06 of this First Supplemental Indenture. After the 123rd day following the deposit referred to in clause (a) of Section 9.05 of this First Supplemental Indenture, the Company’s obligations
set forth in Sections 6.01 through 6.06 of this First Supplemental Indenture and clauses (c), (d), (e), (f) and (g) of Section 7.01 of this First Supplemental Indenture will no longer constitute Events of Default
(“covenant defeasance”), provided the following conditions have been satisfied: 
 (a) The Company has complied
with clauses (a), (b), (c), d(ii), (e) and (f) of Section 9.05 of this First Supplemental Indenture; and 
 (b) the
Company has delivered to the Trustee an Opinion of Counsel to the effect that the beneficial owners of the Notes to be defeased will not recognize income, gain or loss for federal income tax purposes as a result of the defeasance and will be subject
to federal income tax on the same amount and in the same manner and at the same times as would otherwise have been the case. 
 Except as
specifically stated above, none of the Company’s obligations under the Indenture will be discharged. 

Section 9.07. Reinstatement. If and for so long as the Trustee is unable to apply any money or U.S. Government
Obligations held in trust pursuant to Section 8.01 of the Indenture, or Sections 9.05 or 9.06 of this First Supplemental Indenture by reason of any legal proceeding or by reason of any order or judgment of any court or governmental authority
enjoining, restraining or otherwise prohibiting such application, the Company’s obligations 

  
 19 








 
under the Indenture, the First Supplemental Indenture and the Notes will be reinstated as though no such deposit in trust had been made. If the Company makes any payment of principal of or
interest on any Notes because of the reinstatement of its obligations, it will be subrogated to the rights of the Holders of such Notes to receive such payment from the money or U.S. Government Obligations held in trust. 

Section 9.08. Modification Without Consent. With respect to the Notes, the following clauses (a) through
(h) shall replace clauses (a) through (h) of Section 9.01 of the Indenture: 
 (a) to cure any ambiguity, omission,
defect or inconsistency that does not adversely affect the rights of any Holder of the Notes in any material respect; 
 (b) to provide
for the assumption by a successor corporation of the Company’s obligations under the Indenture and this First Supplemental Indenture, in accordance with Article 5 of the Indenture, as amended by Section 9.02 of this First Supplemental
Indenture; 
 (c) to secure the Notes; 

(d) to add to the Covenants of the Company for the benefit of the Holders of the Notes or to surrender any right or power conferred upon
the Company; 
 (e) to provide for uncertificated Notes, at any time that the Notes are in certificated form; 

(f) to evidence and provide for the acceptance of appointment of a successor Trustee with respect to the Notes; 

(g) to comply with the requirements of the TIA and any rules promulgated under the TIA; and 

(h) to make any other change that does not adversely affect the rights of any Holder of the Notes in any material respect; 

Section 9.09. Modification With Consent. With respect to the Notes, the following clauses (a) through
(k) shall replace clauses (a) through (l) of Section 9.03 of the Indenture: 
 (a) change the stated maturity of
the principal of, or any interest on, the Notes; 
 (b) reduce the principal amount of, or interest on, the Notes; 

(c) change the interest rate applicable to the Notes; 

(d) change the currency of payment of principal of, or interest on, the Notes or change any Note’s place of payment; 

(e) impair the right of any Holder to receive payment of principal of, and interest on, such Holder’s Notes on or after the due
dates therefor or to institute suit for the enforcement of any payment on, or with respect to, the Notes; 
 (f) modify the provisions
with respect to the purchase rights of the Holders pursuant to Section 4.01 and Section 6.06 of this First Supplemental Indenture in a manner adverse to the Holders of Notes; 

(g) change the ranking of the Notes; 

(h) change the Company’s obligation to pay Additional Amounts on any Note; 

  
 20 








 (i) waive a default or Event of Default in the payment of principal of, or interest, if any,
on any Note (except a rescission of acceleration of the Notes by the Holders of at least a majority in principal amount of the outstanding Notes and a waiver of the payment default that resulted from such acceleration); 

(j) waive a redemption payment with respect to any Note or change any of the provisions with respect to the redemption of the Notes in a
manner adverse to the Holders of Notes; and 
 (k) modify provisions with respect to modification, amendment or waiver (including
waiver of Events of Default), except to increase the percentage required for modification, amendment or waiver or to provide for consent of each affected Holder of the Notes. 

ARTICLE X 

MISCELLANEOUS 

Section 10.01. Ratification of Indenture. This First Supplemental Indenture is executed and shall be constructed as an
indenture supplement to the Indenture, and as supplemented and modified hereby, the Indenture is in all respects ratified and confirmed, and the Indenture and this First Supplemental Indenture shall be read, taken and constructed as one and the same
instrument. 
 Section 10.02. Trust Indenture Act Controls. If any provision of this First Supplemental Indenture
limits, qualifies or conflicts with another provision that is required or deemed to be included in this First Supplemental Indenture by the Trust Indenture Act, the required or deemed provision shall control. 

Section 10.03. Notices. All notices and other communications shall be given as provided in the Indenture. 

Section 10.04. Governing Law. With respect to the Notes, Section 10.11 of the Indenture shall be superseded in its
entirety by the following 
 THE INDENTURE, THIS FIRST SUPPLEMENTAL INDENTURE AND THE NOTES SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS
OF THE STATE OF NEW YORK APPLICABLE TO AGREEMENTS MADE OR INSTRUMENTS ENTERED INTO AND, IN EACH CASE, PERFORMED IN THE STATE OF NEW YORK. 

(a) Any legal suit, action or proceeding arising out of or based upon this Indenture (each a “Related Proceeding”) may
be instituted in the federal courts of the United States of America located in the City and County of New York, Borough of Manhattan, or the courts of the State of New York in each case located in the City and County of New York, Borough of
Manhattan (collectively, the “Specified Courts”), and each party irrevocably submits to the exclusive jurisdiction (except for proceedings instituted in regard to the enforcement of a judgment of any such court (a
“Related Judgment”), as to which such jurisdiction is non-exclusive) of such courts in any such suit, action or proceeding. Service of any process, summons, notice or document by mail to such party’s address set forth
above shall be effective service of process for any suit, action or other proceeding brought in any such court. The parties irrevocably and unconditionally waive any objection to the laying of venue of any suit, action or other proceeding in
the Specified Courts and irrevocably and unconditionally waive and agree not to plead or claim in any such court that any such suit, action or other proceeding brought in any such court has been brought in an inconvenient forum. Each of the
Company and its subsidiaries not located in the United States irrevocably appoints Sting, LLC, a Delaware limited liability company, as its agent to receive service of process or other legal summons for purposes of any such suit, action or
proceeding that may be instituted in any state or federal court in the City and County of New York. 
 (b) With respect to any Related
Proceeding, each party irrevocably waives, to the fullest extent permitted by applicable law, all immunity (whether on the basis of sovereignty or otherwise) from jurisdiction, service of process, attachment (both before and after judgment) and
execution to which it might otherwise be entitled in the Specified Courts, and with respect to any Related Judgment, each party waives any such immunity in the Specified Courts or any other court of competent jurisdiction, and will not raise or
claim or cause to be pleaded any such immunity at or in respect of any such Related Proceeding or Related Judgment, including, without limitation, any immunity pursuant to the United States Foreign Sovereign Immunities Act of 1976, as amended. 

  
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 Section 10.05. Successors. All covenants and agreements in this First
Supplemental Indenture and the Notes by the Company shall bind its successors and assigns, whether so expressed or not. 

Section 10.06. Counterparts. This First Supplemental Indenture may be executed in several counterparts, each of which
shall be an original and all of which shall constitute but one and the same instrument. The exchange of copies of this Indenture and of signature pages by facsimile or PDF transmission shall constitute effective execution and delivery of this
Indenture as to parties hereto and may be issued in lieu of the original Indenture and signature pages for all purposes. 

Section 10.07. Headings. The Article and Section headings of this First Supplemental Indenture are for convenience only
and shall not affect the construction hereof. 
 Section 10.08. Cross-References. To the extent this First
Supplemental Indenture supersedes or replaces a section of the Indenture, references to such section elsewhere in the Indenture shall be understood to refer to the section of this First Supplemental Indenture superseding or replacing such section.

 Section 10.09. Trustee Not Responsible for Recitals. The recitals contained herein and in the Notes, except the
Trustee’s certificate of authentication shall be taken as the statements of the Company and neither the Trustee nor any Authenticating Agent assumes any responsibility for their correctness. The Trustee makes no representations as to the
validity or sufficiency of this First Supplemental Indenture or of the Notes, except that the Trustee represents that it is duly authorized to execute and deliver this First Supplemental Indenture, authenticate the Notes and perform its obligations
hereunder and that the statements made by it in a Statement of Eligibility on Form T-1 supplied to the Company are true and accurate, subject to the qualifications set forth therein. Neither the Trustee nor any Authenticating Agent shall be
accountable for the use or application by the Company of the Notes or the proceeds thereof. 
 The Trustee shall not be responsible in any
manner whatsoever for or with respect to (i) the proper authorization hereof by the Company by action or otherwise, (ii) the due execution hereof by the Company, or (iii) the consequences of any amendment herein provided for. 

  
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 IN WITNESS WHEREOF, the parties have caused this First Supplemental Indenture to be duly executed
as of the date first written above. 
  

			
	COMPANY:
	
	PARAGON SHIPPING INC.
		
	By:	 	 /s/ Robert Perri

		
	Name:	 	Robert Perri
	Title:	 	Chief Financial Officer


 [First Supplemental Indenture] 







 
			
	TRUSTEE:
	
	DEUTSCHE BANK TRUST COMPANY AMERICAS, as trustee
	
	By: Deutsche Bank National Trust Company
	
	 /s/ Jacqueline Bartnick

	Name:	 	Jacqueline Bartnick
	Title:	 	Director
	
	 /s/ Wanda Camacho

	Name:	 	Wanda Camacho
	Title:	 	Vice President


 [First Supplemental Indenture] 







 EXHIBIT A 

FORM OF NOTE 
 THIS NOTE
IS A GLOBAL SECURITY WITHIN THE MEANING OF THE INDENTURE HEREINAFTER REFERRED TO AND IS REGISTERED IN THE NAME OF A DEPOSITORY (AS DEFINED IN THE INDENTURE) OR A NOMINEE THEREOF. THIS NOTE IS EXCHANGEABLE FOR NOTES REGISTERED IN THE NAME OF A
PERSON OTHER THAN THE DEPOSITORY OR ITS NOMINEE ONLY IN THE LIMITED CIRCUMSTANCES DESCRIBED IN THE INDENTURE AND, UNLESS AND UNTIL IT IS EXCHANGED IN WHOLE OR IN PART FOR NOTES IN DEFINITIVE FORM, THIS NOTE MAY NOT BE TRANSFERRED EXCEPT AS A WHOLE
BY THE DEPOSITORY TO A NOMINEE OF THE DEPOSITORY, OR BY A NOMINEE OF THE DEPOSITORY TO THE DEPOSITORY OR ANOTHER NOMINEE OF THE DEPOSITORY, OR BY THE DEPOSITORY OR ANY SUCH NOMINEE TO A SUCCESSOR DEPOSITORY OR A NOMINEE OF SUCH SUCCESSOR DEPOSITORY.

 UNLESS THIS NOTE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION
(“DTC”), TO THE COMPANY (AS DEFINED BELOW) OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY NOTE ISSUED IS REGISTERED IN THE NAME OF CEDE & CO. OR IN SUCH OTHER NAME AS REQUESTED BY AN AUTHORIZED
REPRESENTATIVE OF DTC (AND ANY PAYMENT IS MADE TO CEDE & CO. OR TO SUCH OTHER ENTITY AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC), ANY TRANSFER, PLEDGE OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL
INASMUCH AS THE REGISTERED OWNER HEREOF, CEDE & CO., HAS AN INTEREST HEREIN. 
 CUSIP NO. 69913R507 

ISIN NO. US69913R5072 
 PARAGON SHIPPING INC.

 8.375% SENIOR NOTE DUE 2021 
  

			
	$25,000,000	 	No.:    1

 PARAGON SHIPPING INC., a Marshall Islands corporation (hereinafter called the “Company”, which term
includes any successor corporation under the Indenture referred to below), for value received, hereby promises to pay to Cede & Co., or registered assigns, the principal sum of $25,000,000.00 (TWENTY-FIVE MILLION DOLLARS) set forth on
Schedule I annexed hereto on August 15, 2021, and to pay interest thereon from and including August 8, 2014 or from the most recent Interest Payment Date on which interest has been paid or duly provided for, quarterly on
February 15, May 15, August 15 and November 15 in each year, commencing November 15, 2014, at the rate of 8.375% per annum, until the principal hereof is paid or made available for payment. Interest on
this Note shall be computed on the basis of a 360-day year of twelve 30-day months. If any Interest Payment Date or the Maturity Date falls on a day that is not a Business Day, the required payment of interest or principal, as the case may be,
shall be made on the next succeeding Business Day as if it were made on the date such payment was due and no interest shall accrue on the amount so payable for the period from and after such Interest Payment Date or the Maturity Date, as the case
may be, to such next Business Day. The interest so payable and punctually paid or duly provided for on any Interest Payment Date will, as provided in the Indenture, be paid to the Person in whose name this Note (or one or more predecessor
Notes) is registered at the close of business on the Regular Record Date for such interest, which shall be the February 1, May 1, August 1 or November 1 (whether or not a


  
 A-1 








 
Business Day), as the case may be, next preceding such Interest Payment Date. Any such interest which is payable but not punctually paid or duly provided for on any Interest Payment Date
shall forthwith cease to be payable to the registered Holder hereof on the relevant Regular Record Date by virtue or having been such Holder, and may be paid to the Person in whose name this Note (or one or more predecessor Notes) is registered at
the close of business on a subsequent special record date (which shall be at least 10 days before the payment date) for the payment of such defaulted interest to be fixed by the Company, notice whereof shall be given to the Holders of Notes not less
than 10 days prior to such Special Record Date, or may be paid at any time in any other lawful manner not inconsistent with the requirements of any securities exchange on which the Notes may be listed, and upon such notice as may be required by such
exchange, all as more fully provided in the Indenture. 
 Payment of the principal of and interest on this Note (including, without
limitation, any purchase price relating to a Change of Control offer to purchase or a Limited Permitted Asset sale offer to purchase) will be made at the office or agency of the Company maintained for that purpose in The Borough of Manhattan, The
City of New York, in such coin or currency of the United States of America as at the time of payment is legal tender for payment of public and private debts; provided, however, that, at the option of the Company, interest may be paid
by check mailed to the address of the Person entitled thereto as such address shall appear in the Security register; provided, further, that payment to DTC or any successor depository may be made by wire transfer to the account
designated by DTC or such successor depository in writing. 
 This Note is one of a duly authorized issue of securities of the Company
designated as its 8.375% Senior Notes due 2021 (herein called the “Notes”), issued and to be issued in one or more series under an Indenture, dated as of August 8, 2014 (the “Base Indenture”), between the
Company and Deutsche Bank Trust Company Americas, as Trustee (herein called the “Trustee,” which term includes any successor trustee under the Indenture), as supplemented by the First Supplemental Indenture, dated August 8,
2014, between the Company and the Trustee (the “First Supplemental Indenture” and, together with the Base Indenture, the “Indenture”), to which Indenture and all indentures supplemental thereto reference is hereby
made for a statement of the respective rights, limitations of rights, duties and immunities thereunder of the Company, the Trustee and the Holders of the Notes, and of the terms upon which the Notes are, and are to be, authenticated and
delivered. This Note is one of the series designated on the face hereof, initially limited (subject to exceptions provided in the Indenture) to the aggregate principal amount of $25,000,000.00. 

If an Event of Default with respect to the Notes shall occur and be continuing, the principal of the Notes may be declared due and payable in
the manner and with the effect provided in the Indenture. 
 The Notes may not be redeemed prior to the Stated Maturity, except as described
in Section 3.01 and 3.02 of the First Supplemental Indenture. The Notes are not subject to any sinking fund. 
 Upon the
occurrence of a Change of Control or a Limited Permitted Asset Sale, each Holder of Notes will have the right to require the Company to purchase all or a portion of such Holder’s Notes at a purchase price equal to 101% of the principal amount
thereof plus accrued and unpaid interest, if any, to but excluding the date of purchase, to the extent provided for in the Indenture. 
 The
Indenture contains provisions permitting, with certain exceptions as therein provided, the amendment thereof and the modification of the rights and obligations of the Company and the rights of the Holders of the Notes of each series issued under the
Indenture at any time by the Company and the Trustee with the written consent of the Holders of not less than a majority in aggregate principal amount of the Notes at the time Outstanding of each series affected thereby. The Indenture also
contains provisions permitting the Holders of specified percentages in aggregate principal amount of the Notes of any series at the time Outstanding, on behalf of the Holders of all Notes of such series, to waive compliance by the Company with
certain provisions of the Indenture and certain past defaults under the Indenture and their consequences. Any such consent or waiver by the Holder of this Note shall be conclusive and binding upon such Holder and upon all future Holders of this
Note and of any Notes issued upon the registration of transfer hereof or in exchange herefor or in lieu hereof, whether or not notation of such consent or waiver is made upon this Note. 

  
 A-2 








 No reference herein to the Indenture and no provision of this Note or of the Indenture shall
alter or impair the obligation of the Company, which is absolute and unconditional, to pay the principal of and interest on this Note, at the times, place and rate, and in the coin or currency, herein and in the Indenture prescribed. 

As provided in the Indenture and subject to certain limitations set forth therein and in this Note, the transfer of this Note may be
registered on the Security register upon surrender of this Note for registration of transfer at the office or agency of the Company maintained for that purpose in any place where the principal of and interest on this Note are payable, duly endorsed
by, or accompanied by a written instrument of transfer in form satisfactory to the Company and the Registrar duly executed by, the Holder hereof or by his attorney duly authorized in writing, and thereupon one or more new Notes of this series and of
like tenor, of authorized denominations and for the same aggregate principal amount, will be issued to the designated transferee or transferees. 

The Notes are issuable only in registered form in the denominations of $25.00 or any integral multiple thereof. As provided in the
Indenture and subject to certain limitations set forth in the Indenture, and in this Note, the Notes are exchangeable for a like aggregate principal amount of Notes of this series in different authorized denominations, as requested by the Holders
surrendering the same. 
 No service charge shall be made for any such registration of transfer or exchange, but the Company may require
payment of a sum sufficient to cover any tax or other governmental charge payable in connection therewith, other than in certain cases provided in the Indenture. 

Prior to due presentment of this Note for registration of transfer, the Company, the Trustee and any agent of the Company or the Trustee may
treat the Person in whose name this Note is registered as the owner hereof for all purposes, whether or not this Note be overdue, and neither the Company, the Trustee nor any such agent shall be affected by notice to the contrary. 

The Indenture contains provisions whereby (i) the Company may be discharged from its obligations with respect to the Notes (subject to
certain exceptions) or (ii) the Company may be released from its obligations under specified covenants and agreements in the Indenture, in each case if the Company irrevocably deposits with the Trustee money or U.S. Government Obligations, or a
combination thereof, in an amount sufficient, without consideration of any reinvestment, to pay and discharge the entire indebtedness on all Notes of this series, and satisfies certain other conditions, all as more fully provided in the Indenture.

 This Note shall be governed by and construed in accordance with the laws of the State of New York applicable to agreements made or
instruments entered into and, in each case, performed in said State. 
 All terms used in this Note without definition that are defined in
the Indenture shall have the meanings assigned to them in the Indenture. 
 [Remainder of Page Intentionally Left Blank] 

  
 A-3 








 IN WITNESS WHEREOF, the Company has caused this Note to be to be duly executed as of the date set
forth below. 
  

			
	PARAGON SHIPPING INC.
		
	By:	 	  

		 	Name:
		 	Title:


  

			
	By:	 	  

		 	Name:
		 	Title:


 Trustee’s Certificate of Authentication 

This is one of the Securities of the series designated therein referred to in the within-mentioned Indenture. 

Dated: August 8, 2014 
  

			
	 DEUTSCHE BANK TRUST COMPANY AMERICAS, as Trustee
  

By: Deutsche Bank National Trust Company

		
	By:	 	  

		 	Name:
		
		 	Title:
		
	By:	 	  

		 	Name:
		
		 	Title:



  
 A-4 








 ASSIGNMENT FORM 

FOR VALUE RECEIVED, the undersigned hereby sell(s), assign(s) and transfer(s) unto 

PLEASE INSERT SOCIAL SECURITY OR OTHER IDENTIFYING NUMBER OF ASSIGNEE 
  

 
 PLEASE PRINT OR TYPEWRITE NAME AND ADDRESS INCLUDING
POSTAL ZIP CODE OF ASSIGNEE 
  

	
	  

	
	  

	
	  


 the within Security and all rights thereunder, hereby irrevocably constituting and appointing attorney to transfer said
Security on the books of the Company, with full power of substitution in the premises. 
  

			
	Dated:	 	  

		
	Signature:	 	  


  

			
	NOTICE:	  	THE SIGNATURE TO THIS ASSIGNMENT MUST CORRESPOND WITH THE NAME AS WRITTEN UPON THE FACE OF THE WITHIN INSTRUMENT IN EVERY PARTICULAR, WITHOUT ALTERATION OR ENLARGEMENT OR ANY CHANGE WHATEVER.

 Signature Guarantee: 

SIGNATURE GUARANTEE 
 Signatures
must be guaranteed by an “eligible guarantor institution” meeting the requirements of the Registrar, which requirements include membership or participation in the Security Transfer Agent Medallion Program (“STAMP”) or such other
“signature guarantee program” as may be determined by the Registrar in addition to, or in substitution for, STAMP, all in accordance with the Securities Exchange Act of 1934, as amended. 

  
 A-5 








 FORM OF PURCHASE NOTICE 

If you want to elect to have this Note purchased by the Company pursuant to Section 5.01 of the First Supplemental Indenture, check the
box: 
  
  ̈ 

If you want to elect to have only part of this Note purchased by the Company pursuant to Section 5.01 of the First Supplemental
Indenture, state the amount in principal amount: $ 
  

									
	 Dated:
	 	  
	 		 	Your Signature:	 	  

					
		 		 		 		 	(Sign exactly as your name appears on the other side of this Note.)

  

			
	Signature Guarantee:	 	  

		
		 	(Signature must be guaranteed)

 Signatures must be guaranteed by an “eligible guarantor institution” meeting the requirements of the Registrar,
which requirements include membership or participation in the Security Transfer Agent Medallion Program (“STAMP”) or such other “signature guarantee program” as may be determined by the Registrar in addition to, or in
substitution for, STAMP, all in accordance with the Securities Exchange Act of 1934, as amended. 

  
 A-6 








 Schedule I 

SCHEDULE OF TRANSFERS AND EXCHANGES 

The initial principal amount of this Global Security is $25,000,000.00 (TWENTY-FIVE MILLION DOLLARS). The following increases or
decreases in principal amount of this Global Security have been made: 
  

									
	 Date of Exchange
	  	 Amount of

Decrease in

Principal
 Amount of
this
 Global Security
	  	Amount of
Increase in
Principal Amount
of this Global
Security	  	Principal
Amount of this
Global Security
following such
Decrease or
Increase	  	Signature of
Authorized
Signatory of
trustee or
Custodian
					
	 Start here
	  		  		  		  	


  
 A-7