Exhibit 4.2


 


FIRST SUPPLEMENTAL INDENTURE


 


Dated as of June 14, 2016


 


Supplementing that Certain


 


INDENTURE


 


Dated as of June 14, 2016


 


Between


 


MAIDEN HOLDINGS, LTD., as Issuer


 


and


 


WILMINGTON, NATIONAL ASSOCIATION, as
Trustee


 


6.625%
NOTES DUE 2046


 




     


     


    

 


Table
of Contents


 


	 	 	Page
	 	 	 
	 	ARTICLE I.	 
	 	 	 
	 	DEFINITIONS	 
	 	 	 
	SECTION 1.1.	Certain Terms Defined in the Indenture	1
	 	 	 
	SECTION 1.2.	Definitions	2
	 	 	 
	 	ARTICLE II.	 
	 	 	 
	 	FORM AND TERMS OF THE NOTES	 
	 	 	 
	SECTION 2.1.	Form and Dating	3
	 	 	 
	SECTION 2.2.	Certain Terms of the Notes	5
	 	 	 
	SECTION 2.3.	Optional Redemption	6
	 	 	 
	SECTION 2.4.	Payment of Additional Amounts	6
	 	 	 
	SECTION 2.5.	Redemption for Changes in Withholding Taxes	8
	 	 	 
	SECTION 2.6.	Limitation on Liens on Stock of Subsidiaries	8
	 	 	 
	SECTION 2.7.	Limitations on Disposition of Stock of Designated Subsidiaries	9
	 	 	 
	 	ARTICLE III.	 
	 	 	 
	 	MISCELLANEOUS	 
	 	 	 
	SECTION 3.1.	Relationship with Indenture	10
	 	 	 
	SECTION 3.2.	Trust Indenture Act Controls	10
	 	 	 
	SECTION 3.3.	Governing Law	10
	 	 	 
	SECTION 3.4.	Multiple Counterparts	10
	 	 	 
	SECTION 3.5.	Severability	10
	 	 	 
	SECTION 3.6.	Ratification	10
	 	 	 
	SECTION 3.7.	Headings	11
	 	 	 
	SECTION 3.8.	Effectiveness	11
	 	 	 
	EXHIBIT A— Form of 6.625% Note due 2046 	A-1


 




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FIRST
SUPPLEMENTAL INDENTURE


 


This First Supplemental Indenture, dated
as of June 14, 2016 (this “First Supplemental Indenture”), between MAIDEN HOLDINGS, LTD., a company duly organized
and existing under the laws of Bermuda (the “Company”), having its principal executive office located at 131
Front Street, 2nd Floor, Hamilton HM12 Bermuda; and Wilmington Trust, National Association, a national banking association
duly organized and existing under the laws of the United States of America, as trustee (the “Trustee”), supplements
that certain Indenture, dated as of June 14, 2016, between the Company and the Trustee (the “Indenture”).


 


RECITALS
OF THE COMPANY


 


WHEREAS, the Company has duly authorized
the execution and delivery of the Indenture to provide for the issuance from time to time of its unsecured debentures, notes or
other evidences of indebtedness to be issued in one or more series as provided for in the Indenture;


 


WHEREAS, the Indenture provides that the
Securities shall be in the form as may be established by or pursuant to a Board Resolution and set forth in an Officers’
Certificate or as may be established in one or more supplemental indentures thereto, in each case with such appropriate insertions,
omissions, substitutions, and other variations as are required or permitted by the Indenture; and


 


WHEREAS, the Company has determined to issue
and deliver, and the Trustee shall authenticate, a series of Securities designated as the Company’s “6.625% Notes due
2046” (hereinafter called the “Notes”) pursuant to the terms of this First Supplemental Indenture and
substantially in the form as herein set forth, with such appropriate insertions, omissions, substitutions and other variations
as are required or permitted by the Indenture and this First Supplemental Indenture.


 


NOW, THEREFORE, THIS FIRST SUPPLEMENTAL
INDENTURE WITNESSETH:


 


For and in consideration of the premises
stated herein and the purchase of the Notes by the Holders thereof, the parties hereto hereby enter into this First Supplemental
Indenture, for the equal and proportionate benefit of all Holders of the Notes, as follows:


 


ARTICLE I.



DEFINITIONS


 


		SECTION
                              1.1.	Certain Terms Defined in the Indenture.



 


For purposes of this First Supplemental
Indenture, all capitalized terms used but not defined herein shall have the meanings ascribed to such terms in the Indenture, as
amended and supplemented hereby.


 




     


     


    

 


		SECTION
                              1.2.	Definitions.



 


For the benefit of the Holders of the Notes,
Section 101 of the Indenture shall be amended by adding or substituting, as applicable, the following new definitions:


 


“Consolidated Net Worth”
means, at any date, the sum of all amounts which would be included under stockholders’ equity on a consolidated balance sheet
of an applicable entity and its subsidiaries determined in accordance with United States generally accepted accounting principles
on such date or, in the event such date is not a fiscal quarter end, as of the immediately preceding fiscal quarter end.


 


“Designated Subsidiary”
means any present or future consolidated Subsidiary of the Company, the Consolidated Net Worth of which constitutes at least 10%
of the Company’s Consolidated Net Worth.


 


“Global Notes” means,
individually and collectively, each of the Notes in the form of global Securities registered in the name of the Depositary or its
nominee, substantially in the form of Exhibit A attached hereto.


 


“Indebtedness” means,
without duplication and solely for the purposes of Section 2.6 herein, with respect to any Person, whether or not contingent:


 


(1)         the
principal of and any premium and interest on (a) indebtedness of such Person for money borrowed or (b) indebtedness evidenced
by notes, debentures, bonds or other similar instruments for the payment of which such person is responsible or liable;


 


(2)         all
capitalized lease obligations of such Person;


 


(3)         all
obligations of such Person issued or assumed as the deferred purchased price of property, all conditional sale obligations and
all obligations under any title retention agreement (but excluding trade accounts payable arising in the ordinary course of business);


 


(4)         all
obligations of such Person for the reimbursement of any obligor on any banker’s acceptance, bank guarantees, surety bonds
or similar credit transaction; and


 


(5)         any
amendments, modifications, refundings, renewals or extensions of any indebtedness or obligation described as “Indebtedness”
in clauses (1) through (4) above;


 


if and to the extent any of the preceding items (other than
letters of credit) would appear as a liability upon a balance sheet of such person prepared in accordance with United States generally
accepted accounting principles; provided, however, the term ‘‘Indebtedness’’ includes all of the
following items, whether or not any such items would appear as a liability on a balance sheet of such Person prepared in accordance
with such generally accepted accounting principles:


 




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		(i)	all Indebtedness of others secured by any mortgage, pledge, lien, security interest or other encumbrance on any property or
asset of such Person (whether or not such Indebtedness is assumed by such Person);



 


		(ii)	to the extent not otherwise included, any guarantee by such person of Indebtedness of any other Person; and



 


		(iii)	preferred stock or other equity interests providing for mandatory redemption or sinking fund or similar payments issued by
any subsidiary of such Person.



 


“Payor” means, in respect
of the Notes, the Company and any of its successors.


 


“Relevant Tax Jurisdiction”
means the jurisdiction, other than the United States, where the Payor is organized or otherwise considered to be a resident for
tax purposes, any jurisdiction, other than the United States, from or through which the Payor makes a payment on the Notes, or,
in each case, any political organization or governmental authority thereof or therein having the power to tax.


 


ARTICLE II.



FORM AND TERMS OF THE NOTES


 


		SECTION
                              2.1.	Form and Dating.



 


The Notes and the Trustee’s certificate
of authentication shall be substantially in the form of Exhibit A attached hereto. The Notes shall be executed on behalf
of the Company by two of the officers of the Company specified in Section 303 of the Indenture. The Notes may have notations, legends
or endorsements required by law, stock exchange rules or usage. Each Note shall be dated the date of its authentication. The Notes
and any beneficial interest in the Notes shall be in minimum denominations of $25.00 and integral multiples of $25.00 in excess
thereof.


 


The terms and notations contained in the
Notes shall constitute, and are hereby expressly made, a part of the Indenture as supplemented by this First Supplemental Indenture;
and the Company and the Trustee, by their execution and delivery of this First Supplemental Indenture, expressly agree to such
terms and provisions and to be bound thereby; provided that, to the extent of any inconsistency between the terms and provisions
in the Indenture, as supplemented by this First Supplemental Indenture, and those contained in the Notes, the Indenture, as supplemented
by this First Supplemental Indenture, shall govern.


 


(a)          Global
Notes. The Notes designated herein shall be issued initially in the form of one or more fully-registered permanent global Securities,
which shall be held by the Trustee as custodian for The Depository Trust Company, New York, New York (the “Depositary”),
and registered in the name of Cede & Co., the Depositary’s nominee, duly executed by the Company and authenticated by
the Trustee. The aggregate principal amount of outstanding Notes may from time to time be increased or decreased by adjustments
made on the records of the Trustee and the Depositary or its nominee as hereinafter provided.




 




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Unless and until the Global Notes are exchanged
in whole or in part for the individual Notes represented thereby pursuant to Section 305 of the Indenture, such Global Notes may
not be transferred except as a whole by the Depositary to its nominee or by its nominee to the Depositary or another nominee of
the Depositary or by the Depositary or any of its nominees to a successor depositary or any nominee of such successor depositary.
Upon the occurrence of the events specified in Section 305 of the Indenture in relation thereto, the Company shall execute, and
the Trustee shall, upon receipt of a Company Order for authentication, authenticate and deliver, Notes in definitive form in an
aggregate principal amount equal to the principal amount of the Global Notes in exchange for such Global Note.


 


(b)          Book-Entry
Provisions. This Section 2.1(b) shall apply only to the Global Notes deposited with or on behalf of the Depositary.


 


The Company shall execute and the Trustee
shall, in accordance with this Section 2.1(b), authenticate and deliver the Global Notes that shall be registered in the name of
the Depositary or the nominee of the Depositary and shall be held by the Trustee as custodian for the Depositary.


 


Participants of the Depositary shall have
no rights either under the Indenture or with respect to any Global Notes. The Depositary shall be treated by the Company, the Trustee
and any agent of the Company or the Trustee as the absolute owner of such Global Note for all purposes under the Indenture. Notwithstanding
the foregoing, nothing herein shall prevent the Company or the Trustee from giving effect to any written certification, proxy or
other authorization furnished by the Depositary or impair, as between the Depositary and its participants, the operation of customary
practices of such Depositary governing the exercise of the rights of an owner of a beneficial interest in the Global Notes.


 


(c)          Definitive
Notes. Definitive Notes issued in physical, certificated form, registered in the name of the beneficial owner thereof, shall
be substantially in the form of Exhibit A attached hereto, but without including the text referred to therein as applying
only to Global Notes. Except as provided above in subsection (a), owners of beneficial interests in the Global Notes will not be
entitled to receive physical delivery of certificated Notes.


 


(d)          Transfer
and Exchange of the Notes. The transfer and exchange of beneficial interests in the Global Notes shall be effected through
the Depositary, in accordance with the Indenture and the procedures of the Depositary therefor. Beneficial interests in the Global
Notes may be transferred to Persons who take delivery thereof in the form of a beneficial interest in the Global Notes.


 


(e)          Paying
Agent. The Company appoints the Trustee as the initial agent of the Company for the payment of the principal of (and premium,
if any) and interest on and any Additional Amounts with respect to the Notes, and the Corporate Trust Office of the Trustee in
Wilmington, Delaware, be and hereby is, designated as the office or agency where the Notes may be presented for payment and where
notices to or demands upon the Company in respect of the Notes and this First Supplemental Indenture and the Indenture pursuant
to which the Notes are to be issued may be made.


 




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		SECTION
                              2.2.	Certain Terms of the Notes.



 


The following terms relating to the Notes
are hereby established:


 


(a)          Title.
The Notes shall constitute a series of Securities having the title “6.625% Notes due 2046.”


 


(b)          Principal
Amount. The aggregate principal amount of the Notes that may be initially authenticated and delivered under the Indenture
(except for Notes authenticated and delivered upon registration of, transfer of, or in exchange for, or in lieu of, other Notes
pursuant to Sections 304, 305, 306, 905 or 1107 of the Indenture) shall be ONE HUNDRED TEN MILLION DOLLARS ($110,000,000). The
Company may, from time to time, without notice to, or the consent of, the Holders of the Notes, issue and sell additional Securities
(“Additional Securities”) ranking equally and ratably with the Notes in all respects (other than the issue date,
and to the extent applicable, issue price, initial date of interest accrual and initial interest payment date of such Additional
Securities), provided that such Additional Securities are fungible with the previously issued Notes for U.S. federal
income tax purposes. Any such Additional Securities shall be consolidated and form a single series with the Notes for all
purposes under the Indenture, including voting.


 


(c)          Maturity
Date. The entire outstanding principal of the Notes shall be payable on June 14, 2046, unless previously redeemed in
full by the Company pursuant to Section 2.3 or 2.5 herein.


 


(d)          Interest
Rate.  The rate at which the Notes shall bear interest shall be 6.625% per annum, computed on the basis of a 360-day
year comprised of twelve 30-day months; the date from which interest shall accrue on the Notes shall be June 14, 2016, or the most
recent Interest Payment Date to which interest has been paid or duly provided for; the Interest Payment Dates for the Notes shall
be the 14th day of March, June, September and December of each year, commencing on September 14, 2016; the interest
so payable, and punctually paid or duly provided for, on any Interest Payment Date, will be paid, in immediately available funds,
to the Persons in whose names the Notes (or one or more Predecessor Securities) is registered at the close of business on the Regular
Record Date for such interest, which shall be the 28th day of February or the 30th day of May, August or
November (whether or not a Business Day), as the case may be, next preceding such Interest Payment Date. Any such interest not
punctually paid or duly provided for shall forthwith cease to be payable to the respective Holders on such Regular Record Date,
and such defaulted interest may be paid to the Persons in whose names the Notes (or one or more Predecessor Securities) is registered
at the close of business on a Special Record Date for the payment of such defaulted interest to be fixed by the Trustee, notice
whereof shall be given to 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 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 said Indenture. Payment of principal of, and
premium, if any, and interest on, and any Additional Amounts with respect to, the Notes will be made at the Corporate Trust Office
of the Trustee or such other office or agency of the Company as may be designated for such purpose, 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 each installment of interest, premium, if any, and principal on, and any Additional Amounts with respect to,
the Notes may at the Company’s option be paid in immediately available funds by wire transfer to an account maintained by
the payee located in the United States.


 




    	 	5	 



     


    

 


(e)          Currency.
The currency of denomination of the Notes is United States dollars. Payment of principal of and interest and premium, if any, on,
and any Additional Amounts with respect to, the Notes will be made in United States dollars.


 


		SECTION
                              2.3.	Optional Redemption.



 


(a)          Applicability
of Article Eleven. The provisions of Article Eleven of the Indenture shall apply to the Notes, as supplemented by Sections
2.3(b) and (c) below.


 


(b)          Redemption
Price. The Notes shall be redeemable, for cash, in whole or in part, on or after June 14, 2021, at the option of the Company,
at any time and from time to time, until the Maturity Date at a Redemption Price equal to 100% of the principal amount of the Notes
to be redeemed, plus (i) accrued but unpaid interest on the principal amount of Notes being redeemed to, but not including, the
Redemption Date and (ii) Additional Amounts, if any (subject, in each case, to the rights of Holders of Notes on the applicable
Regular Record Date to receive interest due on the applicable Interest Payment Date).


 


(c)          Interest
Payable. On and after any Redemption Date for the Notes, interest will cease to accrue on the Notes or any portion thereof
called for redemption, unless the Company defaults in the payment of the Redemption Price.


 


		SECTION
                              2.4.	Payment of Additional Amounts.



 


(a)          Additional
Amounts. If any taxes, assessments or other governmental charges are imposed by the Relevant Tax Jurisdiction in respect of
any payments under the Notes, the Payor shall pay to each Holder of the Notes, to the extent it may lawfully do so, such Additional
Amounts as may be necessary in order that the net amounts paid to such Holder will be not less than the amount specified in the
Notes to which such Holder is otherwise entitled.


 


(b)          Exceptions
to Payments of Additional Amounts. Notwithstanding the foregoing clause (a), the Payor shall not be required to make any payment
of Additional Amounts for or on account of:


 


(1)         any
tax, assessment or other governmental charge which would not have been imposed but for (i) the existence of any present or
former connection between such Holder (or between a fiduciary, settlor, beneficiary, member or shareholder of, or possessor of
a power over, such Holder, if such Holder is an estate, trust, partnership, limited liability company or corporation) and the Relevant
Tax Jurisdiction (other than by reason of the mere ownership of, or receipt of payment under, the Notes), including, without limitation,
such Holder (or such fiduciary, settlor, beneficiary, member, shareholder or possessor) being or having been a citizen or resident
thereof or being or having been present or engaged in trade or business therein or having or having had a permanent establishment
therein or (ii) the presentation of a Note (where presentation is required) for payment on a date more than 30 days after
(x) the date on which such payment became due and payable or (y) the date on which payment thereof is duly provided for, whichever
occurs later;


 




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


 


(3)         any
tax, assessment or other governmental charge which is payable otherwise than by withholding from payment of (or in respect of)
principal of, premium, if any, or any interest on, the Notes;


 


(4)         any
tax, assessment or other governmental charge that is imposed or withheld by reason of the failure by the Holder or the beneficial
owner of the Notes to comply with a request of the Payor addressed to such Holder to provide information, documents or other evidence
concerning the nationality, residence or identity of such Holder or such beneficial owner which is required by a statute, treaty,
regulation or administrative practice of the Relevant Tax Jurisdiction as a precondition to exemption from all or part of such
tax, assessment or other governmental charge;


 


(5)         any
withholding or deduction that is imposed on a payment pursuant to Sections 1471 through 1474 of the Code and related Treasury regulations
and pronouncements (the Foreign Account Tax Compliance Act, or “FATCA”) or any successor provisions and any regulations
or official law, agreement or interpretations thereof implementing an intergovernmental approach thereto; or


 


(6)         any
combination of the above;


 


nor shall Additional Amounts be paid with respect
to any payment of the principal of, or any premium or interest on, any Notes to any Holder who is a fiduciary or partnership or
limited liability company or other than the sole beneficial owner of such payment to the extent such payment would be required
by the laws of the Relevant Tax Jurisdiction to be included in the income for tax purposes of a beneficiary or settlor with respect
to such fiduciary or a member of such partnership or limited liability company or beneficial owner who would not have been entitled
to such Additional Amounts had it been the Holder of such Notes.


 


(c)          Delivery
of Documentation. The Payor shall provide the Trustee with the official acknowledgment of the relevant tax authority (or, if
such acknowledgment is not available, a certified copy thereof) evidencing the payment of any withholding taxes by the Payor. Upon
written request, the Payor shall make copies of such documentation available to the Holders of the Notes or the Paying Agent, as
applicable.


 




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		SECTION
                              2.5.	Redemption for Changes in Withholding Taxes.



 


(a)          Redemption
for Changes in Withholding Taxes. The Company may redeem the Notes, at its option, at any time, for cash, in whole but not
in part, upon not less than 30 nor more than 60 days’ prior written notice to Holders (with a copy to the Trustee), at a
Redemption Price equal to 100% of the principal amount thereof, plus (i) any accrued but unpaid interest to, but excluding, the
Redemption Date and (ii) Additional Amounts, if any (subject, in each case, to the rights of Holders of Notes on the applicable
Regular Record Date, whether or not a Business Day, to receive interest due on the applicable Interest Payment Date), in the event
that the Payor has become or would become obligated to pay, on the next date on which any amount would be payable with respect
to the Notes, any Additional Amounts as a result of:


 


(1)         a
change in or an amendment to the laws (including any regulations promulgated thereunder) of a Relevant Tax Jurisdiction, which
change or amendment is announced: (1) in the case of the Company, after June 7, 2016 and (2) in the case of any successor
to the Company, after the date such successor becomes the successor to the Company; or


 


(2)         any
change in or amendment to any official position regarding the application or interpretation of such laws or regulations, which
change or amendment is announced: (1) in the case of the Company, after June 7, 2016 and (2) in the case of any successor
to the Company, after the date such successor becomes the successor to the Company,


 


and, in each case, the Payor cannot avoid such obligation
by taking reasonable measures available to it.


 


(b)          Deliverables.
Before any notice of redemption of the Notes is delivered to a Holder as described in clause (a) above, the Company shall deliver
to the Trustee, at least 30 days before the Redemption Date, in each case, an Officers’ Certificate and an Opinion of Counsel,
which counsel shall be independent of the Company and of recognized standing, stating that the Payor has or will become obligated
to pay Additional Amounts as a result of a change in tax laws or regulations or the application or interpretation of such laws
or regulations.


 


		SECTION
                              2.6.	Limitation on Liens on Stock of Subsidiaries.



 


The Company covenants and agrees for the
benefit of the Holders of the Notes that, for so long as any of the Notes are Outstanding, the Company will not, nor will the Company
permit any Subsidiary to, create, assume, incur, guarantee or otherwise permit to exist any Indebtedness secured by any mortgage,
pledge, lien, security interest or other encumbrance upon any shares of Capital Stock of any Designated Subsidiary (whether such
shares of Capital Stock are now owned or hereafter acquired) without effectively providing concurrently that the Notes (and, if
the Company so elects, any other Indebtedness of the Company that is not subordinate to the Notes and with respect to which the
governing instruments of such Indebtedness require, or pursuant to which the Company is otherwise obligated, to provide such security)
will be secured equally and ratably with, or prior to, such Indebtedness for at least the time period such other Indebtedness is
so secured.


 




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		SECTION
                              2.7.	Limitations on Disposition of Stock of Designated Subsidiaries



 


(a)          Limitations
on Dispositions. So long as any of the Notes are Outstanding, and except in a transaction otherwise governed by the Indenture,
the Company shall not:


 


(1)         issue,
sell, assign, transfer or otherwise dispose of any shares of, securities convertible into, or warrants, rights or options to subscribe
for or purchase shares of, Capital Stock (other than preferred stock having no voting rights of any kind) of any Designated Subsidiary
(other than to the Company or another Designated Subsidiary); or


 


(2)         permit
any Designated Subsidiary to issue (other than to the Company or another Designated Subsidiary) any shares (other than director’s
qualifying shares) of, or securities convertible into, or warrants rights or options to subscribe for or purchase shares of, Capital
Stock (other than preferred stock having no voting rights of any kind) of any Designated Subsidiary;


 


if, after giving effect to any transaction
described in clauses (1) or (2) above and the issuance of the maximum number of shares issuable upon the conversion or exercise
of all such convertible securities, warrants, rights or options, the Company would own, directly or indirectly, less than 80% of
the shares of Capital Stock of such Designated Subsidiary (other than non-voting preferred stock); provided, however, that
(i) any issuance, sale, assignment, transfer or other disposition permitted by the Company pursuant to this Section 2.7 shall
only be made for at least a fair market value consideration as determined by the Board of Directors of the Company pursuant to
a resolution adopted in good faith and (ii) this Section 2.7(a) shall not prohibit any such issuance or disposition of securities
if required by any law or any regulation or order of any applicable governmental or insurance regulatory authority.


 


(b)          Permitted
Dispositions. Notwithstanding the foregoing clause (a), the Company shall be permitted:


 


(1)         to
merge or consolidate any Designated Subsidiary into or with another direct or indirect subsidiary of the Company, the shares of
Capital Stock of which the Company owns at least 70%; and


 


(2)         subject
to Article Eight of the Indenture, sell, assign, transfer or otherwise dispose of the entire Capital Stock of any Designated Subsidiary
at one time for at least a fair market value consideration as determined by the Board of Directors of the Company pursuant to a
resolution adopted in good faith.


 




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ARTICLE III.



MISCELLANEOUS


 


		SECTION
                              3.1.	Relationship with Indenture.



 


The terms and provisions contained in the
Indenture will constitute, and are hereby expressly made, a part of this First Supplemental Indenture. However, to the extent any
provision of the Indenture conflicts with the express provisions of this First Supplemental Indenture, the provisions of this First
Supplemental Indenture will govern and be controlling.


 


		SECTION
                              3.2.	Trust Indenture Act Controls.



 


If any provision of this First Supplemental
Indenture limits, qualifies or conflicts with another provision which is required to be included in this First Supplemental Indenture
by the Trust Indenture Act, the required provision shall control. If any provision of this First Supplemental Indenture modifies
or excludes any provision of the Trust Indenture Act which may be so modified or excluded, the latter provision shall be deemed
to apply to this First Supplemental Indenture as so modified or to be excluded, as the case may be.


 


		SECTION
                              3.3.	Governing Law.



 


This
First Supplemental Indenture and the Notes shall be governed by and construed in accordance with the laws of the State of New York
without regard to conflicts of law principles of such State other than New York General Obligations Law Section 5-1401.


 


		SECTION
                              3.4.	Multiple Counterparts.



 


The parties may sign multiple counterparts
of this First Supplemental Indenture. Each signed counterpart shall be deemed an original, but all of them together represent one
and the same First Supplemental Indenture.


 


		SECTION
                              3.5.	Severability.



 


Each provision of this First Supplemental
Indenture shall be considered separable and if for any reason any provision which is not essential to the effectuation of the basic
purpose of this First Supplemental Indenture or the Notes shall be invalid, illegal or unenforceable, the validity, legality and
enforceability of the remaining provisions shall not in any way be affected or impaired thereby and a Holder shall have no claim
therefor against any party hereto.


 


		SECTION
                              3.6.	Ratification.



 


The Indenture, as supplemented and amended
by this First Supplemental Indenture, is in all respects ratified and confirmed. The Indenture and this First Supplemental Indenture
shall be read, taken and construed as one and the same instrument. All provisions included in this First Supplemental Indenture
supersede any conflicting provisions included in the Indenture unless not permitted by law. The Trustee accepts the trusts created
by the Indenture, as supplemented by this First Supplemental Indenture, and agrees to perform the same upon the terms and conditions
of the Indenture, as supplemented by this First Supplemental Indenture.


 




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		SECTION
                              3.7.	Headings.



 


The Section headings in this First Supplemental
Indenture are for convenience only and shall not affect the construction thereof.


 


		SECTION
                              3.8.	Effectiveness.



 


The provisions of this First Supplemental
Indenture shall become effective as of the date hereof.


 


[Remainder of Page Intentionally Left
Blank]


 




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


 


	 	MAIDEN HOLDINGS, LTD.,
	 	as Issuer
	 	 	 
	 	By:	/s/ Lawrence F. Metz
	 	 	Name: Lawrence F. Metz
	 	 	Title: Executive Vice President, General
	 	 	Counsel and Secretary
	 	 	 
	 	Wilmington Trust, NATIONAL

 ASSOCIATION
	 	as Trustee
	 	 	 
	 	By:	/s/ Michael H. Wass
	 	 	Name: Michael H. Wass
	 	 	Title: Vice President


 




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EXHIBIT A


 


Form of 6.625% Note due 2046


 


[Include the following legend on each Note that is a Global
Note:


 


THIS NOTE IS A GLOBAL SECURITY WITHIN THE
MEANING OF THE INDENTURE HEREINAFTER REFERRED TO AND IS REGISTERED IN THE NAME OF THE DEPOSITARY OR A NOMINEE OF THE DEPOSITARY.
THIS NOTE IS EXCHANGEABLE FOR NOTES REGISTERED IN THE NAME OF A PERSON OTHER THAN THE DEPOSITARY OR ITS NOMINEE ONLY IN THE LIMITED
CIRCUMSTANCES DESCRIBED IN THE INDENTURE, AND MAY NOT BE TRANSFERRED EXCEPT AS A WHOLE BY THE DEPOSITARY TO A NOMINEE OF THE DEPOSITARY,
BY A NOMINEE OF THE DEPOSITARY TO THE DEPOSITARY OR ANOTHER NOMINEE OF THE DEPOSITARY OR BY THE DEPOSITARY OR ANY SUCH NOMINEE
TO A SUCCESSOR DEPOSITARY OR A NOMINEE OF SUCH A SUCCESSOR DEPOSITARY.]


 


MAIDEN HOLDINGS, LTD.


 


6.625% Note due 2046


 


	REGISTERED	PRINCIPAL AMOUNT: $110,000,000
	No. R-1	UNITS: 4,400,000
	 	 
	CUSIP:  560292 302	 


 


Maiden
Holdings, Ltd., a company duly organized and existing under the laws of Bermuda (herein called the “Company,”
which term includes any successor Person under the Indenture hereinafter referred to), for value received, hereby promises to pay
to Cede & Co., or registered assigns, the principal sum of ONE HUNDRED TEN MILLION DOLLARS ($110,000,000) on June 14, 2046
(the “Maturity Date”) (except to the extent redeemed or repaid prior to the Maturity Date) and to pay interest
thereon from June 14, 2016 (the “Original Issue Date”) or from the most recent Interest Payment Date to which
interest has been paid or duly provided for at the rate of 6.625% per annum, on the 14th day of March, June, September
and December (of each year each such date, an “Interest Payment Date”), commencing on September 14, 2016, until
the principal hereof is paid or made available for payment.


 


Payment
of Interest. The interest so payable, and punctually paid or made available for payment, on any Interest Payment Date,
will, as provided in the Indenture, be paid, in immediately available funds, to the Person in whose name this Note (or one or more
Predecessor Securities) is registered at the close of business on the 28th day of February or the 30th day
of May, August or November (whether or not a Business Day, as defined in the Indenture referred to herein), as the case may be,
next preceding such Interest Payment Date (the “Regular Record Date”). Any such interest not punctually paid
or duly provided for (“Defaulted Interest”) will forthwith cease to be payable to the Holder on such Regular
Record Date, and such Defaulted Interest may be paid to the Person in whose name this Note (or one or more Predecessor Securities)
is registered at the close of business on a special record date (the “Special Record Date”) for the payment
of such Defaulted Interest to be fixed by the Trustee, notice whereof shall be given to 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 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 said Indenture.


 




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Place
of Payment. Payment of principal, premium, if any, and interest on, and any Additional Amounts with respect to, this
Note will be made at the Corporate Trust Office of the Trustee or such other office or agency of the Company as may be designated
for such purpose, 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 each installment of interest, premium, if any, and principal
on, and any Additional Amounts with respect to, this Note may at the Company’s option be paid in immediately available funds
by wire transfer to an account maintained by the payee located in the United States.


 


Time
of Payment. In any case where any Interest Payment Date, the Maturity Date or any date fixed for redemption of the Notes
shall not be a Business Day, then (notwithstanding any other provision of the Indenture or this Note), payment of principal, premium,
if any, or interest, if any, need not be made on such date, but may be made on the next succeeding Business Day with the same force
and effect as if made on such Interest Payment Date, the Maturity Date or the date so fixed for redemption or repayment, as the
case may be, and no interest shall accrue in respect of the delay.


 


General.
This Note is one of a duly authorized issue of Securities of the Company, issued and to be issued in one or more series under an
indenture (the “Base Indenture”), dated as of June 14, 2016, between the Company and Wilmington Trust, National
Association, as trustee (herein called the “Trustee,” which term includes any successor trustee under the Indenture
with respect to the series of which this Note is a part), as supplemented by a First Supplemental Indenture thereto, dated as of
June 14, 2016 (the “First Supplemental Indenture” and, together with the Base Indenture, the “Indenture”),
between the Company and the Trustee. Reference is hereby made to the Indenture for a statement of the respective rights, limitations
of rights, duties and immunities thereunder of the Company, the Trustee and the Holders of the Securities, and of the terms upon
which the Securities are, and are to be, authenticated and delivered; provided that to the extent of any inconsistency between
the terms and provisions in the Indenture and those contained in this Note, the Indenture shall govern. This Note is one of a duly
authorized series of Securities designated as “6.625% Notes due 2046” (collectively, the “Notes”),
initially limited in aggregate principal amount to ONE HUNDRED TEN MILLION DOLLARS ($110,000,000).


 


Further
Issuance. The Company may, from time to time, without notice to, or the consent of, the Holders of the Notes, issue
and sell additional Securities (“Additional Securities”) ranking equally and ratably with the Notes in all respects
(other than the issue date, and to the extent applicable, issue price, initial date of interest accrual and initial interest payment
date of such Additional Securities), provided that such Additional Securities are fungible with the previously issued Notes
for U.S. federal income tax purposes. Any such Additional Securities shall be consolidated and form a single series with
the Notes for all purposes under the Indenture, including voting.


 




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Events
of Default. If an Event of Default with respect to the Notes shall have occurred 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.


 


Sinking
Fund. The Notes are not subject to any sinking fund.


 


Optional
Redemption. The Notes shall be redeemable, for cash, in whole or in part, on or after June 14, 2021, at the option of
the Company, at any time and from time to time, until the Maturity Date at a Redemption Price equal to 100% of the principal amount
of the Notes to be redeemed, plus (i) accrued but unpaid interest on the principal amount of Notes being redeemed to, but not including,
the Redemption Date and (ii) Additional Amounts, if any (subject to the right of Holders on the applicable Regular Record Date
to receive interest due on the applicable Interest Payment Date). In the case of any partial redemption, selection of the Notes
for redemption will be made by the Trustee by such methods, as the Trustee shall deem fair and appropriate. If any Note is to be
redeemed in part only, the notice of redemption relating to such Note shall state the portion of the principal amount thereof to
be redeemed. A new Note in principal amount equal to the unredeemed portion thereof will be issued in the name of the Holder thereof
upon cancellation of this Note.


 


Payment
of Additional Amounts. Subject to certain exceptions set forth in the First Supplemental Indenture, if any taxes, assessments
or other governmental charges are imposed by the Relevant Tax Jurisdiction in respect of any payments on the Notes, the Payor shall
pay to the Holder, to the extent the Payor may lawfully do so, such Additional Amounts as may be necessary in order that the net
amounts paid to the Holder will be not less than the amount specified herein to which such Holder is entitled.


 


Redemption
for Changes in Withholding Taxes. The Company may redeem the Notes, at its option, at any time, for cash, in whole but
not in part, upon not less than 30 nor more than 60 days’ prior written notice to Holders (with a copy to the Trustee), at
a Redemption Price equal to 100% of the principal amount thereof, plus (i) any accrued but unpaid interest to, but excluding, the
Redemption Date and (ii) Additional Amounts, if any (subject, in each case, to the right of Holders on the applicable Regular Record
Date, whether or not a business day, to receive interest due on the applicable Interest Payment Date), in the event that the Payor
has become or would become obligated to pay, on the next date on which any amount would be payable with respect to this Note, any
Additional Amounts as a result of certain changes or amendments to the laws or official positions of the Relevant Tax Jurisdiction,
as set forth in the First Supplemental Indenture, and such Payor cannot avoid such obligation by taking reasonable measures available
to it.


 


Defeasance
and Covenant Defeasance. The Indenture contains provisions for defeasance at any time of (a) the entire indebtedness
of the Company on this Note and (b) certain restrictive covenants and the related Events of Default, in each case which provisions
shall apply to this Note.


 




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Modification
and Waivers; Obligations of the Company Absolute. The Indenture permits, 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 Securities.
Such amendment may be effected under the Indenture at any time by the Company and the Trustee with the consent of the Holders of
not less than a majority in aggregate principal amount of the outstanding Notes affected thereby. The Indenture also contains provisions
permitting the Holders of not less than a majority in aggregate principal amount of the Securities at the time outstanding, on
behalf of the Holders of all outstanding Securities, to waive compliance by the Company with certain provisions of the Indenture.
Furthermore, provisions in the Indenture permit the Holders of not less than a majority in aggregate principal amount of the outstanding
Securities of individual series to waive on behalf of all of the Holders of Securities of such individual series certain past defaults
under the Indenture and their consequences. Any such consent or waiver shall be conclusive and binding upon the Holder of this
Note and upon all future Holders of this Note and of any Note issued upon the registration of transfer hereof or in exchange hereof
or in lieu hereof, whether or not notation of such consent or waiver is made upon this Note.


 


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, and any Additional Amounts with respect to, this Note at the time, place, and rate, and
in the coin or currency, herein prescribed.


 


Limitation
on Suits. As set forth in, and subject to, the provisions of the Indenture, no Holder of any Note will have any right
to institute any proceeding with respect to the Indenture or for any remedy thereunder, unless such Holder shall have previously
given to the Trustee written notice of a continuing Event of Default with respect to the Notes, the Holders of not less than 25%
in principal amount of the outstanding Notes shall have made written request, and offered reasonable indemnity, to the Trustee
to institute such proceedings as trustee, and the Trustee shall not have received from the Holders of a majority in principal amount
of the outstanding Notes a direction inconsistent with such request and shall have failed to institute such proceeding within 60
days; provided, however, that such limitations do not apply to a suit instituted by the Holder hereof for the enforcement
of payment of the principal of or interest on, and any Additional Amounts with respect to, this Note on or after the respective
due dates expressed herein.


 


Authorized
Denominations. The Notes are issuable only in registered form without coupons in minimum denominations of $25.00 and
integral multiples of $25.00 in excess thereof.


 


Registration
of Transfer or Exchange. As provided in the Indenture and subject to certain limitations herein and therein set forth,
the transfer of this Note is registrable in the register of the Notes maintained by the Registrar upon surrender of this Note for
registration of transfer, at the office or agency of the Company 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 his attorney duly authorized in writing, and thereupon one or more new Notes, of authorized
denominations and for the same aggregate principal amount, will be issued to the designated transferee or transferees.


 




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As provided in the Indenture and subject to
certain limitations herein and therein set forth, the Notes are exchangeable for a like aggregate principal amount of Notes of
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.


 


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 Holder 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.


 


Defined
Terms. All terms used in this Note, which are defined in the Indenture and are not otherwise defined herein, shall have
the meanings assigned to them in the Indenture.


 


Governing
Law. The Indenture and the Notes shall be governed by and construed in
accordance with the laws of the State of New York without regard to conflicts of law principles of such State other than New York
General Obligations Law Section 5-1401.


 


Unless the certificate of authentication hereon
has been executed by the Trustee by manual signature, this Note shall not be entitled to any benefit under the Indenture or be
valid or obligatory for any purpose.


 


[Remainder of Page
Intentionally Left Blank]


 




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IN WITNESS WHEREOF, the Company has caused
this instrument to be duly executed.


 


	Dated:  June 14, 2016	 
	 	 
	 	MAIDEN HOLDINGS, LTD.
	 	 
	 	By:	 
	 	 	Name:
	 	 	Title:
	 	 	 
	Attest:	 	 
	 	 	 
	By:	 	 	 
	 	Name:	 	 
	 	Title:	 	 


 




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TRUSTEE’S CERTIFICATE OF AUTHENTICATION


 


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


 


	 	WILMINGTON TRUST, NATIONAL 

ASSOCIATION,

as Trustee
	 	 
	 	By:	 
	 	 	 
	 	 	 
	Dated:  June 14, 2016	 	 


 




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ASSIGNMENT


 


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


 





 



 





 



 


PLEASE INSERT SOCIAL SECURITY NUMBER OR OTHER IDENTIFYING NUMBER
OF ASSIGNEE


 


	 


 





 



 





 



 


(Please print or typewrite name and address,


including postal zip code, of assignee)


 


the within Note and all rights thereunder, and hereby irrevocably
constitutes and appoints


 





 



 





 



 





 



 


to transfer said Note on the books of the Trustee, with full
power of substitution in the premises.


 


	Dated:__________________	 	 
	 	 	NOTICE:  The signature to this assignment must 
	 	 	correspond with the name as written upon the face
	 	 	of the within Note in every particular, without
	 	 	alteration or enlargement or any change whatsoever.


 


	 	 
	Signature Guarantee	 


 




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