Exhibit 4.4


                                    EXHIBIT A

      FIXED/FLOATING RATE JUNIOR SUBORDINATED DEFERRABLE INTEREST DEBENTURE

                               [FACE OF SECURITY]

        THIS SECURITY HAS NOT BEEN REGISTERED  UNDER THE SECURITIES ACT OF 1933,
AS  AMENDED  (THE  "SECURITIES  ACT"),  ANY STATE  SECURITIES  LAWS OR ANY OTHER
APPLICABLE   SECURITIES   LAW.   NEITHER  THIS  SECURITY  NOR  ANY  INTEREST  OR
PARTICIPATION  HEREIN MAY BE REOFFERED,  SOLD, ASSIGNED,  TRANSFERRED,  PLEDGED,
ENCUMBERED  OR  OTHERWISE  DISPOSED  OF IN THE ABSENCE OF SUCH  REGISTRATION  OR
UNLESS SUCH  TRANSACTION  IS EXEMPT  FROM,  OR NOT SUBJECT TO, THE  REGISTRATION
REQUIREMENTS OF THE SECURITIES ACT AND ANY APPLICABLE STATE SECURITIES LAWS. THE
HOLDER OF THIS  SECURITY  BY ITS  ACCEPTANCE  HEREOF  AGREES  TO OFFER,  SELL OR
OTHERWISE TRANSFER THIS SECURITY ONLY (A) TO CASTLEPOINT BERMUDA HOLDINGS,  LTD.
(THE "COMPANY"), (B) PURSUANT TO A REGISTRATION STATEMENT THAT HAS BEEN DECLARED
EFFECTIVE UNDER THE SECURITIES  ACT, (C) TO A PERSON WHOM THE SELLER  REASONABLY
BELIEVES  IS A  QUALIFIED  INSTITUTIONAL  BUYER  IN A  TRANSACTION  MEETING  THE
REQUIREMENTS  OF RULE  144A SO LONG AS THIS  SECURITY  IS  ELIGIBLE  FOR  RESALE
PURSUANT TO RULE 144A IN ACCORDANCE WITH RULE 144A, (D) TO A NON-U.S.  PERSON IN
AN OFFSHORE  TRANSACTION IN ACCORDANCE WITH RULE 903 OR RULE 904 (AS APPLICABLE)
OF REGULATION S UNDER THE SECURITIES  ACT, (E) TO AN  INSTITUTIONAL  "ACCREDITED
INVESTOR"  WITHIN  THE  MEANING  OF  SUBPARAGRAPH  (A) OF  RULE  501  UNDER  THE
SECURITIES ACT THAT IS ACQUIRING  THIS SECURITY FOR ITS OWN ACCOUNT,  OR FOR THE
ACCOUNT OF SUCH AN INSTITUTIONAL  ACCREDITED  INVESTOR,  FOR INVESTMENT PURPOSES
AND  NOT  WITH A  VIEW  TO,  OR FOR  OFFER  OR  SALE  IN  CONNECTION  WITH,  ANY
DISTRIBUTION  IN VIOLATION OF THE  SECURITIES  ACT, OR (F) PURSUANT TO ANY OTHER
AVAILABLE  EXEMPTION FROM THE  REGISTRATION  REQUIREMENTS OF THE SECURITIES ACT,
SUBJECT TO THE  COMPANY'S  RIGHT  PRIOR TO ANY SUCH  OFFER,  SALE OR TRANSFER TO
REQUIRE  THE  DELIVERY  OF AN OPINION OF  COUNSEL,  CERTIFICATION  AND/OR  OTHER
INFORMATION SATISFACTORY TO IT IN ACCORDANCE WITH THE INDENTURE, A COPY OF WHICH
MAY BE OBTAINED FROM THE COMPANY.  HEDGING TRANSACTIONS  INVOLVING THIS SECURITY
MAY NOT BE CONDUCTED UNLESS IN COMPLIANCE WITH THE SECURITIES ACT.

        HEDGING TRANSACTIONS INVOLVING THIS SECURITY MAY NOT BE CONDUCTED UNLESS
IN COMPLIANCE WITH THE SECURITIES ACT.

        THE  HOLDER OF THIS  SECURITY  BY ITS  ACCEPTANCE  HEREOF  ALSO  AGREES,
REPRESENTS  AND  WARRANTS  THAT  IT  IS  NOT  AN  EMPLOYEE  BENEFIT,  INDIVIDUAL
RETIREMENT  ACCOUNT  OR  OTHER  PLAN OR  ARRANGEMENT  SUBJECT  TO TITLE I OF THE
EMPLOYEE  RETIREMENT  INCOME  SECURITY  ACT OF

<PAGE>


1974,  AS AMENDED  ("ERISA"),  OR SECTION 4975 OF THE  INTERNAL  REVENUE CODE OF
1986,  AS AMENDED (THE "CODE")  (EACH A "PLAN"),  OR AN ENTITY WHOSE  UNDERLYING
ASSETS  INCLUDE "PLAN ASSETS" BY REASON OF ANY PLAN'S  INVESTMENT IN THE ENTITY,
AND NO PERSON  INVESTING  "PLAN  ASSETS"  OF ANY PLAN MAY  ACQUIRE  OR HOLD THIS
SECURITY OR ANY INTEREST  THEREIN,  UNLESS SUCH  PURCHASER OR HOLDER IS ELIGIBLE
FOR  EXEMPTIVE  RELIEF  AVAILABLE  UNDER  U.S.  DEPARTMENT  OF LABOR  PROHIBITED
TRANSACTION  CLASS  EXEMPTION  96-23,  95-60,  91-38,  90-1 OR 84-14 OR  ANOTHER
APPLICABLE  EXEMPTION  OR ITS  PURCHASE  AND  HOLDING  OF THIS  SECURITY  IS NOT
PROHIBITED  BY SECTION 406 OF ERISA OR SECTION  4975 OF THE CODE WITH RESPECT TO
SUCH  PURCHASE  OR  HOLDING.  ANY  PURCHASER  OR HOLDER OF THIS  SECURITY OR ANY
INTEREST  THEREIN WILL BE DEEMED TO HAVE REPRESENTED BY ITS PURCHASE AND HOLDING
THEREOF THAT EITHER (i) IT IS NOT AN EMPLOYEE BENEFIT PLAN WITHIN THE MEANING OF
SECTION  3(3)  OF  ERISA,  OR A PLAN  TO  WHICH  SECTION  4975  OF THE  CODE  IS
APPLICABLE,  A TRUSTEE OR OTHER PERSON  ACTING ON BEHALF OF AN EMPLOYEE  BENEFIT
PLAN OR PLAN,  OR ANY OTHER  PERSON OR ENTITY  USING THE ASSETS OF ANY  EMPLOYEE
BENEFIT PLAN OR PLAN TO FINANCE SUCH  PURCHASE,  OR (ii) SUCH  PURCHASE WILL NOT
RESULT IN A PROHIBITED TRANSACTION UNDER SECTION 406 OF ERISA OR SECTION 4975 OF
THE CODE FOR WHICH THERE IS NO APPLICABLE STATUTORY OR ADMINISTRATIVE EXEMPTION.

        THIS  SECURITY  WILL BE  ISSUED  AND MAY BE  TRANSFERRED  ONLY IN BLOCKS
HAVING AN AGGREGATE  PRINCIPAL AMOUNT OF NOT LESS THAN $100,000.00 AND MULTIPLES
OF $1,000.00 IN EXCESS  THEREOF.  ANY  ATTEMPTED  TRANSFER OF THIS SECURITY IN A
BLOCK HAVING AN AGGREGATE  PRINCIPAL  AMOUNT OF LESS THAN  $100,000.00  SHALL BE
DEEMED TO BE VOID AND OF NO LEGAL EFFECT WHATSOEVER.

        THE  HOLDER  OF  THIS  SECURITY  AGREES  THAT IT WILL  COMPLY  WITH  THE
FOREGOING RESTRICTIONS.

        THIS  SECURITY  IS IN  REGISTERED  FORM  WITHIN THE  MEANING OF TREASURY
REGULATIONS  SECTION  1.871-14(c)(1)(i)  FOR U.S. FEDERAL INCOME AND WITHHOLDING
TAX PURPOSES.

        IN  CONNECTION  WITH  ANY  TRANSFER,  THE  HOLDER  WILL  DELIVER  TO THE
REGISTRAR AND TRANSFER AGENT SUCH  CERTIFICATES AND OTHER  INFORMATION AS MAY BE
REQUIRED  BY THE  INDENTURE  TO  CONFIRM  THAT THE  TRANSFER  COMPLIES  WITH THE
FOREGOING RESTRICTIONS.


                                      - 2 -
<PAGE>



      Fixed/Floating Rate Junior Subordinated Deferrable Interest Debenture

                                       of

                       CastlePoint Bermuda Holdings, Ltd.

                               September 27, 2007

        CastlePoint  Bermuda  Holdings,  Ltd., a company  limited by shares duly
organized  and  existing  under the laws of Bermuda (the  "Company,"  which term
includes any successor Person under the Indenture  hereinafter referred to), for
value  received  promises  to  pay  to  Wilmington  Trust  Company,  not  in its
individual capacity but solely as Institutional  Trustee for CastlePoint Bermuda
Holdings Statutory Trust I (the "Holder") or registered  assigns,  the principal
sum of Thirty Million Nine Hundred Twenty Eight Thousand  dollars  ($30,928,000)
on December 15, 2037,  and to pay interest on said  principal sum from September
27, 2007, or from the most recent  Interest  Payment Date (as defined herein) to
which  interest  has been  paid or duly  provided  for,  quarterly  (subject  to
deferral as set forth herein) in arrears on March 15, June 15,  September 15 and
December  15 of each year or if such day is not a  Business  Day,  then the next
succeeding  Business Day (each such date, an "Interest Payment Date") commencing
on the Interest  Payment Date in December 2007, at an annual rate equal to 8.39%
beginning on (and  including)  the date of original  issuance and ending on (but
excluding) the Interest  Payment Date in December 2012 and at an annual rate for
each successive  Distribution  Period  beginning on (and including) the Interest
Payment Date in December 2012, and each  succeeding  Interest  Payment Date, and
ending on (but  excluding)  the next  succeeding  Interest  Payment Date (each a
"Distribution  Period"),  equal to 3-Month LIBOR, determined as described below,
plus 3.50% (the "Coupon Rate");  applied to the principal  amount hereof,  until
the principal hereof is paid or duly provided for or made available for payment,
and on any overdue  principal  and (without  duplication  and to the extent that
payment of such interest is  enforceable  under  applicable  law) on any overdue
installment of interest (including  Additional Interest) at the Interest Rate in
effect for each applicable  period,  compounded  quarterly,  from the dates such
amounts are due until they are paid or made available for payment. The amount of
interest payable (i) for any Distribution Period commencing on or after the date
of original  issuance but before the Interest Payment Date in December 2012 will
be computed on the basis of a 360-day  year of twelve  30-day  months,  it being
understood that no additional interest shall accrue on non-Business Days for the
given Distribution Period, and (ii) for the Distribution Period commencing on or
after  the  Interest   Payment  Date  in  December  2012  and  each   succeeding
Distribution  Period will be computed on the basis of the actual  number of days
in the Distribution Period concerned divided by 360. The interest installment 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
Debenture (or one or more Predecessor  Securities) is registered at the close of
business on the regular record date for such interest  installment,  which shall
be fifteen  days prior to the day on which the  relevant  Interest  Payment Date
occurs.  Any such interest  installment  not so punctually paid or duly provided
for shall  forthwith  cease to be payable to the Holder on such  regular  record
date and may be paid to the Person in whose name this  Debenture (or one or more
Predecessor  Securities)  is  registered  at the close of  business on a special
record date.

                                      - 3 -
<PAGE>


        Capitalized  terms used and not defined in this Debenture shall have the
meanings  assigned in the Indenture dated as of the date of original issuance of
this Debenture between the Trustee and the Company.

        "3-Month  LIBOR" as used  herein,  means the  London  interbank  offered
interest rate for three-month U.S. dollar deposits  determined by the Trustee in
the following  order of priority:  (i) the rate  (expressed as a percentage  per
annum) for U.S. dollar  deposits  having a three-month  maturity that appears on
the Reuters  Screen  LIBOR01 Page as of 11:00 a.m.  (London time) on the related
Determination  Date ("Reuters Screen LIBOR01 Page" means the display  designated
as the  "Reuters  Screen  LIBOR01  Page" or such other page as may  replace  the
Reuters Screen LIBOR01 Page on that service or such other service or services as
may be nominated by the British Bankers'  Association as the information  vendor
for the purpose of displaying  London  interbank  offered rates for U.S.  dollar
deposits);  (ii) if such rate cannot be identified on the related  Determination
Date,  the Trustee will  request the  principal  London  offices of four leading
banks in the London interbank  market to provide such banks' offered  quotations
(expressed  as  percentages  per annum) to prime  banks in the London  interbank
market for U.S. dollar  deposits having a three-month  maturity as of 11:00 a.m.
(London  time) on such  Determination  Date.  If at  least  two  quotations  are
provided, 3-Month LIBOR will be the arithmetic mean of such quotations; (iii) if
fewer than two such  quotations  are provided as requested in clause (ii) above,
the Trustee  will  request four major New York City banks to provide such banks'
offered  quotations  (expressed as  percentages  per annum) to leading  European
banks  for  loans  in U.S.  dollars  as of  11:00  a.m.  (London  time)  on such
Determination Date. If at least two such quotations are provided,  3-Month LIBOR
will be the arithmetic mean of such quotations;  and (iv) if fewer than two such
quotations  are provided as requested in clause (iii) above,  3-Month LIBOR will
be  a  3-Month  LIBOR  determined  with  respect  to  the  Distribution   Period
immediately  preceding such current  Distribution  Period.  If the rate for U.S.
dollar  deposits  having a three-month  maturity that  initially  appears on the
Reuters  Screen  LIBOR01  Page as of 11:00  a.m.  (London  time) on the  related
Determination  Date  is  superseded  on the  Reuters  Screen  LIBOR01  Page by a
corrected rate by 12:00 noon (London time) on such Determination  Date, then the
corrected rate as so  substituted on the applicable  page will be the applicable
3-Month LIBOR for such Determination Date. As used herein,  "Determination Date"
means the date that is two London  Banking  Days (i.e.,  a business day in which
dealings in deposits in U.S.  dollars  are  transacted  in the London  interbank
market) preceding the commencement of the relevant Distribution Period.

        "Interest  Rate" means for the period  beginning on (and  including) the
date of original  issuance and ending on (but  excluding)  the Interest  Payment
Date in  December  2012 the rate per  annum of 8.39%  and for each  Distribution
Period thereafter, the Coupon Rate.

        The Interest Rate for any Distribution  Period will at no time be higher
than the maximum rate then permitted by New York law as the same may be modified
by United States law.

        All percentages  resulting from any  calculations on the Debentures will
be rounded, if necessary,  to the nearest one hundred-thousandth of a percentage
point,  with five  one-millionths  of a percentage  point rounded  upward (e.g.,
9.876545% (or .09876545) being rounded to 9.87655% (or .0987655), and all dollar
amounts  used in or  resulting  from such  calculation  will be  rounded  to the
nearest cent (with one-half cent being rounded upward)).

                                      - 4 -
<PAGE>


        The principal of and interest on this Debenture  shall be payable at the
office or agency of the Trustee (or other paying agent appointed by the Company)
maintained  for that  purpose in any coin or  currency  of the United  States of
America  that at the time of payment is legal  tender for  payment of public and
private debts; provided,  however, that payment of interest may be made by check
mailed to the registered holder at such address as shall appear in the Debenture
Register if a request for a wire  transfer by such holder has not been  received
by the Company or by wire transfer to an account appropriately designated by the
holder  hereof.  Notwithstanding  the  foregoing,  so long as the holder of this
Debenture  is the  Institutional  Trustee,  the payment of the  principal of and
interest on this Debenture will be made in immediately  available  funds at such
place and to such account as may be designated by the Trustee.

        So long as (i) no Event of Default has  occurred and is  continuing  and
(ii) a parent guarantee agreement between CastlePoint Holdings,  Ltd., a Bermuda
exempted company and the parent of the Company, and Wilmington Trust Company, as
Guarantee  Trustee,  is in full force and  effect,  in the form  attached to the
Indenture (the "Parent Guarantee"),  the Company shall have the right, from time
to time, and without causing an Event of Default,  to defer payments of interest
on the Debentures by extending the interest  payment period on the Debentures at
any time and from time to time during the term of the  Debentures,  for up to 20
consecutive  quarterly  periods (each such extended  interest payment period, an
"Extension  Period"),  during  which  Extension  Period no  interest  (including
Additional  Interest)  shall be due and payable (except any Additional Sums that
may be due and payable);  provided, however, that the Company shall not have the
right to defer  payments of interest on the Debentures at any time if the Parent
Guarantee  is not in full force and effect by November 15, 2007 or if the Parent
Guarantee Opinion, as defined in Section 3.1 of the Placement Agreement,  is not
delivered to the Placement Agents as contemplated  therein.  No Extension Period
may end on a date other  than an  Interest  Payment  Date.  During an  Extension
Period, interest will continue to accrue on the Debentures, and interest on such
accrued  interest  will accrue at an annual rate equal to the  Interest  Rate in
effect  for such  Extension  Period,  compounded  quarterly  from the date  such
interest  would have been payable were it not for the Extension  Period,  to the
extent  permitted  by law (such  interest  referred  to  herein  as  "Additional
Interest").  At the end of any such  Extension  Period the Company shall pay all
interest then accrued and unpaid on the  Debentures  (together  with  Additional
Interest thereon); provided, however, that no Extension Period may extend beyond
the Maturity Date;  provided  further,  however,  that during any such Extension
Period,  the Company shall not and shall not permit any Affiliate of the Company
controlled  by the Company to engage in any of the  activities  or  transactions
described  on  the  reverse  side  hereof  and in the  Indenture.  Prior  to the
termination of any Extension Period, the Company may further extend such period,
provided  that  such  period   together  with  all  such  previous  and  further
consecutive  extensions  thereof  shall  not  exceed  20  consecutive  quarterly
periods,  or extend  beyond  the  Maturity  Date.  Upon the  termination  of any
Extension  Period and upon the payment of all accrued  and unpaid  interest  and
Additional Interest, the Company may commence a new Extension Period, subject to
the foregoing requirements.  No interest or Additional Interest shall be due and
payable  during  an  Extension  Period,  except  at the end  thereof,  but  each
installment of interest that would otherwise have been due and payable during an
Extension  Period  shall bear  Additional  Interest to the extent  permitted  by
applicable  law.  The Company  must give the Trustee  notice of its  election to
begin or  extend  an  Extension  Period at least 5  Business  Days  prior to the
regular  record  date (as such  term is used in  Section  2.8 of the  Indenture)
immediately  preceding the Interest  Payment Date with respect to which interest
on the  Debentures  would have

                                      - 5 -
<PAGE>


been payable except for the election to begin or extend an Extension Period. The
Trustee  shall give notice of the  Company's  election to begin a new  Extension
Period to the holders of the Debentures.

        The indebtedness  evidenced by this Debenture is, to the extent provided
in the  Indenture,  subordinate  and  junior  in right of  payment  to the prior
payment in full of all Senior Indebtedness, and this Debenture is issued subject
to the  provisions of the Indenture  with respect  thereto.  Each holder of this
Debenture,  by  accepting  the  same,  (a)  agrees to and shall be bound by such
provisions,  (b) authorizes and directs the Trustee on his or her behalf to take
such action as may be necessary or  appropriate to acknowledge or effectuate the
subordination   so   provided   and  (c)   appoints   the  Trustee  his  or  her
attorney-in-fact  for any and all such purposes.  Each holder hereof,  by his or
her  acceptance  hereof,  hereby  waives  all  notice of the  acceptance  of the
subordination provisions contained herein and in the Indenture by each holder of
Senior Indebtedness,  whether now outstanding or hereafter incurred,  and waives
reliance by each such holder upon said provisions.

        This Debenture  shall not be entitled to any benefit under the Indenture
hereinafter referred to, be valid or become obligatory for any purpose until the
certificate of  authentication  hereon shall have been signed by or on behalf of
the Trustee.

        The  provisions  of this  Debenture  are  continued  on the reverse side
hereof and such provisions shall for all purposes have the same effect as though
fully set forth at this place.


                                      - 6 -
<PAGE>



         IN WITNESS WHEREOF, the Company has duly executed this certificate.

                                            CASTLEPOINT BERMUDA HOLDINGS, LTD.

                                            By:
                                               ---------------------------------
                                               Name:
                                               Title:


                          CERTIFICATE OF AUTHENTICATION
                          -----------------------------

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

                                            WILMINGTON TRUST COMPANY, as Trustee

                                            By:
                                               ---------------------------------
                                               Authorized Officer






                                      - 7 -
<PAGE>



                             [REVERSE OF DEBENTURE]

        This  Debenture is one of the  fixed/floating  rate junior  subordinated
deferrable interest debentures of the Company,  all issued or to be issued under
and pursuant to the Indenture dated as of September 27, 2007 (the  "Indenture"),
duly  executed  and  delivered  between the Company  and the  Trustee,  to which
Indenture reference is hereby made for a description of the rights,  limitations
of rights,  obligations,  duties and immunities  thereunder of the Trustee,  the
Company  and the  holders  of the  Debentures.  The  Debentures  are  limited in
aggregate principal amount as specified in the Indenture.

        Upon the  occurrence  and  continuation  of a Special Event prior to the
Interest  Payment  Date in December  2012,  the Company  shall have the right to
redeem the Debentures in whole,  but not in part, at any Interest  Payment Date,
within 120 days following the  occurrence of such Special Event,  at the Special
Redemption Price.

        In addition,  the Company shall have the right to redeem the Debentures,
in whole or in  part,  but in all  cases in a  principal  amount  with  integral
multiples of  $1,000.00,  on any Interest  Payment Date on or after the Interest
Payment Date in December 2012, at the Optional Redemption Price.

        Prior to 10:00 a.m. New York City time on the Optional  Redemption  Date
or Special  Redemption  Date, as  applicable,  the Company will deposit with the
Trustee  or with one or more  paying  agents an amount  of money  sufficient  to
redeem on the  Optional  Redemption  Date or the  Special  Redemption  Date,  as
applicable,  all the  Debentures  so called for  redemption  at the  appropriate
Optional Redemption Price or Special Redemption Price.

        If all, or less than all, the Debentures are to be redeemed, the Company
will give the Trustee notice not less than 45 nor more than 60 days prior to the
Optional  Redemption Date or Special  Redemption Date, as applicable,  as to the
aggregate  principal  amount of  Debentures to be redeemed and the Trustee shall
select,  in such manner as in its sole discretion it shall deem  appropriate and
fair, the Debentures or portions thereof (in integral multiples of $1,000.00) to
be redeemed.

        Notwithstanding  the  foregoing,  any  redemption  of  Debentures by the
Company  shall be subject  to the  receipt  of any and all  required  regulatory
approvals.

        In case an Event of Default shall have occurred and be continuing,  upon
demand of the Trustee,  the principal of all of the Debentures  shall become due
and  payable  in the  manner,  with the effect  and  subject  to the  conditions
provided in the Indenture.

        The  Indenture  contains  provisions  permitting  the  Company  and  the
Trustee,  with the  consent  of the  holders  of not  less  than a  majority  in
aggregate principal amount of the Debentures at the time outstanding, to execute
supplemental  indentures for the purpose of adding any provisions to or changing
in any manner or  eliminating  any of the provisions of this Indenture or of any
supplemental  indenture  or of modifying in any manner the rights of the holders
of the Debentures;  provided, however, that no such supplemental indenture shall
without  the  consent of the  holders of each  Debenture  then  outstanding  and
affected  thereby (i) change the fixed maturity of any Debenture,  or reduce the
principal  amount thereof or any premium  thereon,  or reduce the rate or extend
the time of  payment  of  interest  thereon,


                                      - 8 -
<PAGE>


or reduce any amount payable on redemption thereof or make the principal thereof
or any interest or premium  thereon  payable in any coin or currency  other than
that  provided  in  the  Debentures,  or  impair  or  affect  the  right  of any
Securityholder  to  institute  suit for  payment  thereof or impair the right of
repayment,  if any,  at the option of the holder,  or (ii) reduce the  aforesaid
percentage  of  Debentures  the holders of which are  required to consent to any
such supplemental indenture.

        The  Indenture  also  contains  provisions  permitting  the holders of a
majority in aggregate principal amount of the Debentures at the time outstanding
on behalf of the  holders  of all of the  Debentures  to waive  (or  modify  any
previously  granted  waiver of) any past  default or Event of  Default,  and its
consequences,  except an Event of Default (a)  specified in Sections  5.1(a) and
(b), (b) in respect of covenants or provisions  hereof or of the Indenture which
cannot  be  modified  or  amended  without  the  consent  of the  holder of each
Debenture affected,  or (c) in respect of the covenants contained in Section 3.9
of the  Indenture;  provided,  however,  that if the  Debentures are held by the
Trust or a trustee of the Trust,  such  waiver or  modification  to such  waiver
shall not be effective until the holders of a majority in Liquidation  Amount of
the Trust Securities shall have consented to such waiver or modification to such
waiver, provided, further, that if the consent of the holder of each outstanding
Debenture is required,  such waiver shall not be effective  until each holder of
the Trust Securities shall have consented to such waiver.  Upon any such waiver,
the default  covered thereby shall be deemed to be cured for all purposes of the
Indenture and the Company,  the Trustee and the holders of the Debentures  shall
be restored to their former positions and rights hereunder, respectively; but no
such waiver shall extend to any  subsequent or other default or Event of Default
or impair any right consequent thereon. Whenever any default or Event of Default
hereunder shall have been waived as permitted by the Indenture,  said default or
Event of Default shall for all purposes of the  Debentures  and the Indenture be
deemed to have been cured and to be not continuing.

        No reference  herein to the Indenture and no provision of this Debenture
or of the Indenture  shall alter or impair the obligation of the Company,  which
is absolute and unconditional,  to pay the principal of and premium, if any, and
interest, including Additional Interest, on this Debenture at the time and place
and at the rate and in the money herein prescribed.

        The Company has agreed that if Debentures  are  initially  issued to the
Trust or a  trustee  of such  Trust in  connection  with the  issuance  of Trust
Securities by the Trust (regardless of whether Debentures continue to be held by
such  Trust) and (i) there shall have  occurred  and be  continuing  an Event of
Default,  (ii) the dollar amount of the Company's  and the  Subsidiaries'  gross
written premiums on a consolidated basis from insurance policies in any calendar
year fails to exceed 51% of the  Company's and the  Subsidiaries'  gross written
premiums  on a  consolidated  basis  from  insurance  policies  in the  previous
calendar  year;  (iii) the  Company  sells  more than 51% of its rights to renew
insurance policies in any single transaction or series of related  transactions;
(iv) any Significant Subsidiary (as defined in Section 1-02(w) of Regulation S-X
to the Securities Act (the "Significant  Subsidiaries")) of the Company which is
rated by A.M.  Best  Company,  Inc. (x) receives a rating from A.M. Best Company
Inc. of B- or lower; or (y) submits a request to withdraw its rating by A.M Best
Company,  Inc.;  (v) the Company shall be in default with respect to its payment
of any obligations under the Capital Securities  Guarantee,  or (vi) the Company
shall have given  notice of its  election  to defer  payments of interest on the
Debentures

                                      - 9 -
<PAGE>


by extending the interest  payment period as provided  herein and such Extension
Period, or any extension  thereof,  shall be continuing,  then the Company shall
not, and shall not permit any Affiliate of the Company controlled by the Company
to, (x) declare or pay any dividends or distributions  on, or redeem,  purchase,
acquire,  or make a liquidation payment with respect to, any of the Company's or
such   Affiliates'   Capital   Stock  (other  than   payments  of  dividends  or
distributions  to the Company or a Subsidiary of the Company)  (the  "Restricted
Payments") or make any payments  with respect to the  Restricted  Payments,  (y)
make any payment of  principal  of or interest or premium,  if any, on or repay,
repurchase or redeem any debt  securities of the Company or any Affiliate of the
Company  controlled  by the Company that rank pari passu in all respects with or
junior in interest  to the  Debentures  or (z) enter  into,  amend or modify any
contract with a shareholder  holding more than 10% of the outstanding  shares of
common  stock of the  Company,  unless  such  contract  contains  terms that are
substantially  at least as  favorable  to the  Company or any  Affiliate  of the
Company controlled by the Company or CastlePoint  Holdings,  Ltd. as would be an
unrelated third party  transaction  (other than, with respect to clauses (x) and
(y) above,  (1)  repurchases,  redemptions  or other  acquisitions  of shares of
Capital Stock of the Company or any Subsidiary of the Company in connection with
any employment  contract,  benefit plan or other similar arrangement with or for
the benefit of one or more employees,  officers,  directors or  consultants,  in
connection with a dividend reinvestment or stockholder stock purchase plan or in
connection  with  the  issuance  of  Capital  Stock  of the  Company  or of such
Subsidiary  (or  securities  convertible  into or  exercisable  for such Capital
Stock) as consideration in an acquisition  transaction entered into prior to the
applicable Extension Period, (2) as a result of any exchange,  reclassification,
or  conversion  of any class or series of the  Company's  Capital  Stock (or any
Capital  Stock of a  Subsidiary  of the  Company) for any class or series of the
Company's  Capital  Stock (or in the case of a Subsidiary  of the  Company,  any
class or series of such Subsidiary's Capital Stock) or of any class or series of
the  Company's  indebtedness  for any class or series of the  Company's  Capital
Stock (or in the case of  indebtedness  of a Subsidiary  of the Company,  of any
class or series of such Subsidiary's indebtedness or any class or series of such
Subsidiary's  Capital Stock), (3) the purchase of fractional interests in shares
of the  Company's  Capital  Stock (or the Capital  Stock of a Subsidiary  of the
Company) pursuant to the conversion or exchange provisions of such Capital Stock
or the security being converted or exchanged,  (4) any declaration of a dividend
in  connection  with any  stockholders'  rights plan, or the issuance of rights,
stock or other property under any  stockholders'  rights plan, or the redemption
or repurchase of rights pursuant thereto, (5) any dividend in the form of stock,
warrants, options or other rights where the dividend stock or the stock issuable
upon  exercise of such  warrants,  options or other  rights is the same stock as
that on which the  dividend  is being paid or ranks pari passu with or junior to
such  stock  and any  cash  payments  in lieu of  fractional  shares  issued  in
connection therewith, or (6) payments under the Capital Securities Guarantee).

        The  Debentures  are  issuable  only in  registered,  certificated  form
without coupons and in minimum  denominations of $100,000.00 and any multiple of
$1,000.00 in excess  thereof.  As provided in the  Indenture  and subject to the
transfer  restrictions  and  limitations as may be contained  herein and therein
from time to time,  this Debenture is  transferable  by the holder hereof on the
Debenture  Register of the Company.  Upon due  presentment  for  registration of
transfer  of any  Debenture  at the  Principal  Office of the  Trustee or at any
office or agency of the  Company  maintained  for such  purpose as  provided  in
Section 3.2 of the  Indenture,  the Company  shall  execute,  the Company or the
Trustee  shall  register  and the  Trustee  or the  Authenticating

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<PAGE>


Agent shall  authenticate  and make  available  for  delivery in the name of the
transferee or transferees a new Debenture for a like aggregate principal amount.
All Debentures presented for registration of transfer or for exchange or payment
shall (if so required by the Company or the Trustee or the Authenticating Agent)
be duly endorsed by, or be accompanied by a written instrument or instruments of
transfer  in  form   satisfactory  to,  the  Company  and  the  Trustee  or  the
Authenticating Agent duly executed by the holder or his attorney duly authorized
in writing.  No service charge shall be made for any exchange or registration of
transfer of Debentures,  but the Company or the Trustee may require payment of a
sum  sufficient to cover any tax, fee or other  governmental  charge that may be
imposed in connection therewith.

        Prior to due presentment for  registration of transfer of any Debenture,
the Company,  the Trustee,  any  Authenticating  Agent,  any paying  agent,  any
transfer  agent and any  Debenture  registrar  may deem the Person in whose name
such Debenture  shall be registered  upon the Debenture  Register to be, and may
treat  him as,  the  absolute  owner  of such  Debenture  (whether  or not  such
Debenture  shall be  overdue)  for the  purpose  of  receiving  payment of or on
account of the principal of, premium, if any, and interest on such Debenture and
for all  other  purposes;  and  neither  the  Company  nor the  Trustee  nor any
Authenticating  Agent  nor any  paying  agent  nor any  transfer  agent  nor any
Debenture  registrar  shall be affected by any notice to the contrary.  All such
payments  so made to any holder  for the time  being or upon his order  shall be
valid,  and, to the extent of the sum or sums so paid,  effectual to satisfy and
discharge the liability for moneys payable upon any such Debenture.

        The  Debentures  are in  registered  form within the meaning of Treasury
Regulations  Section  1.871-14(c)(1)(i)  for U.S. federal income and withholding
tax purposes.

        No recourse for the payment of the  principal of or premium,  if any, or
interest  on any  Debenture,  or for any claim  based  thereon or  otherwise  in
respect  thereof,  and no  recourse  under or upon any  obligation,  covenant or
agreement of the Company in the Indenture or in any supplemental  indenture,  or
in  any  such  Debenture,  or  because  of  the  creation  of  any  indebtedness
represented  thereby,  shall  be  had  against  any  incorporator,  stockholder,
employee,  officer or director, as such, past, present or future, of the Company
or of any  successor  Person of the  Company,  either  directly  or through  the
Company  or any  successor  Person  of the  Company,  whether  by  virtue of any
constitution, statute or rule of law, or by the enforcement of any assessment or
penalty or otherwise,  it being expressly  understood that all such liability is
hereby  expressly  waived and released as a condition of, and as a consideration
for, the execution of the Indenture and the issue of the Debentures.

PURSUANT TO SECTION  5-1401 OF THE GENERAL  OBLIGATIONS  LAW OF THE STATE OF NEW
YORK,  THE  INDENTURE AND THIS  DEBENTURE  SHALL BE GOVERNED BY AND CONSTRUED IN
ACCORDANCE  WITH  THE  LAWS OF THE  STATE  OF NEW  YORK  WITHOUT  REGARD  TO ITS
CONFLICTS OF LAWS PROVISIONS.


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