Document:

<PAGE>

                                                                     Exhibit 4.5

                                    EXHIBIT B

                        ASPECT COMMUNICATIONS CORPORATION

              AMENDMENT NO. 3 TO PREFERRED SHARES RIGHTS AGREEMENT

      This Amendment No. 3 to Preferred Shares Rights Agreement (this
"Amendment") is effective as of --, 2004 and amends the Preferred Shares Rights
Agreement dated as of May 11, 1999, as amended on December 12, 2001 and November
14, 2002 (the "Rights Agreement") by and between Aspect Communications
Corporation , a California corporation (the "Company"), and Equiserve Trust
Company, N.A. as "Rights Agent" (successor to original rights agent, BankBoston,
N.A.).

                                    RECITALS

      A.    The Board of Directors of the Company has determined that it is in
the best interests of the Company and its shareholders to (i) request that Vista
Equity Fund II, L.P. (the "Investor") convert 50,000 shares of Series B
Convertible Preferred Stock, par value $0.01 per share, of the Company (the
"Conversion") into an aggregate of 22,222,222 shares of Common Stock, par value
$0.01 per share, of the Company pursuant to the Certificate of Determination of
Rights, Preferences and Privileges of Series B Convertible Preferred Stock,
dated as of January 21, 2003, (ii) agree that in connection with the Conversion,
the Company shall execute, deliver and perform certain obligations pursuant to a
Conversion Agreement (the "Conversion Agreement"), dated as of February 13,
2004, among the Company, the Investor and Vista Equity Partners, LLC ("Vista
VEP"), and (iii) agree that in connection with the Conversion, the Company shall
issue 200,000 shares (the "VEP Shares") of Common Stock to Vista VEP or its
permitted assigns pursuant to the Conversion Agreement.

      B.    Pursuant to the Conversion Agreement, the Company is obligated to
amend the Rights Agreement in certain respects.

      C.    In accordance with Section 27 of the Rights Agreement, the Company
has the power to supplement or amend the Rights Agreement in any respect without
the approval of the Rights Agent or any holders of "Rights" prior to the
"Distribution Date" (as such terms are defined in the Rights Agreement).

      D.    As of the date of this Amendment, the Distribution Date has not
occurred.

                                    AMENDMENT

        In consideration of the foregoing, the parties agree as follows:

      1.    Amendment to Rights Agreement. The second paragraph of the
definition of "Acquiring Person" set forth in Section 1(a) of the Rights
Agreement is hereby amended and restated in its entirety to read as follows:
<PAGE>
            Furthermore, notwithstanding the foregoing paragraph, the term
"Acquiring Person" shall not be deemed to include either Vista Equity Fund II,
L.P. ("Vista"), Vista Equity Partners, LLC ("VEP") or their respective
Associates and Affiliates (collectively, the "Vista Entities") so long as the
Vista Entities collectively shall be the Beneficial Owners of no more than 34.9%
of the Common Shares then outstanding. In addition to the foregoing, none of the
Vista Entities shall be deemed to be an Acquiring Person as the result of an
acquisition of Common Shares by the Company which, by reducing the number of
shares outstanding, increases the proportionate number of shares beneficially
owned by the Vista Entities to 34.9% or more of the Common Shares of the Company
then outstanding; provided, however, that if the Vista Entities shall
collectively become the Beneficial Owners of 34.9% or more of the Common Shares
of the Company then outstanding by reason of share purchases by the Company and
shall, after such share purchases by the Company collectively become the
Beneficial Owners of any additional Common Shares of the Company (other than
pursuant to a dividend or distribution paid or made by the Company on the
outstanding Common Shares in Common Shares or shares convertible into Common
Shares or pursuant to a split or subdivision of the outstanding Common Shares),
then the Vista Entities shall be deemed to be an Acquiring Person unless upon
becoming the Beneficial Owner of such additional Common Shares of the Company
the Vista Entities do not collectively beneficially own 34.9% or more of the
Common Shares of the Company then outstanding. The exemptions contemplated by
this paragraph for the Vista Entities shall automatically terminate without any
action on the part of the Company or the Vista Entities in their entirety
immediately upon the time at which the Vista Entities shall be Beneficial Owners
of less than 15% of the Common Shares outstanding."

      2.    Governing Law. This Amendment shall be deemed to be a contract made
under the laws of the State of California and for all purposes shall be governed
by and construed in accordance with laws of such State applicable to contracts
to be made and performed entirely within such State.
<PAGE>
      3.    Counterparts. This Amendment may be executed in any number of
counterparts, each of which shall be an original and all such counterparts shall
together constitute one and the same instrument.

      4.    Effective Time. This Amendment shall be effective immediately prior
to the Closing (as defined in the Conversion Agreement).

            Terms used herein but not defined herein shall have the meaning set
forth in the Rights Agreement.

                            [Signature page follows.]
<PAGE>
            The parties have caused this Amendment to be duly executed as of the
date first written above.

                                        ASPECT COMMUNICATIONS
                                        CORPORATION

                                        By:
                                           ---------------------------------
                                           Name:  Gary Barnett
                                           Title: President and Chief Executive
                                                  Officer

                                        Address:  1310 Ridder Park Drive
                                                  San Jose, CA  95131
                                        Fax:      (408) 325-2260

                                        EQUISERVE TRUST COMPANY, N.A.

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

                                        Address:

                                        Fax:
<PAGE>
                                    EXHIBIT A

                              OFFICER'S CERTIFICATE
                                       OF
                        ASPECT COMMUNICATIONS CORPORATION

            The undersigned, Gary Wetsel, hereby certifies as follows:

            1.    The undersigned is the duly elected Executive Vice President,
Finance, Chief Financial Officer and Chief Administrative Officer of Aspect
Communications Corporation, a California corporation (the "Company").

            2.    Pursuant to the Preferred Shares Rights Agreement dated as of
May 11, 1999, as amended on December 12, 2001 and November 14, 2002, entered
into by and among the Company and BankBoston N.A., as Rights Agent (the "Rights
Agreement"), the Company proposes to amend the Rights Agreement pursuant to
Amendment No. 3 to Preferred Shares Rights Agreement dates of the date hereof
(the "Amendment").

            3.    The undersigned has examined the requirements of Section 27 of
the Rights Agreement regarding amendments and supplements to the Rights
Agreement.

            4.    The undersigned is of the opinion that the Amendment is in
compliance with the terms of Section 27 of the Rights Agreement.

            The undersigned has executed this certificate as an officer of the
Company this -- day of --, 2004.

                                        ----------------------------------
                                        Gary Wetsel
                                        Executive Vice President, Finance,
                                        Chief Financial Officer and
                                        Chief Administrative Officerexv4w6

 

Exhibit 4.6

     UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF
THE DEPOSITORY TRUST COMPANY TO THE ISSUER OR ITS AGENT FOR REGISTRATION OF
TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE
NAME OF CEDE & CO. OR IN SUCH OTHER NAME AS IS REQUESTED BY AN AUTHORIZED
REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY (AND ANY PAYMENT HEREON IS MADE
TO CEDE & CO. OR TO SUCH OTHER ENTITY AS IS REQUESTED BY AN AUTHORIZED
REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY), 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.

     TRANSFERS OF THIS GLOBAL SECURITY SHALL BE LIMITED TO TRANSFERS TO
NOMINEES OF THE DEPOSITORY TRUST COMPANY, OR TO A SUCCESSOR THEREOF OR SUCH
SUCCESSOR’S NOMINEE AND TRANSFERS OF PORTIONS OF THIS GLOBAL SECURITY SHALL BE
LIMITED TO TRANSFERS MADE IN ACCORDANCE WITH THE RESTRICTIONS SET FORTH IN
ARTICLE THREE OF THE INDENTURE REFERRED TO ON THE REVERSE HEREOF.

     THIS GLOBAL SECURITY IS IN FULLY REGISTERED FORM, WITHOUT COUPONS. THE
HOLDER OF THIS GLOBAL SECURITY MAY NOT TRANSFER OR EXCHANGE THIS GLOBAL
SECURITY FOR BEARER SECURITIES.

ODYSSEY RE HOLDINGS CORP.

7.65% Senior Notes due 2013

	 	 	 	 	 
	No. 2	 	CUSIP: 67612W AC 2
	Issue Date: November 18, 2003	 	Principal Amount: $75,000,000

     ODYSSEY RE HOLDINGS CORP., a Delaware corporation, promises to pay to Cede
& Co., or registered assigns, the principal amount of SEVENTY-FIVE MILLION
DOLLARS ($75,000,000) on November 1, 2013.

     Interest Payment Dates: May 1 and November 1 commencing May 1, 2004.

     Regular Record Dates: April 15 and October 15.

     Reference is hereby made to the further provisions of this Security set
forth on the reverse side of this Security, which further provisions shall for
all purposes have the same effect as if set forth at this place.

 

 

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

	 	 	 
	 	
ODYSSEY RE HOLDINGS CORP.
	 	 	 
	 	 	 
	 	By:	   /s/ Donald L. Smith
	 	 	

	 	Title:	   Senior Vice President
	 	 	

Dated: November 18, 2003

TRUSTEE’S CERTIFICATE OF AUTHENTICATION

THE BANK OF NEW YORK,

as Trustee, certifies that this is one

of the Securities referred to in the

within-mentioned Indenture.

	 	 	 
	By:	   /s/ Geovanni Barris
	 	
Authorized
Signatory	 

Dated: November 18, 2003

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7.65% Senior Notes due 2013

     This Security is one of a duly authorized issue of 7.65% Senior Notes due
2013 (the “Securities”) of Odyssey Re Holdings Corp., a Delaware corporation
(including any successor corporation under the Indenture hereinafter referred
to, the “Company”), initially issued in an aggregate principal amount of
$150,000,000 on October 31, 2003 and, as a result of the further issuance of
$75,000,000 aggregate principal amount of Securities on November 18, 2003, now
issued in an aggregate principal amount of $225,000,000, issued under an
Indenture, dated as of October 31, 2003 (the “Indenture”), between the Company
and The Bank of New York, as trustee (the “Trustee”). The terms of this
Security include those stated in the Indenture, those made part of the
Indenture by reference to the Trust Indenture Act of 1939, as amended (“TIA”),
and those set forth in this Security. This Security is subject to all such
terms, and Holders are referred to the Indenture and the TIA for a statement of
all such terms. To the extent permitted by applicable law, in the event of any
inconsistency between the terms of this Security and the terms of the
Indenture, the terms of the Indenture shall control; provided that a Holder may
not transfer or exchange Securities for Bearer Securities, notwithstanding the
Indenture or any supplemental indenture. Capitalized terms used but not
defined herein have the meanings assigned to them in the Indenture referred to
below unless otherwise indicated.

	1.	 	Interest

     General. The Company promises to pay interest on the principal amount of
the Securities plus accrued and unpaid interest, if any, at the interest rate
specified herein (the “Interest Rate”) from the date of issuance until
repayment in full at November 1, 2013 or redemption to the Persons in whose
names the Securities are registered at the close of business on the Regular
Record Date, whether or not a Business Day, immediately preceding such Interest
Payment Date, except as set forth in Section 1(c) below. The Company will pay
interest on this Security semi-annually in arrears on May 1 and November 1 of
each year (each, an “Interest Payment Date”), commencing May 1, 2004.

     (a)  The Securities shall bear interest from October 31, 2003 until the
principal amount thereof is paid or made available for payment, or until such
date on which the Securities are redeemed as provided herein, at a rate of
7.65% per annum.

     (b)  Interest on the Securities shall be computed (i) for any full
semi-annual period for which a particular Interest Rate is applicable, on the
basis of a 360-day year of twelve 30-day months and (ii) for any period for
which a particular Interest Rate is applicable for less than a full semi-annual
period for which interest is calculated, on the basis of a 30-day month and,
for such periods of less than a month, the actual number of days elapsed over a
30-day month.

     (c)  If this Security is redeemed on a date that is after the record date
and prior to the corresponding Interest Payment Date, interest, accrued and
unpaid hereon to but not including the applicable Redemption Date, will be paid
to the same Holder to whom the Company pays the principal of this Security.

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     If the principal amount hereof or any portion of such principal amount or
any interest on any Security is not paid when due (whether upon acceleration
pursuant to Section 502 of the Indenture, upon the date set for payment of the
Redemption Price pursuant to Section 6 hereof or upon the Stated Maturity of
this Security), then in each such case the overdue amount shall, to the extent
permitted by law, bear interest at the applicable Interest Rate, compounded
semi-annually, which interest shall accrue from the date such overdue amount
was originally due to the date payment of such amount, including interest
thereon, has been made or duly provided for. All such interest shall be
payable on demand.

	2.	 	Method of Payment.

     Except as provided below, interest will be paid (i) on the global
Securities to The Depository Trust Company (“DTC”) in immediately available
funds, (ii) on any definitive Securities having an aggregate principal amount
of $10,000,000 or less, by check mailed to the Holders of such Securities; and
(iii) on any definitive Securities having an aggregate principal amount of more
than $10,000,000, by wire transfer in immediately available funds at the
election of the Holders of these Securities to an account specified by the
Holder at a bank in New York City.

     Principal on definitive Securities will be payable, upon Stated Maturity
or when due, at the office or agency of the Company in New York City,
maintained for such purpose, initially the Corporate Trust Office of the
Trustee in New York City.

     The Company will pay cash amounts in money of the United States that at
the time of payment is legal tender for payment of public and private debts.
However, the Company may make such cash payments by check payable in such
money.

	3.	 	Paying Agent, Conversion Agent and Security Registrar.

     Initially, the Trustee will act as Paying Agent, and Security Registrar at
its Corporate Trust Office in New York City. The Company may appoint and change
any Paying Agent or Security Registrar without notice, other than notice to the
Trustee; provided that the Company will maintain at least one Paying Agent in
the State of New York, The City of New York, Borough of Manhattan, which shall
initially be an office or agency of the Trustee. The Company or any of its
subsidiaries or any of their Affiliates may act as Paying Agent or Security
Registrar.

	4.	 	Indenture.

     The Securities are general unsecured obligations of the Company. The
Indenture does not limit other indebtedness of the Company, secured or
unsecured.

	5.	 	Additional Securities.

     The Company may from time to time without notice to, or the consent of,
any Holder, create and issue additional Securities under the Indenture, equal
in rank to the Securities in all respects (or in all respects except for the
payment of interest accruing prior to the issue date of the new Securities, or
except for the first payment of interest following the issue date of the

4

 

new Securities) so that the new Securities may be consolidated and form a
single series with the Securities and have the same terms as to status,
redemption and otherwise as the Securities.

	6.	 	Redemption at the Option of the Company.

     No sinking fund is provided for the Securities.

     The Company may redeem the Securities, in whole or in part, at the
Company’s option, at any time at a Redemption Price equal to the greater of (1)
100% of the principal amount of the Securities and (2) the sum of the present
values of the remaining scheduled payments of principal and interest thereon
(exclusive of interest accrued to the Redemption Date) discounted to the
Redemption Date on a semi-annual basis (assuming a 360-day year consisting of
twelve 30-day months) at the Treasury Rate plus 50 basis points, plus, in each
case, interest accrued thereon to the Redemption Date.

     “Treasury Rate” means, with respect to any Redemption Date, the rate per
year equal to the semi-annual equivalent Yield to Maturity or interpolated (on
a day count basis) of the Comparable Treasury Issue, assuming a price for the
Comparable Treasury Issue (expressed as a percentage of its principal amount)
equal to the Comparable Treasury Price for such Redemption Date.

     “Comparable Treasury Issue” means the United States Treasury security or
securities selected by an Independent Investment Banker as having an actual or
interpolated maturity comparable to the remaining term of the Securities to be
redeemed that would be utilized, at the time of selection and in accordance
with customary financial practice, in pricing new issues of corporate debt
securities of a comparable maturity to the remaining term of such Securities.

     “Independent Investment Banker” means one of the Reference Treasury
Dealers appointed by the Trustee after consultation with the Company.

     “Comparable Treasury Price” means, with respect to any redemption date,
(1) the average of the Reference Treasury Dealer Quotations for such Redemption
Date, after excluding the highest and lowest such Reference Treasury Dealer
Quotations, or (2) if the Trustee obtains fewer than four such Reference
Treasury Dealer Quotations, the average of all such quotations.

     “Reference Treasury Dealer Quotations” means, with respect to each
Reference Treasury Dealer and any Redemption Date, the average, as determined
by the Trustee, of the bid and asked prices for the Comparable Treasury Issue
(expressed in each case as a percentage of its principal amount) quoted in
writing to the Trustee by such Reference Treasury Dealer at 3:30 p.m. New York
time on the third Business Day preceding such Redemption Date.

     “Reference Treasury Dealer” means each of (1) Banc of America Securities
LLC, Credit Suisse First Boston LLC and J.P. Morgan Securities Inc. or their
Affiliates which are primary U.S. Government securities dealers in The City of
New York (a “Primary Treasury Dealer”), and their respective successors and (2)
two other Primary Treasury Dealers; provided, however, that if any of the
foregoing or their Affiliates shall cease to be a Primary Treasury

5

 

Dealer, the Company shall substitute therefor another Primary Treasury
Dealer.

     Unless the Company defaults in payment of the Redemption Price, on and
after the Redemption Date, interest will cease to accrue on the Securities or
portions thereof called for redemption.

	7.	 	Notice of Redemption.

     Notice of redemption pursuant to Section 6 of this Security will be mailed
at least 30 days but not more than 60 days before the Redemption Date to each
Holder of Securities to be redeemed at the Holder’s registered address. If
money sufficient to pay the Redemption Price of all Securities (or portions
thereof) to be redeemed on the Redemption Date is deposited with the Paying
Agent prior to or on the Redemption Date, immediately after such Redemption
Date interest ceases to accrue on such Securities or portions thereof.
Securities in denominations larger than $1,000 of principal amount may be
redeemed in part but only in integral multiples of $1,000 of principal amount.

	8.	 	Denominations; Transfer; Exchange.

     The Securities are in fully registered form, without coupons, in
denominations of $1,000 of principal amount and integral multiples of $1,000.
A Holder may transfer or exchange Securities in accordance with the Indenture
(or supplemental indenture, if any), except that a Holder may not transfer or
exchange Securities for Bearer Securities notwithstanding the Indenture or any
supplemental indenture. The Security Registrar may require a Holder, among
other things, to furnish appropriate endorsements and transfer documents and to
pay any taxes and fees required by law or permitted by the Indenture. The
Security Registrar need not transfer or exchange any Securities that may be
among those selected for redemption for a period of 15 days before the mailing
of a notice of redemption of Securities to be redeemed.

	9.	 	Persons Deemed Owners.

     The registered Holder of this Security may be treated as the owner of this
Security for all purposes.

	10.	 	Unclaimed Money or Securities.

     The Trustee and the Paying Agent shall return to the Company upon written
request any money or securities held by them for the payment of any amount with
respect to the Securities that remains unclaimed for two years, subject to
applicable unclaimed property law. After return to the Company, Holders
entitled to the money or securities must look to the Company for payment as
general creditors unless an applicable abandoned property law designates
another person.

	11.	 	Amendment; Waiver.

     Subject to certain exceptions set forth in the Indenture, (i) the
Indenture or the Securities may be amended with the written consent of the
Holders of at least a majority in aggregate principal amount of the outstanding
Securities and (ii) certain Defaults may be waived

6

 

with the written consent of the Holders of a majority in aggregate
principal amount of the outstanding Securities. Subject to certain exceptions
set forth in the Indenture, without the consent of any Holder, the Company and
the Trustee may amend the Indenture or the Securities (i) to evidence the
succession of another Person to the Company and the assumption by any such
successor of the covenants of the Company contained in the Indenture and the
Securities; (ii) to add to the covenants of the Company for the benefit of the
Holders of the Securities or to surrender any right or power conferred upon the
Company under the Indenture; (iii) to add any additional Events of Default for
the benefit of the Holders of the Securities; (iv) to add to or change any of
the provisions of the Indenture to provide that Bearer Securities may be
registerable as to principal, to change or eliminate any restrictions on the
payment of principal of or any premium or interest on Bearer Securities, to
permit Bearer Securities to be issued in exchange for Registered Securities (if
permitted by applicable laws or regulations), to permit Bearer Securities to be
issued in exchange for Bearer Securities of other authorized denominations or
to permit or facilitate the issuance of Securities in uncertificated form; (v)
to change or eliminate any of the provisions of the Indenture; (vi) to
establish the form or terms of the Securities; (vii) to evidence and provide
for the acceptance of appointment under the Indenture by a successor Trustee
with respect to the Securities and to add to or change any of the provisions of
the Indenture as shall be necessary to provide for or facilitate the
administration of the trusts thereunder by more than one Trustee; (viii) to
cure any ambiguity, to correct or supplement any provision in the Indenture
which may be inconsistent with any other provision therein, or to make any
other provisions with respect to matters or questions arising thereunder; or
(ix) to supplement any of the provisions of the Indenture to such extent as
shall be necessary to permit or facilitate the defeasance and discharge of the
Securities.

	12.	 	Merger or Consolidation.

     The Company shall not consolidate with or merge with or into any other
Person or convey or transfer its properties and assets substantially as an
entirety to any Person, unless:

     (a)  either the Company shall be the continuing corporation, or the Person
(if other than the Company) formed by such consolidation or into which the
Company is merged or the Person which acquires by conveyance or transfer the
properties and assets of the Company substantially as an entirety (i) shall be
organized and validly existing under the laws of (A) the United States or any
State thereof or the District of Columbia or (B) Bermuda or the Cayman Islands
and (ii) shall expressly assume, by an indenture supplemental to the Indenture,
executed and delivered to the Trustee, in form satisfactory to the Trustee, the
due and punctual payment of the principal of (and premium, if any) and
interest, if any, on all the Securities and the performance of every covenant
of the Indenture on the part of the Company to be performed or observed;

     (b)  immediately after giving effect to such transaction, no Default or
Event of Default shall have happened and be continuing; and

     (c)  the Company and the successor Person have delivered to the Trustee an
Officers’ Certificate and an Opinion of Counsel each stating that (i) such
consolidation, merger, conveyance or transfer and such supplemental indenture
comply with Article VIII of the Indenture and that all conditions precedent
provided for in the Indenture relating to such

7

 

transaction have been complied with, and (ii) in the case of a merger or
consolidation in which the Company is not the continuing corporation and in
which the successor to the Company is an entity organized under the laws of
Bermuda or the Cayman Islands, that such merger will not result in any material
adverse tax consequences to any Holders of the Securities.

	13.	 	Defaults and Remedies.

     If any Event of Default with respect to Securities shall occur and be
continuing, the principal of all the Securities may be declared due and payable
in the manner and with the effect provided in the Indenture.

     “Event of Default,” wherever used with respect to the Securities, means
any one of the following events (whatever the reason for such Event of Default
and whether or not it shall be voluntary or involuntary or be effected by
operation of law or pursuant to any judgment, decree or order of any court or
any order, rule or regulation of any administrative or governmental body):

     (a)  default in the payment of any interest upon any Security, when such
interest becomes due and payable, and continuance of such default for a period
of 30 days; or

     (b)  default in the payment of the principal of (or premium, if any, on)
any Security when it becomes due and payable at its Maturity; or

     (c)  default in the performance, or breach, of any covenant or agreement of
the Company in the Indenture with respect to any Security (other than a
covenant or agreement a default in whose performance or whose breach is
elsewhere in this Section specifically dealt with), 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 Securities a written notice specifying such default or breach and
requiring it to be remedied and stating that such notice is a “Notice of
Default”; or

     (d)  a failure to pay when due at maturity or a default that results in the
acceleration of maturity of any indebtedness for borrowed money of the Company
or any Designated Subsidiary in an aggregate amount of $25,000,000 or more,
unless the acceleration is rescinded, stayed or annulled within 30 days after
written notice of default is given to the Company by the Trustee or Holders of
not less than 25% in aggregate principal amount of the Outstanding Securities;
or

     (e)  the Company or any Designated Subsidiary, or any group of two or more
Subsidiaries that, taken as a whole, would constitute a Designated Subsidiary,
pursuant to or under or within the meaning of any Bankruptcy Law:

		
	 	     (i)  commences a voluntary case or proceeding,

		
	 	     (ii) consents to the entry of any order for relief against it in
an involuntary case or proceeding or the commencement of any case
against it,

8

 

		
	 	     (iii) consents to the appointment of a Custodian of it or for any
substantial part of its property,

		
	 	     (iv) makes a general assignment for the benefit of its creditors,

		
	 	     (v) files a petition in bankruptcy or answer or consent seeking
reorganization or relief, or

		
	 	     (vi) consents to the filing of such petition or the appointment of
or taking possession by a Custodian; or

     (f)  a court of competent jurisdiction enters an order or decree under any
Bankruptcy Law that:

		
	 	     (i) is for relief against the Company or any Designated Subsidiary,
or any group of two or more subsidiaries that, taken as whole,
would constitute a Designated Subsidiary, in an involuntary case or
proceeding, or adjudicates the Company or any Designated
Subsidiary, or any group of two or more subsidiaries that, taken as
whole, would constitute a Designated Subsidiary, insolvent or
bankrupt, or

		
	 	     (ii) appoints a Custodian of the Company or any Designated
Subsidiary, or any group of two or more subsidiaries that, taken as
whole, would constitute a Designated Subsidiary, or for any
substantial part of its property, or

		
	 	     (iii) orders the winding up or liquidation of the Company or any
Designated Subsidiary, or any group of two or more subsidiaries
that, taken as whole, would constitute a Designated Subsidiary,

and the order or decree remains unstayed and in effect for 60 days; or

     (g) the commencement by the Company or any of its subsidiaries that is a
Designated Subsidiary or any group of two or more subsidiaries that, taken as a
whole, would constitute a Designated Subsidiary, of a voluntary case or
proceeding under any applicable bankruptcy, insolvency, reorganization or other
similar law or of any other case or proceeding to be adjudicated a bankrupt or
insolvent, or the consent by the Company or any of its subsidiaries that is a
Designated Subsidiary or any group of two or more subsidiaries that, taken as a
whole, would constitute a Designated Subsidiary, to the entry of a decree or
order for relief in respect of the Company or any of its subsidiaries that is a
Designated Subsidiary or any group of two or more subsidiaries that, taken as a
whole, would constitute a Designated Subsidiary, in an involuntary case or
proceeding under any applicable bankruptcy, insolvency, reorganization or other
similar law or to the commencement of any bankruptcy or insolvency case or
proceeding against the Company, or the filing by the Company or any of its
subsidiaries that is a Designated Subsidiary or any group of two or more
subsidiaries that, taken as a whole, would constitute a Designated Subsidiary,
of a petition or answer or consent seeking reorganization or relief under

9

 

any applicable law, or the consent by the Company to the filing of such
petition or to the appointment of or the taking possession by a custodian,
receiver, liquidator, assignee, trustee, sequestrator or other similar official
of the Company or of any substantial part of its property, or the making by the
Company or any of its subsidiaries that is a Designated Subsidiary or any group
of two or more subsidiaries that, taken as a whole, would constitute a
Designated Subsidiary, of an assignment for the benefit of creditors, or the
admission by the Company or any of its subsidiaries that is a Designated
Subsidiary or any group of two or more subsidiaries that, taken as a whole,
would constitute a Designated Subsidiary, in writing of its inability to pay
its debts generally as they become due, or the taking of corporate action by
the Company or any of its subsidiaries that is a Designated Subsidiary or any
group of two or more subsidiaries that, taken as a whole, would constitute a
Designated Subsidiary, expressly in furtherance of any such action.

     “Bankruptcy Law” means Title 11, United States Code, or any similar
Federal or state law for the relief of debtors.

     “Custodian” means any receiver, trustee, assignee, liquidator, custodian
or similar official under any Bankruptcy Law.

     “Designated Subsidiary” shall mean any existing or future, direct or
indirect, subsidiary of the Company whose assets constitute 15% or more of the
total assets of the Company on a consolidated basis.

	14.	 	Defeasance and Covenant Defeasance.

     The Indenture contains provisions for defeasance at any time of (a) the
entire indebtedness of the Company on this Security and (b) certain restrictive
covenants and the related Events of Default, upon compliance by the Company
with certain conditions set forth therein, which provisions apply to this
Security.

	15.	 	Definitive Securities

     This Security is a global Security. If (a) the depositary with respect to
the Securities (which shall initially be The Depository Trust Company) shall
notify the Company that it is at any time unwilling, unable or no longer
qualified to continue as depositary and a successor depositary is not appointed
by the Company within 60 days or (b) an Event of Default has occurred and is
continuing and has not been cured or waived, the Company will issue Securities
in definitive registered form without coupons, in any authorized denominations,
of like tenor, in an aggregate principal amount equal to the principal amount
of the Registered Securities in global form (the “Registered Global
Securities”), in exchange for such Registered Global Securities. In addition,
the Company may at any time and in its sole discretion determine that the
Securities will no longer be represented by Registered Global Securities and,
in such event, will issue Securities in definitive registered form, in such
tenor, in any authorized denominations and in an aggregate principal amount
equal to the principal amount of the Registered Global Securities representing
such Securities, in exchange for such Registered Global Securities.
Securities so issued in definitive registered form will be issued in
denominations of $1,000 or

10

 

any amount in excess thereof which is an integral multiple of $1,000 and
will be issued in registered form only, without coupons.

	16.	 	Trustee Dealings with the Company.

     Subject to certain limitations imposed by the TIA, the Trustee under the
Indenture, in its individual or any other capacity, may become the owner or
pledgee of Securities and may otherwise deal with and collect obligations owed
to it by the Company or its Affiliates and may otherwise deal with the Company
or its Affiliates with the same rights it would have if it were not Trustee.

	17.	 	Calculations in Respect of Securities.

     The Company or its agents will be responsible for making all calculations
called for under the Securities. Any calculations made in good faith and
without manifest error will be final and binding on Holders of the Securities.
The Company or its agents will be required to deliver to the Trustee a schedule
of its calculations and the Trustee will be entitled to conclusively rely upon
the accuracy of such calculations without independent verification.

	18.	 	No Recourse Against Others.

     No recourse under or upon any obligation, covenant or agreement contained
in the Indenture, or in this Security, or because of any indebtedness evidenced
thereby, shall be had against any incorporator, as such, or against any past,
present or future stockholder, officer or director, as such, of the Company or
of any successor, either directly or through the Company or any successor,
under any rule of law, statute or constitutional provision or by the
enforcement of any assessment or by any legal or equitable proceeding or
otherwise, all such liability being expressly waived and released by the
acceptance of the Securities by the Holders and as part of the consideration
for the issue of the Securities.

	19.	 	Authentication.

     This Security shall not be valid until an authorized signatory of the
Trustee manually signs the Trustee’s Certificate of Authentication on the other
side of this Security.

	20.	 	Abbreviations.

     Customary abbreviations may be used in the name of a Holder or an
assignee, such as TEN COM (=tenants in common), TEN ENT (=tenants by the
entireties), JT TEN (=joint tenants with right of survivorship and not as
tenants in common), CUST (=custodian), and U/G/M/A (=Uniform Gift to Minors
Act).

	21.	 	GOVERNING LAW.

     THE LAWS OF THE STATE OF NEW YORK SHALL GOVERN THE INDENTURE AND THIS
SECURITY.

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     The Company will furnish to any Holder upon written request and without
charge a copy of the Indenture. Requests may be made to:

	 		 	Odyssey Re Holdings Corp.

140 Broadway, 39th Floor

New York, New York 10005

Attn: General Counsel

Facsimile No. (212) 978-4700

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ASSIGNMENT FORM

To assign this Security, fill in the form below:

I or we assign and transfer this Security to

(Insert assignee’s soc. sec. or tax ID no.)

(Print or type assignee’s name, address and zip code)

and irrevocably appoint

                     agent to transfer this Security on the books of the

Company. The agent may substitute another to act for him.

Date:                     Your Signature:                                  

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

Signature Guaranteed

Participant in a Recognized Signature

Guarantee Medallion Program

By:                                                                      

              Authorized Signatory

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