Document:

Exhibit 10.2

Exhibit 10.2

Sanlam Health Addendum to Robertson Technologies Licensing,

Distribution Agreement with Montana Health

PHASE 1

Robertson Technologies Licensing, LLC (“Robertson”) and Montana Healthcare Solutions (Pty) Ltd
(“Montana Health”) entered into a contract entitled Product Distribution Agreement dated December
6, 2010. The parties wish to enter into an agreement with Sanlam Health (“Sanlam”) for the purpose
of delivering diagnostics, electronic health records (“EHR”), and health insurance applications to
subscribers of MTN, a mobile telephone service provider in Africa. Effective as of December 6,
2010 the contract will be supplemented as follows:

I. PROJECT SUMMARY. PHASE 1.

MTN subscribers will download the RHealth Advisor (“RHA”) mobile application. Users will enter
their age and gender, initiating the EHR, and have the ability to self diagnose. Depending on level
of severity; the user will be guided to treatments available or appropriate next level of care.
This diagnosis will be passed from RHA to Sanlam (via reports) for follow up through voice call
back to initiate risk management protocols.

II. PERFORMANCE MEASURES

	 	A.	 	Robertson Deliverables:

	 	1.	 	Robertson will provide a Mobile applet to be made available by Sanlam and MTN
subscribers

	 	2.	 	Robertson will provide tailored medical data for the South Africa consumer user
base for this project and continue to maintain and update the data for the duration of
the project.

	 	3.	 	Robertson will investigate and, if found to be possible, will provide the
ability to save each diagnosis generated into the EHR. Currently users have the option
to save, however, Sanlam prefers to have symptoms and diagnostic information to
automatically save in the EHR for each case.

	 	4.	 	Support. Robertson will support its business technology systems, deliverance of
technology to consumer sector, and expertise in handling medical and technical
questions. Robertson will be available as Tier 3 support for queries referred from
Montana Health regarding medical or technological questions that are related to RHealth
Advisor applet.

	 	5.	 	Robertson will provide training on its products and services to Montana Health
and its agents and contractors. Once trained, Montana Health will become a technical
implementation partner with Robertson with the capabilities of training all future
contractors, agents, distribution outlets.

	 	B.	 	Montana Deliverables:

	 	1.	 	Montana Health will provide business analysis services, technology consulting
services and regulatory consulting services to Sanlam

	 	2.	 	Account management. Montana Health will maintain the relationship with Sanlam.
	 
	 	3.	 	Montana Health will provide tier 1 and 2 support during hours (8am to 5pm SAST)
to Sanlam. Montana Health will be responsible for escalating any issues unable to be
resolved immediately to RGHS.

 

 

 

III. Revenue Sharing.

Implementation Fee: $41, 500.00 USD (this is a 1-time payment)

Robertson Health: 100%

	 	 	 
	* 	 	To be paid upon signature of contract between Montana Health and Sanlam Health

	 	 	 	 	 	 	 	 	 
	Element	 	Response	 	Amount	 	 	Responsible Party
	Infrastructure Support
	 	 	 	 	 	 	 	 
	Build-out & Setup
	 	No	 	$	0	 	 	 
	Hosting
	 	No	 	$	0	 	 	 
	Implementation
	 	 	 	 	 	 	 	 
	Application Configuration
	 	Yes	 	$	16,500	 	 	Robertson
	Mobile Configuration
	 	No	 	$	0	 	 	 
	Regionalization
	 	Yes	 	$	10,000	 	 	Robertson
	Training
	 	Yes	 	$	5,000	 	 	Robertson & Montana Health
	Post-Implementation Support
	 	Yes	 	$	10,000	 	 	Robertson & Montana Health
	 	 	 	 	 	 	 	 
	Total
	 	 	 	$	41,500	 	 	 
	 	 	 	 	 	 	 	 

Contracted Minimum: $10,000.00 USD per month

Montana Health: 30%

Robertson Health: 70%

Module License: Transactional Based

Montana Health: 30%

Robertson Health: 70%

	 	 	 
	Note: 	 	The transactions are billed in addition to the minimum contracted amount above each month.

 

 

 

License Price / Module / Year

	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	MTN	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	Annual	 
	 	 	 	 	 	 	 	Data	 	 	Health	 	 	 	 	 	 	User	 
	Min	 	Max	 	 	NxOpinion	 	 	Collection	 	 	Tips	 	 	EHR	 	 	Registration	 
	Transaction Volume	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	1
	 	 	50,000	 	 	$	0.25	 	 	$	0.25	 	 	$	0.15	 	 	$	0.25	 	 	$	0.90	 
	50,001
	 	 	100,000	 	 	$	0.25	 	 	$	0.25	 	 	$	0.15	 	 	$	0.25	 	 	$	0.90	 
	100,001
	 	 	500,000	 	 	$	0.15	 	 	$	0.15	 	 	$	0.10	 	 	$	0.20	 	 	$	0.60	 
	500,001
	 	 	1,000,000	 	 	$	0.15	 	 	$	0.15	 	 	$	0.10	 	 	$	0.20	 	 	$	0.60	 
	1,000,001
	 	 	5,000,000	 	 	$	0.05	 	 	$	0.05	 	 	$	0.05	 	 	$	0.15	 	 	$	0.30	 
	5,000,001
	 	 	10,000,000	 	 	$	0.05	 	 	$	0.05	 	 	$	0.05	 	 	$	0.15	 	 	$	0.30	 
	10,000,001
	 	 	999,999,999	 	 	$	0.05	 	 	$	0.05	 	 	$	0.05	 	 	$	0.15	 	 	$	0.30	 

IV. Billing.

Montana Health will bill Sanlam Health each month for the total MTN user registrations based
upon the license price (aggregate annual volume tier) / module / year chart within this agreement
(in local currency equivalent as set at the date of the contract signing between Sanlam Health and
Montana Health). Montana Health will distribute funds to Robertson Health according to the revenue
sharing percentages agreed upon in this agreement; distributions are to be within 30 days of
payment from Sanlam Health. Montana Health will invoice Sanlam Health on a 30 day basis.

 

 

 

[SIGNATURE PAGE]

This Amendment to the Agreement is entered into by the parties as of the Effective Date.

DATE: December 6, 2010

	 	 	 	 	 	 	 	 	 

	Technology Provider:	 	Technology Distributor:	 	 
	Robertson Technologies Licensing, LLC	 	Montana Healthcare Solutions (Pty) Ltd	 	 
	 
	 	 	 	 	 	 	 	 
	Sign: 

	/s/ Joel Robertson
 

	 	Sign: 
	/s/ Nicola Brink
 

	 	 
	 

	Name: 	Joel Robertson
	 	 	Name: 	Nicola Brink

	 	 
	 

	Title: 	CEO

	 	 
	Title: 	Directorexv4w1

Exhibit 4.1

SECOND SUPPLEMENTAL INDENTURE

BY AND BETWEEN

ASPEN INSURANCE HOLDINGS LIMITED,

AS ISSUER

AND

DEUTSCHE BANK TRUST COMPANY AMERICAS,

AS TRUSTEE

 
Dated as of December 10, 2010 

$250,000,000

ASPEN INSURANCE HOLDINGS LIMITED

6.00% SENIOR NOTES DUE 2020

 

 

SECOND SUPPLEMENTAL INDENTURE

          This Second Supplemental Indenture, dated as of December 10, 2010 (the “Second Supplemental
Indenture”), to the Indenture, dated as of August 16, 2004 (the “Original Indenture”) by and
between Aspen Insurance Holdings Limited, a limited company duly organized and existing under the
laws of Bermuda, having its principal executive office located at Maxwell Roberts Building, 1
Church Street, Hamilton HM 11, Bermuda (the “Company”), as issuer, and Deutsche Bank Trust Company
Americas, a New York banking corporation duly organized and existing under the laws of the State of
New York, having its corporate trust office located at 60 Wall Street, New York, NY 10005 (the
“Trustee”), as trustee, is effective upon the execution hereof by the parties hereto.

RECITALS

          WHEREAS, the Company has heretofore executed and delivered to the Trustee the Original
Indenture providing for the issuance from time to time of its notes, debentures or other evidences
of its unsecured indebtedness (the “Securities”), unlimited as to principal amount;

          WHEREAS, the Original Indenture is incorporated herein by reference and the Original
Indenture, as supplemented by this Second Supplemental Indenture, is herein called the “Indenture”;

          WHEREAS, Section 3.1 of the Original Indenture provides that, with respect to any series of
Securities to be authenticated and delivered under the Indenture, the terms of such series of
Securities shall be established by (i) a resolution of the Board of Directors and set forth in an
Officer’s Certificate or (ii) one or more indentures supplemental to the Original Indenture;

          WHEREAS, the Company desires to create, under the Indenture, a series of Securities to be
known as its 6.00% Senior Notes due 2020 (the “Senior Notes”), the form and substance of such notes
and the terms, provisions and conditions thereof to be set forth as provided in the Original
Indenture and this Second Supplemental Indenture; and

          WHEREAS, all conditions necessary to authorize the execution and delivery of this Supplemental
Indenture and to make it a valid and binding obligation of the Company have been done or performed;

          NOW, THEREFORE, in consideration of the foregoing and for other good and valuable consideration,
the receipt of which is hereby acknowledged, the Company and the Trustee mutually covenant and
agree as follows:

 

 

Article I.

DEFINITIONS

          Section 1.1. Definitions. The following defined terms used herein shall have the meanings
specified below. Capitalized terms used herein without definition shall have the respective
meanings assigned such terms in the Original Indenture.

          “Interest Payment Date” means, with respect to the Senior Notes only, June 15 and
December 15 of each year.

          “Regular Record Date” means, with respect to the Senior Notes only, 5:00 p.m., New
York City time, on June 1 or December 1, as the case may be, immediately preceding each
Interest Payment Date.

Article II.

GENERAL TERMS AND CONDITIONS OF THE SENIOR NOTES

          There is hereby established a new series of Securities under the Indenture with the following
terms:

          Section 2.1. Title. The title of the series is “6.00% Senior Notes due 2020”.

          Section 2.2. Principal Amount. There are to be issued by the Company, and authenticated and
delivered by the Trustee on the date hereof, $250,000,000 principal amount of Senior Notes, and
such principal amount of Senior Notes may be increased from time to time pursuant to Section 3.1 of
the Original Indenture. All Senior Notes need not be issued on the same date and such series may
be reopened at any time, without the consent of any Holder, for issuances of additional Senior
Notes, unlimited in principal amount, upon delivery by the Company to the Trustee of either a
resolution of the Board of Directors and set forth in an Officer’s Certificate or an indenture
supplemental to the Original Indenture, setting forth the original issuance date of such additional
Senior Notes. The terms of any such additional Senior Notes will be identical (except as to
denomination, and the date from which interest shall accrue, the issue price and the first Interest
Payment Date) to the terms of the Senior Notes initially issued, authenticated and delivered on the
date hereof. Any such additional Senior Notes will, together with the previously issued Senior
Notes, constitute a single series of Securities under the Indenture.

          Section 2.3. Payment of Principal and Interest.

          (a) The principal of the Senior Notes shall be due on December 15, 2020 which date shall be
the Stated Maturity, subject to the provisions of the Indenture relating to acceleration of
maturity. The Senior Notes will bear interest from December 10, 2010 or from the most recent
Interest Payment Date to which interest has been paid or duly provided for, at a rate of 6.00% per
annum, payable semi-annually in arrears on June 15 and December 15 of each year, commencing on June
15, 2011, and at the Stated Maturity. The Company will pay interest to the Persons in whose names
the Senior Notes are registered on the Regular Record Date for

2

 

such Interest Payment Date. Interest will be computed on the basis of a 360-day year of twelve
30-day months.

          (b) If any Interest Payment Date falls on a day that is not a Business Day, the interest
payment will be postponed to the next day that is a Business Day, and no interest on such payment
will accrue for the period from and after such Interest Payment Date. If the maturity date of the
Senior Notes falls on a day that is not a Business Day, the payment of interest and principal may
be made on the next succeeding Business Day, and no interest on such payment will accrue for the
period from and after the maturity date. Interest payments for the Senior Notes will include
accrued interest from and including the date of issue or from and including the last date in
respect of which interest has been paid, as the case may be, to, but excluding, the Interest
Payment Date or the date of maturity, as the case may be. Interest on the Senior Notes which have
a Redemption Date after a Regular Record Date, and on or before the following Interest Payment
Date, will also be payable to the Persons in whose names the Senior Notes are registered on such
Regular Record Date.

          (c) Payment of the principal and interest due at maturity of the Senior Notes shall be made
upon surrender of the Senior Notes at the Corporate Trust Office of the Trustee. The principal of
and interest on the Senior Notes shall be paid in Dollars. Payments of principal of or interest on
the Senior Notes will be made, subject to such surrender where applicable, at the option of the
Company, (i) by check mailed to the address of the Person entitled thereto as such address shall
appear in the Security Register or (ii) by wire transfer to an account maintained by the payee with
a bank located in the United States.

          Section 2.4. Optional Redemption.

          (a) The Senior Notes will be redeemable as a whole at any time or in part from time to time,
at the option of the Company, at a “make-whole” redemption price equal to the greater of (i) 100%
of the principal amount of the Senior Notes being redeemed or (ii) the sum of the present values of
the remaining scheduled payments of principal and interest (other than accrued interest) on the
Senior Notes being redeemed, 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 45 basis points, plus,
in either case, any accrued and unpaid interest to, but excluding, the date of redemption. Notice
of any redemption will be mailed at least 30 days but no more than 60 days before the redemption
date to each Holder of the Senior Notes to be redeemed. Unless the Company defaults in payment of
the redemption price, on and after the redemption date, interest will cease to accrue on the Senior
Notes or portions thereof called for redemption.

          (b) For the purposes of this Section 2.4,

          “Comparable Treasury Issue” means the United States Treasury security selected by a
Quotation Agent (as defined below) as having a maturity comparable to the remaining term of
the Senior Notes being 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 comparable maturity to the remaining term of such Senior Notes.

3

 

          “Comparable Treasury Price” means, with respect to any redemption date for the Senior
Notes, (1) the average of the Reference Treasury Dealer Quotations (as defined below) 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, or (3) if only one Reference Treasury Dealer
Quotation is received, such Reference Treasury Dealer Quotation.

          “Quotation Agent” means one of the Reference Treasury Dealers appointed by the Company.

          “Reference Treasury Dealer” means (1) each of Citigroup Global Markets Inc. and
Deutsche Bank Securities Inc. (or their respective affiliates that are Primary Treasury
Dealers) and their respective successors; provided, however, that if any of
the foregoing shall cease to be a primary U.S. Government securities dealer in New York City
(a “Primary Treasury Dealer”), the Company shall appoint therefor another Primary Treasury
Dealer as a substitute and (2) any other Primary Treasury Dealer selected by the Company.

          “Reference Treasury Dealer Quotations” means, for each Reference Treasury Dealer and
any redemption date, the average, as determined by the Quotation Agent, 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 Quotation Agent by such Reference Treasury Dealer
at 5:00 p.m., New York City time, on the third business day preceding the redemption date
for the Senior Notes being redeemed.

          “Treasury Rate” means, with respect to any redemption date for the Senior Notes, the
rate per year equal to the semi-annual equivalent yield to maturity 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 the
redemption date.

          Section 2.5. Amendments to Event of Default. The provisos in Section 6.1(a) and Section
6.1(b) of the Original Indenture shall not be applicable with respect to the Senior Notes.

          Section 2.6. Form, Currency and Denominations. The Senior Notes shall be issued in fully
registered form, without coupons, in minimum denominations of $2,000 and integral multiples of
$1,000 in excess thereof. The Senior Notes will be issued in substantially the form set forth in
Exhibit A hereto. The Depository with respect to the Senior Notes shall be The Depository Trust
Company, New York, New York.

          Section 2.7. Global Securities.

          (a) The Senior Notes will be issued in the form of one or more Global Securities registered in
the name of the Depository or its nominee. Except under the circumstances set forth in Section 3.6
of the Original Indenture, the Global Securities will not be exchangeable for, and will not
otherwise be issuable as, Senior Notes in definitive form. Owners

4

 

of beneficial interests in such a Global Security will not be considered the registered owners
or Holders of Senior Notes for any purpose.

          (b) No Security representing a Senior Note shall be exchangeable, except for another Global
Security of like denomination and tenor to be registered in the name of the Depository or its
nominee or to a successor Depository or its nominee. Payment of principal of, any premium or
interest on, and any Additional Amounts, if applicable, in respect of, any Senior Note in global
form shall be made to the registered Holder thereof.

          Section 2.8. Ranking. The Senior Notes will represent the Company’s direct, unsecured
obligations and will rank equally in right of payment with all the Company’s current and future
unsecured and unsubordinated indebtedness.

          Section 2.9. Miscellaneous. The Company is not obligated to redeem or purchase any Senior
Notes pursuant to any sinking fund or analogous provision. The Senior Notes will not be
convertible into shares of Common Stock of the Company and/or exchangeable for other securities.
The amount of payments of principal with respect to the Senior Notes shall not be determined with
reference to an index, formula or other method or methods. No Senior Notes are issuable upon the
exercise of warrants. Each of Section 12.2(b) of the Original Indenture relating to defeasance and
Section 12.2(c) of the Original Indenture relating to covenant defeasance shall be applicable to
the Senior Notes. Except as set forth in Section 4.4 of the Original Indenture, there will be no
Additional Amounts payable on the Senior Notes. The Company may exercise its option to redeem the
Senior Notes for tax purposes pursuant to Section 4.5 of the Original Indenture.

          Section 2.10. Amendments to Section 10.1 of the Original Indenture. Pursuant to Sections
3.1(y) and 10.1(o) of the Original Indenture and only with respect to the Senior Notes issued
hereunder;

          (a) Section 10.1(j) of the Original Indenture shall be deleted in its entirety; and

          (b) in place of the deleted Section 10.1(j) described in (a) above, the following clause shall
be inserted as a new Section 10.1(j): “to provide collateral security for the Securities;”.

Article III.

MISCELLANEOUS PROVISIONS

          Section 3.1. Ratification and Incorporation of the Original Indenture. As amended and
supplemented hereby, the Original Indenture is in all respects ratified and confirmed, and the
Original Indenture, as amended and supplemented by this Second Supplemental Indenture, shall be
read, taken and construed as one and the same instrument.

          Section 3.2. Counterparts. This Second Supplemental Indenture may be executed in several
counterparts, each of which shall be an original and all of which shall constitute but one and the
same instrument.

5

 

          Section 3.3. Governing Law. This Second Supplemental Indenture shall be governed by and
construed in accordance with the laws of the State of New York applicable to agreements made and
performed in said state.

          Section 3.4. Headings. The Article and Section headings herein are for convenience only and
shall not affect the construction hereof.

          Section 3.5. Trustee. The Trustee makes no representations as to the validity or
sufficiency of this Second Supplemental Indenture. The recitals and statements herein are deemed
to be those of the Company and not of the Trustee.

[The remainder of this page is intentionally left blank.]

6

 

          IN WITNESS WHEREOF, Aspen Insurance Holdings Limited has caused this Second Supplemental
Indenture to be duly executed as of the date first above written.

	 	 	 	 	 
	 	 	 
	 	By:  	
/s/ Christopher O’Kane	 
	 	 	Name:  	Christopher O’Kane 	 
	 	 	Title:  	Chief Executive Officer 	 

	 	 	 	 	 
	 	 	 
	 	By:  	/s/ Richard Houghton	 
	 	 	Name:  	Richard Houghton 	 
	 	 	Title:  	Chief Financial Officer 	 
	 

          IN WITNESS WHEREOF, the undersigned, being duly authorized, has executed this Second
Supplemental Indenture as of the date first above written.

	 	 	 	 	 
	 	DEUTSCHE BANK TRUST COMPANY AMERICAS, AS TRUSTEE

 	 
	 	By: Deutsche Bank National Trust Company

 	 
	 	By:  	                                  /s/ Kenneth R. Ring 	 
	 	 	Name:  	Kenneth R. Ring 	 
	 	 	Title:  	Vice President 	 
	 

	 	 	 	 	 
	 	By:  	                                  /s/ David Contino 	 
	 	 	Name:  	David Contino 	 
	 	 	Title:  	Vice President 	 

7

 

	 	 	 	 	 

EXHIBIT A

FORM OF SECURITY CERTIFICATE REPRESENTING SENIOR NOTES

ASPEN INSURANCE HOLDINGS LIMITED

6.00% SENIOR NOTES DUE 2020

UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST
COMPANY, A NEW YORK CORPORATION (“DTC”), TO ASPEN INSURANCE HOLDINGS LIMITED 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 DTC (AND
SUCH PAYMENT IS MADE TO CEDE & CO. OR TO SUCH OTHER ENTITY AS IS REQUESTED BY AN AUTHORIZED
REPRESENTATIVE OF DTC), ANY TRANSFER, PLEDGE OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO
ANY PERSON IS WRONGFUL INASMUCH AS THE REGISTERED OWNER, CEDE & CO., HAS AN INTEREST HEREIN.

UNLESS AND UNTIL THIS CERTIFICATE IS EXCHANGED IN WHOLE OR IN PART FOR SENIOR NOTES IN CERTIFICATED
FORM, THIS CERTIFICATE MAY NOT BE TRANSFERRED EXCEPT AS A WHOLE BY DTC TO A NOMINEE THEREOF OR BY A
NOMINEE THEREOF TO DTC OR ANOTHER NOMINEE OF DTC OR BY DTC OR ANY SUCH NOMINEE TO A SUCCESSOR OF
DTC OR A NOMINEE OF SUCH SUCCESSOR.

 

 

ASPEN INSURANCE HOLDINGS LIMITED

6.00% SENIOR NOTES DUE 2020

	 	 	 

	No. R1

	 	CUSIP No.: 04530DAC6; ISIN No.: US04530DAC65
	 
	 	 
	Principal Amount:

	 	$250,000,000
	 
	 	 
	Regular Record Date:

	 	June 1 or December 1, as the case may be,
immediately preceding each Interest Payment Date
	 
	 	 
	Original Issue Date:

	 	December 10, 2010
	 
	 	 
	Maturity Date:

	 	December 15, 2020
	 
	 	 
	Interest Payment Dates:

	 	June 15 and December 15
	 
	 	 
	Interest Rate:

	 	6.00% per annum
	 
	 	 
	Authorized Denomination:

	 	$2,000, or any integral multiple of $1,000 in
excess thereof

          Aspen Insurance Holdings Limited, a company duly existing and organized under the laws of
Bermuda (the “Company,” which term includes any successor corporation under the Indenture referred
to on the reverse hereof), for value received, hereby promises to pay to CEDE & CO., or registered
assigns, the Principal Amount shown above on the Maturity Date shown above, and to pay interest
thereon from the Original Issuance Date shown above, or from the most recent Interest Payment Date
to which interest has been paid or duly provided for, semi-annually in arrears on each Interest
Payment Date as specified above (including the Maturity Date), commencing on June 15, 2011, at the
rate of 6.00% per annum until the principal hereof is paid or duly provided for. Interest not
timely paid or provided for shall, to the extent permitted by applicable laws, bear simple interest
at the rate of 6.00% per annum. As provided in the Indenture, the Company under certain
circumstances would be required to pay Additional Amounts to the Holders of the Senior Notes.

          The interest so payable, and punctually paid or duly provided for, on any Interest Payment
Date (including the Maturity Date) will, as provided in the Indenture, be paid to the Person in
whose name this Senior Note is registered at the close of business on the Regular Record Date as
specified above next preceding each Interest Payment Date. Any such interest not so punctually
paid or duly provided for will forthwith cease to be payable to the Holder on such Regular Record
Date and may either be paid to the Person in whose name this Senior Note is registered at the close
of business on a Special Record Date for the payment of such defaulted interest established by
notice given by or on behalf of the Company to the Holders of Senior Notes not less than 15 days
prior to such Special Record Date, such Special Record Date to be not less than 10 days prior to
the date for payment of such defaulted interest, or be paid at any time in any other lawful manner
not inconsistent with the requirements of any securities exchange, if any, on which the Senior
Notes shall be listed, and upon such notice as may be required by any such exchange, all as more
fully provided in the Indenture.

 

 

          Payments of interest on this Senior Note will include interest accrued to but excluding the
respective Interest Payment Dates. Interest payments for this Senior Note shall be computed and
paid on the basis of a 360-day year of twelve 30-day months. In the event that any date on which
interest is payable on this Senior Note is not a Business Day, then payment of the interest payable
on such date will be made on the next succeeding day that is a Business Day, with the same force
and effect as if made on the date the payment was originally payable. A “Business Day” shall mean
each Monday, Tuesday, Wednesday, Thursday and Friday which is not a day on which banking
institutions in New York City are generally authorized or obligated, by law, regulation or
executive order to close.

          Payment of the principal of and interest due on the Maturity Date of this Senior Note shall be
made upon surrender of this Senior Note at the Corporate Trust Office of the Trustee. The
principal of and interest on this Senior Note shall be paid in Dollars. Payments of principal of
or interest will be made, subject to such surrender where applicable, at the option of the Company,
(i) by check mailed to the address of the Person entitled thereto as such address shall appear in
the Security Register or (ii) by wire transfer to an account maintained by the payee with a bank
located in the United States.

          REFERENCE IS HEREBY MADE TO THE FURTHER PROVISIONS OF THIS SENIOR NOTE SET FORTH ON THE
REVERSE HEREOF, WHICH FURTHER PROVISIONS SHALL FOR ALL PURPOSES HAVE THE SAME EFFECT AS IF SET
FORTH AT THIS PLACE.

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

 

 

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

Dated: December 10, 2010

	 	 	 	 	 
	 	ASPEN INSURANCE HOLDINGS LIMITED

 	 
	 	By:  	 	 
	 	 	Name:  	Christopher O’Kane 	 
	 	 	Title:  	Chief Executive Officer 	 
	 

	 	 	 	 	 
	 	By:  	
 	 
	 	 	Name:  	Richard Houghton 	 
	 	 	Title:  	Chief Financial Officer 	 

 

 

	 	 	 	 	 

CERTIFICATE OF AUTHENTICATION

          This is one of the 6.00% Senior Notes due 2020 referred to in the within-mentioned Indenture.

Dated: December 10, 2010

	 	 	 	 	 
	 	DEUTSCHE BANK TRUST COMPANY AMERICAS, as Trustee

 	 
	 	By:  	Deutsche Bank National Trust Company
 	 
	 	 	 	 

	 	 	 	 	 
	 	By:  	
 	 
	 	 	Authorized Signatory 	 
	 	 	 	 

 

 

	 	 	 	 	 

(reverse side of security)

          This security is one of a duly authorized issue of debt securities of the Company (hereinafter
called the “Securities”), all issued or to be issued under and pursuant to an Indenture, dated as
of August 16, 2004 (the “Original Indenture”), between the Company and Deutsche Bank Trust Company Americas,
as trustee (the “Trustee,” which term includes any successor trustee under the Indenture),
as supplemented by the Second Supplemental Indenture dated as of December 10, 2010
(the “Second Supplemental Indenture,” and together with the
Original Indenture, the “Indenture”), to which Indenture and all indentures supplemental thereto relating to this security (including, without
limitation, the Second Supplemental Indenture, dated as of December 10, 2010, between the Company
and the Trustee) reference is hereby made for a statement of the respective rights, limitation of
rights, duties and immunities thereunder of the Company, the Trustee and the Holders of the
Securities issued thereunder and of the terms upon which said Securities are, and are to be,
authenticated and delivered. The Securities may be issued in one or more series, which different
series may be issued in various aggregate principal amounts, may mature at different times, may
bear interest at different rates and may otherwise vary as provided in the Indenture or any
indenture supplemental thereto. This security is one of a series designated on the face as 6.00%
Senior Notes due 2020 (the “Senior Notes”), initially limited in aggregate principal amount to
$250,000,000, subject to increase as provided in Section 3.1 of the Indenture. Capitalized terms
used herein for which no definition is provided herein shall have the meanings set forth in the
Indenture.

          While this Senior Note is represented by one or more global notes registered in the name of
DTC or its nominee, the Company will cause payments of principal of, premium, if any, and interest
on this Senior Note to be made to DTC or its nominee, as the case may be, by wire transfer to the
extent, in the funds and in the manner required by agreements with, or regulations or procedures
prescribed from time to time by, DTC or its nominee, and otherwise in accordance with such
agreements, regulations and procedures.

          The Senior Notes will not have a sinking fund.

          The Senior Notes will be redeemable as a whole at any time or in part from time to time, at
the option of the Company, at a “make-whole” redemption price equal to the greater of (i) 100% of
the principal amount of the Senior Notes being redeemed or (ii) the sum of the present values of
the remaining scheduled payments of principal and interest (other than accrued interest) on the
Senior Notes being redeemed, 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 45 basis points, plus,
in either case, any interest accrued but not paid to the date of redemption. Notice of any
redemption will be mailed at least 30 days but no more than 60 days before the redemption date to
each Holder of the Senior Notes to be redeemed. Unless the Company defaults in payment of the
redemption price, on and after the redemption date, interest will cease to accrue on the Senior
Notes or portions thereof called for redemption.

          “Comparable Treasury Issue” means the United States Treasury security selected by a
Quotation Agent (as defined below) as having a maturity comparable to the remaining term of
the Senior Notes being 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 comparable maturity to the remaining term of such Senior Notes.

 

 

          “Comparable Treasury Price” means, with respect to any redemption date for the Senior
Notes, (1) the average of the Reference Treasury Dealer Quotations (as defined below) 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, or (3) if only one Reference Treasury Dealer
Quotation is received, such Reference Treasury Dealer Quotation.

          “Quotation Agent” means one of the Reference Treasury Dealers appointed by the Company.

          “Reference Treasury Dealer” means (1) each of Citigroup Global Markets Inc. and
Deutsche Bank Securities Inc. (or their respective affiliates that are Primary Treasury
Dealers) and their respective successors; provided, however, that if any of
the foregoing shall cease to be a primary U.S. Government securities dealer in New York City
(a “Primary Treasury Dealer”), the Company shall appoint therefor another Primary Treasury
Dealer as a substitute and (2) any other Primary Treasury Dealer selected by the Company.

          “Reference Treasury Dealer Quotations” means, for each Reference Treasury Dealer and
any redemption date, the average, as determined by the Quotation Agent, 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 Quotation Agent by such Reference Treasury Dealer
at 5:00 p.m., New York City time, on the third business day preceding the redemption date
for the Senior Notes being redeemed.

          “Treasury Rate” means, with respect to any redemption date for the Senior Notes, the
rate per year equal to the semi-annual equivalent yield to maturity 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 the
redemption date.

          The Company will mail a notice of redemption at least 30 days but no more than 60 days before
the redemption date to each Holder of the Securities to be redeemed. If less than all of the
Securities are to be redeemed, the Trustee will select, by such method as it will deem fair and
appropriate, including pro rata or by lot, the Securities to be redeemed in whole or in part.

          The Indenture contains provisions for redemption of the Senior Notes for tax purposes in whole
but not in part at the option of the Company.

          The Indenture also contains provisions for defeasance at any time of the entire indebtedness
of the Senior Notes or of certain restrictive covenants with respect to the Senior Notes, in each
case upon compliance with certain conditions set forth in the Indenture.

          If an Event of Default with respect to the Senior Notes shall occur and be continuing, the
principal of the Senior Notes may be declared due and payable in the manner, with the effect and
subject to the conditions provided in the Indenture.

 

 

          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
Senior Notes to be affected 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 principal amount of the Senior Notes at the
time Outstanding affected thereby. The Indenture also contains provisions permitting the Holders
of not less than a majority in principal amount of the Senior Notes at the time Outstanding, on
behalf of the Holders of all Senior Notes, to waive compliance by the Company with certain
provisions of the Indenture and certain past defaults under the Indenture and their consequences.
Any such consent or waiver by the Holder of this Senior Note shall be conclusive and binding upon
such Holder and upon all future Holders of this Senior Note and of any Senior 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 Senior Note.

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

          As provided in the Indenture and subject to certain limitations therein set forth, the
transfer of this Senior Note is registrable in the Security Register, upon surrender of this Senior
Note for registration of transfer at the office or agency of the Company for such purpose, duly
endorsed by, or accompanied by a written instrument of transfer in form satisfactory to the Company
and the Security Registrar and duly executed by, the Holder hereof or his attorney duly authorized
in writing, and thereupon one or more new Senior Notes, of authorized denominations and of like
tenor and for the same aggregate principal amount, will be issued to the designated transferee or
transferees. 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 or certain other expenses payable in connection therewith.

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

          The Senior Notes are issuable only in registered form without coupons in minimum denominations
of $2,000 and any integral multiple of $1,000 in excess thereof. As provided in the Indenture and
subject to certain limitations therein set forth, Senior Notes are exchangeable for a like
aggregate principal amount of Senior Notes of a different authorized denomination, as requested by
the Holder surrendering the same upon surrender of the Senior Note or Notes to be exchanged at the
office or agency of the Company.

          This Senior Note shall be governed by, and construed in accordance with, the laws of the State
of New York applicable to agreements made and performed in said state.

 

 

ABBREVIATIONS

          The following abbreviations, when used in the inscription on the face of this instrument,
shall be construed as though they were written out in full according to applicable laws or
regulations:

TEN
COM—as tenants in common                                                                         UNIF
GIFT MIN
ACT - __________ Custodian ___________

(Cust)                       (Minor)      

under Uniform Gifts to Minors

Act______________________

(State)

TEN ENT—as tenants by the entireties

	JT TEN— 	as joint tenants with rights of

survivorship and not as tenants

in common

Additional abbreviations may also be used though not on the above list.

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

(please
insert Social Security or other identifying number of ___________ assignee)

 

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

 

 

the within Senior Note and all rights thereunder, hereby irrevocably constituting and appointing

 

agent to transfer said Senior Note on the books of the Company 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 instrument in every particular
without alteration or enlargement, or
any change whatever. 	 
	 

9

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