Document:

Exhibit 4.5 

PREFERRED SECURITIES GUARANTEE AGREEMENT

BY AND BETWEEN

TOMPKINS FINANCIAL CORPORATION

AND

WILMINGTON TRUST COMPANY

DATED AS OF APRIL 10, 2009

TABLE OF CONTENTS

	
  

 	
  

 	
  

 	
  

 
	
 ARTICLE
 I. DEFINITIONS AND INTERPRETATION

 	
 1

 
	
 

 	
 Section
 1.1.

 	
 Definitions and Interpretation

 	
 1

 
	
 ARTICLE
 II. TRUST INDENTURE ACT

 	
 5

 
	
 

 	
 Section
 2.1.

 	
 Trust Indenture Act; Application

 	
 5

 
	
 

 	
 Section
 2.2.

 	
 The List of Holders of the Securities

 	
 5

 
	
 

 	
 Section
 2.3.

 	
 Reports by the Guarantor

 	
 5

 
	
 

 	
 Section
 2.4.

 	
 Periodic Reports to the Preferred Guarantee
 Trustee

 	
 5

 
	
 

 	
 Section
 2.5.

 	
 Evidence of Compliance with Conditions
 Precedent

 	
 5

 
	
 

 	
 Section
 2.6.

 	
 Events of Default; Waiver

 	
 6

 
	
 

 	
 Section 2.7.

 	
 Event of Default; Notice

 	
 6

 
	
 

 	
 Section 2.8.

 	
 Conflicting Interests

 	
 6

 
	
 ARTICLE III. POWERS, DUTIES AND RIGHTS OF THE PREFERRED GUARANTEE
 TRUSTEE

 	
 6

 
	
 

 	
 Section 3.1.

 	
 Powers and Duties of the Preferred
 Guarantee Trustee

 	
 6

 
	
 

 	
 Section 3.2.

 	
 Certain Rights of the Preferred Guarantee
 Trustee

 	
 8

 
	
 

 	
 Section 3.3.

 	
 Not Responsible for Recitals or Issuance of
 Guarantee

 	
 9

 
	
 ARTICLE IV. THE PREFERRED GUARANTEE TRUSTEE

 	
 10

 
	
 

 	
 Section 4.1.

 	
 The Preferred Guarantee Trustee;
 Eligibility

 	
 10

 
	
 

 	
 Section 4.2.

 	
 Appointment, Removal and Resignation of the
 Preferred Guarantee Trustee

 	
 10

 
	
 ARTICLE V. GUARANTEE

 	
 11

 
	
 

 	
 Section 5.1.

 	
 Guarantee

 	
 11

 
	
 

 	
 Section 5.2.

 	
 Waiver of Notice and Demand

 	
 11

 
	
 

 	
 Section 5.3.

 	
 Obligations not Affected

 	
 11

 
	
 

 	
 Section 5.4.

 	
 Rights of the Holders

 	
 12

 
	
 

 	
 Section 5.5.

 	
 Guarantee of Payment

 	
 13

 
	
 

 	
 Section 5.6.

 	
 Subrogation

 	
 13

 
	
 

 	
 Section 5.7.

 	
 Independent Obligations

 	
 13

 
	
 ARTICLE VI. LIMITATION OF TRANSACTIONS; SUBORDINATION

 	
 13

 
	
 

 	
 Section 6.1.

 	
 Limitation on Transactions

 	
 13

 
	
 

 	
 Section 6.2.

 	
 Ranking

 	
 13

 
	
 ARTICLE VII. TERMINATION

 	
 14

 
	
 

 	
 Section 7.1.

 	
 Termination

 	
 14

 
	
 ARTICLE VIII. INDEMNIFICATION AND COMPENSATION

 	
 14

 
	
 

 	
 Section 8.1.

 	
 Exculpation

 	
 14

 
	
 

 	
 Section 8.2.

 	
 Indemnification

 	
 15

 
	
 

 	
 Section 8.3.

 	
 Compensation

 	
 15

 
	
 ARTICLE IX. MISCELLANEOUS

 	
 16

 
	
 

 	
 Section 9.1.

 	
 Successors and Assigns

 	
 16

 
	
 

 	
 Section 9.2.

 	
 Amendments

 	
 16

 
	
 

 	
 Section 9.3.

 	
 Notices

 	
 16

 
	
 

 	
 Section 9.4.

 	
 Benefit

 	
 17

 
	
 

 	
 Section 9.5.

 	
 Governing Law

 	
 17

 
	
 

 	
 Section 9.6.

 	
 Counterparts

 	
 17

 
	
 

 	
 Section 9.7.

 	
 Separability

 	
 17

 
	
 

 	
 Section 9.8.

 	
 Limitation

 	
 17

 

2

PREFERRED SECURITIES GUARANTEE AGREEMENT

          This
PREFERRED SECURITIES GUARANTEE AGREEMENT (this “Preferred Securities
Guarantee”), dated as of April 10, 2009, is executed and delivered by TOMPKINS
FINANCIAL CORPORATION, a New York corporation (the “Guarantor”), and WILMINGTON
TRUST COMPANY, a banking corporation organized and existing under the laws of
Delaware, as trustee (the “Preferred Guarantee Trustee”), for the benefit of
the Holders (as defined herein) from time to time of the Preferred Securities
(as defined herein) of TOMPKINS CAPITAL TRUST I, a Delaware statutory trust
(the “Trust”). 

RECITALS

          WHEREAS,
pursuant to an Amended and Restated Trust Agreement (the “Trust Agreement”),
dated as of April 10, 2009, among the trustees of the Trust named therein, the
Guarantor, as depositor, and the holders from time to time of undivided
beneficial interests in the assets of the Trust, the Trust is issuing, in one
or more closings, the first of which is on the date hereof up to 30,000
preferred securities, having an aggregate liquidation amount of up to $30,000,000,
designated the 7.00% Cumulative Trust Preferred Securities (the “Preferred
Securities”); 

          WHEREAS, as
incentive for the Holders to purchase the Preferred Securities, the Guarantor
desires irrevocably and unconditionally to agree, to the extent set forth in
this Preferred Securities Guarantee, to pay to the Holders of the Preferred
Securities the Guarantee Payments (as defined herein) and to make certain other
payments on the terms and conditions set forth herein. 

          NOW,
THEREFORE, in consideration of the purchase by each Holder of Preferred
Securities, which purchase the Guarantor hereby agrees shall benefit the
Guarantor, the Guarantor executes and delivers this Preferred Securities
Guarantee for the benefit of the Holders. 

ARTICLE I.

DEFINITIONS AND INTERPRETATION

Section 1.1.     Definitions and Interpretation. In
this
Preferred Securities Guarantee, unless the context otherwise requires: 

          (a)     capitalized
terms used in this Preferred Securities Guarantee but not defined in the
preamble above have the respective meanings assigned to them in this Section
1.1; 

          (b)     terms
defined in the Trust Agreement as at the date of execution of this Preferred
Securities Guarantee have the same meaning when used in this Preferred
Securities Guarantee, unless otherwise defined in this Preferred Securities
Guarantee; 

          (c)     a
term defined anywhere in this Preferred Securities Guarantee has the same
meaning throughout; 

1

          (d)     all
references to “the Preferred Securities Guarantee” or “this Preferred
Securities Guarantee” are to this Preferred Securities Guarantee as modified,
supplemented or amended from time to time; 

          (e)     all
references in this Preferred Securities Guarantee to Articles and Sections are
to Articles and Sections of this Preferred Securities Guarantee, unless
otherwise specified; 

          (f)     a
term defined in the Trust Indenture Act has the same meaning when used in this
Preferred Securities Guarantee, unless otherwise defined in this Preferred
Securities Guarantee or unless the context otherwise requires; and 

          (g)     a
reference to the singular includes the plural and vice versa. 

          “Affiliate”
has the same meaning as given to that term in Rule 405 of the Securities Act of
1933, as amended, or any successor rule thereunder. 

          “Business
Day” means any day other than a Saturday, Sunday, a day on which federal or
state banking institutions in the Borough of Manhattan, the City of New York,
are authorized or required by law, executive order or regulation to close or a
day on which the Corporate Trust Office of the Preferred Guarantee Trustee is
closed for business. 

          “Code”
means the Internal Revenue Code of 1986, as amended. 

          “Corporate
Trust Office” means the office of the Preferred Guarantee Trustee at which the
corporate trust business of the Preferred Guarantee Trustee shall, at any
particular time, be principally administered, which office at the date of
execution of this Preferred Securities Guarantee is located at Rodney Square
North, 1100 North Market Street, Wilmington, Delaware 19890-0001, Attention:
Corporate Trust Administration. 

          “Covered
Person” means any Holder or beneficial owner of Preferred Securities. 

          “Debentures”
means the 7.00% Subordinated Debentures due 2039, of the Debenture Issuer held
by the Property Trustee of the Trust. 

          “Debenture
Issuer” means Tompkins Financial Corporation, issuer of the Debentures under
the Indenture. 

          “Event of
Default” means a default by the Guarantor on any of its payments or other
obligations under this Preferred Securities Guarantee. 

          “Guarantee
Payments” means the following payments or distributions, without duplication,
with respect to the Preferred Securities, to the extent not paid or made by the
Trust: (i) any accrued and unpaid Distributions that are required to be paid on
such Preferred Securities, to the extent the Trust shall have funds available
therefor, (ii) the redemption price, including all accrued and unpaid
Distributions to the date of redemption (the “Redemption Price”), to the extent
the Trust has funds available therefor, with respect to any Preferred
Securities called for redemption by the Trust, and (iii) upon a voluntary or
involuntary dissolution, winding-up or termination of the Trust (other than in
connection with the distribution of the Debentures to the Holders in exchange
for the Preferred Securities as provided in the Trust Agreement), the lesser of
(A) the aggregate of the Liquidation Amount and all accrued and unpaid
Distributions on the Preferred Securities to the date of payment, to the extent
the Trust shall have funds available therefor (the “Liquidation Distribution”),
and (B) the amount of assets of the Trust remaining available for distribution
to Holders in liquidation of the Trust.

2

          “Guarantor”
means Tompkins Financial Corporation, a New York corporation. 

          “Holder”
means a Person in whose name a Preferred Security is or Preferred Securities
are registered in the Securities Register; provided, however, that, in
determining whether the holders of the requisite percentage of the Preferred
Securities have given any request, notice, consent or waiver hereunder, “Holder”
shall not include the Guarantor, the Preferred Guarantee Trustee or any of
their respective Affiliates. 

          “Indemnified
Person” means the Preferred Guarantee Trustee, any Affiliate of the Preferred
Guarantee Trustee, or any officers, directors, shareholders, members, partners,
employees, representatives, nominees, custodians or agents of the Preferred
Guarantee Trustee. 

          “Indenture”
means the Indenture, dated as of April 10, 2009, among the Debenture Issuer and
Wilmington Trust Company, as trustee, and any indenture supplemental thereto
pursuant to which the Debentures are to be issued to the Property Trustee of
the Trust. 

          “Liquidation
Amount” means the stated value of $1,000 per Preferred Security. 

          “Liquidation
Distribution” has the meaning provided therefor in the definition of Guarantee
Payments. 

          “List of
Holders” has the meaning set forth in Section 2.2 of this Preferred Securities
Guarantee. 

          “Majority
in Liquidation Amount of the Preferred Securities” means the Holders of
more than 50% of the Liquidation Amount (including the stated amount that would
be paid on redemption, liquidation or otherwise, plus accrued and unpaid
Distributions to the date upon which the voting percentages are determined) of
all of the Preferred Securities. 

          “Officers’
Certificate” means, with respect to any Person, a certificate signed by two
authorized officers of such Person, at least one of whom shall be the principal
executive officer, principal financial officer, principal accounting officer,
treasurer or any vice president of such Person. Any Officers’ Certificate
delivered with respect to compliance with a condition or covenant provided for
in this Preferred Securities Guarantee shall include: 

          (a)     a
statement that each officer signing the Officers’ Certificate has read the
covenant or condition and the definition relating thereto; 

          (b)     a
brief statement of the nature and scope of the examination or investigation
undertaken by each officer in rendering the Officers’ Certificate; 

3

          (c)     a
statement that each such officer has made such examination or investigation as,
in such officer’s opinion, is necessary to enable such officer to express an informed
opinion as to whether or not such covenant or condition has been complied with;
and 

          (d)     a
statement as to whether, in the opinion of each such officer, such condition or
covenant has been complied with. 

          “Person”
means a legal person, including any individual, corporation, estate,
partnership, joint venture, association, joint stock company, limited liability
company, trust, unincorporated association, or government or any agency or
political subdivision thereof, or any other entity of whatever nature.” 

          “Preferred
Guarantee Trustee” means Wilmington Trust Company, until a Successor Preferred
Guarantee Trustee has been appointed and has accepted such appointment pursuant
to the terms of this Preferred Securities Guarantee and thereafter means each
such Successor Preferred Guarantee Trustee. 

          “Preferred
Securities” means the 7.00% Cumulative Trust Preferred Securities representing
undivided beneficial interests in the assets of the Trust which rank pari passu
with Common Securities issued by the Trust; provided, however, that upon the
occurrence of an Event of Default, the rights of holders of Commons Securities
to payment in respect of distributions and payments upon liquidation,
redemption and otherwise are subordinated to the rights of holders of Preferred
Securities. 

          “Redemption
Price” has the meaning provided therefor in the definition of Guarantee
Payments. 

          “Responsible
Officer” means, with respect to the Preferred Guarantee Trustee, any officer within
the Corporate Trust Office of the Preferred Guarantee Trustee with direct
responsibility for the administration of this Preferred Securities Guarantee,
including any vice-president, any assistant vice-president, the secretary, any
assistant secretary, the treasurer, any assistant treasurer or other officer of
the Corporate Trust Office of the Preferred Guarantee Trustee customarily
performing functions similar to those performed by any of the above designated
officers and also means, with respect to a particular corporate trust matter,
any other officer to whom such matter is referred because of that officer’s
knowledge of and familiarity with the particular subject. 

          “Securities
Register” and “Securities Registrar” have the meanings assigned to such terms
as in the Trust Agreement (as defined in the Indenture). 

          “Successor
Preferred Guarantee Trustee” means a successor Preferred Guarantee Trustee
possessing the qualifications to act as Preferred Guarantee Trustee under
Section 4.1. 

          “Trust
Indenture Act” means the Trust Indenture Act of 1939, as amended, as in force
at the date of which this instrument was executed; provided, however, that in
the event the Trust Indenture Act of 1939, as amended, is amended after such
date, “Trust Indenture Act” means, to the extent required by any such
amendment, the Trust Indenture Act of 1939, as so amended. 

4

ARTICLE II.

TRUST INDENTURE ACT

Section 2.1.     Trust Indenture Act; Application.

          (a)
     Notwithstanding any contrary provision herein
relating to the applicability of the Trust Indenture Act: 

                    (i)
     Any provision of the Trust Indenture Act, which
by its terms would apply to this Agreement (a “Mandatory TIA Provision”), will
control over any contrary terms contained herein; and, 

                    (ii)
     The terms of this Agreement will control over all
provisions of the Trust Indenture Act, except for Mandatory TIA Provisions. 

Section 2.2.     The List of Holders of the
Securities. 

          (a)
     In the event the Preferred Guarantee Trustee is
not also the Securities Registrar, the Guarantor shall provide the Preferred
Guarantee Trustee with a list, in such form as the Preferred Guarantee Trustee
may reasonably require, of the names and addresses of the Holders of the
Preferred Securities (the “List of Holders”) (i) within five (5) Business Days
after March 15, June 15, September 15 and December 15 of each year, and (ii) at
any other time within thirty (30) days of receipt by the Guarantor of a written
request for a List of Holders as of a date no more than fifteen (15) days
before such List of Holders is given to the Preferred Guarantee Trustee;
provided, that the Guarantor shall not be obligated to provide such List of
Holders at any time the List of Holders does not differ from the most recent
List of Holders given to the Preferred Guarantee Trustee by the Guarantor. The
Preferred Guarantee Trustee may destroy any List of Holders previously given to
it on receipt of a new List of Holders. 

          (b)
     The Preferred Guarantee Trustee shall comply with
its obligations under Sections 311(a), 311(b) and Section 312(b) of the Trust
Indenture Act. 

Section 2.3.     Reports by the Guarantor. The
Guarantor
shall provide directly to all Holders of the Preferred Securities, within
fifteen (15) days after the Guarantor files the same with the Commission,
copies of the annual reports and of the information, documents and other
reports (or copies of such portions of any of the foregoing as the Commission
may from time to time by rules and regulations prescribe) that the Guarantor is
required to provide to shareholders pursuant to the Exchange Act. 

Section 2.4.     Periodic Reports to the Preferred
Guarantee Trustee.
The Guarantor shall provide to the Preferred Guarantee Trustee such documents,
reports and information as required by Section 314 (if any) and the compliance
certificate required by Section 314 of the Trust Indenture Act in the form, in
the manner and at the times required by Section 314 of the Trust Indenture Act.

Section 2.5.     Evidence of Compliance with Conditions
Precedent.
The Guarantor shall provide to the Preferred Guarantee Trustee such evidence of
compliance with any conditions precedent, if any, provided for in this Preferred
Securities Guarantee that relate to any of the matters set forth in Section
314(c) of the Trust Indenture Act. Any certificate or opinion required to be
given by an officer pursuant to Section 314(c)(1) may be given in the form of
an Officers’ Certificate.

5

Section 2.6.     Events of Default; Waiver. The
Holders of
a Majority in Liquidation Amount of the Preferred Securities may, by vote, on
behalf of the Holders of all of the Preferred Securities, waive any past Event
of Default and its consequences. Upon such waiver, any such Event of Default
shall cease to exist, and any Event of Default arising therefrom shall be
deemed to have been cured, for every purpose of this Preferred Securities
Guarantee, but no such waiver shall extend to any subsequent or other default
or Event of Default or impair any right consequent thereon. 

Section 2.7.      Event of Default; Notice. 

          (a)
     The Preferred Guarantee Trustee shall, within
ninety (90) days after the occurrence of an Event of Default, transmit by mail,
first class postage prepaid, to the Holders of the Preferred Securities,
notices of all Events of Default actually known to a Responsible Officer of the
Preferred Guarantee Trustee, unless such defaults have been cured before the
giving of such notice; provided, that the Preferred Guarantee Trustee shall be
protected in withholding such notice if and so long as a Responsible Officer of
the Preferred Guarantee Trustee in good faith determines that the withholding
of such notice is in the interests of the Holders of the Preferred Securities. 

          (b)
     The Preferred Guarantee Trustee shall not be
deemed to have knowledge of any Event of Default unless the Preferred Guarantee
Trustee shall have received written notice, or a Responsible Officer of the
Preferred Guarantee Trustee charged with the administration of the Trust
Agreement shall have obtained actual knowledge of such Event of Default. 

Section 2.8.     Conflicting Interests. The Trust
Agreement
shall be deemed to be specifically described in this Preferred Securities
Guarantee for the purposes of clause (i) of the first proviso contained in
Section 310(b) of the Trust Indenture Act. 

ARTICLE III.

POWERS, DUTIES AND RIGHTS

OF THE PREFERRED GUARANTEE TRUSTEE

Section 3.1.     Powers and Duties of the Preferred
Guarantee Trustee.

          (a)
     This Preferred Securities Guarantee shall be held
by the Preferred Guarantee Trustee for the benefit of the Holders of the
Preferred Securities, and the Preferred Guarantee Trustee shall not transfer
this Preferred Securities Guarantee to any Person except a Holder of Preferred
Securities exercising his or her rights pursuant to Section 5.4(b) or to a
Successor Preferred Guarantee Trustee on acceptance by such Successor Preferred
Guarantee Trustee of its appointment to act as Successor Preferred Guarantee
Trustee. The right, title and interest of the Preferred Guarantee Trustee shall
automatically vest in any Successor Preferred Guarantee Trustee, and such
vesting and cessation of title shall be effective whether or not conveyancing
documents have been executed and delivered pursuant to the appointment of such
Successor Preferred Guarantee Trustee. 

6

          (b)
     If an Event of Default actually known to a
Responsible Officer of the Preferred Guarantee Trustee has occurred and is
continuing, the Preferred Guarantee Trustee shall enforce this Preferred
Securities Guarantee for the benefit of the Holders of the Preferred
Securities. 

          (c)
     The Preferred Guarantee Trustee, before the
occurrence of any Event of Default and after the curing of all Events of
Default that may have occurred, shall undertake to perform only such duties as
are specifically set forth in this Preferred Securities Guarantee, and no
implied covenants shall be read into this Preferred Securities Guarantee
against the Preferred Guarantee Trustee. In case an Event of Default has
occurred (that has not been cured or waived pursuant to Section 2.6) and is
actually known to a Responsible Officer of the Preferred Guarantee Trustee, the
Preferred Guarantee Trustee shall exercise such of the rights and powers vested
in it by this Preferred Securities Guarantee, and use the same degree of care
and skill in its exercise thereof, as a prudent man would exercise or use under
the circumstances in the conduct of his own affairs. 

          (d)
     No provision of this Preferred Securities
Guarantee shall be construed to relieve the Preferred Guarantee Trustee from
liability for its own negligent action, its own negligent failure to act, or
its own willful misconduct, except that: 

                    (i)
     prior to the occurrence of any Event of Default
and after the curing or waiving of all such Events of Default that may have
occurred: 

                              (a)
     the duties and obligations of the Preferred
Guarantee Trustee shall be determined solely by the express provisions of this
Preferred Securities Guarantee, and the Preferred Guarantee Trustee shall not
be liable except for the performance of such duties and obligations as are
specifically set forth in this Preferred Securities Guarantee, and no implied
covenants or obligations shall be read into this Preferred Securities Guarantee
against the Preferred Guarantee Trustee; and 

                              (b)
     in the absence of bad faith on the part of the
Preferred Guarantee Trustee, the Preferred Guarantee Trustee may conclusively
rely, as to the truth of the statements and the correctness of the opinions
expressed therein, upon any certificates or opinions furnished to the Preferred
Guarantee Trustee and conforming to the requirements of this Preferred
Securities Guarantee; but in the case of any such certificates or opinions that
by any provision hereof are specifically required to be furnished to the
Preferred Guarantee Trustee, the Preferred Guarantee Trustee shall be under a
duty to examine the same to determine whether or not they conform to the
requirements of this Preferred Securities Guarantee; 

                    (ii)
     the Preferred Guarantee Trustee shall not be
liable for any error of judgment made in good faith by a Responsible Officer of
the Preferred Guarantee Trustee, unless it shall be proved that the Preferred
Guarantee Trustee was negligent in ascertaining the pertinent facts upon which
such judgment was made; 

                    (iii)
the Preferred Guarantee Trustee shall not be liable with respect to any action
taken or omitted to be taken by it in good faith in accordance with the
direction of the Holders of not less than a Majority in Liquidation Amount of
the Preferred Securities relating to the time, method and place of conducting
any proceeding for any remedy available to the Preferred Guarantee Trustee, or
exercising any trust or power conferred upon the Preferred Guarantee Trustee
under this Preferred Securities Guarantee; an

7

                    (iv)
no provision of this Preferred Securities Guarantee shall require the Preferred
Guarantee Trustee to expend or risk its own funds or otherwise incur personal
financial liability in the performance of any of its duties or in the exercise
of any of its rights or powers, if the Preferred Guarantee Trustee shall have
reasonable grounds for believing that the repayment of such funds or liability
is not reasonably assured to it under the terms of this Preferred Securities
Guarantee or indemnity, reasonably satisfactory to the Preferred Guarantee
Trustee, against such risk or liability is not reasonably assured to it. 

Section 3.2.     Certain Rights of the Preferred Guarantee
Trustee.

          (a)
     Subject to the provisions of Section 3.1: 

                    (i)
     the Preferred Guarantee Trustee may conclusively
rely, and shall be fully protected in acting or refraining from acting upon,
any written resolution, certificate, statement, instrument, opinion, report,
notice, request, direction, consent, order, bond, debenture, note, other
evidence of indebtedness or other paper or document believed by it to be
genuine and to have been signed, sent or presented by the proper party or
parties; 

                    (ii)
     any direction or act of the Guarantor
contemplated by this Preferred Securities Guarantee shall be sufficiently
evidenced by an Officers’ Certificate; 

                    (iii)     whenever,
in the administration of this Preferred Securities Guarantee, the Preferred
Guarantee Trustee shall deem it desirable that a matter be proved or
established before taking, suffering or omitting any action hereunder, the
Preferred Guarantee Trustee (unless other evidence is herein specifically
prescribed) may, in the absence of bad faith on its part, request and
conclusively rely upon an Officers’ Certificate which, upon receipt of such
request, shall be promptly delivered by the Guarantor; 

                    (iv)     the
Preferred Guarantee Trustee shall have no duty to see to any recording, filing
or registration of any instrument (or any rerecording, refiling or registration
thereof); 

                    
(v)      the Preferred Guarantee Trustee may consult
with counsel, and the written advice or opinion of such counsel with respect to
legal matters shall be full and complete authorization and protection in
respect of any action taken, suffered or omitted by it hereunder in good faith
and in accordance with such advice or opinion. Such counsel may be counsel to
the Guarantor or any of its Affiliates and may include any of its employees.
The Preferred Guarantee Trustee shall have the right at any time to seek
instructions concerning the administration of this Preferred Securities
Guarantee from any court of competent jurisdiction; 

                    (vi)     the
Preferred Guarantee Trustee shall be under no obligation to exercise any of the
rights or powers vested in it by this Preferred Securities Guarantee at the request
or direction of any Holder, unless such Holder shall have provided to the
Preferred Guarantee Trustee such security and indemnity, reasonably
satisfactory to the Preferred Guarantee Trustee, against the costs, expenses
(including reasonable attorneys’ fees and expenses and the expenses of the
Preferred Guarantee Trustee’s agents, nominees or custodians) and liabilities
that might be incurred by it in complying with such request or direction,
including such reasonable advances as may be requested by the Preferred
Guarantee Trustee; provided that, nothing contained in this Section 3.2(a)(vi)
shall be taken to relieve the Preferred Guarantee Trustee, upon the occurrence
and during the continuance of an Event of Default, of its obligation to
exercise the rights and powers vested in it by this Preferred Securities
Guarantee;

8

                    (vii)          the
Preferred Guarantee Trustee shall not be bound to make any investigation into
the facts or matters stated in any written resolution, certificate, statement,
instrument, opinion, report, notice, request, direction, consent, order, bond,
debenture, note, other evidence of indebtedness or other paper or document, but
the Preferred Guarantee Trustee, in its discretion, may make such further
inquiry or investigation into such facts or matters as it may see fit; 

                    (viii)     the
Preferred Guarantee Trustee may execute any of the trusts or powers hereunder
or perform any duties hereunder either directly or by or through agents, nominees,
custodians or attorneys, and the Preferred Guarantee Trustee shall not be
responsible for any misconduct or negligence on the part of any agent or
attorney appointed with due care by it hereunder; 

                    (ix)     no
third party shall be required to inquire as to the authority of the Preferred
Guarantee Trustee to so act or as to its compliance with any of the terms and
provisions of this Preferred Securities Guarantee, both of which shall be
conclusively evidenced by the Preferred Guarantee Trustee’s or its agent’s
taking such action; 

                    (x)     whenever
in the administration of this Preferred Securities Guarantee the Preferred
Guarantee Trustee shall deem it desirable to receive instructions with respect
to enforcing any remedy or right or taking any other action hereunder, the
Preferred Guarantee Trustee (A) may request instructions from the Holders of a
Majority in Liquidation Amount of the Preferred Securities, (B) may refrain
from enforcing such remedy or right or taking such other action until such
instructions are received, and (C) shall be protected in conclusively relying
on or acting in accordance with such instructions. 

          (b)     No
provision of this Preferred Securities Guarantee shall be deemed to impose any
duty or obligation on the Preferred Guarantee Trustee to perform any act or
acts or exercise any right, power, duty or obligation conferred or imposed on
it in any jurisdiction in which it shall be illegal, or in which the Preferred
Guarantee Trustee shall be unqualified or incompetent in accordance with
applicable law, to perform any such act or acts or to exercise any such right,
power, duty or obligation. No permissive power or authority available to the
Preferred Guarantee Trustee shall be construed to be a duty. 

Section 3.3.     Not Responsible for Recitals or Issuance
of Guarantee.
The Recitals contained in this Guarantee shall be taken as the statements of
the Guarantor, and the Preferred Guarantee Trustee does not assume any
responsibility for their correctness. The Preferred Guarantee Trustee makes no
representation as to the validity or sufficiency of this Preferred Securities
Guarantee. 

9

ARTICLE IV.

THE PREFERRED GUARANTEE TRUSTEE

Section 4.1.     The Preferred Guarantee Trustee;
Eligibility.

          (a)     There
shall at all times be a Preferred Guarantee Trustee which shall: 

                    (i)     not
be an Affiliate of the Guarantor; and 

                    (ii)     be
a corporation organized and doing business under the laws of the United States
or any state or territory thereof or of the District of Columbia, or a
corporation or Person permitted by the Securities and Exchange Commission to
act as an institutional trustee under the Trust Indenture Act, authorized under
such laws to exercise corporate trust powers, having a combined capital and
surplus of at least $50,000,000, and subject to supervision or examination by
federal, state, territorial or District of Columbia authority. If such
corporation publishes reports of condition at least annually, pursuant to law
or to the requirements of the supervising or examining authority referred to
above, then, for the purposes of this Section 4.1(a)(ii), the combined capital
and surplus of such corporation shall be deemed to be its combined capital and
surplus as set forth in its most recent report of condition so published. 

          (b)     If
at any time the Preferred Guarantee Trustee shall cease to be eligible to so
act under Section 4.1(a), the Preferred Guarantee Trustee shall immediately
resign in the manner and with the effect set out in Section 4.2(c). 

          (c)     If
the Preferred Guarantee Trustee has or shall acquire any “conflicting interest”
within the meaning of Section 310(b) of the Trust Indenture Act, the Preferred
Guarantee Trustee and the Guarantor shall in all respects comply with the
provisions of Section 310(b) of the Trust Indenture Act. 

Section 4.2.     Appointment, Removal and Resignation of
the Preferred
Guarantee Trustee. 

          (a)     Subject
to Section 4.2(b), the Preferred Guarantee Trustee may be appointed or removed
without cause at any time by the Guarantor except during an Event of Default. 

          (b)     The
Preferred Guarantee Trustee shall not be removed in accordance with Section 4.2(a)
until a Successor Preferred Guarantee Trustee has been appointed and has
accepted such appointment by written instrument executed by such Successor
Preferred Guarantee Trustee and delivered to the Guarantor. 

          (c)     The
Preferred Guarantee Trustee appointed to office shall hold office until a
Successor Preferred Guarantee Trustee shall have been appointed or until its
removal or resignation. The Preferred Guarantee Trustee may resign from office
(without need for prior or subsequent accounting) by an instrument in writing
executed by the Preferred Guarantee Trustee and delivered to the Guarantor,
which resignation shall not take effect until a Successor Preferred Guarantee
Trustee has been appointed and has accepted such appointment by instrument in
writing executed by such Successor Preferred Guarantee Trustee and delivered to
the Guarantor and the resigning Preferred Guarantee Trustee. 

10

          (d)     If
no Successor Preferred Guarantee Trustee shall have been appointed and accepted
appointment as provided in this Section 4.2 within sixty (60) days after
delivery to the Guarantor of an instrument of resignation, the resigning
Preferred Guarantee Trustee, at the expense of the Guarantor, may petition any
court of competent jurisdiction for appointment of a Successor Preferred
Guarantee Trustee. Such court may thereupon, after prescribing such notice, if
any, as it may deem proper, appoint a Successor Preferred Guarantee Trustee. 

          (e)     No
Preferred Guarantee Trustee shall be liable for the acts or omissions to act of
any Successor Preferred Guarantee Trustee. 

          (f)     Upon
termination of this Preferred Securities Guarantee or removal or resignation of
the Preferred Guarantee Trustee pursuant to this Section 4.2, the Guarantor
shall pay to the Preferred Guarantee Trustee all fees and expenses accrued to
the date of such termination, removal or resignation. 

ARTICLE V.

GUARANTEE

Section 5.1.     Guarantee. The Guarantor irrevocably
and
unconditionally agrees to pay in full to the Holders the Guarantee Payments
(without duplication of amounts theretofore paid by the Trust), as and when
due, regardless of any defense, right of set-off or counterclaim that the Trust
may have or assert. The Guarantor’s obligation to make a Guarantee Payment may
be satisfied by direct payment of the required amounts by the Guarantor to the
Holders or by causing the Trust to pay such amounts to the Holders. 

Section 5.2.     Waiver of Notice and Demand. The
Guarantor
hereby waives notice of acceptance of this Preferred Securities Guarantee and
of any liability to which it applies or may apply, presentment, demand for
payment, any right to require a proceeding first against the Trust or any other
Person before proceeding against the Guarantor, protest, notice of nonpayment,
notice of dishonor, notice of redemption and all other notices and demands. 

Section 5.3.     Obligations not Affected. The
obligations,
covenants, agreements and duties of the Guarantor under this Preferred
Securities Guarantee shall in no way be affected or impaired by reason of the
happening from time to time of any of the following: 

          (a)     the
release or waiver, by operation of law or otherwise, of the performance or
observance by the Trust of any express or implied agreement, covenant, term or
condition relating to the Preferred Securities to be performed or observed by
the Trust; 

          (b)     the
extension of time for the payment by the Trust of all or any portion of the
Distributions, Redemption Price, Liquidation Distribution or any other sums
payable under the terms of the Preferred Securities or the extension of time
for the performance of any other obligation under, arising out of, or in
connection with, the Preferred Securities (other than an extension of time for
payment of Distributions, Redemption Price, Liquidation Distribution or other
sum payable that results from the extension of any interest payment period on
the Debentures permitted by the Indenture); 

11

          (c)     any
failure, omission, delay or lack of diligence on the part of the Holders to
enforce, assert or exercise any right, privilege, power or remedy conferred on
the Holders pursuant to the terms of the Preferred Securities, or any action on
the part of the Trust granting indulgence or extension of any kind; 

          (d)     the
voluntary or involuntary liquidation, dissolution, sale of any collateral,
receivership, insolvency, bankruptcy, assignment for the benefit of creditors,
reorganization, arrangement, composition or readjustment of debt of, or other
similar proceedings affecting, the Trust or any of the assets of the Trust; 

          (e)     any
invalidity of, or defect or deficiency in, the Preferred Securities; 

          (f)     any
failure or omission to receive any regulatory approval or consent required in
connection with the Preferred Securities (or the common equity securities
issued by the Trust), including the failure to receive any approval of the
Board of Governors of the Federal Reserve System required for the redemption of
the Preferred Securities; 

          (g)     the
settlement or compromise of any obligation guaranteed hereby or hereby
incurred; or 

          (h)     any
other circumstance whatsoever that might otherwise constitute a legal or equitable
discharge or defense of a guarantor, it being the intent of this Section 5.3
that the obligations of the Guarantor hereunder shall be absolute and
unconditional under any and all circumstances. 

          There shall
be no obligation of the Holders to give notice to, or obtain consent of, the
Guarantor with respect to the happening of any of the foregoing. 

Section 5.4.     Rights of the Holders. 

          (a)     The
Holders of a Majority in Liquidation Amount of the Preferred Securities have
the right to direct the time, method and place of conducting any proceeding for
any remedy available to the Preferred Guarantee Trustee in respect of this
Preferred Securities Guarantee or exercising any trust or power conferred upon
the Preferred Guarantee Trustee under this Preferred Securities Guarantee;
provided, however, that (subject to Section 3.1) the Preferred Guarantee
Trustee shall have the right to decline to follow any such direction if the
Preferred Guarantee Trustee being advised in writing by counsel determines that
the action or proceeding so directed may not lawfully be taken or if the
Preferred Guarantee Trustee in good faith by its board of directors or
trustees, executive committees or a trust committee of directors or trustees
and/or Responsible Officers shall determine that the action or proceedings so
directed would involve the Preferred Guarantee Trustee in personal liability. 

          (b)     Any
Holder of Preferred Securities may institute and prosecute a legal proceeding
directly against the Guarantor to enforce its rights under this Preferred
Securities Guarantee, without first instituting a legal proceeding against the
Trust, the Preferred Guarantee Trustee or any other Person. 

12

Section 5.5.     Guarantee of Payment. This Preferred
Securities Guarantee creates a guarantee of payment and not of collection. 

Section 5.6.     Subrogation. The Guarantor shall be
subrogated to all (if any) rights of the Holders of the Preferred Securities
against the Trust in respect of any amounts paid to such Holders by the
Guarantor under this Preferred Securities Guarantee; provided, however, that
the Guarantor shall not (except to the extent required by mandatory provisions
of law) be entitled to enforce or exercise any right that it may acquire by way
of subrogation or any indemnity, reimbursement or other agreement, in all cases
as a result of payment under this Preferred Securities Guarantee, if, at the
time of any such payment, any amounts are due and unpaid under this Preferred
Securities Guarantee. If any amount shall be paid to the Guarantor in violation
of the preceding sentence, the Guarantor agrees to hold such amount in trust
for the Holders and to pay over such amount to the Holders. 

Section 5.7.     Independent Obligations. The
Guarantor acknowledges
that its obligations hereunder are independent of the obligations of the Trust
with respect to the Preferred Securities, and that the Guarantor shall be
liable as principal and as debtor hereunder to make Guarantee Payments pursuant
to the terms of this Preferred Securities Guarantee notwithstanding the
occurrence of any event referred to in subsections (a) through (h), inclusive,
of Section 5.3 hereof. 

ARTICLE VI.

LIMITATION OF TRANSACTIONS; SUBORDINATION 

Section 6.1.     Limitation on Transactions. So long
as any
of the Preferred Securities remain outstanding, if any of the circumstances
described in Section 5.6 of the Indenture shall have occurred, then (a) neither
the Guarantor nor any of its Subsidiaries (as defined in the Indenture) shall
declare or pay any dividend on, make any distributions with respect to, or
redeem, purchase, acquire or make a liquidation payment with respect to, any of
its capital stock (other than (i) dividends or distributions in common stock of
the Guarantor or any declaration of a non-cash dividend in connection with the
implementation of a shareholder rights plan, or the issuance of stock under any
such plan in the future, or the redemption or repurchase of any such rights
pursuant thereto, (ii) purchases of common stock of the Guarantor related to
the rights under any of the Guarantor’s benefit plans for its directors,
officers or employees, (iii) as a result of a reclassification of its capital
stock, (iv) dividends or distributions made by a Subsidiary to the Company, or
(v) dividends or distributions made by a Subsidiary to a Subsidiary), and (b)
neither the Guarantor nor any Subsidiary shall make any payment of principal or
interest on or repay, repurchase or redeem any debt securities issued by the
Guarantor or any Subsidiary which rank pari passu with or junior to the
Debentures or make any guarantee payments with respect to any guarantee by the
Guarantor of any debt securities if such guarantee ranks pari passu or junior
in interest to the Debentures, other than payments under this Preferred
Securities Guarantee. 

Section 6.2.     Ranking. This Preferred Securities
Guarantee will constitute an unsecured obligation of the Guarantor and will
rank (a) subordinate and junior in right of payment to all Senior Debt,
Subordinated Debt and Additional Senior Obligations (as defined in the
Indenture) of the Guarantor, (b) pari passu with any guarantee now or hereafter
entered into by the Guarantor in respect of any preferred securities or
preference stock of any Affiliate of the Guarantor and (c) senior to the most
senior preferred securities or preference stock now or hereafter issued by the
Guarantor and senior to the Guarantor’s common stock.

13

          The right
of the Guarantor to participate in any distribution of assets of any of its
Subsidiaries upon any such Subsidiary’s liquidation or reorganization or
otherwise is subject to the prior claims of creditors of that Subsidiary,
except to the extent the Guarantor may itself be recognized as a creditor of
that Subsidiary. Accordingly, the Guarantor’s obligations under this Preferred
Securities Guarantee will be effectively subordinated to all existing and
future liabilities of the Guarantor’s Subsidiaries, and claimants should look
only to the assets of the Guarantor for payments hereunder. This Preferred
Securities Guarantee does not limit the incurrence or issuance of other secured
or unsecured debt of the Guarantor, including Senior Debt of the Guarantor,
under any indenture that the Guarantor may enter into in the future or
otherwise. 

ARTICLE VII.

TERMINATION

Section 7.1.     Termination. This Preferred Securities
Guarantee shall terminate upon (a) full payment of the Redemption Price of all
the Preferred Securities, (b) full payment of the amounts payable in accordance
with the Trust Agreement upon liquidation of the Trust, or (c) distribution of
the Debentures to the Holders of the Preferred Securities. Notwithstanding the
foregoing, this Preferred Securities Guarantee shall continue to be effective
or shall be reinstated, as the case may be, if at any time any Holder of
Preferred Securities must restore payment of any sums paid under the Preferred
Securities or under this Preferred Securities Guarantee. 

ARTICLE VIII.

INDEMNIFICATION AND COMPENSATION 

Section 8.1.     Exculpation. 

          (a)     No
Indemnified Person shall be liable, responsible or accountable in damages or
otherwise to the Guarantor or any Covered Person for any loss, damage or claim
incurred by reason of any act or omission performed or omitted by such
Indemnified Person in good faith in accordance with this Preferred Securities
Guarantee and in a manner that such Indemnified Person reasonably believed to
be within the scope of the authority conferred on such Indemnified Person by
this Preferred Securities Guarantee or by law, except that an Indemnified
Person shall be liable for any such loss, damage or claim incurred by reason of
such Indemnified Person’s negligence or willful misconduct with respect to such
acts or omissions. 

          (b)     An
Indemnified Person shall be fully protected in relying in good faith upon the
records of the Guarantor and upon such information, opinions, reports or
statements presented to the Guarantor by any Person as to matters the
Indemnified Person reasonably believes are within such other Person’s
professional or expert competence, including information, opinions, reports or
statements as to the value and amount of the assets, liabilities, profits,
losses, or any other facts pertinent to the existence and amount of assets from
which Distributions to the Holders of the Preferred Securities might properly
be paid. 

14

Section 8.2.     Indemnification. 

          (a)     The
Guarantor agrees to indemnify each Indemnified Person for, and to hold each
Indemnified Person harmless against, any loss, liability or expense incurred
without negligence or bad faith on its part, arising out of or in connection
with the acceptance or administration of the trust or trusts hereunder,
including the costs and expenses (including reasonable legal fees and expenses)
of defending itself against, or investigating, any claim or liability in
connection with the exercise or performance of any of its powers or duties
hereunder. The obligation to indemnify as set forth in this Section 8.2 shall
survive the termination of this Preferred Securities Guarantee. 

          (b)     Promptly
after receipt by an Indemnified Person under this Section 8.2 of notice of the
commencement of any action, such Indemnified Person will, if a claim in respect
thereof is to be made against the Guarantor under this Section 8.2, notify the
Guarantor in writing of the commencement thereof; but the failure so to notify
the Guarantor (i) will not relieve the Guarantor from liability under paragraph
(a) above unless and to the extent that the Guarantor did not otherwise learn
of such action and such failure results in the forfeiture by the Guarantor of
substantial rights and defenses and (ii) will not, in any event, relieve the
Guarantor from any obligations to any Indemnified Person other than the
indemnification obligation provided in paragraph (a) above. The Guarantor shall
be entitled to appoint counsel of the Guarantor’s choice at the Guarantor’s
expense to represent the Indemnified Person in any action for which
indemnification is sought (in which case the Guarantor shall not thereafter be
responsible for the fees and expenses of any separate counsel retained by the
Indemnified Person or Persons except as set forth below); provided, however,
that such counsel shall be reasonably satisfactory to the Indemnified Person.
Notwithstanding the Guarantor’s election to appoint counsel to represent the
Guarantor in an action, the Indemnified Person shall have the right to employ
separate counsel (including local counsel), and the Guarantor shall bear the
reasonable fees, costs and expenses of such separate counsel if (i) the use of
counsel chosen by the Guarantor to represent the Indemnified Person would
present such counsel with a conflict of interest, (ii) the actual or potential
defendants in, or targets of, any such action include both the Indemnified
Person and the Guarantor and the Indemnified Person shall have reasonably
concluded that there may be legal defenses available to it and/or other
Indemnified Person(s) which are different from or additional to those available
to the Guarantor, (iii) the Guarantor shall not have employed counsel
satisfactory to the Indemnified Person to represent the Indemnified Person
within a reasonable time after notice of the institution of such action or (iv)
the Guarantor shall authorize the Indemnified Person to employ separate counsel
at the expense of the Guarantor. The Guarantor will not, without the prior
written consent of the Indemnified Persons, settle or compromise or consent to
the entry of any judgment with respect to any pending or threatened claim,
action, suit or proceeding in respect of which indemnification or contribution
may be sought hereunder (whether or not the Indemnified Persons are actual or
potential parties to such claim or action) unless such settlement, compromise
or consent includes an unconditional release of each Indemnified Person from
all liability arising out of such claim, action, suit or proceeding. 

Section 8.3.     Compensation. The Guarantor agrees
(i) to pay to the
Guarantee Trustee from time to time such reasonable compensation for all
services rendered by it hereunder as may be agreed by the Guarantor and the
Guarantee Trustee from time to time (which compensation shall not be limited by
any provision of law in regard to the compensation of a trustee of an express
trust) and (ii) except as otherwise expressly provided herein, to reimburse the
Guarantee Trustee upon request for all reasonable expenses, disbursements and
advances incurred or made by the Guarantee Trustee in accordance with any
provision of this Guarantee Agreement (including the reasonable compensation
and the expenses and disbursements of its agents and counsel), except any such
expense, disbursement or advance as may be attributable to its negligence or
willful misconduct.

15

ARTICLE IX.

MISCELLANEOUS

Section 9.1.     Successors and Assigns. All
guarantees and agreements
contained in this Preferred Securities Guarantee shall bind the successors,
assigns, receivers, trustees and representatives of the Guarantor and shall
inure to the benefit of the Holders of the Preferred Securities then
outstanding. Except in connection with any merger or consolidation of the
Guarantor with or into another entity or any sale, transfer or lease of the
Guarantor’s assets to another entity, in each case, to the extent permitted
under the Indenture, the Guarantor may not assign its rights or delegate its
obligations under this Guarantee without the prior approval of the Holders of
at least a Majority in Liquidation Amount of the Preferred Securities.

Section 9.2.     Amendments. Except with respect to
any changes that do not
adversely affect the rights of the Holders (in which case no consent of the
Holders will be required), this Preferred Securities Guarantee may only be
amended with the prior approval of the Holders of at least a Majority in
Liquidation Amount of the Preferred Securities. The provisions of Article VI of
the Trust Agreement with respect to meetings of the Holders of the Preferred Securities
apply to the giving of such approval.

Section 9.3.     Notices. All notices provided for in
this Preferred
Securities Guarantee shall be in writing, duly signed by the party giving such
notice, and shall be delivered, telecopied or mailed by registered or certified
mail, as follows: 

          (a)     If
given to the Preferred Guarantee Trustee, at the Preferred Guarantee Trustee’s
mailing address set forth below (or such other address as the Preferred Guarantee
Trustee may give notice of to the Holders of the Preferred Securities):

Wilmington Trust Company
Rodney Square North
1100 North Market Street

Wilmington, Delaware 19890-0001
Attention: Corporate Trust Administration

          (b)     If
given to the Guarantor, at the Guarantor’s mailing address set forth below (or
such other address as the Guarantor may give notice of to the Holders of the
Preferred Securities):

Tompkins Financial Corporation
110 North Tioga Street
Ithaca, New York 14850
Attention: Chief Financial Officer

16

          (c)     If
given to any Holder of Preferred Securities, at the address set forth on the
books and records of the Trust. 

          All such
notices shall be deemed to have been given when received in person, telecopied
with receipt confirmed, or mailed by first class mail, postage prepaid except
that if a notice or other document is refused delivery or cannot be delivered
because of a changed address of which no notice was given, such notice or other
document shall be deemed to have been delivered on the date of such refusal or
inability to deliver. 

Section 9.4.     Benefit. This Preferred Securities
Guarantee is solely for the benefit of the Holders of the Preferred Securities
and, subject to Section 3.1(a), is not separately transferable from the
Preferred Securities. 

Section 9.5.     Governing Law. THIS PREFERRED
SECURITIES
GUARANTEE SHALL BE GOVERNED BY, AND CONSTRUED AND INTERPRETED IN ACCORDANCE
WITH THE LAWS OF THE STATE OF DELAWARE (WITHOUT REGARD TO CONFLICT OF LAWS
PRINCIPLES). 

Section 9.6.     Counterparts. This Preferred
Securities
Guarantee may be executed in one or more counterparts, each of which shall be
an original, but all of which taken together shall constitute one and the same
instrument. 

Section 9.7.     Separability. In case one or more of
the
provisions contained in this Preferred Securities Guarantee shall for any
reason be held to be invalid, illegal or unenforceable in any respect, such
invalidity, illegality or unenforceability shall not affect any other
provisions of this Preferred Securities Guarantee, but this Preferred
Securities Guarantee shall be construed as if such invalid or illegal or
unenforceable provision had never been contained herein. 

Section 9.8.     Limitation. To the extent that the
laws of
the Commonwealth of Kentucky are applicable to any matters of construction,
validity or performance of this Preferred Securities Guarantee, (a) the maximum
aggregate liability of the Guarantor under this Preferred Securities Guarantee
shall not exceed $30,000,000 plus interest accruing on the guaranteed
indebtedness (and interest accruing on such interest), and fees, charges and
costs of collecting such guaranteed indebtedness, including reasonable
attorney’s fees, and (b) unless terminated earlier in accordance with the terms
hereof, this Preferred Securities Guarantee will terminate on March 31, 2039,
but such termination shall not relieve the Guarantor from liability with
respect to renewals of interest accruing on, or fees, costs or expenses
incurred with respect to such obligation on or after such date. 

 [Signature Page Immediately Follows.]

17

This Preferred Securities Guarantee is executed as of the day and year
first above written. 

	
  

 	
  

 	
  

 
	
  

 	
 TOMPKINS
 FINANCIAL CORPORATION,

 
	
  

 	
 as Guarantor

 
	
  

 	
  

 	
  

 
	
  

 	
 By:

 	
 /s/ Francis
 M. Fetsko

 
	
  

 	
  

 	 

 
	
  

 	
 Name:

 	
 Francis M.
 Fetsko

 
	
  

 	
 Title:

 	
 Executive
 Vice President & Chief Financial Officer

 
	
  

 	
  

 	
  

 
	
  

 	
 WILMINGTON
 TRUST COMPANY,

 
	
  

 	
 as Preferred
 Guarantee Trustee

 
	
  

 	
  

 	
  

 
	
  

 	
 By:

 	
 /s/ Lori
 Donahue

 
	
  

 	
  

 	 

 
	
  

 	
 Name:

 	
 Lori Donahue

 
	
  

 	
 Title:

 	
 Assistant
 Vice President

 

18Exhibit 4.6

AGREEMENT AS TO EXPENSES AND LIABILITIES

          AGREEMENT
AS TO EXPENSES AND LIABILITIES (this “Agreement”) dated as of April 10, 2009,
between TOMPKINS FINANCIAL CORPORATION, a New York corporation (the “Company”),
and TOMPKINS CAPITAL TRUST I, a Delaware statutory trust (the “Trust”).

RECITALS

          WHEREAS,
the Trust intends to issue its common securities (the “Common Securities”) to,
and receive 7.00% Subordinated Debentures (the “Debentures”) from, the Company
and to issue and sell up to 30,000 7.00% Cumulative Trust Preferred Securities
(the “Preferred Securities”) with such powers, preferences and special rights
and restrictions as are set forth in the Amended and Restated Trust Agreement
of the Trust dated as of April 10, 2009, as the same may be amended from time
to time (the “Trust Agreement”);

          WHEREAS,
the Company shall directly or indirectly own all of the Common Securities of
the Trust and shall issue the Debentures;

          NOW,
THEREFORE, in consideration of the purchase by each holder of the Preferred
Securities, which purchase the Company hereby agrees shall benefit the Company
and which purchase the Company acknowledges shall be made in reliance upon the
execution and delivery of this Agreement, the Company, including in its
capacity as holder of the Common Securities, and the Trust hereby agree as
follows:

ARTICLE I.

Section
1.1.     Guarantee
by the Company. Subject to the terms and conditions hereof, the
Company, including in its capacity as holder of the Common Securities, hereby
irrevocably and unconditionally guarantees to each person or entity to whom the
Trust is now or hereafter becomes indebted or liable (the “Beneficiaries”) the
full payment when and as due, of any and all Obligations (as hereinafter defined)
to such Beneficiaries. As used herein, “Obligations” means any costs, expenses
or liabilities of the Trust other than obligations of the Trust to pay to the
holders of any Preferred Securities or other similar interests in the Trust the
amounts due such holders pursuant to the terms of the Preferred Securities or
such other similar interests, as the case may be. This Agreement is intended to
be for the benefit of, and to be enforceable by, all such Beneficiaries,
whether or not such Beneficiaries have received notice hereof.

Section
1.2.     Term of
Agreement. This Agreement shall terminate and be of no further force
and effect upon the later of (a) the date on which full payment has been made
of all amounts payable to all holders of all the Preferred Securities (whether
upon redemption, liquidation, exchange or otherwise); and (b) the date on which
there are no Beneficiaries remaining; provided, however, that this Agreement
shall continue to be effective or shall be reinstated, as the case may be, if at
any time any holder of the Preferred Securities or any Beneficiary must restore
payment of any sums paid under the Preferred Securities, under any obligation
under the Preferred Securities Guarantee Agreement dated the date hereof by the
Company and Wilmington
Trust Company as guarantee trustee, or under this Agreement for any reason
whatsoever. This Agreement is continuing, irrevocable, unconditional and
absolute.

Section
1.3.     Waiver of
Notice. The Company hereby waives notice of acceptance of this
Agreement and of any obligation to which it applies or may apply, and the
Company hereby waives presentment, demand for payment, protest, notice of
nonpayment, notice of dishonor, notice of redemption and all other notices and
demands.

Section
1.4.     No
Impairment. The obligations, covenants, agreements and duties of the
Company under this Agreement shall in no way be affected or impaired by reason
of the happening from time to time of any of the following:

          (a)     the
extension of time for the payment by the Trust of all or any portion of the
Obligations or for the performance of any other obligation under, arising out
of, or in connection with, the Obligations;

          (b)     
any failure, omission, delay or lack of diligence on the part of the
Beneficiaries to enforce, assert or exercise any right, privilege, power or
remedy conferred on the Beneficiaries with respect to the Obligations or any
action on the part of the Trust granting indulgence or extension of any kind;
or

          (c)     
the voluntary or involuntary liquidation, dissolution, sale of any collateral,
receivership, insolvency, bankruptcy, assignment for the benefit of creditors,
reorganization, arrangement, composition or readjustment of debt of, or other
similar proceedings affecting, the Trust or any of the assets of the Trust.

          There
shall be no obligation of the Beneficiaries to give notice to, or obtain the
consent of, the Company with respect to the happening of any of the foregoing.

Section
1.5.     Enforcement.
A Beneficiary may enforce this Agreement directly against the Company, and the
Company waives any right or remedy to require that any action be brought
against the Trust or any other person or entity before proceeding against the
Company.

ARTICLE II.

Section
2.1.     Binding
Effect. All guarantees and agreements contained in this Agreement
shall bind the successors, assigns, receivers, trustees and representatives of
the Company and shall inure to the benefit of the Beneficiaries.

Section
2.2.     Amendment.
So long as there remains any Beneficiary or any Preferred Securities of any
series are outstanding, this Agreement shall not be modified or amended in any
manner adverse to such Beneficiary or to the holders of the Preferred
Securities.

Section 2.3.     Notices. Any notice, request or other
communication required or permitted to be given hereunder shall be given in
writing by delivering the same by facsimile transmission (confirmed by mail),
telex, or by registered or certified mail, addressed as follows (and if so
given, shall be deemed given when mailed or upon receipt of an answer back, if
sent by telex):

Tompkins
Capital Trust I 

c/o Tompkins Financial Corporation 

110 North Tioga Street 

Ithaca, New York 14850 

ATTN: Chief Financial Officer

Section
2.4.      Governing
Law. This Agreement shall be governed by and construed and
interpreted in accordance with the laws of the State of Delaware (without
regard to conflict of laws principles).

 [The remainder of this page has been left
blank intentionally]

THIS AGREEMENT
is executed as of the day and year first above written.

	
  

 	
  

 	
  

 	
  

 
	
  

 	
 TOMPKINS
 FINANCIAL CORPORATION

 	
  

 
	
  

 	
  

 	
  

 	
  

 
	
  

 	
 By:

 	
 /s/ Francis
 M. Fetsko

 	
  

 
	
  

 	 

 	
  

 
	
  

 	
 Francis M.
 Fetsko

 	
  

 
	
  

 	
 Executive
 Vice President and Chief Financial Officer

 	
  

 
	
  

 	
  

 	
  

 
	
  

 	
 TOMPKINS
 CAPITAL TRUST I

 	
  

 
	
  

 	
  

 	
  

 	
  

 
	
  

 	
 By:

 	
 /s/ David K.
 Kershaw

 	
  

 
	
  

 	
  

 	 

 	
  

 
	
  

 	
  

 	
 David K.
 Kershaw

 	
  

 
	
  

 	
  

 	
 Administrative
 Trustee

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