Document:

Exhibit 4.2

 

FIRST SUPPLEMENTAL INDENTURE

 

THIS FIRST SUPPLEMENTAL INDENTURE dated as of
October 16, 2014 is by and among Wilmington Trust Company, a Delaware trust company, as Trustee (herein, together with its successors
in interest, the “Trustee”), Pathfinder Bancorp, Inc., a Maryland corporation (the “Successor Company”),
and Pathfinder Bancorp, Inc., a federal corporation (the “Company”), under the Indenture referred to below.

 

NOW, THEREFORE, in consideration of the premises
and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged by the parties hereto,
the Trustee, the Company and the Successor Company hereby agree as follows:

 

PRELIMINARY STATEMENTS

 

The Trustee and the Company are parties to that
certain Indenture dated as of March 22, 2007 (the “Indenture”), pursuant to which the Company issued U.S. $5,155,000.00
of its Floating Rate Junior Subordinated Deferrable Interest Debentures due 2037.

 

As permitted by the terms of the Indenture,
the Company, simultaneously with the effectiveness of this First Supplemental Indenture, shall merge (referred to herein for purposes
of Article XI of the Indenture as the “Merger”) with and into the Successor Company with the Successor Company as the
surviving corporation. The parties hereto are entering into this First Supplemental Indenture pursuant to, and in accordance with,
Articles IX and XI of the Indenture.

 

SECTION 1. Definitions. All capitalized
terms used herein that are defined in the Indenture, either directly or by reference therein, shall have the respective meanings
assigned them in the Indenture except as otherwise provided herein or unless the context otherwise requires.

 

SECTION 2. Interpretation.

 

		(a)	In this First Supplemental Indenture, unless a clear contrary intention appears:

 

		(i)	the singular number includes the plural number and vice versa;

 

		(ii)	reference to any gender includes the other gender;

 

		(iii)	the words “herein,” “hereof” and “hereunder” and other words of similar import refer to
this First Supplemental Indenture as a whole and not to any particular Section or other subdivision;

 

		(iv)	reference to any Person includes such Person’s successors and assigns but, if applicable, only if such
successors and assigns are permitted by this First Supplemental Indenture or the Indenture,

 

    	 

    	 

    

 

and reference to a Person in a particular
capacity excludes such Person in any other capacity or individually provided that nothing in this clause (iv) is intended to authorize
any assignment not otherwise permitted by this First Supplemental Indenture or the Indenture;

 

		(v)	reference to any agreement, document or instrument means such agreement, document or instrument as amended, supplemented or
modified and in effect from time to time in accordance with the terms thereof and, if applicable, the terms hereof, as well as
any substitution or replacement therefor and reference to any note includes modifications thereof and any note issued in extension
or renewal thereof or in substitution or replacement therefor;

 

		(vi)	reference to any Section means such Section of this First Supplemental Indenture; and

 

		(vii)	the word “including” (and with correlative meaning “include”) means including without limiting the
generality of any description preceding such term.

 

		(b)	No provision in this First Supplemental Indenture shall be interpreted or construed against any Person because that Person
or its legal representative drafted such provision.

 

SECTION 3. Assumption of Obligations.

 

		(a)	Pursuant to, and in compliance and accordance with, Section 11.1 and Section 11.2 of the Indenture, the Successor Company hereby
expressly assumes the due and punctual payment of the principal of and premium, if any, and interest on all of the Debentures in
accordance with their terms, according to their tenor, and the due and punctual performance and observance of all of the covenants
and conditions of the Indenture to be kept, performed, or observed by the Company under the Indenture.

 

		(b)	Pursuant to, and in compliance and accordance with, Section 11.2 of the Indenture, the Successor Company succeeds to and is
substituted for the Company, with the same effect as if the Successor Company had originally been named in the Indenture as the
Company.

 

		(c)	The Successor Company also succeeds to and is substituted for the Company with the same effect
as if the Successor Company had originally been named in (i) the Amended and Restated Declaration of Trust of the Trust, dated
as of March 7, 2007 (the “Trust Agreement”), as Sponsor (as defined in the Trust Agreement) and (ii) the Guarantee
Agreement, dated

 

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as of March 22,
2007 (the “Guarantee”), as Guarantor (as defined in the Guarantee).

 

SECTION 4. Representations and Warranties.
The Successor Company represents and warrants that (a) it has all necessary power and authority to execute and deliver this First
Supplemental Indenture and to perform the Indenture, (b) that it is the successor of the Company pursuant to the Merger effected
in accordance with applicable law, (c) that it is a corporation organized and existing under the laws of Maryland, (d) that both
immediately before and after giving effect to the Merger and this First Supplemental Indenture, no Default or Event of Default,
and no event which, after notice or lapse of time or both, would become an Event of Default, has occurred and is continuing and
(e) that this First Supplemental Indenture is executed and delivered pursuant to Section 9.1(a) and Article XI of the Indenture
and does not require the consent of the Securityholders.

 

SECTION 5. Conditions of Effectiveness.
This First Supplemental Indenture shall become effective simultaneously with the effectiveness of the Merger, provided, however,
that:

 

		(a)	the Trustee shall have executed a counterpart of this First Supplemental Indenture and shall have received one or more counterparts
of this First Supplemental Indenture executed by the Successor Company and the Company;

 

		(b)	the Trustee shall have received an Officers’ Certificate stating that (i) this First Supplemental Indenture complies
with the requirements of Article IX of the Indenture; and (ii) in the opinion of the signers, all conditions precedent, if any,
provided for in the Indenture relating to the Merger and this First Supplemental Indenture have been complied with;

 

		(c)	the Trustee shall have received an Opinion of Counsel to the effect that (i) all conditions precedent provided for in the Indenture
relating to the Merger and this First Supplemental Indenture have been complied with; (ii) this First Supplemental Indenture complies
with the requirements of Article IX of the Indenture and is authorized or permitted by, and conforms to, the terms of Article IX
of the Indenture; (iii) it is proper for the Trustee, under the provisions of Article IX of the Indenture, to join in the execution
of this First Supplemental Indenture; and (iv) the Merger and the assumption by the Successor Company under this First Supplemental
Indenture comply with the provisions of Article XI of the Indenture; and

 

		(d)	the Successor Company and the Company shall have duly executed and filed with the State Department of Assessments and Taxation
of the State of Maryland Articles of Merger in connection with the Merger.

 

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SECTION 6. Reference to the Indenture.

 

		(a)	Upon the effectiveness of this First Supplemental Indenture, each reference in the Indenture to “this Indenture,”
“hereunder,” “herein” or words of like import shall mean and be a reference to the Indenture, as affected,
amended and supplemented hereby.

 

		(b)	Upon the effectiveness of this First Supplemental Indenture, each reference in the Debentures to the Indenture including each
term defined by reference to the Indenture shall mean and be a reference to the Indenture or such term, as the case may be, as
affected, amended and supplemented hereby.

 

		(c)	The Indenture, as amended and supplemented hereby shall remain in full force and effect and is hereby ratified and confirmed.

 

SECTION 7. Execution in Counterparts.
This First Supplemental Indenture may be executed in any number of counterparts and by different parties hereto in separate counterparts,
each of which when so executed and delivered shall be deemed to be an original and all of which when taken together shall constitute
but one and the same instrument.

 

SECTION 8. Governing Law; Binding Effect.
This First Supplemental Indenture shall be governed by and construed in accordance with the laws of the State of New York and shall
be binding upon the parties hereto and their respective successors and assigns.

 

SECTION 9. The Trustee. The Trustee
shall not be responsible in any manner whatsoever for or in respect of the validity or sufficiency of this First Supplemental Indenture
or the due execution thereof by the Company or the Successor Company. The recitals of fact contained herein shall be taken as the
statements solely of the Company or the Successor Company, and the Trustee assumes no responsibility for the correctness thereof.

 

[Signatures on following page]

 

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

 

	 	PATHFINDER BANCORP, INC., a federal corporation
	 	 	 
	 	By:	/s/ Thomas W. Schneider	 
	 	 	Name: Thomas W. Schneider
	 	 	Title: President and Chief Executive Officer
	 	 	 
	 	PATHFINDER BANCORP, INC., a Maryland corporation
	 	 	 
	 	By:	/s/ Thomas W. Schneider	 
	 	 	Name: Thomas W. Schneider
	 	 	Title: President and Chief Executive Officer
	 	 	 
	 	WILMINGTON TRUST COMPANY, not in its individual capacity, but solely as Trustee
	 	 	 
		By:	/s/ Michael H. Wass	 
	 	Name:	Michael H. Wass	 
	 	Title:	Assistant Vice President	 

 

    	5Exhibit 4.3

 

INCORPORATED UNDER THE LAWS OF MARYLAND

 

	No. 1	Pathfinder Bancorp, Inc.	
        Thirteen Thousand

        (13,000)

        Shares

 

FULLY
PAID AND NON-ASSESSABLE

PAR VALUE $0.01 PER SHARE

LIQUIDATION PREFERENCE $1,000.00 PER SHARE

 

THE SHARES REPRESENTED BY THIS

CERTIFICATE ARE SUBJECT TO

RESTRICTIONS, SEE REVERSE SIDE

 

THIS CERTIFIES that the Secretary of the Treasury
is the owner of

 

THIRTEEN THOUSAND (13,000) FULLY PAID AND NON-ASSESSABLE
SHARES OF SENIOR NON-CUMULATIVE PERPETUAL PREFERRED STOCK, SERIES A

of

Pathfinder Bancorp, Inc.

a Maryland corporation

 

The shares
evidenced by this certificate are transferable only on the books of Pathfinder Bancorp, Inc. by the holder hereof, in person or
by attorney, upon surrender of this certificate properly endorsed. The capital stock evidenced hereby is not an account of an insurable
type and is not insured by the Federal Deposit Insurance Corporation or any other Federal or state governmental agency.

 

IN WITNESS
WHEREOF, Pathfinder Bancorp, Inc. has caused this certificate to be executed by its duly authorized officers and has caused its
seal to be hereunto affixed this ___ day of October, 2014.

 

	By	 	 	[SEAL]	By	 
	 	EDWARD A. MERVINE	 	 	 	THOMAS W. SCHNEIDER
	 	CORPORATE SECRETARY	 	 	 	PRESIDENT AND 
	 	 	 	 	 	CHIEF EXECUTIVE OFFICER

 

SBLF0626

 

    	 

    	 

    

 

THE SECURITIES REPRESENTED BY THIS INSTRUMENT
ARE NOT SAVINGS ACCOUNTS, DEPOSITS OR OTHER OBLIGATIONS OF A BANK AND ARE NOT INSURED BY THE FEDERAL DEPOSIT INSURANCE CORPORATION
OR ANY OTHER GOVERNMENTAL AGENCY.

 

THE SECURITIES REPRESENTED BY THIS INSTRUMENT
HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), OR THE SECURITIES LAWS
OF ANY STATE AND MAY NOT BE TRANSFERRED, SOLD OR OTHERWISE DISPOSED OF EXCEPT WHILE A REGISTRATION STATEMENT RELATING THERETO IS
IN EFFECT UNDER SUCH ACT AND APPLICABLE STATE SECURITIES LAWS OR PURSUANT TO AN EXEMPTION FROM REGISTRATION UNDER SUCH ACT OR SUCH
LAWS. EACH PURCHASER OF THE SECURITIES REPRESENTED BY THIS INSTRUMENT IS NOTIFIED THAT THE SELLER MAY BE RELYING ON THE EXEMPTION
FROM SECTION 5 OF THE SECURITIES ACT PROVIDED BY RULE 144A THEREUNDER (THE “144A EXEMPTION”). IF ANY TRANSFEREE OF
THE SECURITIES REPRESENTED BY THIS INSTRUMENT IS ADVISED BY THE TRANSFEROR THAT SUCH TRANSFEROR IS RELYING ON THE 144A EXEMPTION,
SUCH TRANSFEREE BY ITS ACCEPTANCE HEREOF (1) REPRESENTS THAT IT IS A “QUALIFIED INSTITUTIONAL BUYER” (AS DEFINED IN
RULE 144A UNDER THE SECURITIES ACT), (2) AGREES THAT IT WILL NOT OFFER, SELL OR OTHERWISE TRANSFER THE SECURITIES REPRESENTED BY
THIS INSTRUMENT EXCEPT (A) PURSUANT TO A REGISTRATION STATEMENT WHICH IS THEN EFFECTIVE UNDER THE SECURITIES ACT, (B) FOR SO LONG
AS THE SECURITIES REPRESENTED BY THIS INSTRUMENT ARE ELIGIBLE FOR RESALE PURSUANT TO RULE 144A, TO A PERSON IT REASONABLY BELIEVES
IS A “QUALIFIED INSTITUTIONAL BUYER” AS DEFINED IN RULE 144A UNDER THE SECURITIES ACT THAT PURCHASES FOR ITS OWN ACCOUNT
OR FOR THE ACCOUNT OF A QUALIFIED INSTITUTIONAL BUYER TO WHOM NOTICE IS GIVEN THAT THE TRANSFER IS BEING MADE IN RELIANCE ON RULE
144A, (C) TO THE ISSUER OR (D) PURSUANT TO ANY OTHER AVAILABLE EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF THE SECURITIES ACT
AND (3) AGREES THAT IT WILL GIVE TO EACH PERSON TO WHOM THE SECURITIES REPRESENTED BY THIS INSTRUMENT ARE TRANSFERRED A NOTICE
SUBSTANTIALLY TO THE EFFECT OF THIS LEGEND.

 

THIS INSTRUMENT IS ISSUED SUBJECT TO THE RESTRICTIONS
ON TRANSFER AND OTHER PROVISIONS OF A SECURITIES PURCHASE AGREEMENT BETWEEN THE ISSUER OF THESE SECURITIES AND TREASURY, A COPY
OF WHICH IS ON FILE WITH THE ISSUER. THE SECURITIES REPRESENTED BY THIS INSTRUMENT MAY NOT BE SOLD OR OTHERWISE TRANSFERRED EXCEPT
IN COMPLIANCE WITH SAID AGREEMENT. ANY SALE OR OTHER TRANSFER NOT IN COMPLIANCE WITH SAID AGREEMENT WILL BE VOID.

 

The following abbreviations
when used in the inscription on the face of this certificate 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)
	TEN ENT	- as tenants by the entireties	 	 
	 	 	 	Under Uniform Gifts to Minors Act
	JT TEN	- as joint tenants with right	 	 
	 	  of survivorship and not as	 	 
	 	  tenants in common	 	(State)

 

Additional abbreviations may also be used though
not in the above list

 

For value received, ______________________________
hereby sell, assign and transfer unto

 

PLEASE INSERT SOCIAL SECURITY NUMBER OR OTHER
IDENTIFYING NUMBER

 

	 

                                               
	 

 

 

 

 (please print or typewrite name and address including
postal zip code of assignee)

 

 

 

_____________________________________________________________________________________
Shares of the Preferred Stock represented by the within Certificate, and do hereby irrevocably constitute
and appoint ________________________________________________________________________ Attorney to transfer the said shares on the books of the within named corporation with full
power of substitution in the premises.

 

	Dated,	 	 	 	 
	 	 	 	 
	In the presence of	 	Signature:	 
	 	 	 	 
	 	 	 	 

 

NOTE: THE SIGNATURE TO THIS ASSIGNMENT MUST
CORRESPOND WITH THE NAME OF THE STOCKHOLDER(S) AS WRITTEN UPON THE FACE OF THE CERTIFICATE, IN EVERY PARTICULAR, WITHOUT ALTERATION
OR ENLARGEMENT, OR ANY CHANGE WHATSOEVER.

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