Document:

EX-4.1

 Exhibit 4.1 

PROOFPOINT, INC. 
 as Issuer 

AND 
 WELLS FARGO BANK, NATIONAL
ASSOCIATION, 
 as Trustee 

FIRST SUPPLEMENTAL INDENTURE 

Dated as of August [•], 2021 

0.25% Convertible Senior Notes due 2024 

 FIRST SUPPLEMENTAL INDENTURE, dated as of August [•], 2021 (this “Supplemental
Indenture”), among Proofpoint, Inc., a Delaware corporation (the “Company”), as issuer, and Wells Fargo Bank, National Association, a national banking association organized under the laws of the United States of America, as
trustee (the “Trustee”), to the Indenture, dated as of August 23, 2019 (as supplemented or otherwise modified prior to the date hereof, the “Indenture”), between the Company and the Trustee. 

WHEREAS, the Company has heretofore executed and delivered the Indenture, pursuant to which the Company issued its 0.25% Convertible Senior
Notes due 2024 (the “Notes”) in the original aggregate principal amount of $920,000,000; 
 WHEREAS, the Company has
entered into an Agreement and Plan of Merger, dated as of April 25, 2021 (as amended, supplemented, restated or otherwise modified, the “Merger Agreement”), by and among Project Kafka Parent, LLC, a Delaware limited liability
company (“Parent”), Project Kafka Merger Sub, Inc., a Delaware corporation and wholly owned subsidiary of Parent (“Merger Sub”) and the Company; 

WHEREAS, pursuant to the terms of the Merger Agreement, Merger Sub will merge with and into the Company (the “Merger”) on the
date hereof with the Company, as the surviving entity in the Merger, becoming a wholly owned subsidiary of Parent as of the date hereof; 

WHEREAS, the Merger constitutes a Merger Event under the Indenture; 

WHEREAS, Section 4.07(a) of the Indenture provides that, at the effective time of any Merger Event, the Company or the successor or
purchasing Person, as the case may be, shall execute with the Trustee, without the consent of Holders of the Notes, a supplemental indenture providing that at and after the effective time of such Merger Event, the right to convert a Note will be
changed into a right to convert such Note as set forth in the Indenture into the kind and amount of shares of stock, other securities or other property or assets (including cash or any combination thereof) that a holder of a number of shares of
Common Stock equal to the Conversion Rate immediately prior to such Merger Event would have owned or been entitled to receive upon such Merger Event; 

WHEREAS, Section 4.07(a) of the Indenture provides that if the holders of the Common Stock receive only cash in such transaction, then
for all conversions that occur after the effective date of such transaction, (i) the consideration due upon conversion of each $1,000 principal amount of Notes shall be solely cash in an amount equal to the Conversion Rate in effect on the
Conversion Date (as may be increased as described in Section 4.06 of the Indenture), multiplied by the price paid per share of Common Stock in such transaction and (ii) the Company shall satisfy its Conversion Obligation by paying cash to
converting Holders on the second Business Day following the Conversion Date; 

  
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 WHEREAS, in connection with the Merger, each outstanding share of Common Stock outstanding
immediately prior to the effective time of the Merger (the “Effective Time”) (subject to certain exceptions, including shares of Common Stock owned by stockholders of the Company who have not voted in favor of the adoption of the
Merger Agreement and have properly exercised appraisal rights in accordance with Section 262 of the General Corporation Law of the State of Delaware) will, at the Effective Time, automatically be converted into the right to receive $176.00 in
cash, subject to applicable withholding taxes; 
 WHEREAS, Section 7.01 of the Indenture provides that the Company, when authorized by
resolutions of the Board of Directors of the Company (the “Board of Directors”), and the Trustee, at the Company’s expense, may amend or supplement the Indenture or the Notes or waive any provision of the Indenture or Notes
without the consent of any Holder for one or more purposes, including, among other things, to, in connection with any transaction described under Section 4.07 of the Indenture, provide that the Notes are convertible into Reference Property,
subject to the provisions of Section 4.03 of the Indenture, and make certain related changes to the terms of the Notes to the extent expressly required by Section 4.07 of the Indenture; 

WHEREAS, the Board of Directors, by resolutions adopted on August [•], has duly authorized the Company’s entry into and delivery of
this Supplemental Indenture, and the entry into this Supplemental Indenture by the parties hereto is permitted or authorized by the provisions of the Indenture; 

WHEREAS, in connection with the execution and delivery of this Supplemental Indenture, the Trustee has received an Officers’ Certificate
and an Opinion of Counsel as contemplated by Sections 6.01, 7.05, 11.02, 11.07 and 14.05 of the Indenture; and 
 WHEREAS, the Company has
requested that the Trustee execute and deliver this Supplemental Indenture and have satisfied all requirements necessary to make this Supplemental Indenture a valid instrument in accordance with its terms. 

W I T N E S S E T H: 

NOW THEREFORE, in consideration of the foregoing and for other good and valuable consideration, the receipt of which is hereby acknowledged,
the Company covenants and agrees with the Trustee as follows for the equal and ratable benefit of the Holders: 
 ARTICLE 1 

Section 1.01 Definitions in the Supplemental Indenture. Unless otherwise specified herein or the context otherwise requires: 

(a) a term defined in the Indenture has the same meaning when used in this Supplemental Indenture unless the definition of such term is
amended or supplemented pursuant to this Supplemental Indenture; 
 (b) the terms defined in this Article and in this Supplemental Indenture
include the plural as well as the singular; and 
 (c) unless otherwise stated, a reference to a Section or Article is to a Section or
Article of this Supplemental Indenture. 

  
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 ARTICLE 2 

EFFECT OF MERGER ON CONVERSION 

Section 2.01 Conversion Right. In accordance with and subject to Section 4.07 of the Indenture, as a result of the Merger, at
the effective time of the Merger, the right to convert a Note will be changed into the right to convert such Note as set forth into the kind and amount of shares of stock, other securities or other property or assets (including cash or any
combination thereof) that a holder of a number of shares of Common Stock equal to the Conversion Rate prior to the Merger would have owned or been entitled to receive upon the Merger. For all conversions that occur after the effective date of the
Merger (i) the consideration due upon conversion of each $1,000 principal amount of Notes shall be solely cash in an amount equal to the Conversion Rate then in effect on the Conversion Date (as may be increased by Section 4.06 of the
Indenture), multiplied by $176.00 and (ii) the Company shall satisfy its Conversion Obligation by paying cash to converting Holders on the second Business Day immediately following the Conversion Date. 

ARTICLE 3 
 MISCELLANEOUS 

Section 3.01 Ratification of Indenture. The Indenture, as supplemented by this Supplemental Indenture, is in all respects ratified
and confirmed, and this Supplemental Indenture shall be deemed part of the Indenture in the manner and to the extent herein and therein provided. 

Section 3.02 Trustee Not Responsible for Recitals. The recitals herein contained are made by the Company and not by the Trustee,
and the Trustee assumes no responsibility for the correctness thereof. The Trustee makes no representation as to the validity or sufficiency of this Supplemental Indenture. All of the provisions contained in the Indenture in respect of the rights,
privileges, immunities, powers, and duties of the Trustee shall be applicable in respect of the Supplemental Indenture as fully and with like force and effect as though set forth in full herein. 

Section 3.03 Successors. All agreements of the Company and the Trustee in this Supplemental Indenture will bind their respective
successors. 
 Section 3.04 Governing Law. THIS SUPPLEMENTAL INDENTURE SHALL BE GOVERNED BY, AND CONSTRUED IN ACCORDANCE
WITH, THE LAWS OF THE STATE OF NEW YORK. 
 Section 3.05 Headings, Etc. The titles and headings of the articles and sections
of this Supplemental Indenture have been inserted for convenience of reference only, are not to be considered a part hereof, and shall in no way modify or restrict any of the terms or provisions hereof. 

  
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 Section 3.06 Execution in Counterparts. This Supplemental Indenture may be
executed in any number of counterparts, each of which shall be an original, but such counterparts shall together constitute but one and the same instrument. This Supplemental Indenture (or any document delivered in connection with this Supplemental
Indenture) shall be valid, binding, and enforceable against a party only when executed and delivered by an authorized individual on behalf of the party by means of (i) any electronic signature permitted by the federal Electronic Signatures in
Global and National Commerce Act, state enactments of the Uniform Electronic Transactions Act, and/or any other relevant electronic signatures law, including relevant provisions of the Uniform Commercial Code (collectively, “Signature
Law”); (ii) an original manual signature; or (iii) a faxed, scanned, or photocopied manual signature. Each electronic signature or faxed, scanned, or photocopied manual signature shall for all purposes have the same validity, legal
effect, and admissibility in evidence as an original manual signature. Each party hereto shall be entitled to conclusively rely upon, and shall have no liability with respect to, any faxed, scanned, or photocopied manual signature, or other
electronic signature, of any party and shall have no duty to investigate, confirm or otherwise verify the validity or authenticity thereof. This Supplemental Indenture may be executed in any number of counterparts, each of which shall be deemed to
be an original, but such counterparts shall, together, constitute one and the same instrument. For avoidance of doubt, original manual signatures shall be used for execution or indorsement of writings when required under the Uniform Commercial Code
or other Signature Law due to the character or intended character of the writings. 
 Section 3.07 Severability. In the event
any provision of this Supplemental Indenture shall be invalid, illegal or unenforceable, then (to the extent permitted by law) the validity, legality or enforceability of the remaining provisions shall not in any way be affected or impaired. 

Section 3.08 Waiver of Jury Trial. EACH OF THE COMPANY AND THE TRUSTEE HEREBY IRREVOCABLY WAIVES, TO THE FULLEST EXTENT
PERMITTED BY APPLICABLE LAW, ANY AND ALL RIGHT TO TRIAL BY JURY IN ANY LEGAL PROCEEDING ARISING OUT OF OR RELATING TO THIS SUPPLEMENTAL INDENTURE OR THE TRANSACTIONS CONTEMPLATED HEREBY. 

Section 3.09 Effectiveness. This Supplemental Indenture shall become effective upon, without further action by the parties hereto,
the effective time of the Merger. 
 [Signature Page Follows] 

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

			
	PROOFPOINT, INC.
		
	By:	 	             

		 	Name:
		 	Title:

 SIGNATURE PAGE TO SUPPLEMENTAL INDENTURE 

 
			
	WELLS FARGO BANK, NATIONAL ASSOCIATION, as Trustee
		
	By:	 	             

		 	Name:
		 	Title:

 SIGNATURE PAGE TO SUPPLEMENTAL INDENTUREEX-10.1

 Exhibit 10.1 

TERMINATION AGREEMENT 

This TERMINATION AGREEMENT (this “Termination Agreement”) with respect to the Call Option Confirmations (as defined below) is
made as of August [•], 2021 between [DEALER] (“Dealer”) and Proofpoint, Inc. (“Counterparty”), a Delaware corporation. 

WHEREAS, Counterparty issued $920,000,000 principal amount of 0.25% Convertible Senior Notes due 2024 (the “Convertible
Notes”) pursuant to an Indenture dated as of August 23, 2019 between Counterparty and Wells Fargo Bank, National Association, as trustee; 

WHEREAS, Dealer and Counterparty are parties to the base capped call option transaction (as amended, modified or supplemented, the
“Base Call Option Transaction”) evidenced by the letter agreement between Dealer and Counterparty, dated as of August 20, 2019 (as amended, modified or supplemented, the “Base Call Option Confirmation”), and
the additional capped call option transaction (as amended, modified or supplemented, the “Additional Call Option Transaction” and, together with the Base Call Option Transaction, the “Call Option Transactions”)
evidenced by the letter agreement between Dealer and Counterparty, dated as of August 21, 2019 (as amended, modified or supplemented, the “Additional Call Option Confirmation” and, together with the Base Call Option
Confirmation, the “Call Option Confirmations”); and 
 WHEREAS, the Counterparty has requested the full termination of both
the Base Call Option Transaction and the Additional Call Option Transaction upon consummation of the acquisition of Counterparty by Project Kafka Parent, LLC, a Delaware limited liability company (“Parent”), pursuant to the
Agreement and Plan of Merger, dated as of April 25, 2021, by and among Parent, Project Kafka Merger Sub, Inc., a Delaware corporation and wholly owned subsidiary of Parent, and Counterparty (the “Merger Agreement”). 

NOW, THEREFORE, in consideration of their mutual covenants contained herein and for other good and valuable consideration, the receipt and
sufficiency of which are hereby acknowledged, the parties hereto, intending to be legally bound, hereby mutually covenant and agree as follows: 
 1.
Defined Terms. Any capitalized term not otherwise defined herein shall have the meaning set forth for such term in the Call Option Confirmations. 

2. Termination of Transactions and Confirmations. Notwithstanding anything to the contrary in the Call Option Confirmations, Counterparty and
Dealer agree that, upon the occurrence of the Closing Date (as defined in the Merger Agreement), (i) the Base Call Option Transaction shall automatically terminate and all of the respective rights and obligations of the parties under the Base Call
Option Confirmation shall be terminated, cancelled and extinguished, (ii) the Additional Call Option Confirmation shall automatically terminate and all of the respective rights and obligations of the parties under the Additional Call Option
Confirmation shall be terminated, cancelled and extinguished and (iii) in consideration of the foregoing, Dealer shall pay to Counterparty, in immediately available funds to the account specified below, cash in US Dollars in an amount equal to
$[•] no later than 11:00 a.m. (New York City time) on the Closing Date (as defined in the Merger Agreement). 
 3. Effectiveness. The
termination of the Call Option Transactions and the Call Option Confirmations as contemplated by this Termination Agreement shall be effective upon the occurrence of the Closing Date (as defined in the Merger Agreement). Counterparty shall notify
Dealer on or before the Closing Date (as defined in the Merger Agreement) of such Closing Date, which notice shall be provided via email to the email address set forth in Section 6 below. 

4. Further Adjustments; Termination. 

(a) Prior to any termination of this Termination Agreement, Dealer agrees that it shall not modify, amend, adjust, cancel or terminate, or
suspend its performance under, any of the Call Option Confirmations, including but not limited to declaring an Early Termination Date thereunder. 

(b) If the Closing Date (as defined in the Merger Agreement) has not occurred and the Merger Agreement is terminated in accordance with its
terms, this Termination Agreement shall immediately terminate and shall be of no force and effect and each of the Call Option Confirmations shall remain in full force and effect pursuant to the terms thereof in effect immediately prior to the
execution of this Termination Agreement. 

  
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 5. Representations and Warranties of Counterparty. Each of Counterparty and Dealer represents
and warrants to the other party on the date hereof that: 
 (a) it is duly organized and validly existing under the laws of the jurisdiction
of its organization or incorporation and, if relevant under such laws, in good standing; 
 (b) it has the power to execute this Termination
Agreement and any other documentation relating to this Termination Agreement, to deliver this Termination Agreement and each such other document relating thereto (if any) and to perform its obligations hereunder and thereunder (as applicable) and
has taken all necessary action to authorize such execution, delivery and performance; 
 (c) such execution, delivery and performance do not
violate or conflict with any law applicable to it, any provision of its constitutional documents, any order or judgment of any court or other agency of government applicable to it or any of its assets or any contractual restriction binding on or
affecting it or any of its assets; 
 (d) all governmental and other consents that are required to have been obtained by it with respect to
this Termination Agreement have been obtained and are in full force and effect and all conditions of any such consents have been complied with; 

(e) its obligations under this Termination Agreement constitute its legal, valid and binding obligations, enforceable in accordance with their
respective terms (subject to applicable bankruptcy, reorganization, insolvency, moratorium or similar laws affecting creditors’ rights generally and subject, as to enforceability, to equitable principles of general application (regardless of
whether enforcement is sought in a proceeding in equity or at law)); and 
 (f) on the date hereof, it remains a party to the Call Option
Transactions to the full extent as on the date of execution thereof and it has not assigned, purported to assign or made any attempt to assign, any interest in the Call Option Transactions to any third party. 

6. Notices. For purposes of this Termination Agreement, the addresses for notices or communications to the parties shall be: 

(a) Counterparty: 

[•] 
 (b) Dealer: 

[•] 
 7. Account Details. For
purposes of this Termination Agreement, the account for payments to Counterparty shall be: 
  

			
	Bank:	  	[•]
	ABA#:	  	[•]
	Acct No.:	  	[•]
	Beneficiary:	  	[•]
	SWIFT ID:	  	[•]

  
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 8. Governing Law. THIS TERMINATION AGREEMENT AND ANY CLAIM, CONTROVERSY OR DISPUTE ARISING
UNDER OR RELATED TO THIS TERMINATION AGREEMENT SHALL BE GOVERNED BY THE LAWS OF THE STATE OF NEW YORK. THE PARTIES HERETO IRREVOCABLY SUBMIT TO THE EXCLUSIVE JURISDICTION OF THE COURTS OF THE STATE OF NEW YORK AND THE UNITED STATES COURT FOR THE
SOUTHERN DISTRICT OF NEW YORK IN CONNECTION WITH ALL MATTERS RELATING HERETO AND WAIVE ANY OBJECTION TO THE LAYING OF VENUE IN, ANY CLAIM OF INCONVENIENT FORUM WITH RESPECT TO, THESE COURTS. 

9. Waiver of Trial by Jury. EACH OF COUNTERPARTY AND DEALER HEREBY IRREVOCABLY WAIVES (ON ITS OWN BEHALF AND, TO THE EXTENT PERMITTED BY
APPLICABLE LAW, ON BEHALF OF ITS STOCKHOLDERS) ALL RIGHT TO TRIAL BY JURY IN ANY ACTION, PROCEEDING OR COUNTERCLAIM (WHETHER BASED ON CONTRACT, TORT OR OTHERWISE) ARISING OUT OF OR RELATING TO THE TRANSACTION OR THE ACTIONS OF DEALER OR ITS
AFFILIATES IN THE NEGOTIATION, PERFORMANCE OR ENFORCEMENT HEREOF. 
 10. Amendment; Continuing Effect. This Termination Agreement may not
be modified, amended or supplemented, except in a written instrument signed by each party hereto. Except as set forth herein, all other terms of the Call Option Transactions and provisions of the Call Option Confirmations shall remain and continue
in full force and effect and are hereby confirmed in all respects. 
 11. Counterparts. This Termination Agreement may be executed by any one
or more of the parties hereto in any number of counterparts, each of which shall be deemed to be an original, but all such counterparts shall together constitute one and the same instrument. Counterparts may be delivered via facsimile, electronic
mail (including any electronic signature covered by the U.S. federal ESIGN Act of 2000, Uniform Electronic Transactions Act, the Electronic Signatures and Records Act or other applicable law, e.g., www.docusign.com) or other transmission method and
any counterpart so delivered shall be deemed to have been duly and validly delivered and be valid and effective for all purposes. 
 [The
remainder of page intentionally left blank] 

  
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 IN WITNESS WHEREOF the parties have executed this Termination Agreement with effect from the
date specified on the first page of this Termination Agreement. 
  

			
	[DEALER]
		
	By:	 	  

		 	Name:
		 	 Title:

 [Signature Page to Termination Agreement] 

			
	Proofpoint, Inc.
		
	By:	 	  

		 	Name:
		 	Title: 

 [Signature Page to Termination Agreement]

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