Document:

EX-4.1

 Exhibit 4.1 

ESCROW RELEASE DATE SUPPLEMENTAL INDENTURE 

First Supplemental Indenture (this “Supplemental Indenture”), dated as of December 1, 2021, among Gray Television, Inc.,
a Georgia corporation (the “Company”), the parties that are signatories hereto as guarantors (each, a “Guaranteeing Subsidiary”) and U.S. Bank National Association, as trustee (in such capacity, the
“Trustee”). 
 W I T N E S S E T H 

WHEREAS, Gray Escrow II, Inc. (the “Escrow Issuer”) has heretofore executed and delivered to the Trustee an indenture (the
“Indenture”), dated as of November 9, 2021, initially in the aggregate principal amount of $1,300,000,000 5.375% Senior Notes due 2031 (the “Notes”); 

WHEREAS, the Indenture permits the Transactions (including, without limitation, the merger of Escrow Issuer with and into the Company on the
Escrow Release Date upon the condition, among other things, that the Company and each Guaranteeing Subsidiary party hereto shall execute and deliver to the Trustee this Supplemental Indenture, (i) which shall evidence the assumption by the
Company of all of the Escrow Issuer’s obligations under the Notes and the Indenture, in each case, on the terms and conditions set forth herein and under the Indenture and (ii) pursuant to which the Guaranteeing Subsidiaries shall
unconditionally guarantee all of the Escrow Issuer’s obligations under the Notes and the Indenture on the terms and conditions set forth herein and under the Indenture; and 

WHEREAS, pursuant to Section 9.01 of the Indenture, the Company, each Guaranteeing Subsidiary and the Trustee is authorized to execute
and deliver this Supplemental Indenture. 
 NOW THEREFORE, in consideration of the foregoing and for other good and valuable consideration,
the receipt of which is hereby acknowledged, the parties mutually covenant and agree for the equal and ratable benefit of the Holders of the Notes as follows: 

(1)    Defined Terms. As used in this Supplemental Indenture, terms defined in the Indenture or in
the preamble or recital hereto are used herein as therein defined. The words “herein,” “hereof” and “hereby” and other words of similar import used in this Supplemental Indenture refer to this Supplemental Indenture as
a whole and not to any particular section hereof. 
 (2)    Assumption of the Escrow Issuer’s
Obligations. The Company hereby confirms that, pursuant to the merger of the Escrow Issuer with and into the Company, occurring contemporaneous with the execution and delivery of this Supplemental Indenture, it has fully and unconditionally
assumed the Escrow Issuer’s obligations under the Indenture and the Notes on the terms and subject to the conditions set forth therein and to be bound by all other applicable provisions of the Indenture and to perform all of the obligations and
agreements of the Escrow Issuer under the Indenture. 
 (2)    Agreement to be Bound. Each
Guaranteeing Subsidiary hereby becomes a party to the Indenture as a Subsidiary Guarantor and as such will have all of the rights and be subject to all of the obligations and agreements of a Subsidiary Guarantor under the Indenture. 

(3)    Guarantee. Each Guaranteeing Subsidiary agrees, on a joint and several basis with all the
other Subsidiary Guarantors, to provide an unconditional Subsidiary Guarantee on the terms and subject to the conditions set forth in Article XI of the Indenture. 

 (4)    Ratification of Indenture; Supplemental
Indentures Part of Indenture. Except as expressly amended hereby, the Indenture is in all respects ratified and confirmed and all the terms, conditions and provisions thereof shall remain in full force and effect. This Supplemental Indenture
shall form a part of the Indenture for all purposes and every holder of Notes heretofore or hereafter authenticated and delivered shall be bound hereby. 

(5)    Governing Law. THIS SUPPLEMENTAL INDENTURE SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE
WITH THE LAWS OF THE STATE OF NEW YORK, WITHOUT REGARD TO PRINCIPLES OF CONFLICTS OF LAW THAT WOULD INDICATE THE APPLICABILITY OF THE LAWS OF ANY OTHER JURISDICTION. 

(6)    Counterparts. The parties may sign any number of copies of this Supplemental Indenture. Each
signed copy shall be an original, but all of them together represent the same agreement. 

(7)    Effect of Headings. The Section headings herein are for convenience only and shall not affect
the construction hereof. 
 (8)    The Trustee. The Trustee shall not be responsible in any manner
whatsoever for or in respect of the validity or sufficiency of this Supplemental Indenture or for or in respect of the recitals contained herein, all of which recitals are made solely by the Guaranteeing Subsidiary. 

(9)    Benefits Acknowledged. Each Guaranteeing Subsidiary’s Guarantee is subject to the terms
and conditions set forth in the Indenture. Each Guaranteeing Subsidiary acknowledges that it will receive direct and indirect benefits from the financing arrangements contemplated by the Indenture and this Supplemental Indenture and that the
guarantee and waivers made by it pursuant to this Subsidiary Guarantee are knowingly made in contemplation of such benefits. 

(10)    Successors. All agreements of each Guaranteeing Subsidiary in this Supplemental Indenture
shall bind its successors, except as otherwise provided in the Indenture. All agreements of the Trustee in this Supplemental Indenture shall bind its successors. 

(11)    Execution and Delivery. Each Guaranteeing Subsidiary agrees that its Subsidiary Guarantee
set forth in Article XI of the Indenture shall remain in full force and effect notwithstanding any failure to endorse on each Note a notation of any such Subsidiary Guarantee. 

  
 2 

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

					
	GRAY TELEVISION, INC.
		
	By:	 	
                /s/ James C.
Ryan

		 	Name:	 	    James C. Ryan
		 	Title:	 	    Executive Vice President and Chief Financial Officer
	
	GUARANTEEING SUBSIDIARIES:
	
	 GRAY MEDIA GROUP, INC.
 WVLT-TV, INC.

		
	By:	 	
                /s/ James C.
Ryan

		 	Name:	 	    James C. Ryan
		 	Title:	 	    Executive Vice President and Chief Financial Officer
	
	 DYNAMIC CAPTIONING LLC
 GRAY
TELEVISION LICENSEE, LLC
 RAYCOM SPORTS NETWORK, INC.
 TUPELO
HONEY RAYCOM, LLC

		
	By:	 	
                /s/ James C.
Ryan

		 	Name:	 	    James C. Ryan
		 	Title:	 	    Treasurer

  
 [Signature Page to
Supplemental Indenture] 

 
					
	 U.S. BANK NATIONAL ASSOCIATION, as Trustee

		
	By:	 	     /s/ Felicia H. Powell

		 	    Name:	 	Felicia H. Powell
		 	    Title:	 	Vice President

  
 [Signature Page to
Supplemental Indenture]EX-4.2

 Exhibit 4.2 

FIRST SUPPLEMENTAL INDENTURE 

FIRST SUPPLEMENTAL INDENTURE (this “Supplemental Indenture”) dated as of December 1, 2021, among Dynamic Captioning LLC
(the “New Guarantor”), a subsidiary of Gray Television, Inc. (or its successor), a Georgia corporation (the “Company”), the Company and U.S. Bank National Association, a national association under the laws of the
United States, as trustee under the indenture referred to below (the “Trustee”). 
 WITNESSETH: 

WHEREAS, the Company and certain subsidiaries of the Company existing as such on October 19, 2020 have heretofore executed and delivered
to the Trustee an Indenture (the “Indenture”), dated as of October 19, 2020, providing for the issuance of an aggregate principal amount of $800,000,000 of 4.750% Senior Notes due 2030 (the “Notes”); 

WHEREAS, Section 4.15 of the Indenture provides that under certain circumstances the Company is required to cause the New Guarantor to
execute and deliver to the Trustee a supplemental indenture pursuant to which the New Guarantor shall unconditionally guarantee all of the Company’s obligations under the Notes pursuant to a Guarantee on the terms and conditions set forth
herein; 
 WHEREAS, pursuant to Section 9.01 of the Indenture, the Trustee, the Company and the New Guarantor are authorized to execute
and deliver this Supplemental Indenture; and 
 WHEREAS, the Company and the New Guarantor have duly authorized the execution and delivery
of this Supplemental Indenture and all things necessary to make this Supplemental Indenture when executed by each of them a valid and binding agreement of the Company, the Subsidiary Guarantors and the New Guarantor have been done and performed;

 NOW THEREFORE, in consideration of the foregoing and for other good and valuable consideration, the receipt of which is hereby
acknowledged, the New Guarantor, the Company, the Subsidiary Guarantors and the Trustee mutually covenant and agree for the equal and ratable benefit of the holders of the Notes as follows: 

1.    Agreement to Guarantee. The New Guarantor hereby agrees, jointly and severally with the Subsidiary
Guarantors, to unconditionally guarantee the Company’s obligations under the Notes on the terms and subject to the conditions set forth in Article XI of the Indenture and to be bound by all other applicable provisions of the Indenture
and the Notes. 
 2.    Ratification of Indenture; Supplemental Indentures Part of Indenture. Except as expressly
amended hereby, the Indenture is in all respects ratified and confirmed and all the terms, conditions and provisions thereof shall remain in full force and effect. This Supplemental Indenture shall form a part of the Indenture for all purposes, and
every Holder heretofore or hereafter authenticated and delivered shall be bound hereby. 

 3.    GOVERNING LAW. THIS SUPPLEMENTAL INDENTURE SHALL BE
GOVERNED BY, AND CONSTRUED IN ACCORDANCE WITH, THE LAWS OF THE STATE OF NEW YORK BUT WITHOUT GIVING EFFECT TO APPLICABLE PRINCIPLES OF CONFLICTS OF LAW TO THE EXTENT THAT THE APPLICATION OF THE LAWS OF ANOTHER JURISDICTION WOULD BE REQUIRED THEREBY.

 4.    Trustee’s Assumption; Trustee Makes No Representation. The Trustee assumes no duties,
responsibilities or liabilities under this Supplemental Indenture other than as set forth in the Indenture. The Trustee makes no representation as to the validity or sufficiency of this Supplemental Indenture. 

5.    Counterparts. The parties may sign any number of copies of this Supplemental Indenture. Each signed copy
shall be an original, but all of them together represent the same agreement. 
 6.    Effect of Headings. The
Section headings herein are for convenience only and shall not affect the construction thereof. 
 7.    Execution
and Delivery. Each New Guarantor agrees that its Subsidiary Guarantee set forth in Article XI of the Indenture shall remain in full force and effect notwithstanding any failure to endorse on each Note a notation of any such Subsidiary
Guarantee. 

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

			
	DYNAMIC CAPTIONING LLC
		
	By:	 	     /s/ James C. Ryan

	Name: James C. Ryan
	Title: Treasurer
	
	GRAY TELEVISION, INC.
		
	By:	 	     /s/ James C. Ryan

	Name: James C. Ryan
	Title: Executive Vice President and Chief Financial Officer

 [Signature Page to First Supplemental Indenture to October 2020 Indenture] 

 
			
	U.S. BANK NATIONAL ASSOCIATION,
as Trustee
		
	By:	 	     /s/ Felicia H. Powell

	Name: Felicia H. Powell
	Title:   Vice President

 [Signature Page to First Supplemental Indenture to October 2020 Indenture]

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