Document:

Exhibit 4.1

 

Execution Version

 

CLOUD PEAK ENERGY RESOURCES LLC

 

and

 

CLOUD PEAK ENERGY FINANCE CORP., as Issuers,

 

CLOUD PEAK ENERGY INC.

 

and

 

CLOUD PEAK ENERGY LOGISTICS I LLC, as Guarantors,

 

WILMINGTON TRUST COMPANY, as Trustee,

 

and

 

CITIBANK, N.A., as Securities Administrator

 

 

SIXTH SUPPLEMENTAL INDENTURE

 

Dated as of September 10, 2015

 

to

 

Indenture

 

Dated as of November 25, 2009

 

 

8.500% Senior Notes due 2019

 

 

THIS SIXTH SUPPLEMENTAL INDENTURE (this “Supplemental Indenture”), dated as of September 10, 2015, is by and among Cloud Peak Energy Resources LLC, a Delaware limited liability company (the “Company”), Cloud Peak Energy Finance Corp., a Delaware corporation (the “Co-Issuer” and together with the Company, the “Issuers”), Cloud Peak Energy Inc., a Delaware corporation (the “Parent Guarantor”), Cloud Peak Energy Logistics I LLC, a Delaware limited liability company (the “New Guarantor”), Wilmington Trust Company, a Delaware trust company, as trustee (the “Trustee”), and Citibank, N.A., a national banking association, as securities administrator (the “Securities Administrator”).

 

WHEREAS, the Issuers, the Guarantors party thereto, the Trustee and the Securities Administrator have heretofore executed and delivered that certain Indenture, dated as of November 25, 2009 (as heretofore supplemented, the “Indenture”);

 

WHEREAS, Section 9.01 of the Indenture provides that, without notice to or the consent of any Noteholders, the Issuers, the Trustee and the Securities Administrator may enter into an indenture supplemental to the Indenture for the purpose of amending or supplementing the Indenture or the Notes in order to, among other things, provide for any Guarantee of the Notes;

 

WHEREAS, the New Guarantor wishes to Guarantee all of the outstanding Notes in accordance with the Indenture;

 

WHEREAS, the execution and delivery of this Supplemental Indenture have been authorized by each of the Issuers, the Parent Guarantor and the New Guarantor;

 

WHEREAS, the Company desires and has requested the Trustee and the Securities Administrator to join with the Issuers, the Parent Guarantor and the New Guarantor in entering into this Supplemental Indenture without the consent of the Noteholders for the purpose of supplementing the Indenture to add the New Guarantor as a Guarantor as permitted by Section 9.01(6) thereof; and

 

NOW, THEREFORE, in consideration of the above premises, each party hereby agrees, for the benefit of the others and for the equal and ratable benefit of the Noteholders, as follows:

 

ARTICLE I

 

ADDITION OF GUARANTOR

 

Section 1.1    Addition of Guarantor.  The New Guarantor, by its execution of this Supplemental Indenture, agrees to be a Guarantor under the Indenture and to be bound by the terms of the Indenture applicable to Guarantors, including, but not limited to Article 10 thereof. The Note Guaranty of the New Guarantor may be released in accordance with the Indenture.

 

ARTICLE II

 

MISCELLANEOUS PROVISIONS

 

Section 2.1    Defined Terms.  For all purposes of this Supplemental Indenture, except as otherwise defined or unless the context otherwise requires, terms used in capitalized form in this Supplemental Indenture and defined in the Indenture have the meanings specified in the Indenture.

 

Section 2.2    Indenture.  Except as supplemented hereby, the Indenture and the Notes are in all respects ratified and confirmed and all the terms 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 under the Indenture shall be bound hereby and all terms and conditions of both shall be read together as though they constitute a single instrument, except that in the case of conflict the provisions of this Supplemental Indenture shall control.

 

Section 2.3    Governing Law.  THIS SUPPLEMENTAL INDENTURE SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK.

 

1

 

Section 2.4    Successors.  All agreements of the New Guarantor in this Supplemental Indenture shall bind its successors.

 

Section 2.5    Duplicate Originals.  All parties may sign any number of copies of this Supplemental Indenture.  Each signed copy shall be an original, but all of them together shall represent the same agreement.  It is the express intent of the parties to be bound by the exchange of signatures on this Supplemental Indenture via telecopy or other form of electronic transmission.

 

Section 2.6    Severability.  In case any one or more of the provisions in this Supplemental Indenture or in the Notes shall be held invalid, illegal or unenforceable, in any respect for any reason, the validity, legality and enforceability of any such provision in every other respect and of the remaining provisions shall not in any way be affected or impaired thereby, it being intended that all of the provisions hereof shall be enforceable to the fullest extent permitted by law.

 

Section 2.7    Disclaimer.  The Trustee and the Securities Administrator accept the amendments of the Indenture effected by this Supplemental Indenture and agree to execute the trust created by the Indenture as hereby amended, but on the terms and conditions set forth in the Indenture, including the terms and provisions defining and limiting the liabilities and responsibilities of the Trustee and the Securities Administrator, which terms and provisions shall in like manner define and limit their respective liabilities and responsibilities in the performance of the trust created by the Indenture as hereby amended, and without limiting the generality of the foregoing, neither the Trustee nor the Securities Administrator shall be responsible in any manner whatsoever for or with respect to any of the recitals or statements contained herein, all of which recitals or statements are made solely by the Issuers, the Parent Guarantor and the New Guarantor and neither the Trustee nor the Securities Administrator makes any representation with respect to any such matters. Additionally, neither the Trustee nor the Securities Administrator makes any representations as to the validity or sufficiency of this Supplemental Indenture.

 

Section 2.8    Effectiveness.  The provisions of this Supplemental Indenture shall be effective upon execution and delivery of this instrument by the parties hereto.

 

Section 2.9    Effect of Headings.  The Section headings herein are for convenience only and shall not affect the construction thereof.

 

[THE REMAINDER OF THIS PAGE IS INTENTIONALLY LEFT BLANK]

 

2

 

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

 

	
 
    	
COMPANY:
    
	
 
    	
 
    
	
 
    	
CLOUD   PEAK ENERGY RESOURCES LLC
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
By:
    	
/s/ Bryan Pechersky
    
	
 
    	
 
    	
Bryan Pechersky
    
	
 
    	
 
    	
Executive Vice   President, General Counsel and
    
	
 
    	
 
    	
Corporate Secretary
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
CO-ISSUER:
    
	
 
    	
 
    
	
 
    	
CLOUD   PEAK ENERGY FINANCE CORP.
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
By:
    	
/s/   Bryan Pechersky
    
	
 
    	
 
    	
Bryan Pechersky
    
	
 
    	
 
    	
Executive Vice   President, General Counsel and
    
	
 
    	
 
    	
Corporate Secretary
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
PARENT GUARANTOR:
    
	
 
    	
 
    
	
 
    	
CLOUD   PEAK ENERGY INC.
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
By:
    	
/s/   Bryan Pechersky
    
	
 
    	
 
    	
Bryan Pechersky
    
	
 
    	
 
    	
Executive Vice   President, General Counsel and
    
	
 
    	
 
    	
Corporate Secretary
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
NEW GUARANTOR:
    
	
 
    	
 
    
	
 
    	
CLOUD   PEAK ENERGY LOGISTICS I LLC
    
	
 
    	
 
    
	
 
    	
By:
    	
/s/ Bryan Pechersky
    
	
 
    	
 
    	
Bryan Pechersky
    
	
 
    	
 
    	
Executive Vice   President, General Counsel and
    
	
 
    	
 
    	
Corporate Secretary
    

 

[Signature Page to Sixth Supplemental Indenture]

 

 

	
 
    	
TRUSTEE:
    
	
 
    	
 
    
	
 
    	
WILMINGTON   TRUST COMPANY, as   Trustee
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
By:
    	
/s/ W. Thomas Morris, II
    
	
 
    	
 
    	
W. Thomas Morris, II
    
	
 
    	
 
    	
Vice President
    

 

[Signature Page to Sixth Supplemental Indenture]

 

 

	
 
    	
SECURITIES   ADMINISTRATOR:
    
	
 
    	
 
    
	
 
    	
CITIBANK,   N. A., as   Securities Administrator
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
By:
    	
/s/ Valerie Delgado
    
	
 
    	
 
    	
Valerie Delgado
    
	
 
    	
 
    	
Vice President
    

 

[Signature Page to Sixth Supplemental Indenture]Exhibit 4.2

 

Execution Version

 

 

CLOUD PEAK ENERGY RESOURCES LLC

 

and

 

CLOUD PEAK ENERGY FINANCE CORP., as Issuers,

 

CLOUD PEAK ENERGY INC., as Parent Guarantor,

 

THE SUBSIDIARIES NAMED HEREIN, as Subsidiary Guarantors

 

and

 

WELLS FARGO BANK, NATIONAL ASSOCIATION, as Trustee

 

 

6.375% Senior Notes due 2024

 

 

 

SECOND SUPPLEMENTAL INDENTURE

 

Dated as of September 1, 2015

 

 

 

This SECOND SUPPLEMENTAL INDENTURE, (this “Supplemental Indenture”) dated as of September 1, 2015, is among Cloud Peak Energy Resources LLC, a Delaware limited liability company (the “Company”), Cloud Peak Energy Finance Corp., a Delaware corporation (the “Co-issuer” and, together with the Company, the “Issuers”), Cloud Peak Energy Inc., a Delaware corporation (the “Parent Guarantor”), each of the parties identified under the caption “Subsidiary Guarantors” on the signature page hereto (the “Subsidiary Guarantors”) and Wells Fargo Bank, National Association, a national banking association, as Trustee.

 

RECITALS

 

WHEREAS, the Issuers, the Parent Guarantor, the initial Subsidiary Guarantors and the Trustee entered into an Indenture, dated as of March 11, 2014 (as supplemented and amended by the First Supplemental Indenture dated as of March 11, 2014, the “Indenture”), pursuant to which the Issuers have issued $200,000,000 in principal amount of 6.375% Senior Notes due 2024 (the “Notes”);

 

WHEREAS, Section 10.01 of the Indenture provides that the Issuers and the Trustee may amend or supplement the Indenture in order to add one or more Subsidiary Guarantors pursuant to Section 5.13 thereof, without the consent of the Holders of the Notes; and

 

WHEREAS, all acts and things prescribed by the Indenture, by law and by the Certificate of Incorporation and the Bylaws (or comparable constituent documents) of the Issuers, of the Parent Guarantors and Subsidiary Guarantors and of the Trustee necessary to make this Supplemental Indenture a valid instrument legally binding on the Issuers, the Parent Guarantor and Subsidiary Guarantors and the Trustee, in accordance with its terms, have been duly done and performed;

 

WHEREAS, the Company desires and has requested the Trustee to join with the Issuers, the Parent Guarantor and the Subsidiary Guarantors in executing this Supplemental Indenture to add Cloud Peak Energy Logistics I LLC as a Subsidiary Guarantor as permitted by Section 5.13 of the Indenture;

 

NOW, THEREFORE, to comply with the provisions of the Indenture and in consideration of the above premises, the Issuers, the Parent Guarantors and Subsidiary Guarantors and the Trustee covenant and agree for the equal and proportionate benefit of the respective Holders of the Notes as follows:

 

ARTICLE 1

 

This Supplemental Indenture is supplemental to the Indenture and does and shall be deemed to form a part of, and shall be construed in connection with and as part of, the Indenture for any and all purposes.

 

This Supplemental Indenture shall become effective immediately upon its execution and delivery by each of the Issuers, the Subsidiary Guarantors and the Trustee.

 

 

ARTICLE II

 

From this date, in accordance with Section 5.13 and by executing this Supplemental Indenture, the Subsidiary Guarantors whose signatures appear below are subject to the provisions of the Indenture to the extent provided for in Article XI thereunder.

 

ARTICLE III

 

Except as specifically modified herein, the Indenture and the Notes are in all respects ratified and confirmed (mutatis mutandis) and shall remain in full force and effect in accordance with their terms with all capitalized terms used herein without definition having the same respective meanings ascribed to them as in the Indenture.

 

The Trustee accepts the amendments of the Indenture effected by this Supplemental Indenture and agrees to execute the trust created by the Indenture as hereby amended, but on the terms and conditions set forth in the Indenture, including the terms and provisions defining and limiting the liabilities and responsibilities of the Trustee, which terms and provisions shall in like manner define and limit its liabilities and responsibilities in the performance of the trust created by the Indenture as hereby amended, and without limiting the generality of the foregoing, the Trustee shall not be responsible in any manner whatsoever for or with respect to any of the recitals or statements contained herein, all of which recitals or statements are made solely by the Issuers and the Subsidiary Guarantors, and the Trustee makes no representation with respect to any such matters.  Additionally, the Trustee makes no representations as to the validity or sufficiency of this Supplemental Indenture

 

THIS SUPPLEMENTAL INDENTURE SHALL BE GOVERNED BY, AND CONSTRUED IN ACCORDANCE WITH, THE LAWS OF THE STATE OF NEW YORK.

 

The parties may sign any number of copies of this Supplemental Indenture.  Each signed copy shall be an original, but all of such executed copies together shall represent the same agreement.

 

[NEXT PAGE IS SIGNATURE PAGE]

 

 

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

 

 

	
 
    	
COMPANY:
    
	
 
    	
 
    
	
 
    	
CLOUD   PEAK ENERGY RESOURCES LLC
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
By:
    	
/s/   Bryan Pechersky
    
	
 
    	
 
    	
Bryan   Pechersky
    
	
 
    	
 
    	
Executive   Vice President, General Counsel
   and Corporate Secretary
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
CO-ISSUER:
    
	
 
    	
 
    
	
 
    	
CLOUD   PEAK ENERGY FINANCE CORP.
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
By:
    	
/s/   Bryan Pechersky
    
	
 
    	
 
    	
Bryan   Pechersky
    
	
 
    	
 
    	
Executive   Vice President, General Counsel
   and Corporate Secretary
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
PARENT   GUARANTOR:
    
	
 
    	
 
    
	
 
    	
CLOUD   PEAK ENERGY INC.
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
By:
    	
/s/   Bryan Pechersky
    
	
 
    	
 
    	
Bryan   Pechersky
    
	
 
    	
 
    	
Executive   Vice President, General Counsel
   and Corporate Secretary
    

 

Signature Page to Second Supplemental Indenture

 

 

	
 
    	
SUBSIDIARY   GUARANTORS:
    
	
 
    	
 
    
	
 
    	
ARROWHEAD   I LLC
    
	
 
    	
ARROWHEAD   II LLC
    
	
 
    	
ARROWHEAD   III LLC
    
	
 
    	
YOUNGS   CREEK HOLDINGS I LLC
    
	
 
    	
YOUNGS   CREEK HOLDINGS II LLC
    
	
 
    	
YOUNGS   CREEK MINING COMPANY, LLC
    
	
 
    	
BIG   METAL COAL CO. LLC
    
	
 
    	
CORDERO   MINING LLC
    
	
 
    	
CORDERO   MINING HOLDINGS LLC
    
	
 
    	
CORDERO   OIL AND GAS LLC
    
	
 
    	
CABALLO   ROJO LLC
    
	
 
    	
CABALLO   ROJO HOLDINGS LLC
    
	
 
    	
NERCO   LLC
    
	
 
    	
NERCO   COAL LLC
    
	
 
    	
ANTELOPE   COAL LLC
    
	
 
    	
SPRING   CREEK COAL LLC
    
	
 
    	
NERCO   COAL SALES LLC
    
	
 
    	
PROSPECT   LAND AND DEVELOPMENT LLC
    
	
 
    	
CLOUD   PEAK ENERGY LOGISTICS LLC
    
	
 
    	
CLOUD   PEAK ENERGY LOGISTICS I LLC
    
	
 
    	
KENNECOTT   COAL SALES LLC
    
	
 
    	
RESOURCE   DEVELOPMENT LLC
    
	
 
    	
WESTERN   MINERALS LLC
    
	
 
    	
SEQUATCHIE   VALLEY COAL CORPORATION
    
	
 
    	
CLOUD   PEAK ENERGY SERVICES COMPANY,
    
	
 
    	
as   Subsidiary Guarantors
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
By:
    	
/s/   Bryan Pechersky
    
	
 
    	
 
    	
Bryan   Pechersky
    
	
 
    	
 
    	
Executive   Vice President, General Counsel
   and Corporate Secretary
    

 

Signature Page to Second Supplemental Indenture

 

 

	
 
    	
WELLS FARGO BANK, NATIONAL   ASSOCIATION, AS   TRUSTEE
    
	
 
    	
 
    
	
 
    	
 
    
	
 
    	
By:
    	
/s/   John C. Stohlmann
    
	
 
    	
 
    	
John   C. Stohlmann
    
	
 
    	
 
    	
Vice   President
    

 

Signature Page to Second Supplemental Indenture

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