CLDP / CLOUD PEAK ENERGY, INC. - Pengajuan SECLaporan Tahunan, Pernyataan Proksi

IN THE UNITED STATES BANKRUPTCY COURT FOR THE DISTRICT OF DELAWARE

Exhibit 99.1 IN THE UNITED STATES BANKRUPTCY COURT FOR THE DISTRICT OF DELAWARE In re CLOUD PEAK ENERGY INC., et al., Debtors.1 ) ) ) ) ) ) ) ) ) Chapter 11 Case No. 19 – 11047 (KG) (Jointly Administered) Re: Docket No. 868 NOTICE OF (I) ENTRY OF ORDER CONFIRMING THe REVISED FIRST AMENDED JOINT CHAPTER 11 PLAN OF CLOUD PEAK ENERGY INC. AND CERTAIN OF ITS DEBTOR AFFILIATES AND (II) OCCURRENCE OF TH

Independent Contractor Agreement, dated December 17, 2019, among Cloud Peak Energy Inc., Jackson Square Advisors LLC, and Mr. Nathan in his individual capacity as the Managing Member of Jackson Square Advisors LLC.

Exhibit 10.3 INDEPENDENT CONTRACTOR AGREEMENT THIS INDEPENDENT CONTRACTOR AGREEMENT (this “Agreement”) is made as of December 17, 2019, by and among Jackson Square Advisors LLC (the “Contractor”), Gilbert Nathan, in his individual capacity as the Managing Member of the Contractor (“Nathan”), and Cloud Peak Energy Inc. (“CPE” or the “Company,” and, together with the Contractor and Nathan, the “Part

Amended and Restated Security Agreement, dated December 12, 2019, among Cloud Peak Energy Resources LLC, Cloud Peak Energy Finance Corp., the guarantors party thereto and Wilmington Trust, FSB, as Collateral Agent.

Exhibit 10.1 EXECUTION VERSION AMENDED AND RESTATED SECURITY AGREEMENT dated as of October 17, 2016, as amended on December 17, 2019 by CLOUD PEAK ENERGY RESOURCES LLC CLOUD PEAK ENERGY FINANCE CORP. THE OTHER GRANTORS FROM TIME TO TIME PARTY HERETO in favor of WILMINGTON SAVINGS FUND SOCIETY, FSB, solely in its capacity as Collateral Agent TABLE OF CONTENTS Section 1. Definitions 1 Section 2. Gra

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Termination of a Material Definitive Agreement, Material Modification to Rights of Security Holders, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Completion of Acquisition or Disposition of Assets

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 17, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commissio

CLD / Cloud Peak Energy Inc. 15-12B - - FORM 15-12B

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13 AND 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. Commission File Number: 001-34547 CLOUD PEAK ENERGY INC. (Exact name of registrant as specified in

Amended and Restated Bylaws of Cloud Peak Energy Inc.

Exhibit 3.2 AMENDED AND RESTATED BYLAWS (the “Bylaws”) (Effective as of December 17, 2019) OF CLOUD PEAK ENERGY INC. (the “Corporation”) * * * * * Article 1 Offices Section 1.01. Registered Office. The registered office of the Corporation, and the registered agent of the Corporation at such address, shall be as fixed in the Corporation’s Amended and Restated Certificate of Incorporation (as it may

Stockholders Agreement, dated December 17, 2019, among Cloud Peak Energy Inc. and holders of common stock in the reorganized Cloud Peak Energy Inc., as Stockholders.

Exhibit 10.2 STOCKHOLDERS AGREEMENT dated as of December 17, 2019 among CLOUD PEAK ENERGY, INC. and EACH OF THE STOCKHOLDERS PARTY HERETO TABLE OF CONTENTS Page Article 1 DEFINITIONS Section 1.01. Definitions 1 Section 1.02. Other Definitional and Interpretative Provisions 2 Article 2 RESTRICTIONS ON TRANSFER Section 2.01. Restrictions on Transfer 3 Section 2.02. Legends 3 Article 3 INFORMATION Se

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 17, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commissio

Amended and Restated Certificate of Incorporation of Cloud Peak Energy Inc.

Exhibit 3.1 AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF CLOUD PEAK ENERGY INC. Pursuant to the provisions of Sections 242 and 245 of the General Corporation Law of the State of Delaware (“Delaware Law”), Cloud Peak Energy Inc., a corporation organized under the laws of the State of Delaware, does hereby certify that: FIRST: The present name of the corporation is Cloud Peak Energy Inc. (th

Amended and Restated Indenture, dated as of October 17 2016, as amended on December 12, 2019, by an among Cloud Peak Energy Resources LLC, Cloud Peak Energy Finance Corp. Cloud Peak Energy Inc., the subsidiaries named therein, as subsidiary guarantors, and Wilmington Savings Fund Society, FSB, as Trustee and Collateral Agent.

Exhibit 4.1 EXECUTION VERSION CLOUD PEAK ENERGY RESOURCES LLC, CLOUD PEAK ENERGY FINANCE CORP., as Issuers, CLOUD PEAK ENERGY INC., as Parent Guarantor, THE SUBSIDIARIES NAMED HEREIN, as Subsidiary Guarantors and WILMINGTON SAVINGS FUND SOCIETY, FSB, as Trustee and Collateral Agent AMENDED AND RESTATED INDENTURE Dated as of October 17, 2016, as amended on December 17, 2019 12% Second Lien Senior S

Financial Statements and Exhibits, Bankruptcy or Receivership

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 5, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

IN THE UNITED STATES BANKRUPTCY COURT FOR THE DISTRICT OF DELAWARE

Exhibit 99.1 IN THE UNITED STATES BANKRUPTCY COURT FOR THE DISTRICT OF DELAWARE ) In re ) Chapter 11 ) CLOUD PEAK ENERGY INC., et al., ) Case No. 19 — 11047 (KG) ) Debtors.(1) ) (Jointly Administered) ) SECOND AMENDED JOINT CHAPTER 11 PLAN OF CLOUD PEAK ENERGY INC. AND CERTAIN OF ITS DEBTOR AFFILIATES Daniel J. DeFranceshci (No. 2732) John H. Knight (No. 3848) One Rodney Square 920 North King Stre

IN THE UNITED STATES BANKRUPTCY COURT FOR THE DISTRICT OF DELAWARE

EX-99.2 3 a19-247931ex99d2.htm EX-99.2 Exhibit 99.2 IN THE UNITED STATES BANKRUPTCY COURT FOR THE DISTRICT OF DELAWARE ) In re ) Chapter 11 ) CLOUD PEAK ENERGY INC., et al., ) Case No. 19 — 11047 (KG) ) Debtors.(1) ) (Jointly Administered) ) ) Re: Docket No. 744, 745, & 854 FINDINGS OF FACT, CONCLUSIONS OF LAW, AND ORDER (I) APPROVING THE DEBTORS’ DISCLOSURE STATEMENT AND (II) CONFIRMING THE REVIS

CLD / Cloud Peak Energy Inc. CORRESP - -

CLOUD PEAK ENERGY RESOURCES LLC CLOUD PEAK ENERGY FINANCE CORP. 748 T-7 Road Gillette, Wyoming 82718 November 25, 2019 VIA EDGAR U.S. Securities & Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, D.C. 20549 Re: Cloud Peak Energy Resources LLC Cloud Peak Energy Finance Corp. Application for Qualification of Indenture on Form T-3 (File No. 022-29081) Ladies and Gentle

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CORPORATION DESIGNATED TO ACT AS TRUSTEE o Check if an Application to Determine Eligibility of a Trustee Pursuant t

Exhibit 25.1 SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CORPORATION DESIGNATED TO ACT AS TRUSTEE o Check if an Application to Determine Eligibility of a Trustee Pursuant to Section 305(b)(2) WILMINGTON SAVINGS FUND SOCIETY, FSB (Exact name of Trustee as specified in its charter) N/A 51-0054940 (Jurisdiction

CLOUD PEAK ENERGY RESOURCES LLC, CLOUD PEAK ENERGY FINANCE CORP., as Issuers, CLOUD PEAK ENERGY INC., as Parent Guarantor, THE SUBSIDIARIES NAMED HEREIN, as Subsidiary Guarantors WILMINGTON SAVINGS FUND SOCIETY, FSB, as Trustee and Collateral Agent A

Exhibit T3C CLOUD PEAK ENERGY RESOURCES LLC, CLOUD PEAK ENERGY FINANCE CORP., as Issuers, CLOUD PEAK ENERGY INC., as Parent Guarantor, THE SUBSIDIARIES NAMED HEREIN, as Subsidiary Guarantors and WILMINGTON SAVINGS FUND SOCIETY, FSB, as Trustee and Collateral Agent AMENDED AND RESTATED INDENTURE Dated as of October 17, 2016, as amended on [ ], 2019 12% Second Lien Senior Secured Notes due 2025 CROS

CLD / Cloud Peak Energy Inc. T-3/A - - T-3

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 1 to FORM T-3 FOR APPLICATIONS FOR QUALIFICATION OF INDENTURES UNDER THE TRUST INDENTURE ACT OF 1939 Cloud Peak Energy Resources LLC Cloud Peak Energy Finance Corp. (Issuers) Cloud Peak Energy Inc. (Parent Guarantor) Antelope Coal LLC Arrowhead I LLC Arrowhead II LLC Arrowhead III LLC Big Metal

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 21, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commissio

10/24/19 - 12/13/19

Exhibit 99.2 Cloud Peak Energy Inc., et al Projected Sources and Uses of Cash Period from October 24, 2019 though Projected Date of Emergence of December 13, 2019 $ in millions Projected Sources of Cash 10/24/19 - 12/13/19 Cash on Hand(1) $ 120.3 Customer and Other AR 44.2 Surety Bond LC Cash Collateral(2) 25.7 Cash Received From NTEC at Closing 16.9 Total Sources of Cash $ 207.1 $ in millions Pro

Week 1

EX-99.1 2 a19-208503ex99d1.htm EX-99.1 Exhibit 99.1 Cloud Peak Energy Inc., et al 13 Week Cash Forecast (Summary) [Post NTEC Sale Transaction] $’s 000s FCST FCST FCST FCST FCST FCST FCST FCST FCST FCST FCST FCST FCST Total Week Number Week 1 Week 2 Week 3 Week 4 Week 5 Week 6 Week 7 Week 8 Week 9 Week 10 Week 11 Week 12 Week 13 28-Oct Week Ending 1-Nov 8-Nov 15-Nov 22-Nov 29-Nov 6-Dec 13-Dec 20-De

IN THE UNITED STATES BANKRUPTCY COURT FOR THE DISTRICT OF DELAWARE ) In re ) Chapter 11 ) CLOUD PEAK ENERGY INC., et al., ) Case No. 19 — 11047 (KG) ) Debtors.(1) ) (Jointly Administered) ) REVISED FIRST AMENDED DISCLOSURE STATEMENT FOR THE JOINT CHA

Exhibit 99.2 IN THE UNITED STATES BANKRUPTCY COURT FOR THE DISTRICT OF DELAWARE ) In re ) Chapter 11 ) CLOUD PEAK ENERGY INC., et al., ) Case No. 19 — 11047 (KG) ) Debtors.(1) ) (Jointly Administered) ) REVISED FIRST AMENDED DISCLOSURE STATEMENT FOR THE JOINT CHAPTER 11 PLAN OF CLOUD PEAK ENERGY INC. AND CERTAIN OF ITS DEBTOR AFFILIATES THIS DISCLOSURE STATEMENT IS NOT AN OFFER TO SELL ANY SECURIT

IN THE UNITED STATES BANKRUPTCY COURT FOR THE DISTRICT OF DELAWARE In re CLOUD PEAK ENERGY INC., et al., Debtors.(1) ) ) ) ) ) ) ) Chapter 11 Case No. 19 — 11047 (KG) (Jointly Administered) REVISED FIRST AMENDED JOINT CHAPTER 11 PLAN OF CLOUD PEAK EN

Exhibit 99.1 IN THE UNITED STATES BANKRUPTCY COURT FOR THE DISTRICT OF DELAWARE In re CLOUD PEAK ENERGY INC., et al., Debtors.(1) ) ) ) ) ) ) ) Chapter 11 Case No. 19 — 11047 (KG) (Jointly Administered) REVISED FIRST AMENDED JOINT CHAPTER 11 PLAN OF CLOUD PEAK ENERGY INC. AND CERTAIN OF ITS DEBTOR AFFILIATES Daniel J. DeFranceshci (No. 2732) John H. Knight (No. 3848) One Rodney Square 920 North Ki

Financial Statements and Exhibits, Bankruptcy or Receivership

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 29, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

CLOUD PEAK ENERGY RESOURCES LLC, CLOUD PEAK ENERGY FINANCE CORP., as Issuers, CLOUD PEAK ENERGY INC., as Parent Guarantor, THE SUBSIDIARIES NAMED HEREIN, as Subsidiary Guarantors WILMINGTON SAVINGS FUND SOCIETY, FSB, as Trustee and Collateral Agent A

Exhibit T3C CLOUD PEAK ENERGY RESOURCES LLC, CLOUD PEAK ENERGY FINANCE CORP., as Issuers, CLOUD PEAK ENERGY INC., as Parent Guarantor, THE SUBSIDIARIES NAMED HEREIN, as Subsidiary Guarantors and WILMINGTON SAVINGS FUND SOCIETY, FSB, as Trustee and Collateral Agent AMENDED AND RESTATED INDENTURE Dated as of October 17, 2016, as amended on [ ], 2019 12% Second Lien Senior Secured Notes due 2025 CROS

CLD / Cloud Peak Energy Inc. T-3 - - T-3

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM T-3 FOR APPLICATIONS FOR QUALIFICATION OF INDENTURES UNDER THE TRUST INDENTURE ACT OF 1939 Cloud Peak Energy Resources LLC Cloud Peak Energy Finance Corp. (Issuers) Cloud Peak Energy Inc. (Parent Guarantor) Antelope Coal LLC Arrowhead I LLC Arrowhead II LLC Arrowhead III LLC Big Metal Coal Co. LLC Caball

IN THE UNITED STATES BANKRUPTCY COURT FOR THE DISTRICT OF DELAWARE ) In re ) Chapter 11 ) CLOUD PEAK ENERGY INC., et al., ) Case No. 19 — 11047 (KG) ) Debtors.(1) ) (Jointly Administered) ) REVISED FIRST AMENDED DISCLOSURE STATEMENT FOR THE JOINT CHA

Exhibit T3E IN THE UNITED STATES BANKRUPTCY COURT FOR THE DISTRICT OF DELAWARE ) In re ) Chapter 11 ) CLOUD PEAK ENERGY INC.

EX-99.T3G

EX-99.T3G 4 a19-208501ex99dt3g.htm EX-99.T3G Exhibit T3G

Amended and Restated Employment Agreement, dated as of October 24, 2019, by and between Cloud Peak Energy Inc. and Bryan Pechersky

Exhibit 10.5 Execution Version AMENDED AND RESTATED EMPLOYMENT AGREEMENT This AMENDED AND RESTATED EMPLOYMENT AGREEMENT (the “Agreement”) is made effective as of October 24, 2019 (the “Effective Date”) by and among Cloud Peak Energy Inc., a Delaware corporation (the “Company”) and Bryan Pechersky (the “Executive”). RECITALS WHEREAS, the Company and the Executive previously entered into that certai

Amended and Restated Employment Agreement, dated as of October 24, 2019, by and between Cloud Peak Energy Inc. and Todd Myers

Exhibit 10.4 Execution Version AMENDED AND RESTATED EMPLOYMENT AGREEMENT This AMENDED AND RESTATED EMPLOYMENT AGREEMENT (the “Agreement”) is made effective as of October 24, 2019 (the “Effective Date”) by and among Cloud Peak Energy Inc., a Delaware corporation (the “Company”) and Todd A. Myers (the “Executive”). RECITALS WHEREAS, the Company and the Executive previously entered into that certain

Royalty Interest Agreement, dated as of October 24, 2019, by and between Cloud Peak Energy Resources LLC and Navajo Transitional Energy Company, LLC

Exhibit 10.2 TERM ROYALTY AGREEMENT THIS TERM ROYALTY AGREEMENT (this “Agreement”) is made and entered into this 24th day of October, 2019 (the “Effective Date”) by and between Navajo Transitional Energy Company, LLC, a limited liability company formed under the laws of the Navajo Nation and having a mailing address of 4801 N. Butler Ave., Bldg. 200, Farmington, New Mexico 87401 (“NTEC” or “Payor”

Amended and Restated Employment Agreement, dated as of October 24, 2019, by and between Cloud Peak Energy Inc. and Heath Hill

Exhibit 10.3 Execution Version AMENDED AND RESTATED EMPLOYMENT AGREEMENT This AMENDED AND RESTATED EMPLOYMENT AGREEMENT (the “Agreement”) is made effective as of October 24, 2019 (the “Effective Date”) by and among Cloud Peak Energy Inc., a Delaware corporation (the “Company”) and Heath Hill (the “Executive”). RECITALS WHEREAS, the Company and the Executive previously entered into that certain Emp

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Termination of a Material Definitive Agreement, Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 21, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

Transition Services Agreement, dated as of October 24, 2019, by and between Cloud Peak Energy Inc. and Navajo Transitional Energy Company, LLC

Exhibit 10.1 Execution Version TRANSITION SERVICES AGREEMENT This TRANSITION SERVICES AGREEMENT, dated as of October 24, 2019 (this “Agreement”), is by and among Navajo Transitional Energy Company, LLC, a Navajo Nation limited liability company (“Purchaser”), Cloud Peak Energy Inc., a Delaware corporation (the “Company” or the “Seller”, and collectively with each Additional Seller, the “Sellers”).

Amendment No. 11 dated as of October 21, 2019 to Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019 by and among Cloud Peak Energy Inc. and its subsidiaries party thereto, the lenders party thereto and Ankura Trust Company, LLC, as Administrative Agent and as Collateral Agent, as amended.

Exhibit 10.2 AMENDMENT NO. 11 AMENDMENT No. 11 dated as of October 21, 2019 (this “Amendment”) to the Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019, by and among Cloud Peak Energy Inc., a Delaware corporation and a debtor and debtor-in-possession under chapter 11 of the Bankruptcy Code (the “CPE”), the other Persons party hereto from time to ti

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 21, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

Second Amendment to the Asset Purchase Agreement dated October 21, 2019, by and among Cloud Peak Energy Inc. and substantially all of its direct and indirect subsidiaries, as Sellers, and Navajo Transitional Energy Company, as Purchaser

Exhibit 10.1 Execution Version SECOND AMENDMENT TO THE ASSET PURCHASE AGREEMENT This SECOND AMENDMENT TO ASSET PURCHASE AGREEMENT (this “Amendment”), dated as of October 21, 2019, by and among Navajo Transitional Energy Company, LLC, a Navajo Nation limited liability company (“Purchaser”), Cloud Peak Energy Inc., a Delaware corporation (the “Company”), and the Additional Sellers (together with the

CLD / Cloud Peak Energy Inc. S-8 POS - - S-8 POS

As filed with the Securities and Exchange Commission on October 21, 2019 Registration No.

CLD / Cloud Peak Energy Inc. S-8 POS - - S-8 POS

As filed with the Securities and Exchange Commission on October 21, 2019 Registration No.

CLD / Cloud Peak Energy Inc. S-8 POS - - S-8 POS

S-8 POS 1 a19-206555s8pos.htm S-8 POS As filed with the Securities and Exchange Commission on October 21, 2019 Registration No. 333-163295 Registration No. 333-175312 Registration No. 333-211350 Registration No. 333-217877 Registration No. 333-224818 Registration No. 333-175311 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Post-Effective Amendment No. 1 to Form S-8 Regist

CLD / Cloud Peak Energy Inc. S-8 POS - - S-8 POS

As filed with the Securities and Exchange Commission on October 21, 2019 Registration No.

CLD / Cloud Peak Energy Inc. S-8 POS - - S-8 POS

S-8 POS 1 a19-206553s8pos.htm S-8 POS As filed with the Securities and Exchange Commission on October 21, 2019 Registration No. 333-163295 Registration No. 333-175312 Registration No. 333-211350 Registration No. 333-217877 Registration No. 333-224818 Registration No. 333-175311 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Post-Effective Amendment No. 1 to Form S-8 Regist

CLD / Cloud Peak Energy Inc. S-8 POS - - S-8 POS

As filed with the Securities and Exchange Commission on October 21, 2019 Registration No.

CLD / Cloud Peak Energy Inc. POS AM - - POS AM

As filed with the Securities and Exchange Commission on October 21, 2019 Registration No.

CLD / Cloud Peak Energy Inc. 10-Q - Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Numbe

Mine Safety Disclosure

Exhibit 95.1 MINE SAFETY DISCLOSURE Strong Safety Performance One of our most important values is ensuring the safety of our employees and contractors by operating in a safe and responsible manner and protecting the environment in which we live and work. We have extensive safety systems that have been developed over many years. We continue to focus on refining these systems and the safety leadersh

Bankruptcy or Receivership

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 2, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

Amendment No. 10 dated as of September 27, 2019 to Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019 by and among Cloud Peak Energy Inc. and its subsidiaries party thereto, the lenders party thereto and Ankura Trust Company, LLC, as Administrative Agent and as Collateral Agent, as amended.

Exhibit 10.2 AMENDMENT NO. 10 AMENDMENT No. 10 dated as of September 27, 2019 (this “Amendment”) to the Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019, by and among Cloud Peak Energy Inc., a Delaware corporation and a debtor and debtor-in-possession under chapter 11 of the Bankruptcy Code (the “CPE”), the other Persons party hereto from time to

First Amendment to the Asset Purchase Agreement dated September 30, 2019, by and among Cloud Peak Energy Inc. and substantially all of its direct and indirect subsidiaries, as Sellers, and Navajo Transitional Energy Company, as Purchaser

Exhibit 10.1 Execution Version FIRST AMENDMENT TO THE ASSET PURCHASE AGREEMENT This FIRST AMENDMENT TO ASSET PURCHASE AGREEMENT (this “Amendment”), dated as of September 30, 2019, by and among Navajo Transitional Energy Company, LLC, a Navajo Nation limited liability company (“Purchaser”), Cloud Peak Energy Inc., a Delaware corporation (the “Company”), and the Additional Sellers (together with the

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Bankruptcy or Receivership

8-K 1 a19-1922718k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 27, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 20, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commissi

Amendment No. 9 dated as of September 20, 2019 to Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019 by and among Cloud Peak Energy Inc. and its subsidiaries party thereto, the lenders party thereto and Ankura Trust Company, LLC, as Administrative Agent and as Collateral Agent, as amended.

Exhibit 10.1 AMENDMENT NO. 9 AMENDMENT No. 9 dated as of September 20, 2019 (this “Amendment”) to the Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019, by and among Cloud Peak Energy Inc., a Delaware corporation and a debtor and debtor-in-possession under chapter 11 of the Bankruptcy Code (the “CPE”), the other Persons party hereto from time to ti

Mine Safety Disclosure

Exhibit 95.1 MINE SAFETY DISCLOSURE Strong Safety Performance One of our most important values is ensuring the safety of our employees and contractors by operating in a safe and responsible manner and protecting the environment in which we live and work. We have extensive safety systems that have been developed over many years. We continue to focus on refining these systems and the safety leadersh

CLD / Cloud Peak Energy Inc. 10-Q - Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 00

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

8-K 1 a19-1879918k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 13, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction

Limited Waiver and Amendment dated as of September 13, 2019 to Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019 by and among Cloud Peak Energy Inc. and its subsidiaries party thereto, the lenders party thereto and Ankura Trust Company, LLC, as Administrative Agent and as Collateral Agent, as amended.

Exhibit 10.1 LIMITED WAIVER AND AMENDMENT LIMITED WAIVER AND AMENDMENT dated as of September 13, 2019 (this “Limited Waiver and Amendment”) to the Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019, by and among Cloud Peak Energy Inc., a Delaware corporation and a debtor and debtor-in-possession under chapter 11 of the Bankruptcy Code (the “CPE”), t

Amendment No. 8 dated as of September 6, 2019 to Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019 by and among Cloud Peak Energy Inc. and its subsidiaries party thereto, the lenders party thereto and Ankura Trust Company, LLC, as Administrative Agent and as Collateral Agent, as amended.

Exhibit 10.1 AMENDMENT NO. 8 AMENDMENT No. 8 dated as of September 6, 2019 (this “Amendment”) to the Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019, by and among Cloud Peak Energy Inc., a Delaware corporation and a debtor and debtor-in-possession under chapter 11 of the Bankruptcy Code (the “CPE”), the other Persons party hereto from time to tim

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

8-K 1 a19-1852318k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 6, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction o

Amendment No. 7 dated as of August 29, 2019 to Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019 by and among Cloud Peak Energy Inc. and its subsidiaries party thereto, the lenders party thereto and Ankura Trust Company, LLC, as Administrative Agent and as Collateral Agent, as amended.

Exhibit 10.1 AMENDMENT NO. 7 AMENDMENT No. 7 dated as of August 29, 2019 (this “Amendment”) to the Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019, by and among Cloud Peak Energy Inc., a Delaware corporation and a debtor and debtor-in-possession under chapter 11 of the Bankruptcy Code (the “CPE”), the other Persons party hereto from time to time

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

8-K 1 a19-1829518k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 29, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of

Amendment No. 6 dated as of August 23, 2019 to Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019 by and among Cloud Peak Energy Inc. and its subsidiaries party thereto, the lenders party thereto and Ankura Trust Company, LLC, as Administrative Agent and as Collateral Agent, as amended.

Exhibit 10.1 AMENDMENT NO. 6 AMENDMENT No. 6 dated as of August 23, 2019 (this “Amendment”) to the Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019, by and among Cloud Peak Energy Inc., a Delaware corporation and a debtor and debtor-in-possession under chapter 11 of the Bankruptcy Code (the “CPE”), the other Persons party hereto from time to time

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 23, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 19, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

Amendment No. 5 dated as of August 19, 2019 to Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019 by and among Cloud Peak Energy Inc. and its subsidiaries party thereto, the lenders party thereto and Ankura Trust Company, LLC, as Administrative Agent and as Collateral Agent, as amended.

Exhibit 10.1 Execution Version AMENDMENT NO. 5 AMENDMENT No. 5 dated as of August 19, 2019 (this “Amendment”) to the Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019, by and among Cloud Peak Energy Inc., a Delaware corporation and a debtor and debtor-in-possession under chapter 11 of the Bankruptcy Code (the “CPE”), the other Persons party hereto

Cloud Peak Energy Announces Navajo Transitional Energy Company as Winning Bidder for Substantially All of Its Assets in Competitive Auction as Part of Chapter 11 Process Cloud Peak Continues to Operate as Normal and Meet Customer Commitments Will See

Exhibit 99.3 Cloud Peak Energy Announces Navajo Transitional Energy Company as Winning Bidder for Substantially All of Its Assets in Competitive Auction as Part of Chapter 11 Process Cloud Peak Continues to Operate as Normal and Meet Customer Commitments Will Seek Court Approval of Transaction at Hearing Scheduled for August 19, 2019 GILLETTE, Wyo.— August 16, 2019— Cloud Peak Energy Inc. (OTC: CL

CONFIDENTIAL - SUBJECT TO SIGNIFICANT CHANGE

Exhibit 99.2 CONFIDENTIAL - SUBJECT TO SIGNIFICANT CHANGE Cloud Peak Energy Inc., et al Projected Sources and Uses of Cash Based on Hypothetical Transaction Closing Date of October 4, 2019 $ in millions Projected Sources of Cash 10/04/19 Cash on Hand $ 98.3 Customer and Other AR 34.4 ARS Facility Collateral 7.8 Cash From NTEC at Closing 15.7 Total Sources of Cash $ 156.3 $ in millions Projected Us

Week 1

Exhibit 99.1 Cloud Peak Energy Inc., et al 13 Week Cash Forecast [DIP Budget No. 4] Effective August 5, 2019 $’s 000s FCST FCST FCST FCST FCST FCST FCST FCST FCST FCST FCST FCST FCST Total Week Number Week 1 Week 2 Week 3 Week 4 Week 5 Week 6 Week 7 Week 8 Week 9 Week 10 Week 11 Week 12 Week 13 5-Aug Week Ending 9-Aug 16-Aug 23-Aug 30-Aug 6-Sep 13-Sep 20-Sep 27-Sep 4-Oct 11-Oct 18-Oct 25-Oct 1-Nov

Asset Purchase Agreement

Exhibit 10.1 Execution Version ASSET PURCHASE AGREEMENT among NAVAJO TRANSITIONAL ENERGY COMPANY, LLC, CLOUD PEAK ENERGY INC., and CERTAIN SUBSIDIARIES OF CLOUD PEAK ENERGY INC. Dated as of August 19, 2019 TABLE OF CONTENTS Page I. DEFINITIONS 1 1.1 Certain Definitions 1 1.2 Other Definitional and Interpretive Matters 11 II. PURCHASE AND SALE OF ASSETS; ASSUMPTION OF LIABILITIES 13 2.1 Purchase an

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 16, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

8-K 1 a19-1655128k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 8, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of I

Amendment No. 4 dated as of August 8, 2019 to Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019 by and among Cloud Peak Energy Inc. and its subsidiaries party thereto, the lenders party thereto and Ankura Trust Company, LLC, as Administrative Agent and as Collateral Agent, as amended.

EX-10.1 2 a19-165512ex10d1.htm EX-10.1 Exhibit 10.1 Execution Version AMENDMENT NO. 4 AMENDMENT No. 4 dated as of August 8, 2019 (this “Amendment”) to the Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019, by and among Cloud Peak Energy Inc., a Delaware corporation and a debtor and debtor-in-possession under chapter 11 of the Bankruptcy Code (the “

CLD / Cloud Peak Energy Inc. NT 10-Q - - NT 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING Commission File Number: 001-34547 (Check one): o Form 10-K o Form 20-F o Form 11-K x Form 10-Q o Form 10-D o Form N-SAR o Form N-CSR For Period Ended: June 30, 2019 o Transition Report on Form 10-K o Transition Report on Form 20-F o Transition Report on Form 11-K o Transition Report on F

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 31, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission Fi

Limited Waiver and Amendment No. 3 dated as of July 16, 2019 to Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019 by and among Cloud Peak Energy Inc. and its subsidiaries party thereto, the lenders party thereto and Ankura Trust Company, LLC, as administrative agent and as collateral agent, as amended.

EX-10.2 3 a19-130421ex10d2.htm EX-10.2 Exhibit 10.2 LIMITED WAIVER AND AMENDMENT NO. 3 LIMITED WAIVER AND AMENDMENT No. 3 dated as of July 16, 2019 (this “Amendment”) to the Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019, by and among Cloud Peak Energy Inc., a Delaware corporation and a debtor and debtor-in-possession under chapter 11 of the Ban

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

8-K 1 a19-1304218k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 16, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of In

Amendment No. 1 to Amended and Restated Sale and Plan Support Agreement

EX-10.1 2 a19-130421ex10d1.htm EX-10.1 Exhibit 10.1 EXECUTION VERSION AMENDMENT NO. 1 This AMENDMENT No. 1 dated as of July 16, 2019 (this “Amendment”) to that certain Amended and Restated Sale and Plan Support Agreement, dated as of May 9, 2019, is by and among (i) Cloud Peak Energy Inc. (“Parent”), Cloud Peak Energy Resources LLC (“CPE Resources”) and Cloud Peak Energy Finance Corp. (the “Co-Iss

Amendment No. 1 dated as of June 19, 2019 to Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019 by and among Cloud Peak Energy Inc. and its subsidiaries party thereto, the lenders party thereto and Ankura Trust Company, LLC, as administrative agent and as collateral agent

Exhibit 10.1 EXECUTION VERSION AMENDMENT NO. 1 AMENDMENT No. 1 dated as of June 19, 2019 (this “Amendment”) to the Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019, by and among Cloud Peak Energy Inc., a Delaware corporation and a debtor and debtor-in-possession under chapter 11 of the Bankruptcy Code, the other Persons party hereto from time to t

Amendment No. 2 dated as of June 25, 2019 to Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019 by and among Cloud Peak Energy Inc. and its subsidiaries party thereto, the lenders party thereto and Ankura Trust Company, LLC, as administrative agent and as collateral agent

Exhibit 10.2 Execution Version AMENDMENT NO. 2 AMENDMENT No. 2 dated as of June 25, 2019 (this “Amendment”) to the Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement dated as of May 15, 2019, by and among Cloud Peak Energy Inc., a Delaware corporation and a debtor and debtor-in-possession under chapter 11 of the Bankruptcy Code (the “CPE”), the other Persons party hereto fr

CLOUD PEAK ENERGY ANNOUNCES EXTENSION OF ITS PREVIOUSLY ANNOUNCED TENDER OFFER FOR HOLDERS OF 2021 NOTES TO PARTICIPATE IN DIP FINANCING

Exhibit 99.1 PRESS RELEASE June 25, 2019 CLOUD PEAK ENERGY ANNOUNCES EXTENSION OF ITS PREVIOUSLY ANNOUNCED TENDER OFFER FOR HOLDERS OF 2021 NOTES TO PARTICIPATE IN DIP FINANCING Gillette, Wyo. — Cloud Peak Energy Inc. (OTC: CLDPQ) (the “Company”, “Cloud Peak Energy” or “we”) announces the extension of its previously announced tender offer providing the opportunity for the holders of record as of M

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Other Events, Bankruptcy or Receivership

8-K 1 a19-1208618k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 19, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of In

Regulation FD Disclosure

8-K 1 a19-1103818k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 4, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Inc

Second Amended and Restated Receivables Purchase Agreement, dated as of May 15, 2019, among Cloud Peak Energy Receivables LLC, as Seller, Cloud Peak Energy Resources LLC, as Initial Servicer, the various conduit purchasers, related committed purchasers, LC Participants and Purchaser Agents from time to time party thereto, PNC Bank, National Association, as Administrator and as LC Bank and PNC Capital Markets LLC, as Structuring Agent (incorporated by reference to Exhibit 10.1 to Cloud Peak Energy Inc.’s Current Report on Form 8-K filed on May 17, 2019 (File No. 001-34547))

Exhibit 10.1 EXECUTION VERSION SECOND AMENDED AND RESTATED RECEIVABLES PURCHASE AGREEMENT dated as of May 15, 2019 among CLOUD PEAK ENERGY RECEIVABLES LLC, as Seller, CLOUD PEAK ENERGY RESOURCES LLC, a debtor and debtor-in-possession under chapter 11 of the Bankruptcy Code, as initial Servicer, THE VARIOUS CONDUIT PURCHASERS, RELATED COMMITTED PURCHASERS, LC PARTICIPANTS AND PURCHASER AGENTS FROM

Cloud Peak Energy Receives Court Approval of “First Day” Motions to Support Business Operations Obtains Interim Approval to Access $10 Million of its $35 Million Debtor-in-Possession Financing Mines to Continue Normal Operations

EX-99.1 4 a19-100161ex99d1.htm EX-99.1 Exhibit 99.1 Cloud Peak Energy Receives Court Approval of “First Day” Motions to Support Business Operations Obtains Interim Approval to Access $10 Million of its $35 Million Debtor-in-Possession Financing Mines to Continue Normal Operations GILLETTE, Wyo.— May 14, 2019— Cloud Peak Energy Inc. (OTC: CLDP) (“Cloud Peak Energy” or the “Company”), the only pure-

Superpriority Senior Secured Priming Debtor-in-Possession Credit Agreement, dated as of May 15, 2019, among Cloud Peak Energy Inc. and the subsidiaries of Cloud Peak Energy Inc. party thereto, as Borrowers, the Lenders party thereto and Ankura Trust Company, LLC, as Administrative Agent and as Collateral Agent (incorporated by reference to Exhibit 10.2 to Cloud Peak Energy Inc.’s Current Report on Form 8-K filed on May 17, 2019 (File No. 001-34547))

Exhibit 10.2 Execution Version SUPERPRIORITY SENIOR SECURED PRIMING DEBTOR-IN-POSSESSION CREDIT AGREEMENT Dated as of May 15, 2019 among CLOUD PEAK ENERGY INC. and THE SUBSIDIARIES OF CLOUD PEAK ENERGY INC. PARTY HERETO, each a Debtor and Debtor-in-Possession under Chapter 11 of the Bankruptcy Code, as Borrowers, THE LENDERS PARTY HERETO, and ANKURA TRUST COMPANY, LLC, as Administrative Agent and

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Bankruptcy or Receivership

8-K 1 a19-1001618k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 14, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Inc

Amended and Restated Sale and Plan Support Agreement, dated May 9, 2019, by and among Cloud Peak Energy Inc. and certain of its direct and indirect subsidiaries, certain holders of 2021 Notes, and certain holders of 2024 Notes

EX-10.1 2 a19-95922ex10d1.htm EX-10.1 Exhibit 10.1 EXECUTION VERSION THIS AMENDED AND RESTATED SALE AND PLAN SUPPORT AGREEMENT IS NOT AN OFFER WITH RESPECT TO ANY SECURITIES. ANY SUCH OFFER OR SOLICITATION WILL COMPLY WITH ALL APPLICABLE SECURITIES LAWS. NOTHING CONTAINED IN THIS AMENDED AND RESTATED SALE AND PLAN SUPPORT AGREEMENT SHALL BE AN ADMISSION OF FACT OR LIABILITY OR, UNTIL THE OCCURRENC

Cloud Peak Energy Discussion Materials May 2019 1

Exhibit 99.1 Cloud Peak Energy Discussion Materials May 2019 1 Disclaimer The information contained herein includes proprietary information regarding Cloud Peak Energy Inc. and its corporate affiliates (jointly and severally, “Cloud Peak”, “CPE”, or the “Company”). The assumptions and financial projections contained herein are those of the management of the Company. While management believes that

Cloud Peak Energy Voluntarily Files for Chapter 11 Operations to Continue as Normal and Marketing and Sale Process to Continue Secures Approximately $35 Million in Debtor-in-Possession Financing Enters into Sale and Plan Support Agreement with Certai

EX-99.2 5 a19-95922ex99d2.htm EX-99.2 Exhibit 99.2 Cloud Peak Energy Voluntarily Files for Chapter 11 Operations to Continue as Normal and Marketing and Sale Process to Continue Secures Approximately $35 Million in Debtor-in-Possession Financing Enters into Sale and Plan Support Agreement with Certain Creditors GILLETTE, Wyo.—May 10, 2019— Cloud Peak Energy Inc. (OTC: CLDP) (“Cloud Peak Energy” or

Receivables Purchase Agreement Amendment, dated as of May 10, 2019, by and among Cloud Peak Energy Receivables LLC, Cloud Peak Energy Resources LLC, and PNC Bank, National Association as the Administrator, a Related Committed Purchaser and Purchaser Agent, an LC Participant and the LC Bank (incorporated by reference to Exhibit 10.2 to Cloud Peak Energy Inc.’s Current Report on Form 8-K filed on May 10, 2019 (File No. 001-34547))

Exhibit 10.2 EXECUTION VERSION SECOND AMENDMENT TO THE AMENDED AND RESTATED RECEIVABLES PURCHASE AGREEMENT THIS SECOND AMENDMENT TO THE AMENDED AND RESTATED RECEIVABLES PURCHASE AGREEMENT (this “Amendment”), dated as of May 10, 2019, is entered into among CLOUD PEAK ENERGY RECEIVABLES LLC, a Delaware limited liability company (the “Seller”), as Seller, CLOUD PEAK ENERGY RESOURCES LLC, a Delaware l

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Triggering Events That Accelerate or Increase a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement, Bankruptcy or Receivership

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 6, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission File

CLD / Cloud Peak Energy Inc. 10-Q Quarterly Report 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 0

Mine Safety Disclosure

Exhibit 95.1 MINE SAFETY DISCLOSURE Strong Safety Performance One of our most important values is ensuring the safety of our employees and contractors by operating in a safe and responsible manner and protecting the environment in which we live and work. We have extensive safety systems that have been developed over many years. We continue to focus on refining these systems and the safety leadersh

Third Amended and Restated Forbearance Agreement, dated May 7, 2019, by and among Cloud Peak Energy Receivables LLC, Cloud Peak Energy Resources LLC, and PNC Bank, National Association as the Administrator, a Purchaser, a Purchaser Agent and the LC Bank (incorporated by reference to Exhibit 10.2 to Cloud Peak Energy Inc.’s Current Report on Form 8-K filed on May 8, 2019 (File No. 001-34547))

Exhibit 10.2 EXECUTION VERSION THIRD AMENDED AND RESTATED FORBEARANCE AGREEMENT This THIRD AMENDED AND RESTATED FORBEARANCE AGREEMENT, dated as of May 7, 2019 (this “Agreement”), is entered into among the undersigned in connection with the AMENDED AND RESTATED RECEIVABLES PURCHASE AGREEMENT, dated as of January 31, 2017 (as amended, supplemented and modified from time to time, the “RPA”) among CLO

Letter Agreement, dated as of May 7, 2019, by and among Cloud Peak Energy Resources LLC, Cloud Peak Energy Inc., Cloud Peak Finance Corp., and Nomura Corporate Research and Asset Management Inc. (incorporated by reference to Exhibit 10.1 to Cloud Peak Energy Inc.’s Current Report on Form 8-K filed on May 8, 2019 (File No. 001-34547))

Exhibit 10.1 NOMURA CORPORATE RESEARCH AND ASSET MANAGEMENT INC. 309 West 49th Street New York, NY 10019 May 7, 2019 Cloud Peak Energy Resources LLC 385 Interlocken Crescent, Suite 400 Broomfield, CO 80021 Attention: Heath A. Hill, Executive V.P. and Chief Financial Officer Ladies and Gentlemen: This letter agreement refers to the Forbearance Agreement, dated April 30, 2019 (as amended by that cer

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Triggering Events That Accelerate or Increase a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 7, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission File

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Triggering Events That Accelerate or Increase a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 30, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission F

Letter Agreement, dated as of April 30, 2019, by and among Cloud Peak Energy Resources LLC, Cloud Peak Energy Inc., Cloud Peak Finance Corp., and Nomura Corporate Research and Asset Management Inc. (incorporated by reference to Exhibit 10.1 to Cloud Peak Energy Inc.’s Current Report on Form 8-K filed on May 1, 2019 (File No. 001-34547))

Exhibit 10.1 NOMURA CORPORATE RESEARCH AND ASSET MANAGEMENT INC. 309 West 49th Street New York, NY 10019 April 30, 2019 Cloud Peak Energy Resources LLC 385 Interlocken Crescent, Suite 400 Broomfield, CO 80021 Attention: Heath A. Hill, Executive V.P. and Chief Financial Officer Ladies and Gentlemen: This letter agreement refers to the Forbearance Agreement, dated April 30, 2019 (the “Forbearance Ag

Second Amended and Restated Forbearance Agreement, dated April 30, 2019, by and among Cloud Peak Energy Receivables LLC, Cloud Peak Energy Resources LLC, and PNC Bank, National Association as the Administrator, a Purchaser, a Purchaser Agent and the LC Bank (incorporated by reference to Exhibit 10.2 to Cloud Peak Energy Inc.’s Current Report on Form 8-K filed on May 1, 2019 (File No. 001-34547))

Exhibit 10.2 SECOND AMENDED AND RESTATED FORBEARANCE AGREEMENT This SECOND AMENDED AND RESTATED FORBEARANCE AGREEMENT, dated as of April 30, 2019 (this “Agreement”), is entered into among the undersigned in connection with the AMENDED AND RESTATED RECEIVABLES PURCHASE AGREEMENT, dated as of January 31, 2017 (as amended, supplemented and modified from time to time, the “RPA”) among CLOUD PEAK ENERG

Amended and Restated Forbearance Agreement, dated April 12, 2019, by and among Cloud Peak Energy Receivables LLC, Cloud Peak Energy Resources LLC, and PNC Bank, National Association as the Administrator, a Purchaser, a Purchaser Agent and the LC Bank (incorporated by reference to Exhibit 10.2 to Cloud Peak Energy Inc.’s Current Report on Form 8-K filed on April 15, 2019 (File No. 001-34547))

Exhibit 10.2 AMENDED AND RESTATED FORBEARANCE AGREEMENT This AMENDED AND RESTATED FORBEARANCE AGREEMENT, dated as of April 12, 2019 (this “Agreement”), is entered into among the undersigned in connection with the AMENDED AND RESTATED RECEIVABLES PURCHASE AGREEMENT, dated as of January 31, 2017 (as amended, supplemented and modified from time to time, the “RPA”) among CLOUD PEAK ENERGY RECEIVABLES

Forbearance Agreement, dated as of April 15, 2019, by and among Cloud Peak Energy Resources LLC, Cloud Peak Energy Inc., Cloud Peak Finance Corp., and Nomura Corporate Research and Asset Management Inc. (incorporated by reference to Exhibit 10.1 to Cloud Peak Energy Inc.’s Current Report on Form 8-K filed on April 15, 2019 (File No. 001-34547))

Exhibit 10.1 FORBEARANCE FORBEARANCE, dated as of April 15, 2019 (this “Agreement”), by and among Cloud Peak Energy Resources LLC, a Delaware limited liability company (the “Company”), Cloud Peak Finance Corp., a Delaware corporation (together with the Company, the “Issuers”), Cloud Peak Energy Inc., a Delaware corporation (the “Parent Guarantor” and, together with the Issuers, the “Note Parties”)

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Triggering Events That Accelerate or Increase a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 12, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission F

EX-99.25

NOTIFICATION OF THE REMOVAL FROM LISTING AND REGISTRATION OF THE STATED SECURITIES The New York Stock Exchange ('NYSE' or the 'Exchange') hereby notifies the Securities and Exchange Commission (the 'Commission') of its intention to remove the Common Stock (the 'Common Stock') of Cloud Peak Energy Inc.

CLOUD PEAK ENERGY ANNOUNCES SUSPENSION OF TRADING AND COMMENCEMENT OF NYSE DELISTING PROCEDURES DUE TO LOW STOCK PRICE; COMMON STOCK EXPECTED TO BEGIN TRADING ON THE OTC PINK

Exhibit 99.1 PRESS RELEASE March 26, 2019 CLOUD PEAK ENERGY ANNOUNCES SUSPENSION OF TRADING AND COMMENCEMENT OF NYSE DELISTING PROCEDURES DUE TO LOW STOCK PRICE; COMMON STOCK EXPECTED TO BEGIN TRADING ON THE OTC PINK Gillette, Wyo. — Cloud Peak Energy Inc. (NYSE: CLD) (the “Company”) announced that on March 26, 2019, the Company was notified by the New York Stock Exchange (“NYSE”) that the NYSE ha

Regulation FD Disclosure, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 26, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission F

Mine Safety Disclosure

Exhibit 95.1 MINE SAFETY DISCLOSURE Strong Safety Performance One of our most important values is ensuring the safety of our employees and contractors by operating in a safe and responsible manner and protecting the environment in which we live and work. We have extensive safety systems that have been developed over many years. We continue to focus on refining these systems and the safety leadersh

2018 Form 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-34547 Cloud Peak Energy Inc.

List of Subsidiaries

Exhibit 21.1 List of Subsidiaries The following is a complete list of the direct and indirect subsidiaries of Cloud Peak Energy Inc., a Delaware corporation, including their respective states of incorporation, as of March 15, 2019: Name Jurisdiction Ownership Antelope Coal LLC Delaware 100 % Arrowhead I LLC Delaware 100 % Arrowhead II LLC Delaware 100 % Arrowhead III LLC Delaware 100 % Big Metal C

Forbearance Agreement, dated as of March 14, 2019, by and among Cloud Peak Energy Receivables LLC, Cloud Peak Energy Resources LLC, and PNC Bank, National Association as the Administrator, a Purchaser, a Purchaser Agent and the LC Bank

Exhibit 10.32 FORBEARANCE AGREEMENT This FORBEARANCE AGREEMENT, dated as of March 14, 2019 (this “Agreement”), is entered into among the undersigned in connection with the AMENDED AND RESTATED RECEIVABLES PURCHASE AGREEMENT, dated as of January 31, 2017 (as amended, supplemented and modified from time to time, the “RPA”) among CLOUD PEAK ENERGY RECEIVABLES LLC, a Delaware limited liability company

CLD / Cloud Peak Energy Inc.

CORRESP 1 filename1.htm February 26, 2019 Joel Parker Senior Assistant Chief Accountant Office of Beverages, Apparel, and Mining Securities and Exchange Commission 100 F Street, N.E. Washington, DC 20549 Re: Cloud Peak Energy Inc. Form 10-Q for the Quarterly Period Ended September 30, 2018 Filed October 26, 2018 File No. 001-34547 Dear Mr. Parker: On behalf of Cloud Peak Energy Inc. (the “Company”

CLD / Cloud Peak Energy Inc. / Kopernik Global Investors, LLC Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 3)* Cloud Peak Energy, Inc (Name of Issuer) Common Stock (Title of Class of Securities) 18911Q102 (CUSIP Number) December 31, 2018 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this

CLD / Cloud Peak Energy Inc. / VANGUARD GROUP INC Passive Investment

cloudpeakenergyinc.htm - Generated by SEC Publisher for SEC Filing SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 1 )* Name of issuer: Cloud Peak Energy Inc Title of Class of Securities: Common Stock CUSIP Number: 18911Q102 Date of Event Which Requires Filing of this Statement: December 31, 2018 Check the appropriate

CLD / Cloud Peak Energy Inc. / DIMENSIONAL FUND ADVISORS LP - SCHEDULE 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 4)* CLOUD PEAK ENERGY INC (Name of Issuer) Common Stock (Title of Class of Securities) 18911Q102 (CUSIP Number) December 31, 2018 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this S

Form of Executive Retention Agreement dated January 29, 2019 (Incorporated herein by reference to Exhibit 10.1 to CPE Inc.’s Current Report on Form 8-K filed on January 29, 2019 (File No. 001-34547)) †

Exhibit 10.1 EXECUTIVE RETENTION AGREEMENT This Executive Retention Agreement (this “Agreement”) is made by and among CLOUD PEAK ENERGY INC. (the “Company”) and (“Executive”) and is entered into as of January 29, 2019 (the “Effective Date”). 1. Purpose. The Company recognizes the important goal of retaining Executive as an employee of the Company, and, in furtherance of that goal, the Company wish

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 29, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

CLOUD PEAK ENERGY PROVIDES UPDATE ON STRATEGIC ALTERNATIVES REVIEW

Exhibit 99.1 PRESS RELEASE January 29, 2019 CLOUD PEAK ENERGY PROVIDES UPDATE ON STRATEGIC ALTERNATIVES REVIEW Gillette, Wyo. — Cloud Peak Energy Inc. (NYSE: CLD) (the “Company”), the only pure-play Powder River Basin (“PRB”) coal company, today announced that it has retained Centerview Partners LLC as its investment banker, Vinson & Elkins LLP as its legal advisor, and FTI Consulting, Inc. as its

CLD / Cloud Peak Energy Inc. 8-A12B

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 26-3088162 (State or other jurisdiction of incorporation) (IRS Employer Identification No.) 748 T-7 Road Gil

CLOUD PEAK ENERGY ADOPTS TAX BENEFIT PRESERVATION PLAN FOR NET OPERATING LOSSES

EX-99.1 4 a19-28062ex99d1.htm EX-99.1 Exhibit 99.1 PRESS RELEASE January 14, 2019 CLOUD PEAK ENERGY ADOPTS TAX BENEFIT PRESERVATION PLAN FOR NET OPERATING LOSSES Gillette, Wyo. — Cloud Peak Energy Inc. (NYSE: CLD) (the “Company”) announced today that its Board of Directors (the “Board”) has adopted a Stockholder Rights Plan (the “Rights Plan”) designed to preserve its substantial federal net opera

Certificate of Designations of Series A Junior Participating Preferred Stock of Cloud Peak Energy Inc.

Exhibit 3.1 CERTIFICATE OF DESIGNATIONS OF SERIES A JUNIOR PARTICIPATING PREFERRED STOCK OF CLOUD PEAK ENERGY INC. (Pursuant to Section 151 of the Delaware General Corporation Law) In accordance with Section 151 of the Delaware General Corporation Law, the undersigned corporation hereby certifies that the following resolution was adopted by the Board of Directors of Cloud Peak Energy Inc., a Delaw

Regulation FD Disclosure, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Material Modification to Rights of Security Holders, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 11, 2019 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other jurisdiction of incorporation) (Commission

Rights Agreement, dated as of January 11, 2019, between Cloud Peak Energy Inc., as the Company, and Computershare Trust Company, N.A., as Rights Agent

Exhibit 4.1 Execution Version RIGHTS AGREEMENT dated as of January 11, 2019 between CLOUD PEAK ENERGY INC., as the Company, and COMPUTERSHARE TRUST COMPANY, N.A., as Rights Agent TABLE OF CONTENTS Page SECTION 1. Certain Definitions 1 SECTION 2. Appointment of Rights Agent 9 SECTION 3. Issue of Rights Certificates 10 SECTION 4. Form of Rights Certificate 12 SECTION 5. Countersignature and Registra

CLOUD PEAK ENERGY ANNOUNCES NYSE NON-COMPLIANCE NOTIFICATION DUE TO MINIMUM AVERAGE SHARE PRICE REQUIREMENT

Exhibit 99.1 PRESS RELEASE December 27, 2018 CLOUD PEAK ENERGY ANNOUNCES NYSE NON-COMPLIANCE NOTIFICATION DUE TO MINIMUM AVERAGE SHARE PRICE REQUIREMENT Gillette, Wyo. — Cloud Peak Energy Inc. (NYSE: CLD) (the “Company”) announced that on December 26, 2018, the Company was notified by the New York Stock Exchange (“NYSE”) that the average closing price of the Company’s shares of common stock had fa

Regulation FD Disclosure, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 26, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commissio

CLD / Cloud Peak Energy Inc.

December 17, 2018 Joel Parker Senior Assistant Chief Accountant Office of Beverages, Apparel, and Mining Securities and Exchange Commission 100 F Street, N.

Filed Form of Executive Retention Agreement, dated November 9, 2018, entered into by Cloud Peak Energy Inc. and each of Mr. Colin Marshall, Mr. Heath Hill, Mr. Bruce Jones, Mr. Bryan Pechersky, Ms. Amy Clemetson, and Mr. Todd Myers

Exhibit 10.1 EXECUTIVE RETENTION AGREEMENT This Executive Retention Agreement (this “Agreement”) is made by and among CLOUD PEAK ENERGY INC. (the “Company”) and (“Executive”) and is entered into as of November 9, 2018 (the “Effective Date”). 1. Purpose. The Company recognizes the important goal of retaining Executive as an employee of the Company, and, in furtherance of that goal, the Company wish

CLOUD PEAK ENERGY ANNOUNCES STRATEGIC ALTERNATIVES REVIEW

Exhibit 99.2 PRESS RELEASE November 13, 2018 CLOUD PEAK ENERGY ANNOUNCES STRATEGIC ALTERNATIVES REVIEW Gillette, Wyo. (BUSINESSWIRE) — Cloud Peak Energy Inc. (NYSE:CLD), one of the largest U.S. coal producers and the only pure-play Powder River Basin (“PRB”) coal company, today announced that its Board of Directors, working together with the Company’s management team and legal and financial adviso

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Termination of a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 9, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

CLOUD PEAK ENERGY ANNOUNCES ITS ELECTION TO TERMINATE ITS UNDRAWN CREDIT AGREEMENT

Exhibit 99.1 PRESS RELEASE November 13, 2018 CLOUD PEAK ENERGY ANNOUNCES ITS ELECTION TO TERMINATE ITS UNDRAWN CREDIT AGREEMENT Gillette, Wyo. (BUSINESSWIRE) — Cloud Peak Energy Inc. (NYSE:CLD), one of the largest U.S. coal producers and the only pure-play Powder River Basin (“PRB”) coal company, today announced that Cloud Peak Energy Resources LLC (“CPE Resources”), a wholly owned subsidiary of C

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 30, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of (Commission File Number) (

INVESTOR Presentation October 2018

Exhibit 99.1 INVESTOR Presentation October 2018 Cautionary Note Regarding Forward-Looking Statements This presentation contains “forward-looking statements” within the meaning of the safe harbor provisions of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Forward-looking statements are not statements of historical facts, and often contain words su

CLD / Cloud Peak Energy Inc. 10-Q (Quarterly Report)

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Numbe

Mine Safety Disclosure

Exhibit 95.1 MINE SAFETY DISCLOSURE Strong Safety Performance One of our most important values is ensuring the safety of our employees and contractors by operating in a safe and responsible manner and protecting the environment in which we live and work. We have extensive safety systems that have been developed over many years. We continue to focus on refining these systems and the safety leadersh

Financial Statements and Exhibits, Results of Operations and Financial Condition

8-K 1 a18-1899038k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 25, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of

CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR THIRD QUARTER AND FIRST NINE MONTHS OF 2018

Exhibit 99.1 PRESS RELEASE October 25, 2018 CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR THIRD QUARTER AND FIRST NINE MONTHS OF 2018 Gillette, Wyo. (BUSINESSWIRE) — Cloud Peak Energy Inc. (NYSE:CLD), one of the largest U.S. coal producers and the only pure-play Powder River Basin (“PRB”) coal company, today announced results for the third quarter and first nine months of 2018. Colin Marshall, Pres

CLOUD PEAK ENERGY COMPLETES PREVIOUSLY ANNOUNCED CORPORATE HEADQUARTERS MOVE

Exhibit 99.1

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES

INVESTOR Presentation July 2018

Exhibit 99.1 INVESTOR Presentation July 2018 Cautionary Note Regarding Forward-Looking Statements This presentation contains “forward-looking statements” within the meaning of the safe harbor provisions of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Forward-looking statements are not statements of historical facts, and often contain words such

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 27, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission Fi

CLD / Cloud Peak Energy Inc. 10-Q (Quarterly Report)

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 00

Mine Safety Disclosure

Exhibit 95.1 MINE SAFETY DISCLOSURE Strong Safety Performance One of our most important values is ensuring the safety of our employees and contractors by operating in a safe and responsible manner and protecting the environment in which we live and work. We have extensive safety systems that have been developed over many years. We continue to focus on refining these systems and the safety leadersh

CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR SECOND QUARTER AND FIRST SIX MONTHS OF 2018

Exhibit 99.1 PRESS RELEASE July 26, 2018 CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR SECOND QUARTER AND FIRST SIX MONTHS OF 2018 Gillette, Wyo. (BUSINESSWIRE) — Cloud Peak Energy Inc. (NYSE:CLD), one of the largest U.S. coal producers and the only pure-play Powder River Basin (“PRB”) coal company, today announced results for the second quarter and first six months of 2018. Colin Marshall, Preside

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 26, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission Fi

CLOUD PEAK ENERGY ANNOUNCES CHIEF OPERATING OFFICER TRANSITION

Exhibit 99.1 FOR IMMEDIATE RELEASE July 11, 2018 CLOUD PEAK ENERGY ANNOUNCES CHIEF OPERATING OFFICER TRANSITION Gillette, Wyo, July 11, 2018 — Cloud Peak Energy Inc. (NYSE:CLD), one of the largest U.S. coal producers and the only pure-play Powder River Basin coal company, today announced that effective July 11, 2018, Bruce Jones, currently Cloud Peak Energy’s Senior Vice President, Technical Servi

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 11, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission Fi

Amended and Restated Bylaws of Cloud Peak Energy Inc., effective July 11, 2018 (incorporated by reference to Exhibit 3.2 to Cloud Peak Energy Inc.’s Current Report on Form 8-K filed on July 11, 2018 (File No. 001-34547))

Exhibit 3.2 AMENDED AND RESTATED BYLAWS OF CLOUD PEAK ENERGY INC. ARTICLE I Offices SECTION 1. Registered Office. The registered office and registered agent of the Company in the State of Delaware shall be as set forth in the Amended and Restated Certificate of Incorporation of the Company, as amended from time to time (the “Certificate of Incorporation”). The registered office and/or registered a

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 7, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission Fil

Amended and Restated Credit Agreement, dated May 24, 2018, between Cloud Peak Energy Resources LLC, the guarantors party thereto, the lenders party thereto and PNC Bank, National Association, as administrative agent.

Exhibit 10.1 EXECUTION VERSION CUSIP: 18911WAC3 AMENDED AND RESTATED CREDIT AGREEMENT dated as of May 24, 2018 among CLOUD PEAK ENERGY RESOURCES LLC, the GUARANTORS party hereto, the LENDERS party hereto, and PNC BANK, NATIONAL ASSOCIATION, as Administrative Agent, Swingline Lender, and Issuing Bank PNC CAPITAL MARKETS LLC as Joint Lead Arranger and Sole Bookrunner THE HUNTINGTON NATIONAL BANK as

CLOUD PEAK ENERGY EXTENDS AND AMENDS REVOLVING CREDIT FACILITY AND RECEIVABLES SECURITIZATION FACILITY

Exhibit 99.1 FOR IMMEDIATE RELEASE May 24, 2018 CLOUD PEAK ENERGY EXTENDS AND AMENDS REVOLVING CREDIT FACILITY AND RECEIVABLES SECURITIZATION FACILITY Gillette, Wyo, May 24, 2018 — Cloud Peak Energy Inc. (NYSE:CLD), one of the largest U.S. coal producers and the only pure-play Powder River Basin coal company, today announced that, effective May 24, 2018, its wholly owned subsidiary Cloud Peak Ener

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 24, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of (Commission File Number) (IRS

Amended and Restated Guarantee and Security Agreement, dated May 24, 2018, between Cloud Peak Energy Resources LLC, the guarantors party thereto, and PNC Bank, National Association, as administrative agent.

Exhibit 10.2 AMENDED AND RESTATED GUARANTEE AND SECURITY AGREEMENT dated as of May 24, 2018 among CLOUD PEAK ENERGY RESOURCES LLC the GUARANTORS party hereto and PNC BANK, NATIONAL ASSOCIATION, as Administrative Agent TABLE OF CONTENTS SECTION 1. Definitions 3 SECTION 2. Guarantees by Guarantors 9 SECTION 3. Grant of Transaction Liens 11 SECTION 4. General Representations and Warranties 13 SECTION

First Amendment to the Amended and Restated Receivables Purchase Agreement, dated May 24, 2018, by and between Cloud Peak Energy Resources LLC, Cloud Peak Energy Receivables LLC, PNC Bank, National Association, as administrator, related committed purchaser and purchaser agent.

EX-10.3 4 a18-142091ex10d3.htm EX-10.3 Exhibit 10.3 EXECUTION VERSION FIRST AMENDMENT TO THE AMENDED AND RESTATED RECEIVABLES PURCHASE AGREEMENT THIS FIRST AMENDMENT TO THE AMENDED AND RESTATED RECEIVABLES PURCHASE AGREEMENT (this “Amendment”), dated as of May 24, 2018, is entered into among CLOUD PEAK ENERGY RECEIVABLES LLC, a Delaware limited liability company, as Seller, CLOUD PEAK ENERGY RESOU

CLD / Cloud Peak Energy Inc. S-8

As filed with the Securities and Exchange Commission on May 10, 2018 Registration No.

Amendment No. 2 to the Cloud Peak Energy Inc. 2009 Long Term Incentive Plan, as amended and restated effective March 3, 2017 (incorporated by reference to Exhibit 10.1 to the Registrant’s Current Report on Form 8-K filed on May 9, 2018 (File No. 001-34547))

Exhibit 10.1 SECOND AMENDMENT TO THE CLOUD PEAK ENERGY INC. 2009 LONG TERM INCENTIVE PLAN (AS AMENDED AND RESTATED EFFECTIVE MARCH 3, 2017) THIS SECOND AMENDMENT (the “Amendment”), dated as of May 9, 2018, to the Cloud Peak Energy Inc. 2009 Long Term Incentive Plan, as amended and restated effective March 3, 2017 and previously amended effective May 10, 2017 (the “Plan”), as approved by the Board

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 9, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission File

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 9, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission File

Annual Stockholders Meeting May 9, 2018

Exhibit 99.1 Annual Stockholders Meeting May 9, 2018 Cautionary Note Regarding Forward-Looking Statements This presentation contains “forward-looking statements” within the meaning of the safe harbor provisions of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Forward-looking statements are not statements of historical facts, and often contain wor

INVESTOR Presentation May 3, 2018

Exhibit 99.1 INVESTOR Presentation May 3, 2018 Cautionary Note Regarding Forward-Looking Statements This presentation contains “forward-looking statements” within the meaning of the safe harbor provisions of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Forward-looking statements are not statements of historical facts, and often contain words suc

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 3, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission File

CLD / Cloud Peak Energy Inc. 10-Q (Quarterly Report)

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 0

Modified Federal Coal Lease, WYW-177903: Antelope Coal LLC effective February 1, 2018

Exhibit 10.5 Serial Number WYW177903 September 1, 2011 UNITED STATES DEPARTMENT OF THE INTERIOR BUREAU OF LAND MANAGEMENT MODIFIED COAL LEASE PART I. THIS MODIFIED COAL LEASE is entered into on FEB 01 2018, by and between the UNITED STATES OF AMERICA, hereinafter called the Lessor, through the Bureau of Land Management, and Antelope Coal LLC P.O. Box 3009 Gillette, WY 82717 hereinafter called Less

Mine Safety Disclosure

Exhibit 95.1 MINE SAFETY DISCLOSURE Strong Safety Performance One of our most important values is ensuring the safety of our employees and contractors by operating in a safe and responsible manner and protecting the environment in which we live and work. We have extensive safety systems that have been developed over many years. We continue to focus on refining these systems and the safety leadersh

First Amendment to the Amended and Restated Deferred Compensation Plan for Cloud Peak Energy Resources LLC, effective April 2, 2018

EX-10.6 3 a18-86151ex10d6.htm EX-10.6 Exhibit 10.6 FIRST AMENDMENT TO THE AMENDED AND RESTATED DEFERRED COMPENSATION PLAN FOR CLOUD PEAK ENERGY RESOURCES LLC WHEREAS, Cloud Peak Energy Resources LLC (the “Company”), a Delaware limited liability company, adopted the Deferred Compensation Plan For Cloud Peak Energy Resources LLC (the “Plan”) and subsequently amended and restated the Plan effective A

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 26, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission F

CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR FIRST QUARTER 2018

Exhibit 99.1 PRESS RELEASE April 26, 2018 CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR FIRST QUARTER 2018 Gillette, Wyo. (BUSINESSWIRE) — Cloud Peak Energy Inc. (NYSE:CLD), one of the largest U.S. coal producers and the only pure-play Powder River Basin (“PRB”) coal company, today announced results for the first quarter of 2018. Colin Marshall, President, Chief Executive Officer and Chief Operatin

CLD / Cloud Peak Energy Inc. DEFA14A

DEFA14A 1 br71534x1.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permit

CLD / Cloud Peak Energy Inc. DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

CLD / Cloud Peak Energy Inc. DEF 14A

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14

Form of 2018 Cloud Peak Energy Inc. 2009 Long Term Incentive Plan Performance Share Unit Award Agreement (Incorporated herein by reference to Exhibit 10.3 to CPE Inc.’s Current Report on 8-K filed on March 5, 2018 (File No. 001-34547))

Exhibit 10.3 For 2018 Awards CLOUD PEAK ENERGY INC. 2009 LONG TERM INCENTIVE PLAN (As Amended and Restated Effective March 3, 2017) FORM OF PERFORMANCE SHARE UNIT AWARD AGREEMENT THIS AGREEMENT is made as of the 2nd day of March 2018 (the “Grant Date”), between Cloud Peak Energy Inc., a Delaware corporation (the “Company”), and (the “Grantee”). WHEREAS, the Company has adopted the Cloud Peak Energ

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 2, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of (Commission File Number) (IRS

Waiver of Employment Agreement for 2018 LTIP Reduction (Colin Marshall)

Exhibit 10.1 Waiver of Executive Employment Agreement For Reduction in 2018 LTIP Grant Date Target Award Value March 2, 2018 WHEREAS, the undersigned (the “Executive”) is subject to an Employment Agreement (the “Employment Agreement”) with Cloud Peak Energy Inc., a Delaware corporation (the “Company”), dated as of the applicable date specified in such Employment Agreement; WHEREAS, all capitalized

Waiver of Employment Agreement for 2018 LTIP Reduction (Heath Hill)

Exhibit 10.2 Waiver of Executive Employment Agreement For Reduction in 2018 LTIP Grant Date Target Award Value March 2, 2018 WHEREAS, the undersigned (the “Executive”) is subject to an Employment Agreement (the “Employment Agreement”) with Cloud Peak Energy Inc., a Delaware corporation (the “Company”), dated as of the applicable date specified in such Employment Agreement; WHEREAS, all capitalized

Form of 2018 Cloud Peak Energy Inc. 2009 Long Term Incentive Plan Restricted Stock Unit Agreement (Incorporated herein by reference to Exhibit 10.4 to CPE Inc.’s Current Report on 8-K filed on March 5, 2018 (File No. 001-34547))

Exhibit 10.4 For 2018 Awards CLOUD PEAK ENERGY INC. 2009 LONG TERM INCENTIVE PLAN (As Amended and Restated Effective March 3, 2017) FORM OF RESTRICTED STOCK UNIT AGREEMENT THIS AGREEMENT is made as of the 2nd day of March 2018 (the “Grant Date”), between Cloud Peak Energy Inc., a Delaware corporation (the “Company”), and (the “Grantee”). WHEREAS, the Company has adopted the Cloud Peak Energy Inc.

INVESTOR Presentation February 2018

Exhibit 99.1 INVESTOR Presentation February 2018 Cautionary Note Regarding Forward-Looking Statements This presentation contains ?forward-looking statements? within the meaning of the safe harbor provisions of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Forward-looking statements are not statements of historical facts, and often contain words s

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 23, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commissio

CLD / Cloud Peak Energy Inc. 10-K (Annual Report)

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2017 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-34547 Cloud Peak Energy Inc.

Form of 2018 Cloud Peak Energy Inc. 2009 Long Term Incentive Plan Director Restricted Stock Unit Agreement

Exhibit 10.55 CLOUD PEAK ENERGY INC. 2009 LONG TERM INCENTIVE PLAN (As Amended and Restated, Effective March 3, 2017) RESTRICTED STOCK UNIT AGREEMENT Directors THIS AGREEMENT is made as of the 10th day of January, 2018 (the “Grant Date”), between Cloud Peak Energy Inc., a Delaware corporation (the “Company”), and (the “Grantee”), a non-employee member of the Company’s Board. WHEREAS, the Company h

Computation of Ratio of Earnings to Fixed Charges

Exhibit 12.1 COMPUTATION OF HISTORICAL RATIOS OF EARNINGS TO FIXED CHARGES (1) (in thousands, except ratio data) CLOUD PEAK ENERGY INC. December 31, 2017 2016 2015 2014 2013 Earnings: Income from continuing operations before income tax benefit (provision), earnings (loss) from unconsolidated affiliates and minority interest $ (36,822 ) $ 18,971 $ (128,720 ) $ 113,294 $ 63,066 Amortization of capit

List of Subsidiaries

Exhibit 21.1 List of Subsidiaries The following is a complete list of the direct and indirect subsidiaries of Cloud Peak Energy Inc., a Delaware corporation, including their respective states of incorporation, as of February 15, 2018: Name Jurisdiction Ownership Antelope Coal LLC Delaware 100 % Arrowhead I LLC Delaware 100 % Arrowhead II LLC Delaware 100 % Arrowhead III LLC Delaware 100 % Big Meta

Mine Safety Disclosure

Exhibit 95.1 MINE SAFETY DISCLOSURE Strong Safety Performance One of our most important values is ensuring the safety of our employees and contractors by operating in a safe and responsible manner and protecting the environment in which we live and work. We have extensive safety systems that have been developed over many years. We continue to focus on refining these systems and the safety leadersh

CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR THE FOURTH QUARTER AND FULL YEAR 2017

Exhibit 99.1 PRESS RELEASE February 15, 2018 CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR THE FOURTH QUARTER AND FULL YEAR 2017 Gillette, Wyo. (BUSINESSWIRE) — Cloud Peak Energy Inc. (NYSE:CLD), one of the largest U.S. coal producers and the only pure-play Powder River Basin (“PRB”) coal company, today announced results for the fourth quarter and full year 2017. Highlights and Recent Developments

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 15, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commissio

CLD / Cloud Peak Energy Inc. / Kopernik Global Investors, LLC Passive Investment

SC 13G/A 1 c90428sc13ga.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2)* Cloud Peak Energy, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 18911Q102 (CUSIP Number) December 31, 2017 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the

CLD / Cloud Peak Energy Inc. / DIMENSIONAL FUND ADVISORS LP - SCHEDULE 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 3)* CLOUD PEAK ENERGY INC (Name of Issuer) Common Stock (Title of Class of Securities) 18911Q102 (CUSIP Number) December 31, 2017 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this S

CLD / Cloud Peak Energy Inc. / VANGUARD GROUP INC Passive Investment

cloudpeakenergyinc.htm - Generated by SEC Publisher for SEC Filing SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 0 )* Name of issuer: Cloud Peak Energy Inc Title of Class of Securities: Common Stock CUSIP Number: 18911Q102 Date of Event Which Requires Filing of this Statement: December 31, 2017 Check the appropriate

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 18, 2018 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 7, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

INVESTOR Presentation November 2017

Exhibit 99.1 INVESTOR Presentation November 2017 Cautionary Note Regarding Forward-Looking Statements This presentation contains ?forward-looking statements? within the meaning of the safe harbor provisions of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Forward-looking statements are not statements of historical facts, and often contain words s

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2017 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Numbe

Mine Safety Disclosure

Exhibit 95.1 MINE SAFETY DISCLOSURE Strong Safety Performance One of our most important values is ensuring the safety of our employees and contractors by operating in a safe and responsible manner and protecting the environment in which we live and work. We have extensive safety systems that have been developed over many years. We continue to focus on refining these systems and the safety leadersh

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 26, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission

CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR THE THIRD QUARTER AND FIRST NINE MONTHS OF 2017

Exhibit 99.1 PRESS RELEASE October 26, 2017 CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR THE THIRD QUARTER AND FIRST NINE MONTHS OF 2017 Gillette, Wyo. (BUSINESSWIRE) ? Cloud Peak Energy Inc. (NYSE:CLD), one of the largest U.S. coal producers and the only pure-play Powder River Basin (?PRB?) coal company, today announced results for the third quarter and first nine months of 2017. Highlights and R

Cloud Peak Energy 8-K/A (Current Report/Significant Event)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 10, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission F

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 7, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission F

INVESTOR Presentation August 2017

Exhibit 99.1 INVESTOR Presentation August 2017 Cautionary Note Regarding Forward-Looking Statements This presentation contains ?forward-looking statements? within the meaning of the safe harbor provisions of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Forward-looking statements are not statements of historical facts, and often contain words suc

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2017 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 00

Mine Safety Disclosure

Exhibit 95.1 MINE SAFETY DISCLOSURE Strong Safety Performance One of our most important values is ensuring the safety of our employees and contractors by operating in a safe and responsible manner and protecting the environment in which we live and work. We have extensive safety systems that have been developed over many years. We continue to focus on refining these systems and the safety leadersh

Employment Agreement between Cloud Peak Energy Inc. and Amy Clemetson, dated as of June 17, 2017 (Incorporated herein by reference to Exhibit 10.3 to CPE Inc.’s Quarterly Report on Form 10-Q filed on July 27, 2017 (File No. 001-34547)) †

Exhibit 10.3 EMPLOYMENT AGREEMENT This EMPLOYMENT AGREEMENT (the ?Employment Agreement?) is made effective as of June 17, 2017 (the ?Effective Date?) by and among Cloud Peak Energy Inc., a Delaware corporation (the ?Company?) and Amy Clemetson (the ?Executive?). RECITALS WHEREAS, the Executive possesses skills, experience and knowledge that are of value to the Company; and WHEREAS, the Company and

CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR THE SECOND QUARTER AND FIRST SIX MONTHS OF 2017

Exhibit 99.1 PRESS RELEASE July 27, 2017 CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR THE SECOND QUARTER AND FIRST SIX MONTHS OF 2017 Gillette, Wyo. (BUSINESSWIRE) ? Cloud Peak Energy Inc. (NYSE:CLD), one of the largest U.S. coal producers and the only pure-play Powder River Basin (?PRB?) coal company, today announced results for the second quarter and first six months of 2017. Highlights and Rece

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 27, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission Fi

POWER OF ATTORNEY

Exhibit 24 POWER OF ATTORNEY Know all by these presents, that the undersigned, in the undersigned?s capacity as an officer and/or director of Cloud Peak Energy Inc.

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

8-K 1 a17-1425618k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 25, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Inc

Cloud Peak Energy S-8

As filed with the Securities and Exchange Commission on May 11, 2017 Registration No.

Amendment No. 1 to the Cloud Peak Energy Inc. 2009 Long Term Incentive Plan (Incorporated herein by reference to Exhibit 10.1 to CPE Inc.’s Current Report on Form 8-K filed on May 10, 2017 (File No. 001-34547)) †

Exhibit 10.1 FIRST AMENDMENT TO THE CLOUD PEAK ENERGY INC. 2009 LONG TERM INCENTIVE PLAN (AS AMENDED AND RESTATED EFFECTIVE MARCH 3, 2017) THIS FIRST AMENDMENT (the ?Amendment?), dated as of May 10, 2017, to the Cloud Peak Energy Inc. 2009 Long Term Incentive Plan, as amended and restated effective March 3, 2017 (the ?Plan?), as approved by the Board of Directors (the ?Board?) of Cloud Peak Energy

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 10, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission Fil

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 10, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission Fil

2017 Annual Stockholders’ Meeting Colin Marshall President and CEO

EX-99.1 2 a17-119003ex99d1.htm EX-99.1 Exhibit 99.1 2017 Annual Stockholders’ Meeting Colin Marshall President and CEO Cautionary Note Regarding Forward-Looking Statements This presentation contains “forward-looking statements” within the meaning of the safe harbor provisions of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Forward-looking statem

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 4, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission File

INVESTOR Presentation May 2017

Exhibit 99.1 INVESTOR Presentation May 2017 Cautionary Note Regarding Forward-Looking Statements This presentation contains ?forward-looking statements? within the meaning of the safe harbor provisions of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Forward-looking statements are not statements of historical facts, and often contain words such a

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2017 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 0

MINE SAFETY DISCLOSURE

Exhibit 95.1 MINE SAFETY DISCLOSURE Strong Safety Performance One of our most important values is ensuring the safety of our employees and contractors by operating in a safe and responsible manner and protecting the environment in which we live and work. We have extensive safety systems that have been developed over many years. We continue to focus on refining these systems and the safety leadersh

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 27, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commission F

CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR THE FIRST QUARTER OF 2017

Exhibit 99.1 PRESS RELEASE April 27, 2017 CLOUD PEAK ENERGY INC. ANNOUNCES RESULTS FOR THE FIRST QUARTER OF 2017 Gillette, Wyo. (BUSINESSWIRE) — Cloud Peak Energy Inc. (NYSE:CLD), one of the largest U.S. coal producers and the only pure-play Powder River Basin (“PRB”) coal company, today announced results for the first quarter of 2017. Highlights and Recent Developments Quarter Ended (in millions,

Cloud Peak Energy DEFA14A

QuickLinks - Click here to rapidly navigate through this document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

Cloud Peak Energy DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Defin

Cloud Peak Energy DEF 14A

DEF 14A 1 a17-21111def14a.htm DEF 14A Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Co

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 3, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of (Commission File Number) (IRS

Form of 2017 Cloud Peak Energy Inc. 2009 Long Term Incentive Plan Performance Share Unit Award Agreement (Incorporated herein by reference to Exhibit 10.2 to CPE Inc.’s Current Report on 8-K filed on March 6, 2017 (File No. 001-34547))

Exhibit 10.2 FOR 2017 AWARDS CLOUD PEAK ENERGY INC. 2009 LONG TERM INCENTIVE PLAN (As Amended and Restated Effective March 3, 2017) FORM OF PERFORMANCE SHARE UNIT AWARD AGREEMENT THIS AGREEMENT is made as of the 3rd day of March 2017 (the ?Grant Date?), between Cloud Peak Energy Inc., a Delaware corporation (the ?Company?), and (the ?Grantee?). WHEREAS, the Company has adopted the Cloud Peak Energ

Form of 2017 Cloud Peak Energy Inc. 2009 Long Term Incentive Plan Restricted Stock Unit Agreement (Incorporated herein by reference to Exhibit 10.3 to CPE Inc.’s Current Report on 8-K filed on March 6, 2017 (File No. 001-34547))

Exhibit 10.3 FOR 2017 AWARDS CLOUD PEAK ENERGY INC. 2009 LONG TERM INCENTIVE PLAN (As Amended and Restated Effective March 3, 2017) FORM OF RESTRICTED STOCK UNIT AGREEMENT THIS AGREEMENT is made as of the 3rd day of March 2017 (the ?Grant Date?), between Cloud Peak Energy Inc., a Delaware corporation (the ?Company?), and (the ?Grantee?). WHEREAS, the Company has adopted the Cloud Peak Energy Inc.

Cloud Peak Energy Inc. 2009 Long Term Incentive Plan, as amended and restated effective March 3, 2017 (Incorporated herein by reference to Exhibit 10.1 to CPE Inc.’s Current Report on Form 8-K filed on March 6, 2017 (File No. 001-34547) †

Exhibit 10.1 CLOUD PEAK ENERGY INC. 2009 LONG TERM INCENTIVE PLAN (As Amended and Restated Effective March 3, 2017) 1. Purpose. The purpose of the Plan is to strengthen Cloud Peak Energy Inc., a Delaware corporation (the ?Company?), by providing an incentive to its and its Subsidiaries? (as defined herein) employees, officers, consultants and directors, thereby encouraging them to devote their abi

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 28, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other jurisdiction of incorporation) (Commissio

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 22, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other jurisdiction of incorporation) (Commissio

13,500,000 Shares CLOUD PEAK ENERGY INC. Common Stock, $0.01 par value UNDERWRITING AGREEMENT

Exhibit 1.1 Execution Version 13,500,000 Shares CLOUD PEAK ENERGY INC. Common Stock, $0.01 par value UNDERWRITING AGREEMENT February 22, 2017 CREDIT SUISSE SECURITIES (USA) LLC As Representative of the Several Underwriters, c/o Credit Suisse Securities (USA) LLC Eleven Madison Avenue New York, New York 10010-3629 Dear Sir/Madam: 1. Introductory. Cloud Peak Energy Inc., a Delaware corporation (?Com

INVESTOR Presentation February 2017

Exhibit 99.1 INVESTOR Presentation February 2017 Cautionary Note Regarding Forward-Looking Statements This presentation contains “forward-looking statements” within the meaning of the safe harbor provisions of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Forward-looking statements are not statements of historical facts, and often contain words s

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 27, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of Incorporation) (Commissio

13,500,000 Shares Common Stock

424B5 1 a2231037z424b5.htm 424B5 Use these links to rapidly review the document TABLE OF CONTENTS Prospectus Supplement TABLE OF CONTENTS Table of Contents Filed Pursuant to Rule 424(b)(5) Registration No.333-214869 PROSPECTUS SUPPLEMENT (To prospectus dated December 20, 2016) 13,500,000 Shares Common Stock We are offering 13,500,000 shares of our common stock at a public offering price of $5.10 p

CLOUD PEAK ENERGY PRICES PUBLIC OFFERING OF COMMON STOCK

Exhibit 99.1 FOR IMMEDIATE RELEASE February 22, 2017 CLOUD PEAK ENERGY PRICES PUBLIC OFFERING OF COMMON STOCK Gillette, Wyo. ? Cloud Peak Energy Inc. (NYSE: CLD) (the ?Company?) announced that it has priced a registered underwritten public offering of 13,500,000 shares of its common stock at a price to the public of $5.10 per share. The Company has granted the underwriters a 30-day option to purch

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 22, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other jurisdiction of incorporation) (Commissio

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 22, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other jurisdiction of incorporation) (Commissio

CLOUD PEAK ENERGY INC. ANNOUNCES PUBLIC OFFERING OF 13,500,000 SHARES OF COMMON STOCK

Exhibit 99.1 FOR IMMEDIATE RELEASE February 22, 2017 CLOUD PEAK ENERGY INC. ANNOUNCES PUBLIC OFFERING OF 13,500,000 SHARES OF COMMON STOCK Gillette, Wyo. — Cloud Peak Energy Inc. (NYSE: CLD) (“CPE Inc.”) announced that it has commenced a registered underwritten public offering of 13,500,000 shares of its common stock. CPE Inc. intends to grant the underwriters a 30-day option to purchase 2,000,000

Subject to Completion dated February 22, 2017

Use these links to rapidly review the document TABLE OF CONTENTS Prospectus Supplement TABLE OF CONTENTS Table of Contents Filed Pursuant to Rule 424(b)(5) Registration No.

COMPUTATION OF HISTORICAL RATIOS OF EARNINGS TO FIXED CHARGES (1) (in thousands, except ratio data)

Exhibit 12.1 COMPUTATION OF HISTORICAL RATIOS OF EARNINGS TO FIXED CHARGES (1) (in thousands, except ratio data) CLOUD PEAK ENERGY INC. December 31, 2016 2015 2014 2013 2012 Earnings: Income from continuing operations before income tax benefit (provision), earnings (loss) from unconsolidated affiliates and minority interest $ 18,971 $ (128,720 ) $ 113,294 $ 63,066 $ 234,778 Amortization of capital

Form of 2017 Cloud Peak Energy Inc. 2009 Long Term Incentive Plan Director Restricted Stock Unit Agreement (Incorporated herein by reference to Exhibit 10.54 to CPE Inc.’s Annual Report on Form 10-K filed on February 15, 2017 (File No. 001-34547)) †

Exhibit 10.54 CLOUD PEAK ENERGY INC. 2009 LONG TERM INCENTIVE PLAN (As Amended and Restated, Effective March 12, 2016) RESTRICTED STOCK UNIT AGREEMENT Directors THIS AGREEMENT is made as of the day of , 2017 (the ?Grant Date?), between Cloud Peak Energy Inc., a Delaware corporation (the ?Company?), and (the ?Grantee?), a non-employee member of the Company?s Board. WHEREAS, the Company has adopted

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2016 or o TRANSITION REPORT PURSU

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2016 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-34547 Cloud Peak Energy Inc.

List of Subsidiaries

Exhibit 21.1 List of Subsidiaries The following is a complete list of the direct and indirect subsidiaries of Cloud Peak Energy Inc., a Delaware corporation, including their respective states of incorporation, as of February 15, 2017: Name Jurisdiction Ownership Antelope Coal LLC Delaware 100 % Arrowhead I LLC Delaware 100 % Arrowhead II LLC Delaware 100 % Arrowhead III LLC Delaware 100 % Big Meta

MINE SAFETY DISCLOSURE

Exhibit 95.1 MINE SAFETY DISCLOSURE Strong Safety Performance One of our most important values is ensuring the safety of our employees and contractors by operating in a safe and responsible manner and protecting the environment in which we live and work. We have extensive safety systems that have been developed over many years. We continue to focus on refining these systems and the safety leadersh

Form of 2015 Cloud Peak Energy Inc. 2009 Long Term Incentive Plan Director Restricted Stock Unit Agreement (Incorporated herein by reference to Exhibit 10.48 to CPE Inc.’s Annual Report on Form 10-K filed on February 15, 2017 (File No. 001-34547))

Exhibit 10.48 FORM OF CLOUD PEAK ENERGY INC. 2009 LONG TERM INCENTIVE PLAN RESTRICTED STOCK UNIT AGREEMENT Directors THIS AGREEMENT, made as of the day of , 2015 (the ?Grant Date?), between Cloud Peak Energy Inc., a Delaware corporation (the ?Company?), and (the ?Grantee?). WHEREAS, the Company has adopted the Cloud Peak Energy Inc. 2009 Long Term Incentive Plan (the ?Plan?), as amended, in order

Second Amended and Restated Employee Stock Purchase Plan dated February 13, 2017 (Incorporated herein by reference to Exhibit 10.57 to CPE Inc.’s Annual Report on Form 10-K filed on February 15, 2017 (File No. 001-34547)) †

Exhibit 10.57 CLOUD PEAK ENERGY INC. SECOND AMENDED AND RESTATED EMPLOYEE STOCK PURCHASE PLAN ARTICLE I PURPOSE AND SCOPE OF THE PLAN Section 1.1Purpose. The Cloud Peak Energy Inc. Employee Stock Purchase Plan is intended to encourage employee participation in the ownership and economic progress of the Company. The Company intends that the Plan qualify as an ?employee stock purchase plan? under Se

CLOUD PEAK ENERGY MODIFIES THROUGHPUT AND TRANSPORTATION AGREEMENTS WITH WESTSHORE TERMINALS AND BNSF RAILWAY

Exhibit 99.2 PRESS RELEASE February 15, 2017 CLOUD PEAK ENERGY MODIFIES THROUGHPUT AND TRANSPORTATION AGREEMENTS WITH WESTSHORE TERMINALS AND BNSF RAILWAY Gillette, Wyo, February 15, 2017 ? Cloud Peak Energy Inc. (NYSE:CLD), one of the largest U.S. coal producers and the only pure-play Powder River Basin (?PRB?) coal company, today announced that Cloud Peak Energy Logistics LLC replaced its throug

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

8-K 1 a17-113248k.htm 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 15, 2017 Cloud Peak Energy Inc. (Exact name of registrant as specified in its charter) Delaware 001-34547 26-3088162 (State or other Jurisdiction of

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clou16a1.htm - Generated by SEC Publisher for SEC Filing CUSIP NO. 18911Q102 13G Page 1 of 13 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* Cloud Peak Energy Inc. (Name of Issuer) Common Stock, par value $0.01 per share (Title of Class of Securities) 18911Q102 (CUSIP Number) December 31, 2016 (Date

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[Signature page follows]

December 16, 2016 VIA EDGAR John Reynolds Assistant Director Office of Beverages, Apparel, and Mining U.

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Exhibit 25.5 File No. SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CORPORATION DESIGNATED TO ACT AS TRUSTEE o CHECK IF AN APPLICATION TO DETERMINE ELIGIBILITY OF A TRUSTEE PURSUANT TO SECTION 305(b)(2) WILMINGTON TRUST, NATIONAL ASSOCIATION (Exact name of trustee as specified in its charter) 16-1486454 (I.R.S

As filed with the Securities and Exchange Commission on December 1, 2016

Use these links to rapidly review the document TABLE OF CONTENTS TABLE OF CONTENTS Table of Contents As filed with the Securities and Exchange Commission on December 1, 2016 Registration No.