v3.26.1
Common Stock Options and Warrants
6 Months Ended
Jun. 30, 2026
Common Stock Options and Warrants [Abstract]  
Common Stock Options and Warrants
Note 14 Common Stock Options and Warrants

On May 3, 2023, the Company completed its merger with Prairie LLC, pursuant to the terms of the Amended and Restated Agreement and Plan of Merger, dated as of May 3, 2023 (the “Merger Agreement”), by and among the Company, Creek Road Merger Sub, LLC (“Merger Sub”), and Prairie LLC, pursuant to which, among other things, Merger Sub merged with and into Prairie LLC, with Prairie LLC surviving and continuing to exist as a Delaware limited liability company and a wholly-owned subsidiary of the Company (the “Merger”). Upon consummation of the Merger, the Company changed its name from “Creek Road Miners, Inc.” to “Prairie Operating Co.”

Legacy Warrants

Upon the Merger, the Company assumed warrants to purchase 53,938 shares of the Common Stock with weighted average exercise prices of $47.61 per share (the “Legacy Warrants”). As of June 30, 2026 and December 31, 2025, 35,388 and 37,138 Legacy Warrants, respectively, providing the right to purchase shares of Common Stock were outstanding. As of June 30, 2026, the Legacy Warrants have a weighted average remaining contractual life of 0.4 years.

Merger Options

On August 31, 2022, Prairie LLC entered into agreements with its members whereby each member was provided non–compensatory options to purchase a 40% membership interest in the Company for an aggregate exercise price of $1.0 million per member. The non–compensatory options were sold to the members for $80,000 per option holder. On May 3, 2023, prior to the closing of the Merger, Prairie LLC entered into a non–compensatory option purchase agreement with its members and Bristol Capital, LLC (“Bristol Capital”), which manages Bristol Investment Fund, Ltd. (“Bristol Investment”) and BOKA Energy LP (“BOKA”), a third–party investor, pursuant to which Bristol Capital and BOKA purchased non–compensatory options for $24,000 and $8,000, respectively, from Prairie LLC’s members.

Upon the Merger, the Company converted the non–compensatory options to purchase the outstanding and unexercised membership interests of Prairie LLC, as of immediately prior to the Merger, into options to acquire an aggregate of 8,000,000 shares of Common Stock for an exercise price of $0.25 per share (the “Merger Options”). The Merger Options only became exercisable in 25% increments upon the achievement of the following production milestones in barrels of oil equivalent per day (“Boe/d”): 2,500 Boe/d, 5,000 Boe/d, 7,500 Boe/d, and 10,000 Boe/d. The Company achieved all of these production milestones upon the closing of the Bayswater Acquisition on March 26, 2025; as such, all of the Merger Options became exercisable.

Subsequent to the Merger, the Company entered into amended and restated non–compensatory option agreements with each of Gary C. Hanna, former President and Director, Edward Kovalik, former Chairman of the Board and Chief Executive Officer, Bristol Capital, and BOKA. On August 30, 2023, the Company, Gary C. Hanna, Edward Kovalik, Bristol Capital, and Georgina Asset Management entered into a non–compensatory option purchase agreement, pursuant to which Georgina Asset Management agreed to purchase, and each of the sellers agreed to sell to Georgina Asset Management, the Merger Options to acquire an aggregate of 200,000 shares of Common Stock, for an exercise price of $0.25 per share for an aggregate purchase price of $2,000. In January 2024, Georgina Asset Management transferred its options to Westwood Financial Holdings LLC (“Westwood”) pursuant to an assignment.
On September 30, 2024, the Company, BOKA, Rose Hill Holdings Limited (“Rose Hill”), Anchorman Holdings Inc. (“Anchorman”), and Blackstem Forest, LLC (“Blackstem” and, together with Rose Hill and Anchorman, the “Option Purchasers”) entered into a non–compensatory option purchase agreement, pursuant to which each of the Option Purchasers agreed to purchase, and BOKA agreed to sell to the Option Purchasers, Merger Options to acquire an aggregate of 800,000 shares of Common Stock, for an exercise price of $0.25 per share. The Company did not receive any proceeds from the transfer of the Merger Options and the terms of the amended and restated non–compensatory option agreements were not amended, modified, or changed in any way in connection with the transfers.

In 2025, Bristol Capital, Westwood, Rose Hill, and Anchorman exercised their options, and received an aggregate 2,993,840 shares of Common Stock. On April 9, 2026, Gary C. Hanna and Edward Kovalik exercised their cashless options and received an aggregate 4,182,572 shares of the Common Stock. As of June 30, 2026, 300,000 shares of Common Stock remained issuable upon the exercise of the Merger Options. As of June 30, 2026, the Merger Options have a weighted average remaining contractual life of 1.2 years.

Series D PIPE Warrants

The Series D PIPE Warrants, upon issuance, provided the warrant holders with the right to purchase an aggregate of 6,950,500 shares of Common Stock at an exercise price of $6.00 per share. The Series D A Warrants expire on May 3, 2028 and the Series D B Warrants expired on May 3, 2024. All such warrants must be exercised for cash.

On April 8, 2024, the Company entered into an Amendment and Waiver of Exercise Limitations Letter Agreement (the “Series D PIPE Letter Agreement”) with Bristol Investment to amend certain terms of the Series D A Warrants and Series D B Warrants held by Bristol Investment. Each of the Series D PIPE Warrants held by Bristol Investment is subject to a limitation on exercise if as a result of such exercise or conversion, the holder would own more than 4.99% of the outstanding shares of the Company’s Common Stock, which may be increased by the holder upon written notice to the Company, to any specified percentage not in excess of 9.99% (the “Beneficial Ownership Limitation Ceiling”). The Series D PIPE Letter Agreement increased the Beneficial Ownership Limitation Ceiling from 9.99% to 19.99%. Pursuant to the Series D PIPE Letter Agreement, Bristol Investment further notified the Company of its intent to immediately increase the Beneficial Ownership Limitation Ceiling to 19.99% and the parties agreed to waive the waiting period with respect to such notice.

No Series D A Warrants were exercised during the year ended December 31, 2025 or the three and six months ended June 30, 2026. As of June 30, 2026 and December 31, 2025, 3,215,761 Series D A Warrants providing the right to purchase shares of Common Stock were outstanding with a remaining contractual life of 1.8 and 2.3 years, respectively.

Series E PIPE Warrants

The Series E PIPE Warrants provide the warrant holders with the right to purchase 8,000,000 shares of Common Stock at an exercise price of $6.00 per share. The Series E A Warrants expire on August 15, 2028 and the Series E B Warrants expired on August 15, 2024. All such warrants must be exercised for cash.

As of June 30, 2026 and December 31, 2025, 4,000,000 Series E A Warrants providing the right to purchase shares of Common Stock with a remaining contractual life of 2.1 and 2.6 years, respectively, were outstanding.

During the year ended December 31, 2024, all of the Series E B Warrants were exercised, resulting in the issuance of 4,000,000 shares of Common Stock, for total proceeds to the Company of $24.0 million, resulting in no outstanding Series E B Warrants as of December 31, 2025 or June 30, 2026.
Exok Warrants

Upon closing of the Merger, the Company consummated the purchase of oil and gas leases from Exok including all of Exok’s right, title, and interest in, to and under certain undeveloped oil and gas leases located in Weld County, Colorado, together with certain other associated assets, data, and records, for $3.0 million (the “First Exok Acquisition”). On August 15, 2023, Prairie LLC exercised the option it acquired in the First Exok Acquisition and purchased additional oil and gas leases from Exok, consisting of approximately 20,300 net leasehold acres in, on and under approximately 32,580 gross acres (the “Second Exok Acquisition”) for total consideration of $25.3 million. The total consideration consisted of $18.0 million in cash to Exok, which was funded with the Series E PIPE, and equity consideration to certain affiliates of Exok consisting of (i) 670,499 shares of Common Stock, and (ii) 670,499 warrants providing the right to purchase shares of Common Stock at $7.43 per share (the “Exok Warrants”). The Exok Warrants provide the warrant holders with the right to purchase shares of Common Stock at an exercise price of $7.43 per share. The Exok Warrants expire on August 15, 2028 and may be exercised in a cashless manner under certain circumstances. On June 30, 2026 and December 31, 2025, 670,499 Exok Warrants providing the right to purchase shares of Common Stock were outstanding with a remaining contractual life of 2.1 and 2.6 years, respectively.

Subordinated Note Warrants

Pursuant to the terms of the Subordinated Note, the Company issued the Subordinated Note Warrants to purchase up to 1,141,552 shares of Common Stock to the Noteholders. The Subordinated Note Warrants vest in equal tranches, beginning on September 30, 2024, every 3 months until the Subordinated Note is repaid. Upon vesting, the Subordinated Note Warrants will be exercisable at any time until September 30, 2029, at an exercise price of $8.89 per warrant, subject to adjustments as provided under the terms of the Subordinated Note Warrants. As of June 30, 2026 and December 31, 2025, Subordinated Note Warrants providing the right to purchase 856,165 shares of Common Stock with a remaining contractual life of 3.3 years and 3.8 years, respectively, had vested and were outstanding.

The Company has determined that the Subordinated Note Warrants should be accounted for as a liability pursuant to ASC 480. In accordance with ASC 815, the Company recorded the Subordinated Note Warrants at fair value and remeasures the fair value at each reporting period with changes in fair value recognized in earnings. As of June 30, 2026 and December 31, 2025, the fair value of the Subordinated Note Warrants was less than $0.1 million and $0.3 million, respectively. Refer to Note 5 – Fair Value Measurements for a further discussion of the fair value of the Subordinated Note Warrants.

Series F Preferred Stock Anniversary Warrants

Pursuant to the Series F Preferred Securities Purchase Agreement with the Series F Preferred Stockholder, as amended, if any shares of Series F Preferred Stock are outstanding on the Series F Preferred Stock Anniversary Warrant Issuance Date, and the other conditions set forth in the Series F Preferred Stock Certificate of Designation have been satisfied, the Company will issue the Series F Preferred Stock Anniversary Warrants to the Series F Preferred Stockholder. The Series F Preferred Stock Anniversary Warrants, as amended, allow the Series F Preferred Stockholder to purchase a number of the Company’s Common Stock shares equal to the quotient of (i) 65% of the Stated Value of all Series F Preferred Stock held on the Series F Preferred Stock Anniversary Warrant Issuance Date, divided by (ii) the average of the 10 daily volume-weighted average per share trading prices of the Common Stock during the 10 trading-days prior to the Series F Preferred Stock Anniversary Warrant Issuance Date.

If issued, the Series F Preferred Stock Anniversary Warrants would be immediately exercisable and would expire on the fifth anniversary of the Series F Preferred Stock Anniversary Warrant Issuance Date. The Series F Preferred Stock Anniversary Warrants would have an initial exercise price per share equal to 110% of the average of the 10 daily per share volume–weighted average prices of the Common Stock during the 10 trading-days prior to the Series F Preferred Stock Anniversary Warrant Issuance Date. The exercise price and number of Common Stock shares issuable upon exercise is subject to appropriate adjustment in the event of certain stock dividends and distributions, stock splits, stock combinations, reclassifications or similar events affecting the Common Stock and also upon any distributions of assets, including cash, stock or other property to the Company’s stockholders.

Series F Preferred Stock Anniversary Warrants Amendments and Letter Agreements. On March 25, 2026, the Company entered into the First Series F Preferred Stock Warrant Amendment, which, among other things, extended the issuance date of the Series F Preferred Stock Anniversary Warrants from March 26, 2026 to April 7, 2026. Pursuant to the First Series F Preferred Stock Warrant Amendment, the Company agreed to pay the Series F Preferred Stockholder a $3.0 million extension fee, which was waived by the Series F Preferred Stockholder on April 8, 2026.

On April 6, 2026, the Company entered into the Second Series F Preferred Stock Warrant Amendment, which among other things, amended and restated the First Series F Preferred Stock Warrant Amendment to extend the issuance date of the Series F Preferred Stock Anniversary Warrants from April 7, 2026 to April 9, 2026.

On April 8, 2026, the Company entered into the First Series F Preferred Stock Letter Agreement, pursuant to which, among other things, the Company repurchased 13,727 shares of Series F Preferred Stock from the Series F Preferred Stockholder for the Series F Preferred Stock Repurchase Price, the cash portion of which was $19.0 million. Additionally, pursuant to the First Series F Preferred Stock Letter Agreement, the Company issued the Series F Preferred Stockholder the Series F Preferred Stock Penny Warrants. Further, pursuant to the First Series F Preferred Stock Letter Agreement, upon the Series F Preferred Stockholder’s receipt of the Series F Preferred Stock Repurchase Price and the issuance of the First Series F Preferred Stock Penny Warrants, the Series F Preferred Stockholder waived the Company’s obligation to pay the $3.0 million extension fee. The Series F Preferred Stockholder exercised the First Series F Preferred Stock Penny Warrants on June 5, 2026, resulting in the issuance of 4,000,000 shares of Common Stock.
Finally, the First Series F Preferred Stock Letter Agreement also extended the issuance date of the Series F Preferred Stock Anniversary Warrants from April 9, 2026 to July 8, 2026 and reduced the number of Common Stock shares issuable upon exercise of the Series F Preferred Stock Anniversary Warrants from (1) a number of shares equal to the quotient of (i) 125% of the Stated Value of all Series F Preferred Stock held on the Series F Preferred Stock Anniversary Warrant Issuance Date, divided by (ii) the average of the 10 daily volume–weighted average per share trading prices of the Company’s Common Stock during the 10 trading-days prior to the Series F Preferred Stock Anniversary Warrant Issuance Date, to (2) a number of shares equal to the quotient of (i) 75% of the Stated Value of all Series F Preferred Stock held on July 8, 2026, divided by (ii) the average of the 10 daily volume–weighted average per share trading prices of the Company’s Common Stock during the 10 trading-days prior to the Series F Preferred Stock Anniversary Warrant Issuance Date.

On June 10, 2026, the Company entered into the Second Series F Preferred Stock Letter Agreement. Pursuant to the Second Series F Preferred Stock Letter Agreement, among other things, the parties further extended the issuance date of the Series F Preferred Stock Anniversary Warrants to August 7, 2026, which date was subsequently extended to August 31, 2026 (refer to Note 18 – Subsequent Events for a discussion of the extensions of the Series F Preferred Stock Anniversary Warrant Issuance Date which occurred subsequent to June 30, 2026), and reduced the number of Common Stock shares issuable upon exercise of the Series F Preferred Stock Anniversary Warrants to a number of shares equal to the quotient of (i) 65% of the Stated Value of all Series F Preferred Stock held on the Series F Preferred Stock Anniversary Warrant Issuance Date, divided by (ii) the average of the 10 daily volume-weighted average per share trading prices of the Common Stock during the 10 trading-days prior to the Series F Preferred Stock Anniversary Warrant Issuance Date.

Series F Preferred Stock Anniversary Warrants Fair Value. The Company has determined that the Series F Preferred Stock Anniversary Warrants are not considered indexed to the Company’s own stock because the potential number of Common Stock shares to be issued upon the exercise of such warrants will vary based on the amount of Series F Preferred Stock outstanding on the Series F Preferred Stock Anniversary Warrant Issuance Date. As such, the Company has determined that the Series F Preferred Stock Anniversary Warrants should be accounted for as liabilities pursuant to ASC 480. In accordance with ASC 815, the Company has recorded the Series F Preferred Stock Anniversary Warrants at fair value and remeasures the fair value each reporting period with changes in fair value recognized in earnings. As of June 30, 2026, the fair value of the Series F Preferred Stock Anniversary Warrants was $9.5 million compared to $90.1 million as of December 31, 2025, which is presented on the Company’s condensed consolidated balance sheet as a liability.

The Company determined that the changes to the Series F Preferred Stock Certificate of Designation set forth in the First Series F Preferred Stock Letter Agreement should be accounted for as modification. Additionally, the Company concluded that the partial redemption of the Series F Preferred Stock pursuant to the First Series F Preferred Stock Letter Agreement should be aggregated and treated as a single transaction with the modification. These amendments decreased the fair value of the Series F Preferred Anniversary Warrants to $35.5 million, resulting in a deemed dividend of $51.3 million, which is presented in the remeasurement of Series F Preferred Stock line item on the condensed consolidated statements of operations for the three and six months ended June 30, 2026.

The Company also determined that the changes to the Series F Preferred Stock Anniversary Warrants set forth in the Second Series F Preferred Stock Letter Agreement should be accounted for as modification. These modifications further decreased the fair value of the Series F Preferred Anniversary Warrants to $11.7 million, resulting in a change of fair value of $2.2 million, which is presented as a component of gain (loss) on adjustment to fair value – financial instrument liabilities on the consolidated statements of operations for the three and six months ended June 30, 2026.

Unrelated to the redemption of the Series F Preferred Stock and modification of the Series F Preferred Stock Anniversary Warrants, the Company recognized $2.2 million and $27.1 million as changes in fair value presented as components of gain (loss) on adjustment to fair value – financial instrument liabilities on its consolidated statements of operations for the three and six months ended June 30, 2026, respectively. For the three and six months ended June 30, 2025, the Company recognized a $21.6 million change in fair value as a component of gain (loss) on adjustment to fair value – financial instrument liabilities on its consolidated statements of operations. Refer to Note 5 – Fair Value Measurements for a further discussion of the fair value of the Series F Preferred Stock Anniversary Warrants.