Gray Jonathan H. 4

4 · Prairie Operating Co. · Filed Jun 9, 2026

AI-generated summary of this filing

Updated Jun 9, 2026

Prairie Operating (PROP) Director Jonathan Gray Acquires 537,398 Shares

What Happened

Jonathan H. Gray, a director of Prairie Operating Co. (PROP), acquired a total of 537,398 common shares on April 20, 2026 via conversion of Series D convertible preferred stock (396,901 shares + 140,497 shares) at $1.81 per share, totaling $972,691. The filing also shows disposals of 720 shares and 254.87 shares on April 20 (reported as derivative-related) and a June 4, 2026 disposition of 15,544 shares (used to satisfy tax withholding) at $0.87 per share ($13,523).

Key Details

Primary acquisition date: 2026-04-20 — 396,901 @ $1.81 ($718,391) and 140,497 @ $1.81 ($254,300); combined = 537,398 shares, $972,691.
Tax withholding: 2026-06-04 — 15,544 shares disposed @ $0.87 = $13,523 (reported as payment of tax liability, code F).
Small derivative disposals on 2026-04-20: 720 shares and 254.87 shares (no per-share price reported).
Footnotes: F1 — these acquisitions resulted from conversion agreements for Series D convertible preferred stock; F2 — withheld shares were used to satisfy tax withholding on vesting; F3 — Series D preferred has no expiration.
Shares owned after these transactions: not specified in the provided filing data.
Filing timeliness: Form 4 was filed on 2026-06-09 for transactions dated 2026-04-20 and 2026-06-04 — this is later than the typical 2-business-day reporting window (a reporting delay).

Context

These were not open-market purchases but conversions of preferred stock into common shares (per F1), which is a non-market acquisition and not necessarily a fresh cash buy signal. The June 4 disposition reflects shares withheld to cover tax obligations on vesting (a common administrative action). The small derivative disposals likely reflect fractional-share or derivative adjustments from the conversion.

Form 4

Period: 2026-04-20

Director

Transactions

Other
Common Stock
[F1]
2026-04-20$1.81/sh+396,901$718,391→ 627,060 total(indirect: By LLC)
Other
Common Stock
[F1]
2026-04-20$1.81/sh+140,497$254,300→ 300,496 total(indirect: Held by First Idea International Ltd.)
Tax Payment
Common Stock
[F2]
2026-06-04$0.87/sh−15,544$13,523→ 660,273 total
Other
Series D Convertible Preferred Stock
[F1][F3]
2026-04-20−720→ 30 total(indirect: By LLC)
Exercise: $5.00From: 2023-05-03→ Common Stock (144,000 underlying)
Other
Series D Convertible Preferred Stock
[F1][F3]
2026-04-20−254.87→ 0 total(indirect: Held by First Idea International Ltd.)
Exercise: $5.00From: 2023-05-03→ Common Stock (50,974 underlying)

Footnotes (3)

[F1]Prairie Operating Co. (the "Company") entered into preferred stock conversion agreements with certain holders of its Series D Convertible Preferred Stock, including First Idea Ventures LLC and First Idea International Ltd., pursuant to which, among other things, the shares of Series D Convertible Preferred Stock held by such holders were converted into shares of the Company's common stock, par value $0.01 per share, upon the terms set forth therein.
[F2]Represents shares that were withheld upon vesting of restricted stock to satisfy tax withholding obligations.
[F3]The Series D Convertible Preferred Stock has no expiration date.

Signature

/s/ Jonathan Gray|2026-06-09

1 file