[Form 4] Heritage Distilling Holding Company, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Justin B. Stiefel, CEO, Treasurer and Director of Heritage Distilling Holding Company (CASK), reported acquiring pre-funded warrants on 08/15/2025. The filing shows Stiefel purchased 3,309,615 pre-funded warrants exercisable for common stock at a stated price of $0.6042 per underlying share. The warrants were issued under a Subscription Agreement dated August 11, 2025, as amended August 15, 2025, and will be automatically exercised on a cashless basis upon receipt of the Stockholder Approval specified in that agreement. The securities are held by Constantine IHSV, LLC, of which Stiefel is sole member, and the Form 4 was signed on 08/19/2025.

Positive

• Acquisition of 3,309,615 pre-funded warrants by the CEO and Director is explicitly disclosed
• Warrants will be automatically exercised on a cashless basis upon Stockholder Approval, as stated in the Subscription Agreement
• Securities are held via Constantine IHSV, LLC, with the reporting person identified as sole member

Negative

• None.

Insights

Financial Analyst

TL;DR: Insider purchased a sizeable block of pre-funded warrants totaling 3,309,615 shares, indicating meaningful insider participation.

The Form 4 documents an acquisition of 3,309,615 pre-funded warrants by the CEO and Director, Justin B. Stiefel, at a referenced per-share figure of $0.6042, via a subscription agreement. These warrants convert into common stock and are held indirectly through Constantine IHSV, LLC. The warrants are structured to be automatically exercised on a cashless basis upon Stockholder Approval, which is a specific conditional trigger disclosed in the filing. For investors, the transaction increases potential future share count if warrants convert, and it reflects direct insider involvement in the financing arrangement disclosed.

Corporate Governance Expert

TL;DR: CEO and Director executed an insider purchase through an affiliated LLC with conversion tied to shareholder approval.

The report clearly identifies the reporting person as CEO, Treasurer and Director and discloses indirect ownership through Constantine IHSV, LLC. The subscription agreement dates (August 11 and amendment August 15, 2025) and the automatic cashless exercise upon Stockholder Approval are explicitly stated. The filing is complete for Section 16 reporting purposes, with a manual signature dated 08/19/2025. This provides transparency on the timing, mechanics and holding vehicle for the securities acquired.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Stiefel Justin B

(Last) (First) (Middle)

C/O HERITAGE DISTILLING HOLDING COMPANY

9668 BUJACICH ROAD

(Street)

GIG HARBOR WA 98332

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Heritage Distilling Holding Company, Inc. [ CASK ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	CEO & Treasurer

3. Date of Earliest Transaction (Month/Day/Year)
08/15/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Pre-Funded Warrant to Purchase Common Stock	$0.0001	08/15/2025		P		3,309,615		(1)	(1)	Common Stock	3,309,615	$0.6042	3,309,615	I	By LLC(2)

Explanation of Responses:

1. The securities reported herein were issued to the reporting person by Heritage Distilling Holding Company, Inc. (the "Issuer") in connection with that certain subscription agreement by and between the reporting person and the Issuer, dated August 11, 2025, as amended on August 15, 2025 (the "Subscription Agreement"), pursuant to which the reporting person purchased pre-funded warrants (the "Warrants") that are exercisable for shares of the Issuer's common stock, par value $0.0001 per share. The Warrants will be automatically exercised on a cashless basis upon the receipt of the Stockholder Approval (as defined in the Subscription Agreement).

2. The reported securities are held by Constantine IHSV, LLC, of which the reporting person is the sole member and may be deemed to beneficially own the securities held by it.

Remarks:

	/s/ Justin B. Stiefel	08/19/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What did Justin B. Stiefel report on the Form 4 for CASK?

The Form 4 reports that Justin B. Stiefel acquired 3,309,615 pre-funded warrants exercisable for common stock, with securities held indirectly through Constantine IHSV, LLC.

When was the transaction dated and when was the Form 4 signed?

The transaction date is 08/15/2025 and the Form 4 was signed on 08/19/2025.

At what price are the underlying shares reported in the filing?

The filing lists a price reference of $0.6042 per underlying share for the common stock related to the warrants.

Under what agreement were the warrants issued?

The warrants were issued pursuant to a Subscription Agreement dated August 11, 2025, as amended on August 15, 2025.

Will the warrants convert automatically?

Yes, the filing states the warrants will be automatically exercised on a cashless basis upon receipt of the Stockholder Approval defined in the Subscription Agreement.