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

Rhea-AI Filing Summary

Heritage Distilling Holding Company (CASK) reporting person Justin B. Stiefel, CEO and Treasurer and a director, notified the company of acquisitions on 09/18/2025. He acquired 3,309,615 pre-funded warrants exercisable into common stock at $0.0001 and tied to a conversion into 3,309,615 shares at an underlying price of $0.6042; these instruments are held indirectly through Constantine IHSV, LLC. The filing also discloses indirect ownership of 330,283 shares held by his spouse and 1,737 shares held in an IRA, and a disposition of 325,921 shares. The warrant includes an initial exercise tied to a requisite stockholder approval and will be cashless-exercised thereafter in accordance with its terms.

Positive

• Transparent disclosure of large insider acquisition through Form 4 with details on amounts, ownership form, and related parties
• Significant insider stake potential: 3,309,615 pre-funded warrants exercisable into common stock increase alignment of CEO with shareholders if converted

Negative

• None.

Insights

Corporate Governance Expert

TL;DR: CEO/director acquired large indirect pre-funded warrants converting to common shares, reflecting significant insider ownership change.

The report shows a concentrated increase in potential share ownership via 3,309,615 pre-funded warrants held through an LLC controlled by the reporting person, which materially increases his economic exposure to the company if exercised. The instrument’s exercise mechanics reference a stockholder approval condition and automatic cashless exercise thereafter, which could affect dilution dynamics and timing of share issuance. The filing also clarifies spouse and IRA holdings and a reported disposition of 325,921 shares, providing a complete view of the reporting person’s current beneficial holdings and relationships.

Securities Analyst

TL;DR: Significant indirect acquisition of warrants tied to future share issuance, with clear ownership disclosures and an associated disposition.

The transaction code indicates acquisition of pre-funded warrants that convert into 3,309,615 common shares at an underlying per-share consideration of $0.6042; the warrants are priced at $0.0001 and are recorded as held indirectly by an LLC of which the reporting person is the sole member. The presence of a disposition of 325,921 existing shares should be noted when calculating net changes to beneficial ownership. These details are precisely disclosed, allowing investors to model potential dilution and timing contingent on specified stockholder approval.

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)
09/18/2025

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
Common Stock	09/18/2025		M		3,309,615	A	$0.0001	3,309,615	I	By LLC(1)
Common Stock								330,283	I	By spouse(2)
Common Stock								325,921(3)	D

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	09/18/2025		M			3,309,615	(4)	(4)	Common Stock	3,309,615	$0.6042	0	I	By LLC(1)

Explanation of Responses:

1. 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.

2. These securities are held by Jennifer D.H. Stiefel, the spouse of the reporting person. For purposes of Section 16 of the Exchange Act, the reporting person disclaims beneficial ownership of any such securities, except to the extent of her pecuniary interest therein, if any, and this report shall not be deemed an admission that such reporting person is the beneficial owner of such securities for purposes of Section 16 or otherwise.

3. Includes 1,737 shares beneficially owned through American Estate and Trust, LC FBO Justin Stiefel IRA account

4. The initial exercise date of the warrant is at any time on or after the effective date of the requisite Stockholder Approval, as defined in the warrant agreement. Following the initial exercise date, the warrant shall be automatically exercised via cashless exercise in accordance with its terms.

Remarks:

	/s/ Justin B. Stiefel	09/22/2025
	** 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 the CASK Form 4 filed by Justin B. Stiefel report?

The filing reports acquisition on 09/18/2025 of 3,309,615 pre-funded warrants (exercisable into 3,309,615 shares) held indirectly through Constantine IHSV, LLC, plus disclosures of spouse and IRA holdings and a disposition of 325,921 shares.

How are the 3,309,615 instruments held according to the Form 4?

They are held indirectly by Constantine IHSV, LLC, of which Justin B. Stiefel is the sole member, and reported as pre-funded warrants with $0.0001 nominal price and underlying share price listed as $0.6042.

Does the Form 4 disclose any conditions on exercising the warrants?

Yes. The initial exercise date is tied to the effective date of the requisite Stockholder Approval per the warrant agreement, and after that the warrant will be automatically cashless-exercised in accordance with its terms.

What other related-party holdings are disclosed in the filing?

The filing discloses 330,283 shares held by the reporting person’s spouse (Jennifer D.H. Stiefel) and 1,737 shares held in an IRA for the reporting person.

Was there any disposition reported by the reporting person?

Yes, the filing reports a disposition of 325,921 common shares by the reporting person.