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

Rhea-AI Filing Summary

Matthew J. Swann, a director of Heritage Distilling Holding Company (ticker: CASK), reports transactions converting preferred shares into common stock and pre-funded warrants. The filing corrects a prior omission that on 06/27/2025 he acquired 10,000 shares of Series B Convertible Preferred Stock. On 08/15/2025 he exchanged those 10,000 Series B shares for 13,315 shares of common stock and pre-funded warrants to purchase an aggregate of 252,994 common shares pursuant to an exchange agreement. The reported common shares owned following the transaction are 119,065 (direct). The pre-funded warrants become exercisable on staged conditions: one set earliest of three months or if stock closes at or above $1.50; the other set earliest of six months or if stock closes at or above $2.00.

Positive

• Conversion to common stock increases the reporting person’s direct common equity stake to 119,065 shares, aligning interests with common shareholders
• Pre-funded warrants provide structured optionality with clear exercisability conditions, creating a path for future investment rather than immediate free dilution
• Correction filed reports an earlier omitted acquisition of 10,000 Series B shares, improving disclosure completeness

Negative

• Potential dilution from pre-funded warrants totaling 252,994 shares if exercised, which could materially increase share supply
• Prior omission of the June 27, 2025 Series B acquisition required a corrective filing, indicating a lapse in timely disclosure

Insights

Financial Analyst

TL;DR: Director swapped preferred for common and large pre-funded warrants, creating potential dilution and optionality tied to price hurdles.

The exchange converts illiquid preferred shares into immediately owned common shares plus pre-funded warrants exercisable on specified conditions, increasing the director's direct common share stake to 119,065 shares and creating contractual rights to an additional 252,994 shares if exercised. For investors this raises potential near- to medium-term supply of common stock depending on warrant exercisability and market price. The correction noting the June acquisition improves disclosure completeness but highlights an earlier reporting omission.

Corporate Governance Expert

TL;DR: Transaction is routine insider conversion but the prior omission required correction, a minor governance flag.

From a governance perspective the filing documents a standard exchange agreement converting preferred into common and pre-funded warrants, aligning the director's economic exposure with common shareholders. The corrected disclosure of the June preferred acquisition resolves an earlier reporting gap; however, timely initial reporting is important for Section 16 transparency. The size of the warrants relative to outstanding shares may be material to shareholder dilution analysis.

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

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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^*

Swann Matthew J

(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
	Officer (give title below)		Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
06/27/2025

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	08/15/2025		J(1)		13,315	A	$0(1)	119,065	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
Series B Convertible Preferred Stock	$0.5	06/27/2025		P(2)		10,000		12/24/2025	06/27/2028	Common Stock	264,000	$10	10,000	D
Series B Convertible Preferred Stock	$0.5	08/15/2025		J(1)			10,000	12/24/2025	06/27/2028	Common Stock	13,315	$0(1)	0	D
Pre-Funded Warrant to Purchase Common Stock	$0.01	08/15/2025		J(1)		133,155		(3)	08/08/2030	Common Stock	133,155	$0(1)	133,155	D
Pre-Funded Warrant to Purchase Common Stock	$0.01	08/15/2025		J(1)		119,839		(4)	08/08/2030	Common Stock	119,839	$0(1)	119,839	D

Explanation of Responses:

1. On August 15, 2025, the reporting person exchanged 10,000 shares of Series B Convertible Preferred Stock for (i) 13,315 shares of common stock, par value $0.0001 per share (the "Common Stock"), of Heritage Distilling Holding Company, Inc. and (ii) pre-funded warrants to purchase an aggregate of 252,994 shares of Common Stock pursuant to an exchange agreement.

2. The reporting person acquired shares of Series B Convertible Preferred Stock on June 27, 2025, which were inadvertently omitted from the reporting person's prior filings. This Form 4 corrects the prior omission by reporting such acquisition.

3. The pre-funded warrant reported herein will become exercisable on the earlier of (i) three months after the date of issuance of such warrant or (ii) the first trading day after the date of issuance of such warrant on which the closing price of the Common Stock equals or exceeds $1.50 per share.

4. The pre-funded warrant reported herein will become exercisable on the earlier of (i) six months after the date of issuance of such warrant or (ii) the first trading day after the date of issuance of such warrant on which the closing price of the Common Stock equals or exceeds $2.00 per share.

Remarks:

	/s/ Justin B. Stiefel, attorney-in-fact for Matthew J. Swann	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 Heritage Distilling director Matthew J. Swann report on Form 4 (CASK)?

He reported acquiring 10,000 Series B Convertible Preferred shares on 06/27/2025 and on 08/15/2025 exchanging those 10,000 preferred shares for 13,315 common shares plus pre-funded warrants to purchase 252,994 common shares.

How many common shares does Matthew J. Swann beneficially own after the reported transactions (CASK)?

The Form 4 shows 119,065 common shares beneficially owned following the reported transactions.

What are the exercisability conditions for the pre-funded warrants reported by the insider (CASK)?

One set of pre-funded warrants becomes exercisable on the earlier of three months after issuance or when the stock closing price reaches $1.50; the other set becomes exercisable on the earlier of six months after issuance or when the stock closing price reaches $2.00.

How many potential shares could be issued if the pre-funded warrants are exercised (CASK)?

The pre-funded warrants reported total 252,994 underlying common shares (133,155 and 119,839 in two tranches).

Was there a correction or amendment in this Form 4 filing for Heritage Distilling (CASK)?

Yes. The Form 4 corrects a prior omission by reporting acquisition of 10,000 Series B Convertible Preferred shares acquired on 06/27/2025.