[Form 4] Beeline Holdings, Inc. Insider Trading Activity

Beeline Holdings, Inc. reported a stock option grant to its Chief Accounting Officer.

Rhea-AI Filing Summary

Beeline Holdings, Inc. reported a stock option grant to its Chief Accounting Officer. The officer was granted 35,000 stock options on 10/02/2025 with an exercise price of $0.9216 per share and an expiration date of 10/02/2035. The options vest annually in equal amounts over two years beginning 05/28/2025, subject to continued service, and were issued under the company’s Amended and Restated 2025 Equity Incentive Plan. The filing notes the grant was board-approved and exempt from Section 16(b) by Rule 16b-3. The reporting person is listed as the company’s Chief Accounting Officer.

Insights

Compensation & Governance Analyst

Grant aligns an officer with shareholder value and ties compensation to tenure.

The 35,000 option award vests over two years from 05/28/2025

and carries a $0.9216 exercise price with a 10/02/2035 expiration. Board approval and Rule 16b-3 exemption indicate the award followed standard governance protocols. The two-year annual vesting schedule creates a near-term retention incentive for the reporting officer.

Key dependencies include continued service through each vesting date and future stock price relative to the $0.9216 strike for economic value. Monitor option vesting milestones over the next two years and any subsequent disclosure of additional awards or exercises.

Insider Trade Summary

Grant/Award: 35,000 shares

Grant/Award 1 txn

Insider Milton Tiffany

Role Chief Accounting Officer

Type	Security	Shares	Price	Value
Grant/Award	Stock Options (Right to Buy)	35,000	$0.00	$0.00

Holdings After Transaction: Stock Options (Right to Buy) — 35,000 contracts (Direct)

Footnotes (1)

1. F1. The grant of stock options was exempt from Section 16(b) of the Securities Exchange Act of 1934 by virtue of Rule 16b-3 promulgated thereunder, as it was approved by the Issuer's Board of Directors. The stock options shall vest annually in equal amounts over two years from May 28, 2025, subject to continued service as an officer on the applicable vesting dates. The stock options were granted under the Issuer's Amended and Restated 2025 Equity Incentive Plan.

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Accepted by SEC EDGAR 10/06/2025 - 04:30 PM Learn about SEC filing dates

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
Estimated average burden
hours per response:			0.5

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^*

Milton Tiffany

(Last) (First) (Middle)

188 VALLEY STREET

SUITE 225

(Street)

PROVIDENCE RI 02909

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Beeline Holdings, Inc. [ BLNE ]

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

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Accounting Officer

3. Date of Earliest Transaction (Month/Day/Year)
10/02/2025

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
Stock Options (Right to Buy)	$0.9216	10/02/2025		A		35,000		(1)	10/02/2035	Common Stock	35,000	$0	35,000	D

Explanation of Responses:

1. The grant of stock options was exempt from Section 16(b) of the Securities Exchange Act of 1934 by virtue of Rule 16b-3 promulgated thereunder, as it was approved by the Issuer's Board of Directors. The stock options shall vest annually in equal amounts over two years from May 28, 2025, subject to continued service as an officer on the applicable vesting dates. The stock options were granted under the Issuer's Amended and Restated 2025 Equity Incentive Plan.

	/s/ Tiffany Milton	10/06/2025
	** 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.