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

Rhea-AI Filing Summary

Beeline Holdings, Inc. (BLNE) director Joseph Caltabiano reported two grants of restricted equity on 10/02/2025. He received 98,984 shares of restricted common stock and 30,000 restricted stock units, bringing his total reported beneficial ownership to 128,984 shares. The restricted stock grant was approved by the board under the 2025 Equity Incentive Plan and includes mixed vesting: 49,818 shares are fully vested in lieu of cash, 10,000 shares vest on 05/28/2026, 30,000 vest in equal annual increments beginning 05/28/2026, and 9,166 shares vest on 05/28/2026 for prior work, all subject to continued service and a restricted stock agreement. The 30,000 RSUs vest on the earlier of 08/05/2026 or delivery of a final committee report, subject to service and standard RSU terms. Both grants were board-approved and exempt from Section 16(b) under Rule 16b-3.

Positive

• Board-approved awards under the 2025 Equity Incentive Plan indicate formal governance review
• 49,818 shares fully vested in lieu of cash, reducing immediate cash compensation needs
• Time-based vesting ties significant equity (30,000+ shares) to continued service through 05/28/2026 and beyond

Negative

• Substantial award size (total 128,984 shares) may cause dilution if issued from authorized shares
• Large portion vests within a year (multiple tranches on 05/28/2026), raising near-term potential share supply

Insights

Compensation & Governance Analyst

Director received equity with multi-year vesting and some immediately vested shares.

The awards combine fully vested shares in lieu of cash and time-based restricted equity, aligning the director’s pay with shareholder value creation while conserving cash. The mix—49,818 vested shares and time‑vested blocks—reduces near-term dilution pressure from new cash payouts.

Key dependencies include continued board service through 05/28/2026 and possible acceleration if a committee delivers its final report before 08/05/2026. Monitor future Form 4 filings for any sales or additional grants within 12 months.

Corporate Insider Activity Specialist

Reported change materially increases an insider’s stake to 128,984 shares.

The reported ownership increase to 128,984 shares is a tangible insider position change to track for governance and signaling. Grants were board‑approved and exempt under Rule 16b-3, which is standard for director awards and limits short-swing liability.

Watch for vesting-trigger events around 05/28/2026 and 08/05/2026 and subsequent Form 4s that would record any dispositions or exercise-related events in the following months.

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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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^*

Caltabiano Joseph

(Last) (First) (Middle)

188 VALLEY ST.,

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)

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

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
Common Stock(1)	10/02/2025		A		98,984	A	$0	98,984	D
Common Stock(2)	10/02/2025		A		30,000	A	$0	128,984	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

Explanation of Responses:

1. The grant of the Issuer's restricted common stock 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 shares of restricted common stock were granted under the Issuer's Amended and Restated 2025 Equity Incentive Plan. The shares of restricted common stock vest as follows: 10,000 shares shall vest on May 28, 2026; 30,000 shares shall vest in equal increments annually over three years with the first vesting date on May 28, 2026; 9,166 shares for prior work shall vest on May 28, 2026; and 49,818 shares in lieu of cash for prior work are fully vested, subject to continued service as a director as of each applicable vesting date and subject to execution of the Issuer's standard Restricted Stock Agreement.

2. Represents restricted stock units. Each restricted stock unit represents a contingent right to receive one share of the Issuer's common stock. The grant 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 units shall vest on the earlier of (i) August 5, 2026 or (ii) the delivery of a final report by the applicable committee, subject to continued service as a director on the applicable vesting date and execution of the Issuer's standard Restricted Stock Unit Agreement.

	/s/ Joseph Caltabiano	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.

FAQ

What equity did Beeline Holdings director Joseph Caltabiano receive (BLNE)?

He was granted 98,984 restricted common shares and 30,000 restricted stock units, totaling 128,984 shares following the grants.

When do Caltabiano's shares vest?

Vesting includes 49,818 fully vested shares; 10,000 and 9,166 shares vest on 05/28/2026; 30,000 shares vest in equal annual increments starting on 05/28/2026; the 30,000 RSUs vest on the earlier of 08/05/2026 or delivery of a final committee report.

Were the grants subject to short-swing profit rules?

No. The grants were approved by the board and were exempt from Section 16(b) short-swing liability under Rule 16b-3.

Do the RSUs convert to common stock one-for-one?

Yes. Each restricted stock unit represents the contingent right to receive one share of common stock upon vesting.

Is continued service required for vesting?

Yes. Vesting of the restricted shares and RSUs is subject to continued service as a director and execution of the issuer’s standard agreements.