STOCKHOLDERS’ EQUITY

6 Months Ended

Jun. 30, 2026

Equity [Abstract]

STOCKHOLDERS’ EQUITY

14. STOCKHOLDERS’ EQUITY

Issuance of Common Stock

2026

In January 2026, the Company issued 100,000 shares of restricted common stock valued at $3.77 per share based on the 2025 grant date fair value to an employee, of which $0.4 million and $6,855 was recognized in 2025 and January 2026, respectively, under the Amended and Restated 2025 Equity Incentive Plan (the “2025 Plan”).

During the six months ended June 30, 2026, the Company issued 40,000 shares of restricted stock awards (RSAs) to the Company’s board of directors under the 2025 Plan subject to certain vesting requirements. The total value of these RSA grants was $0.1 million for the six months ended June 30, 2026, see Note 15 – Stock-Based Compensation.

During the six months ended June 30, 2026, the Company issued 7,010 shares of restricted common stock to a member of the board of directors under its the 2025 Plan with a value of $15,000 in lieu of cash for board fees, see Note 15 – Stock-Based Compensation.

In February 2026, the Company issued 1,875 shares of common stock upon the exercise of stock options issued under its 2025 Plan for proceeds of $1,725.

In June 2026, the Company’s Chief Executive Officer surrendered to the Company 70,454 shares of the Company’s common stock in lieu of repaying cash of $0.1 million.

On June 30, 2026, the Company issued 211,679 shares of common stock value of $1.22 per share to acquire its remaining outstanding ownership interest of 52.4% in MagicBlocks.

During the six months ended June 30, 2026, the Company issued 521,753 shares of common stock upon the exercise of 579,360 Warrants related to the Company’s Series G Preferred Stock offering for proceeds of $0.2 million, including 169,080 shares of common stock issued under the cashless exercise provision upon the exercise of 226,687 Warrants.

Beeline Holdings, Inc.

Notes to Consolidated Financial Statements

June 30, 2026 and 2025

(unaudited)

During the six months ended June 30, 2026, the Company issued 318,168 shares of common stock for gross proceeds of $0.8 million pursuant to the At the Market Agreement.

During the six months ended June 30, 2026, the Company issued a total of 1,581,030 shares of common stock as a result of various preferred stock conversions as noted below.

2025

On March 12, 2025, the Company implemented a 1-for-10 reverse stock split of its common stock. All share and per share data in these consolidated financial statements have been retrospectively adjusted to give effect to the stock split.

From June 26, 2025 through June 30, 2025, certain holders of the Notes converted $1.0 million of their Notes into 747,221 shares of common stock.

In June 2025, the Company issued 10,000 shares of common stock in satisfaction of the former Chief Executive Officer’s employment agreement which was recorded as stock issuable of $14,300 as of March 31, 2025.

In February 2025, the Company issued 13,115 shares of common stock related to a legal settlement agreed upon in October 2024 where $0.1 million was recorded as stock to be issued as of December 31, 2024.

During 2025, the Company sold a total of 5,540,043 shares of common stock for gross proceeds of $7.0 million in its registered at-the-market offering. The Company recorded related offering costs of $0.3 million as of June 30, 2025.

During 2025, the Company issued a total of 6,564,947 shares of common stock as a result of various preferred stock conversions as noted below.

ELOC Agreement

On December 31, 2024, the Company entered into entered into a Common Stock Purchase Agreement and related Registration Rights Agreement (collectively, the “ELOC Agreement”) with an institutional investor (the “Purchaser”) pursuant to which the Company agreed to sell, and the Purchaser agreed to purchase, up to $35 million of the Company’s common stock, subject to a sale limit of 19.99% of the outstanding shares of the Company’s common stock.

On March 7, 2025, the Company entered into an Amended ELOC Agreement to reduce the maximum amount under the ELOC Agreement from $35 million to $10 million. On September 8, 2025, the Company again amended the ELOC Agreement to increase the commitment amount by $10 million, to maximum total sales of up to $20 million, and to remove minimum closing price conditions for effecting purchases under the ELOC Agreement. As a result, the Company may sell up to $12.5 million under the ELOC Agreement (after giving effect to prior sales) beginning after January 11, 2026. During the six months ended June 30, 2026, the Company sold and issued a total of 2,114,575 shares of common stock for an aggregate purchase price of $3.2 million to the Purchaser. The Company recorded offering costs related to the ELOC Agreement of $0.1 million as of June 30, 2026. During the six months ended June 30, 2025, the Company sold and issued a total of 5,018,437 shares of common stock for an aggregate purchase price of $6.3 million to the Purchaser. The Company recorded offering costs related to the ELOC of $0.4 million as of June 30, 2025.

Preferred Stock

The Company has 100 million shares of preferred stock authorized at a par value of $0.0001 per share.

Issuance of Series A Preferred Stock

On July 23, 2025, the Company entered into an agreement with a holder of and effected the exchange of 8,356,151 shares of Series F Preferred Stock and 68,951 shares of Series F-1 Preferred Stock of the Company in exchange for the issuance to the holder of 8,425,102 shares of a newly designated Series A Convertible Redeemable Preferred Stock (the “Series A Preferred Stock”).

Beeline Holdings, Inc.

Notes to Consolidated Financial Statements

June 30, 2026 and 2025

(unaudited)

On July 23, 2025, the Company filed a Certificate of Designation, Preferences and Rights of the Series A Convertible Redeemable Preferred Stock of the Company (the “Certificate of Designations”) with the Nevada Secretary of State designating and authorizing the issuance of up to 8,425,102 shares of Series A Preferred Stock. Each share of Series A Preferred Stock had a stated value of $0.50. Beginning on the initial issuance date of the Series A Preferred Stock, the holder may convert up to $1.0 million in stated value of Series A Preferred Stock (the “Special Conversion Amount”) at a conversion price of $1.75 per share, subject to adjustment as provided therein and subject to beneficial ownership limitations. The conversion price was subject to customary adjustments including for reverse stock splits, forward stock splits, and similar corporate events, and was also subject to price protection adjustment in connection with subsequent sales or issuances of securities at a per-share price that is lower than the conversion price, subject to certain exceptions and limitations.

Beginning on the issuance date of the Series A Preferred Stock on July 23, 2025 and for a period of one-year thereafter, the Company had the right to redeem the shares of Series A Preferred Stock, other than the Special Conversion Amount, at a redemption price of $2.00 per underlying share of common stock (based on the $1.75 per share conversion price, subject to adjustment). At the end of the one-year redemption period, all remaining shares of Series A Preferred Stock (in addition to the Special Conversion Amount) would become convertible at the option of the holder.

Each share of Series A Preferred Stock was convertible into common stock by a conversion ratio equal to the stated value of the Series A Preferred Stock share divided by the Series A Preferred Stock conversion price. The Series A Preferred Stock was entitled to vote with the Company’s common stock on an as-converted basis, subject to the 4.99% beneficial ownership limitation.

During the three months ended March 31, 2026, the remaining 6,425,102 shares of Series A Preferred Stock were converted or exchanged into a total of 1,483,356 shares of common stock resulting in no gain or loss being recognized.

In March 2026, the Certificate of Designation was withdrawn for the Series A Preferred Stock.

Issuance of Series B Preferred Stock

On October 19, 2021, the Company entered into a securities purchase agreement (“Purchase Agreement”) with an accredited investor for its purchase of 2.5 million shares of Series B Convertible Preferred Stock (“Series B”) at a purchase price of $1.00 per Preferred Share, which Preferred Shares are convertible into shares of the Company’s common stock pursuant to the terms and conditions set forth in a Certificate of Designation establishing Series B of the Company with an initial conversion price of $620.00 per share. 4,250 shares of common stock were reserved for issuance in the event of conversion of the Preferred Shares. The holder of Series B has voting rights on an as-converted basis.

The Series B accrues dividends at a rate of 6% per annum, payable annually on the last day of December of each year. Dividends shall accrue from day to day, whether or not declared, and shall be cumulative. Dividends are payable at the Company’s option either in cash or “in kind” in shares of common stock; provided, however that dividends may only be paid in cash following the fiscal year in which the Company has net income (as shown in its audited financial statements contained in its Annual Report on Form 10-K for such year) of at least $0.5 million. For “in-kind” dividends, holders will receive that number of shares of common stock equal to (i) the amount of the dividend payment due such stockholder divided by (ii) the volume weighted average price of the common stock for the 90 trading days immediately preceding a dividend date (“VWAP”). For both the six months ended June 30, 2026 and 2025, the Company accrued $0.1 million of preferred dividends.

Issuance of Series C Preferred Stock

In January 2025, the Certificate of Designation was withdrawn for the Series C Preferred Stock.

Issuance of Series D Preferred Stock

Each share of Series D Preferred Stock has a stated value of $10.00 and is convertible into shares of the Company’s common stock pursuant to the terms and conditions set forth in a Certificate of Designation establishing Series D Preferred Stock with an initial conversion price of $18.00 per share. Each share of Series D Preferred Stock is convertible into common stock by a conversion ratio equal to the stated value of the Series D Preferred Stock share divided by the Series D Preferred Stock conversion price. In the event that the Company declares a dividend payable in cash or stock to holders of any class of the Company’s stock (including the Series B Preferred Stock), the holder of a share of Series D Preferred Stock will be entitled to receive an equivalent dividend on an as-converted basis. In the event of a liquidation of the Company, the holders of Series D Preferred Stock will share in the distribution of the Company’s net assets on an as-converted basis equally with the Series C Preferred Stock and Series E Preferred Stock, subordinate only to the senior position of the Series B. The number of shares of common stock into which a holder may convert Series D Preferred Stock is limited by a beneficial ownership limitation of 9.99%. The Series D Preferred Stock conversion price and the floor price will be subject to equitable adjustment in the event of stock splits, reverse splits and similar events. The Series D Preferred Stock is non-voting. In January 2026, the Certificate of Designation was withdrawn for the Series D Preferred Stock.

Beeline Holdings, Inc.

Notes to Consolidated Financial Statements

June 30, 2026 and 2025

(unaudited)

In conjunction with the Senior Secured Notes entered into on November 14, 2024, the Company entered in two side letters with two institutional investors to each convert $0.3 million of Series D Preferred Stock beginning on April 7, 2025 at a conversion price equal to the lower of $5.00 per share or the five-day VWAP price ending on April 7, 2025, but not less than $2.50 per share.

During the six months ended June 30, 2025, 188,808 shares of Series D Preferred Stock were converted into 104,893 shares of common stock.

In January 2026, the Certificate of Designation was withdrawn for the Series D Preferred Stock.

Issuance of Series E Preferred Stock

Each share of Series E Preferred Stock has a stated value of $10.00 and is convertible into shares of the Company’s common stock pursuant to the terms and conditions set forth in a Certificate of Designation establishing Series E Preferred Stock with an initial conversion price of $20.00, subject to an automatic adjustment on October 31, 2025 equal to the average of the VWAPs for the five trading days immediately preceding the Measurement Date (390 days after the closing under the Debt Exchange Agreement), subject to a “Floor Price” of $2.50 per share. The Series E Preferred Stock conversion price and the floor price will be subject to equitable adjustment in the event of stock splits, reverse splits and similar events. Each share of Series E Preferred Stock is convertible into common stock by a conversion ratio equal to the stated value of the Series E Preferred Stock share divided by the Series E Preferred Stock conversion price. The number of shares of common stock into which a holder may convert Series E Preferred Stock is limited by a beneficial ownership limitation, which restricts the number of shares of common stock that the holder and its affiliates may beneficially own after the conversion to 9.99%. The Series E Preferred Stock is non-voting.

On October 21, 2025, the Company entered into a letter agreement with the investors pursuant to which they agreed to the redemption of their shares of Series E Preferred Stock in exchange for payment of $2.0 million. The Company redeemed the Series E Preferred Stock on November 12, 2025 and recorded a deemed dividend of $1.4 million. The deemed dividend was computed as the difference between the redemption cost of $2.0 million less the original equity recorded upon issuance of $0.6 million. The shares were returned to the Company’s treasury and cancelled and subsequently the Certificate of Designation was withdrawn for the Series E Preferred Stock.

Issuance of Series F and F-1 Preferred Stock

The Merger that closed on October 7, 2024, was structured as an all-stock transaction. The stockholders of Beeline Financial received 69,482,229 preferred shares of Series F and 517,775 preferred shares of Series F-1. Each share of Series F and F-1 Preferred Stock has a stated value of $0.50 and is convertible into shares of the Company’s common stock pursuant to the terms and conditions set forth in a Certificate of Designation establishing Series F and F-1 Preferred Stock with an initial conversion price of $5.00 per share. Each share of Series F and F-1 Preferred Stock is convertible into common stock by a conversion ratio equal to the stated value of the Series F and F-1 Preferred Stock share divided by the Series F and F-1 Preferred Stock conversion price. The number of shares of common stock into which a holder may convert Series F and F-1 Preferred Stock is limited by a beneficial ownership limitation, which restricts the number of shares of the Company’s common stock that the holder and its affiliates may beneficially own after the conversion to 4.99%. That beneficial ownership limitation does not, however, apply to holders who are subject to Section 16 of the Exchange Act by virtue of being an executive officer or director of the Company which presently only applies to the Company’s Chief Executive Officer.

The Series F and F-1 Preferred Stock was valued at $48.2 million per the Merger. The conversion of Series F and F-1 Preferred Stock was approved at a special meeting of stockholders on March 7, 2025.

Beeline Holdings, Inc.

Notes to Consolidated Financial Statements

June 30, 2026 and 2025

(unaudited)

During the six months ended June 30, 2026, investors converted 256,242 and 1,910 shares of Series F and F-1 Preferred Stock, respectively, into 25,815 shares of common stock. During the six months ended June 30, 2025, 57,020,394 and 421,186 shares of Series F and F-1 Preferred Stock, respectively, were converted into 5,744,158 shares of common stock. No gain or loss was recognized as a result of these conversions for both the six months ended June 30, 2026 and 2025.

On July 23, 2025, the Company entered into an agreement with a holder of and effected the exchange of 8,356,151 shares of Series F Preferred Stock and 68,951 shares of Series F-1 Preferred Stock of the Company in exchange for the issuance to the holder of 8,425,102 shares of Series A Preferred Stock.

In conjunction with the Senior Secured Notes entered into on November 14, 2024, the Company entered in a side letter which permitted an affiliate who invested $0.4 million to exchange that amount of stated value of shares of Series F Preferred Stock for a $0.4 million 120-day promissory note and has substantially identical terms to the Senior Secured Notes, except it is subordinated with respect to its security interest. This affiliate exchanged 896,667 shares of Series F Preferred Stock. Additional side letters permitted two investors to each receive 250,000 shares of Series F Preferred Stock. The net amount of these side letters was (396,667) shares.

Issuance of Series G Preferred Stock

Each share of Series G Preferred Stock has a stated value of $0.51 and is convertible into shares of the Company’s common stock pursuant to the terms and conditions set forth in a Certificate of Designation establishing Series G Preferred Stock with an initial conversion price of $5.10 per share. The conversion price is subject to adjustment as provided therein including that in the event of an issuance of common stock or common stock equivalents at a price per share that is less than the conversion price, the conversion price then in effect will be reduced to such lower price per share, subject to certain exceptions and to a floor price of 20% of the Nasdaq Minimum Price as of the initial closing date of the offering of such Series G Preferred Stock (see below for triggering event). The result of such provision is that more shares of common stock will be issuable upon conversions of the Series G Preferred Stock if there is a subsequent issuance at a lower price per share. Each share of Series G Preferred Stock is convertible into common stock by a conversion ratio equal to the stated value of the Series G Preferred Stock share divided by the Series G Preferred Stock conversion price. The Series G Preferred Stock conversion price is subject to equitable adjustment in the event of a stock split, reverse split, and similar events. The number of shares of common stock into which a holder may convert Series G Preferred Stock will be limited by a beneficial ownership limitation, which restricts the number of shares of the Company’s common stock that the holder and its affiliates may beneficially own after the conversion to 4.99%. The holder of Series G Preferred Stock has no conversion or voting rights prior to stockholder approval of such actions. In the event of a liquidation of the Company, the holders of Series G Preferred Stock will share in the distribution of the Company’s net assets on an as-converted basis, subordinate only to the Series B Preferred Stock, Series C Preferred Stock, Series D Preferred Stock, and Series E Preferred Stock. The conversion of Series G Preferred Stock was approved at a special meeting of stockholders on March 7, 2025.

On April 25, 2025, the Company filed with the Nevada Secretary of State a Certificate of Amendment to the Series G Preferred Stock Certificate of Designations. The Certificate of Amendment provides that (i) the beneficial ownership limitation on conversion set forth in the Certificate of Designation will not apply to a holder who is otherwise subject to Section 16(a) of the Securities Exchange Act of 1934 by virtue of being an executive officer or director of Company, and (ii) the anti-dilution price protection adjustment rights with respect to subsequent offerings or issuances of securities will not apply to an equity line of credit or at-the-market offering facility or as otherwise determined by the holder(s) of a majority of the Series G Preferred Stock.

During the six months ended June 30, 2025, the Company sold 6,417,159 shares of Series G Preferred Stock and five-year Warrants to purchase a total of 320,862 shares of common stock for total gross proceeds of $3.3 million. The Company incurred offering costs of $6,270 related to the offering. In addition, in February 2025, the Company’s Chief Executive Officer converted his $0.7 million bridge loan into $0.7 million of units comprised of 1,372,549 shares of Series G Preferred Stock and five-year Warrants to purchase a total of 68,628 shares of common stock.

On March 25, 2025 (“the trigger date”), the Company sold common stock under the ELOC Agreement at $1.67 per share, which was less than the Series G Preferred Stock original conversion price of $5.10 per share, resulting in the reduction of the conversion price of the Series G Preferred Stock to $1.67 per share as a result of the price protection adjustment related to the conversion of the Series G Preferred Stock. The Company recorded a deemed dividend related to the Series G Preferred Stock price protection of $1.5 million. The deemed dividend was computed as the fair value of the embedded conversion option with the reduced conversion price of $1.67 less the fair value of the embedded conversion option with the original conversion price of $5.10 as computed on the trigger date. See below for the warrant related deemed dividend allocation and assumptions used in the Black-Scholes model.

Beeline Holdings, Inc.

Notes to Consolidated Financial Statements

June 30, 2026 and 2025

(unaudited)

During the six months ended June 30, 2026, 235,293 shares of Series G Preferred Stock were converted into 71,859 shares of common stock. During the six months ended June 30, 2025, 3,980,664 shares of Series G Preferred Stock were converted into 398,066 shares of common stock. No gain or loss was recognized as a result of these conversions for both the six months ended June 30, 2026 and 2025.

In January 2025, the Company issued a consultant 245,098 shares of Series G Preferred Stock that were issuable as of December 31, 2024. In addition, in January 2025, the Company issued 19,698 shares of Series G Preferred Stock for legal services of $10,000.

Warrants

During six months ended June 30, 2026, 579,360 Warrants were exercised for proceeds of $0.2 million related to Series G Preferred Stock and the Company issued 521,753 shares of common stock, including 169,080 shares of common stock issued under the cashless exercise provision upon the exercise of 226,687 Warrants.

There were no new warrants issued during the six months ended June 30, 2026. A summary of all Warrant share activity as of and for the six months ended June 30, 2026 is presented below:

	Warrant Shares			Weighted-Average Remaining Life (Years)		Weighted-Average Exercise Price			Aggregate Intrinsic Value (in millions)
Outstanding as of December 31, 2024		315,056			4.6	$	28.00		$	1.0
Additions due to price protection adjustment		5,430,468			4.3		0.66			5.8
Issued with Series G Preferred Stock units sold		389,490			4.0		0.66			0.4
Granted		302,200			4.7		2.36			-
Exercised		(25,000	)		-		(1.00	)		-
Expired		(1,083	)		-		(767.54	)		-
Outstanding as of December 31, 2025		6,411,131			4.1	$	1.76		$	6.4
Exercised		(579,360	)		-		(0.66	)		(0.8	)
Expired		(4,500	)		-		-			-
Outstanding as of June 30, 2026		5,827,271			3.3	$	1.41		$	3.1

On March 25, 2025, the Company sold shares under the ELOC at $1.67 per share, which was less than the exercise price of the Warrants issued in the Company’s Series G Preferred Stock offering, resulting in the reduction of the exercise price of the warrants to $1.67 per share and an increase in common shares issuable upon exercise of 1,774,986 under the full price protection adjustment of the Warrants. The Company recorded a deemed dividend related to the Warrants price protection of $3.1 million. On June 16, 2025, the Company sold shares under the ELOC at $0.66 per share, which was less than the exercise price of the Warrants adjusted in March 2025, resulting in the reduction of the exercise price of the warrants to $0.66 per share and an increase in common shares issuable upon exercise of 3,655,482 under the full price protection adjustment of the Warrants. The Company recorded an additional deemed dividend related to the Warrants price protection of $5.2 million for the six months ended June 30, 2025.

The estimated fair value of the deemed dividend relating to the price protection adjustment is computed as the fair value of the warrants with the reduced exercise price of $1.67 less the fair value of the warrants at the original exercise price of $6.50 as computed on the trigger date. The Black-Scholes option-pricing model used the assumptions below for the six months ended June 30, 2025:

Volatility	100-131%
Risk-free interest rate	3.94% - 4.46%
Expected term (in years)	5.0
Expected dividend yield	-
Fair value of common stock	$0.66 - $8.60

Beeline Warrants

In the merger agreement, the Company agreed to assume 5,868 outstanding Beeline Warrants with an exercise price of $231.20 per share. The new Warrants have not been issued as of the date of this Report.

Beeline Holdings, Inc.

Notes to Consolidated Financial Statements

June 30, 2026 and 2025

(unaudited)