[Form 4] Airship AI Holdings, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Insider transactions by Paul M. Allen, President and Officer of Airship AI Holdings, Inc. (AISP). The Form 4 reports a sale of 51,948 shares of common stock on 09/03/2025. The filing also details multiple option holdings and earnout rights converted from pre-merger Airship AI awards, including Converted Stock Options exercisable into 100,000, 150,000, 100,000, 300,000 and a newly acquired option for 50,000 shares vesting per stated schedules. Total underlying shares shown after transactions include 835,058, 155,843, and other option pools by grant. Some options have exercise prices from $0.57 to $4.25 and various expiration dates through 2035. Earnout shares are contingent on future performance and continued service. The report is signed on 09/04/2025.

Insights

Securities Analyst

TL;DR: Insider sold a modest block and retains substantial option exposure from converted pre-merger awards.

The sale of 51,948 shares on 09/03/2025 represents a discrete disposition by the company President but is small relative to total reported underlying option exposure. The filing highlights converted options from the Merger Agreement and multiple option grants with staggered vesting and expirations through 2035. Exercise prices range from $0.57 to $4.25, implying differing intrinsic value depending on current market price. Earnout rights remain contingent on performance and continued service, creating potential future dilution if achieved. Overall, this is routine insider activity following a merger conversion and option schedule rather than an unusual corporate event.

Corporate Governance Expert

TL;DR: Transactions reflect standard post-merger option conversion and vesting mechanics, with contingent earnouts noted.

The Form 4 documents Converted Stock Options received under the Merger Agreement and subsequent option grants that vest quarterly over four years where specified. The presence of earnout rights tied to operating and share price milestones is material to potential future share issuance but is explicitly conditional. The direct ownership and options are reported as direct holdings. The filing appears complete and properly signed, with no amendments indicated. For governance, key points are the vesting schedules and earnout contingencies which align management incentives with performance.

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^*

Allen Paul M.

(Last) (First) (Middle)

C/O AIRSHIP AI HOLDINGS, INC.

8210 154TH AVE NE

(Street)

REDMOND WA 98052

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Airship AI Holdings, Inc. [ AISP ]

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

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

3. Date of Earliest Transaction (Month/Day/Year)
09/03/2025

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								51,948	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
Options(1)	$0.57							12/21/2023	01/15/2032	Common Stock	100,000		835,058	D
Earnout Rights	(2)							(2)	(2)	Common Stock	51,948		155,843	D
Options	$2.86							(3)	08/16/2034	Common Stock	150,000		150,000	D
Options	$3.27							03/04/2025	03/04/2035	Common Stock	100,000		100,000	D
Options	$3.27							(3)	03/04/2035	Common Stock	300,000		300,000	D
Options	$4.25	09/03/2025		A		50,000		(3)	09/03/2035	Common Stock	50,000	$0	50,000	D

Explanation of Responses:

1. Represents options to purchase shares of common stock of the Issuer received on December 21, 2023 (the "Converted Stock Options"), pursuant to that certain Merger Agreement, dated as of June 27, 2023 (as amended on September 22, 2023 and as may be further amended and/or restated from time to time, the "Merger Agreement"), by and among Airship AI Holdings, Inc., a Delaware corporation (the "Issuer") (formerly known as BYTE Acquisition Corp., a Cayman Island exempted company limited by shares, prior to its domestication as a Delaware corporation), BYTE Merger Sub, Inc., a Washington corporation and a direct, wholly-owned subsidiary of the Issuer, and Airship AI, Inc., a Washington company (formerly known as Airship AI Holdings, Inc., "Airship AI"). The Reporting Person received the reported options upon the conversion of options to purchase shares of common stock of Airship AI at the Conversion Ratio, as defined in the Merger Agreement, as of the Effective Time of the Merger.

2. Pursuant to earnout provisions in the Merger Agreement and subject to the Reporting Person's continued service to the Issuer and the vesting conditions applicable to the Converted Stock Options, the holder of such Earnout Rights is entitled to receive shares of common stock of the Issuer upon the occurrence of certain operating performance and share price performance milestones during the applicable earnout periods set forth in the Merger Agreement.

3. Options vest quarterly over 4 years.

	By: /s/ Paul Allen	09/04/2025
	** 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).
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FAQ

What did Paul M. Allen report on the Form 4 for AISP?

The Form 4 reports a sale of 51,948 common shares on 09/03/2025 and discloses multiple option holdings and earnout rights converted under the Merger Agreement.

How many shares does the filing show were disposed of by the insider?

The filing shows a disposition of 51,948 shares of common stock.

What types of derivative securities are reported in the AISP Form 4?

The filing reports multiple options with exercise prices from $0.57 to $4.25, various exercisable and expiration dates through 2035, and earnout rights convertible to common stock upon milestones.

Are the earnout shares in the filing guaranteed?

No. The earnout rights are contingent on specified operating performance and share price milestones and the reporting person’s continued service, per the Merger Agreement.

When was the Form 4 signed by the reporting person?

The Form 4 is signed by Paul Allen on 09/04/2025.