Strategy Inc (MSTR) VP trades shares to cover RSU tax obligations

Filing Impact

(Neutral)

Filing Sentiment

(Negative)

Form Type

Rhea-AI Filing Summary

Strategy Inc VP & CAO Jeanine Montgomery reported routine equity transactions linked to restricted stock units (RSUs). On March 23, 2026, she acquired 1,560 shares of Class A common stock at $0.00 per share through the vesting and settlement of RSUs. The next day, she sold a total of 470 shares of Class A common stock in open-market transactions at weighted average prices between $137.370 and $139.550. According to the disclosure, these sales were made under a pre-arranged Rule 10b5-1 instruction letter solely to satisfy tax withholding obligations from the RSU vesting. After the transactions, she directly held 10,423 shares of Class A common stock, 3,120 RSUs scheduled to vest in equal installments in 2027 and 2028, and 5,000 shares of Series A perpetual preferred stock.

Insider Trade Summary 10b5-1

Net Seller: 470 shares ($65,016)

Net Sell 6 txns

Insider Montgomery Jeanine

Role VP & CAO

Sold 470 shs ($65K)

Type	Security	Shares	Price	Value
Sale	Class A Common Stock	250	$137.73	$34K
Sale	Class A Common Stock	201	$138.976	$28K
Sale	Class A Common Stock	19	$139.453	$3K
Exercise	Restricted Stock Units	1,560	$0.00	--
Exercise	Class A Common Stock	1,560	$0.00	--
holding	Series A Perpetual Stretch Preferred Stock	--	--	--

Holdings After Transaction: Class A Common Stock — 10,643 shares (Direct); Restricted Stock Units — 3,120 shares (Direct); Series A Perpetual Stretch Preferred Stock — 5,000 shares (Direct)

Footnotes (1)

Each restricted stock unit represents a contingent right to receive one share of class A common stock of Strategy Inc ("Strategy"). The sales were effected pursuant to a Rule 10b5-1 instruction letter entered into on May 3, 2024 to satisfy the reporting person's tax withholding obligation upon the vesting of previously granted equity awards. Such sales were made solely to pay Strategy the tax withholding obligation due upon the vesting of restricted stock units on March 21, 2026 and their settlement on March 23, 2026. The reported price is a weighted average price. These shares were sold in multiple transactions at prices ranging from $137.370 to $138.350, inclusive. The reporting person undertakes to provide to Strategy, any security holder of Strategy, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each price within the range set forth in this footnote. The reported price is a weighted average price. These shares were sold in multiple transactions at prices ranging from $138.390 to $139.380, inclusive. The reporting person undertakes to provide to Strategy, any security holder of Strategy, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each price within the range set forth in this footnote. The reported price is a weighted average price. These shares were sold in multiple transactions at prices ranging from $139.385 to $139.550, inclusive. The reporting person undertakes to provide to Strategy, any security holder of Strategy, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each price within the range set forth in this footnote. The remaining 3,120 RSUs will vest in equal annual installments over a two-year period, with 1,560 RSUs vesting on March 21, 2027 and 1,560 RSUs vesting on March 21, 2028.

Form 4 Insider Transactions: What Each Field Means →

03/25/2026 - 08:28 PM

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^*

Montgomery Jeanine

(Last)

(First)

(Middle)

C/O STRATEGY INC

1850 TOWERS CRESCENT PLAZA

(Street)

TYSONS CORNER

VIRGINIA

22182

(City)

(State)

(Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Strategy Inc [ MSTR ]

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

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
03/23/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Class A Common Stock	03/23/2026		M		1,560	A	⁽¹⁾	10,893	D
Class A Common Stock	03/24/2026		S⁽²⁾		250	D	$137.73⁽³⁾	10,643	D
Class A Common Stock	03/24/2026		S⁽²⁾		201	D	$138.976⁽⁴⁾	10,442	D
Class A Common Stock	03/24/2026		S⁽²⁾		19	D	$139.453⁽⁵⁾	10,423	D
Series A Perpetual Stretch Preferred Stock								5,000	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)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Restricted Stock Units	⁽¹⁾	03/23/2026		M			1,560	⁽⁶⁾	⁽⁶⁾	Class A Common Stock	1,560	$0	3,120	D

Explanation of Responses:

1. Each restricted stock unit represents a contingent right to receive one share of class A common stock of Strategy Inc ("Strategy").

2. The sales were effected pursuant to a Rule 10b5-1 instruction letter entered into on May 3, 2024 to satisfy the reporting person's tax withholding obligation upon the vesting of previously granted equity awards. Such sales were made solely to pay Strategy the tax withholding obligation due upon the vesting of restricted stock units on March 21, 2026 and their settlement on March 23, 2026.

3. The reported price is a weighted average price. These shares were sold in multiple transactions at prices ranging from $137.370 to $138.350, inclusive. The reporting person undertakes to provide to Strategy, any security holder of Strategy, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each price within the range set forth in this footnote.

4. The reported price is a weighted average price. These shares were sold in multiple transactions at prices ranging from $138.390 to $139.380, inclusive. The reporting person undertakes to provide to Strategy, any security holder of Strategy, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each price within the range set forth in this footnote.

5. The reported price is a weighted average price. These shares were sold in multiple transactions at prices ranging from $139.385 to $139.550, inclusive. The reporting person undertakes to provide to Strategy, any security holder of Strategy, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each price within the range set forth in this footnote.

6. The remaining 3,120 RSUs will vest in equal annual installments over a two-year period, with 1,560 RSUs vesting on March 21, 2027 and 1,560 RSUs vesting on March 21, 2028.

	/s/ Allein Sabel, Attorney-in-Fact	03/25/2026
	** 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.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transactions did Strategy Inc (MSTR) report for Jeanine Montgomery?

Strategy Inc reported that VP & CAO Jeanine Montgomery had RSUs vest into 1,560 Class A shares, then sold 470 shares in open-market trades. The sales were tied to tax withholding obligations under a pre-arranged Rule 10b5-1 instruction letter.

How many Strategy Inc (MSTR) shares did the VP sell and at what prices?

Jeanine Montgomery sold 470 shares of Strategy Inc Class A common stock in three open-market transactions. Weighted average prices ranged from $137.370 to $139.550 per share, reflecting multiple individual trades within each reported price range on March 24, 2026.

Were the Strategy Inc (MSTR) insider sales part of a Rule 10b5-1 plan?

Yes, the filing states the sales were effected under a Rule 10b5-1 instruction letter entered on May 3, 2024. The transactions were made solely to satisfy tax withholding obligations arising from the vesting and settlement of restricted stock units.

How many Strategy Inc (MSTR) shares and RSUs does the VP hold after these transactions?

Following the reported transactions, Jeanine Montgomery directly held 10,423 shares of Strategy Inc Class A common stock and 3,120 restricted stock units. The RSUs are scheduled to vest in two equal annual installments in 2027 and 2028, subject to continued conditions.

What is the nature of the RSU vesting for Strategy Inc (MSTR) reported here?

The filing shows 1,560 restricted stock units converted into an equal number of Class A shares as part of equity compensation. The remaining 3,120 RSUs will vest in two equal annual installments on March 21, 2027 and March 21, 2028, respectively.

Does the Strategy Inc (MSTR) insider also hold preferred stock?

Yes, the report lists a direct holding of 5,000 shares of Series A perpetual preferred stock. This line is shown as a holding entry rather than a new transaction, indicating the preferred position after the reported equity compensation and related common share sales.