MicroStrategy (MSTR) updates proceeds language; agents' holdings may trigger FINRA Rule 5121

Rhea-AI Filing Summary

MicroStrategy files Supplement No. 2 to its base prospectus supplement to amend the Use of Proceeds disclosure and rename the Plan of Distribution section to Plan of Distribution (Conflicts of Interest). The supplement states offerings may include Class A common stock and series of preferred stock under an Omnibus Sales Agreement and reiterates that certain agents or their affiliates may hold the company's equity or convertible notes and could receive proceeds if repurchases occur. The supplement adds a Conflicts of Interest subsection referencing FINRA Rule 5121 and notes bitcoin price volatility in the prior 12 months, citing trades below $65,000 and above $120,000.

Insights

Securities Offerings Specialist

Supplement revises proceeds use and adds explicit conflict rules tied to agent holdings.

The filing amends the Use of Proceeds language and inserts a Conflicts of Interest clause that ties certain dealer behavior to FINRA Rule 5121. The text flags that agents or their affiliates may receive proceeds if the company repurchases securities they hold.

Practical dependencies include whether repurchases occur and whether any single agent receives at least 5% of net proceeds, which would trigger the Rule 5121 distribution requirements. Subsequent prospectus updates or sales notices would disclose any such arrangements.

Corporate Finance Analyst

Use-of-proceeds remains broad; management retains allocation discretion.

The supplement states management has not allocated specific net proceeds amounts and will exercise broad discretion in applying proceeds, including potential bitcoin purchases and debt repurchases. Bitcoin price volatility is cited as a realization risk for cash generation from crypto holdings.

Material outcomes depend on future allocation decisions; cash‑flow effects from bitcoin purchases or repurchases will appear in later filings if implemented.

Key Figures

Bitcoin price range cited: $65,000 and $120,000 FINRA conflict threshold: 5% 0.625% Convertible Notes: 0.625% interest +2 more

5 metrics

Bitcoin price range cited $65,000 and $120,000 traded below $65,000 and above $120,000 in the 12 months preceding the base prospectus supplement

FINRA conflict threshold 5% agent or affiliate receiving at least 5% of net proceeds triggers FINRA Rule 5121

0.625% Convertible Notes 0.625% interest 0.625% Convertible Senior Notes due 2028 and due 2030 shown in annex table

0% Convertible Notes 0.000% interest 0% Convertible Senior Notes due 2029 and 2030 shown in annex table

2.25% Convertible Notes 2.250% interest 2.25% Convertible Senior Notes due 2032 shown in annex table

Key Terms

Omnibus Sales Agreement, FINRA Rule 5121, bona fide public market, qualified independent underwriter, +1 more

5 terms

Omnibus Sales Agreement financial

"offer and sale ... pursuant to the Omnibus Sales Agreement, dated as of November 4, 2025"

FINRA Rule 5121 regulatory

"To the extent such Agents ... would be deemed to have a conflict of interest under FINRA Rule 5121"

bona fide public market regulatory

"the securities being offered have a "bona fide public market" (as defined in FINRA Rule 5121)"

qualified independent underwriter financial

"The appointment of a "qualified independent underwriter" ("as defined in FINRA Rule 5121) is not necessary"

A qualified independent underwriter is a financial firm that is both eligible under regulatory rules and free of close ties to the issuing company, so it can buy, price and sell a new batch of securities without conflicts of interest. Investors treat its involvement like a neutral referee: its role helps set a fair market price, adds credibility to the deal and reduces the risk that shares are being pushed on biased or poorly vetted terms.

Convertible Senior Notes financial

"0.625% Convertible Senior Notes due 2028 ... 2.25% Convertible Senior Notes due 2032"

Convertible senior notes are a type of loan that a company issues to investors, which can be turned into company shares later on. They are called "senior" because they are paid back before other debts if the company runs into trouble. This allows investors to earn interest like a loan but also have the chance to own part of the company if its value rises.

Offering Details

ATM

Offering

Offering Type ATM

Use of Proceeds Net proceeds may be used for purposes listed in the base prospectus and annexes, potentially including purchases of bitcoin and repurchases of equity or convertible notes; management has broad discretion

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 05/06/2026 - 04:12 PM Learn about SEC filing dates

FAQ

What does MicroStrategy's Supplement No. 2 change about the offering?

The supplement amends the Use of Proceeds section and revises the Plan of Distribution to add a Conflicts of Interest subsection. It clarifies agent holdings could create FINRA Rule 5121 implications when repurchases occur.

Does the supplement state how MicroStrategy will use net proceeds?

No specific allocations are provided; management will have broad discretion. The supplement says net proceeds may include purchases of bitcoin, repurchases of equity or convertible notes, and other purposes listed in the base prospectus and annexes.

How does the filing address conflicts of interest for selling agents (MSTR)?

The filing warns certain Agents or affiliates may hold company securities and, if they receive at least 5% of net proceeds, distribution must follow FINRA Rule 5121, including limits on confirming sales to discretionary accounts without prior consent.

What bitcoin risk does MicroStrategy disclose in the supplement (MSTR)?

The supplement notes bitcoin traded below $65,000 and above $120,000 in the prior 12 months and states bitcoin does not pay interest; cash generation depends on sales and prices realized when converted to cash.

Are there limits on appointing a qualified independent underwriter?

The supplement states a qualified independent underwriter is not required because the securities have a "bona fide public market" as defined in FINRA Rule 5121, per the supplement language.

As Filed Pursuant to Rule 424(b)(3)
Registration No. 333-284510

Supplement No. 2 dated May 6, 2026

(To Base Prospectus Supplement Dated November 4, 2025

To Prospectus Dated January 27, 2025)

Class A Common Stock

Preferred Stock

This supplement relates to the offer and sale of shares of our class A common stock, $0.001 par value per share, and shares of several series of our preferred stock, $0.001 par value per share, pursuant to the Omnibus Sales Agreement, dated as of November 4, 2025, as amended, supplemented or otherwise modified from time to time (the “Sales Agreement”), by and among us and the sales agents identified therein (the “Agents”) and supplements the base prospectus supplement dated November 4, 2025 related thereto. This supplement should be read in conjunction with the base prospectus supplement, as supplemented by supplement no. 1 thereto, the annexes to the base prospectus supplement, and the accompanying prospectus dated January 27, 2025. Except as set forth herein, the base prospectus supplement, as supplemented, and the accompanying prospectus remain unchanged.

We are filing this supplement to (i) amend and restate the disclosure under the section heading “Use of Proceeds” in the base prospectus supplement in its entirety as set forth below and (ii) to revise the section heading “Plan of Distribution” in the base prospectus supplement to be “Plan of Distribution (Conflicts of Interest)” and insert the Conflicts of Interest subsection set forth below at the end of such section.

Use of Proceeds:

We intend to use the net proceeds from the offerings of securities under this base prospectus supplement, the supplements to this base prospectus supplement and the annexes to this base prospectus supplement for the purposes set forth in this base prospectus supplement, the supplements to this base prospectus supplement and in the applicable annex, which may include:

• general corporate purposes, including the acquisition of bitcoin and for working capital;

• the payment of cash dividends declared or expected to be declared by the board of directors from time to time on shares of one or more series of our preferred stock;

• subject to market conditions, the repurchase of outstanding shares of one or more classes or series of our equity securities, including our class A common stock and outstanding series of preferred stock; and

• the repayment or, subject to market conditions, the repurchase or redemption of the following convertible notes:

Convertible Notes		Interest Rate				Maturity Date(1)
0.625% Convertible Senior Notes due 2028			0.625	%			9/15/2028
0% Convertible Senior Notes due 2029			0.000	%			12/1/2029
0.625% Convertible Senior Notes due 2030			0.625	%			3/15/2030
0% Convertible Senior Notes due 2030			0.000	%			3/1/2030
0.875% Convertible Senior Notes due 2031			0.875	%			3/15/2031
2.25% Convertible Senior Notes due 2032			2.250	%			6/15/2032
(1)   Unless earlier converted, redeemed, or repurchased in accordance with their respective terms.

Bitcoin is a highly volatile asset that has traded below $65,000 per bitcoin and above $120,000 per bitcoin in our principal market in the 12 months preceding the date of this base prospectus supplement. Bitcoin does not pay interest or other returns and so our ability to generate cash from our bitcoin holdings depends on sales. Future fluctuations in bitcoin trading prices may result in our converting bitcoin purchased with the net proceeds from the offerings of securities under this base prospectus supplement into cash with a value substantially below the net proceeds from these offerings, and there can be no assurance as to whether or when we will realize any cash proceeds from our contemplated acquisition of bitcoin.

We have not determined the amount of net proceeds to be used specifically for any of these purposes. As a result, our management will have broad discretion in the application of the net proceeds from these offerings and you will not have the opportunity as part of your investment decision to assess whether the net proceeds are being used in a manner of which you approve.

Certain of the Agents and/or their affiliates may from time to time be holders of our equity securities and/or convertible notes. To the extent we use the net proceeds from any of these offerings to repurchase such equity securities and/or convertible notes, such Agents and/or their affiliates may receive a portion of the net proceeds of such offerings. See “Plan of Distribution (Conflicts of Interest) — Conflicts of Interest” in this base prospectus supplement.

********************

Plan of Distribution (Conflicts of Interest):

Conflicts of Interest

Certain of the Agents and/or their affiliates may from time to time be holders of our equity securities and/or convertible notes. To the extent we use the net proceeds from any of these offerings to repurchase such equity securities and/or convertible notes, such Agents and/or their affiliates may receive a portion of the net proceeds of such offerings. To the extent such Agents and/or their affiliates receive at least 5% of the net proceeds of any offering, such Agents would be deemed to have a conflict of interest under FINRA Rule 5121. Any Agent deemed to have a conflict of interest would be required to conduct the distribution of our securities in accordance with FINRA Rule 5121. If the offerings are conducted in accordance with FINRA Rule 5121, any such Agent with a conflict of interest would not be permitted to confirm a sale to an account over which it exercises discretionary authority without first receiving specific written approval from the account holder. The appointment of a “qualified independent underwriter” (“as defined in FINRA Rule 5121) is not necessary for these offerings because the securities being offered have a “bona fide public market” (as defined in FINRA Rule 5121).

Our business and an investment in our securities involve significant risks. These risks are described under the caption “Risk Factors Related to the ATM Offering Programs” beginning on page S-9 of the base prospectus supplement, and under the captions “Risk Factors” and “Risk Factor Updates” in each applicable annex to the base prospectus supplement and in the documents incorporated by reference into the base prospectus supplement.

Neither the Securities and Exchange Commission nor any state or foreign securities commission or regulatory authority has approved or disapproved of these securities or passed upon the adequacy or accuracy of this supplement, the base prospectus supplement, any applicable annex to the base prospectus supplement or the accompanying prospectus. Any representation to the contrary is a criminal offense.

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