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10.00% Series A Perpetual Stride Preferred Stock MicroStrategy Incorporated d/b/a Strategy is offering 2,500,000 shares of our 10.00% Series A Perpetual Stride Preferred Stock,which we refer to as our “STRD Stock.” The STRD Stock will have a stated amount of $100 per share and an initial liquidationpreference of $100 per share. The liquidation preference will be subject to adjustment in the manner described in this prospectussupplement. However, the liquidation preference will not be adjusted to an amount that is less than $100 per share. DIVIDENDS Dividends on shares of the STRD Stock will not be mandatory. Holders of the STRD Stock will be entitled to receivenon-cumulativedividends, which we refer to as “regular dividends,” at a rate per annum equal to 10.00% on the stated amountthereof, which is $100 per share of STRD Stock, out of funds legally available for their payment to the extent paid in cash, onlywhen, as, and if declared by our board of directors or any duly authorized committee thereof. If declared, regular dividends onthe STRD Stock will be payable quarterly in arrears on March31, June30, September30 and December31 of each year,beginning on September30, 2025. Since regular dividends are not cumulative, we will not have any obligation to pay anyregular dividend for any regular dividend period unless we declare such regular dividend prior to the regular dividend paymentdate for such regular dividend period. No dividend, interest or other amount will accumulate or accrue on any unpaid regulardividends, regardless of whether regular dividends are declared for any future regular dividend period. Declared regulardividends on the STRD Stock will be payable, solely in cash in the manner, and subject to the provisions, described in thisprospectus supplement. REDEMPTION AND REPURCHASE We will have the right, at our election, to redeem all, and not less than all, of the STRD Stock, at any time, for cash if the totalnumber of shares of all STRD Stock then outstanding is less than 25% of the total number of shares of STRD Stock originallyissued in this offering and in any future offering taken together. In addition, we will have the right to redeem all, but not lessthan all, of the STRD Stock if a “tax event” (as defined in this prospectus supplement) occurs. The redemption price for anySTRD Stock to be redeemed will be a cash amount equal to the liquidation preference of the STRD Stock to be redeemed as ofthe business day before the date we send the related redemption notice, plus declared and unpaid regular dividends, if any, thatwill have accrued to, but excluding, the redemption date. For the avoidance of doubt, the redemption price will not includepayment of any undeclared regular dividends. The information in this preliminary prospectus supplement is not complete and may be changed. This preliminary prospectussupplement and the accompanying prospectus are not an offer to sell these securities or a solicitation of an offer to buy these securitiesin any jurisdiction where the offer and sale is not permitted.If a “fundamental change” (as defined in this prospectus supplement) occurs, then, except as described in this prospectussupplement, preferred stockholders will have the right (which we refer to as the “fundamental change repurchase right”) torequire us to repurchase some or all of their shares of STRD Stock at a cash repurchase price equal to the stated amount of theSTRD Stock to be repurchased, plus declared and unpaid regular dividends, if any, that will have accrued to, but excluding thefundamental change repurchase date. For the Table of Contents avoidance of doubt, the fundamental change repurchase price will not include payment of any undeclared regular dividends. LISTING No public market currently exists for the STRD Stock. We have applied to list the STRD Stock on The Nasdaq Global Select Market under the symbol“STRD.” If the listing is approved, we expect trading to commence within 30 days after the date the STRD Stock is first issued. (1)For additional information about underwriting compensation, see “Underwriting.” Our business and an investment in the STRD Stock involve significant risks. These risks are described under thecaption “Risk Factors” beginning on pageS-14of this prospectus supplement and in the documents incorporated byreference into this prospectus supplement. Neither the Securities and Exchange Commission nor any state or foreign securities commission has approved or disapproved of the STRDStock or passed upon the adequacy or accuracy of this prospectus supplement or the accompanying prospectus. Any representation to thecontrary is a criminal offense. At our request, the underwriters have reserved up toshares of STRD Stock, or% of the STRD Stock offered by this prospectussupplement, for sale at the public offering price through a directed share program to certain of our employees, officers and directors based in the UnitedStates. See “Underwriting—Directed Sh