Montgomery Jeanine 4

What Happened

• Jeanine Montgomery, VP & CAO of Strategy Inc (MSTR), had 1,560 restricted stock units (RSUs) vest/settle on March 23, 2026 (converted to shares) and, pursuant to a pre-existing 10b5-1 instruction, sold a portion of the shares to cover taxes.
• She sold 470 shares in open-market transactions on March 24, 2026 for total proceeds of approximately $65,017 (250 shares at a weighted avg $137.73 = $34,433; 201 shares at a weighted avg $138.98 = $27,934; 19 shares at a weighted avg $139.45 = $2,650). An additional 1,560 shares were reported disposed at $0.00 (share withholding/surrender to Strategy to satisfy tax withholding on the vested RSUs).

Key Details

• Transaction dates: RSU settlement/exercise on 2026-03-23; open-market sales on 2026-03-24.
• Sale prices: weighted averages shown — $137.73 (250 shares), $138.98 (201 shares), $139.45 (19 shares). Footnotes report transaction price ranges for each block and offer to provide per-price detail on request.
• Total cash proceeds from open-market sales: ~$65,017.
• The 1,560 shares shown as disposed at $0.00 reflect shares withheld/surrendered to Strategy to cover tax withholding on the vested RSUs.
• Plan/footnotes: Sales were effected pursuant to a Rule 10b5-1 instruction (entered May 3, 2024) specifically to satisfy the reporting person’s tax withholding obligation (F2). Each RSU represents a right to one share (F1).
• Remaining RSUs: 3,120 RSUs remain unvested and will vest in equal installments on March 21, 2027 and March 21, 2028 (F6).
• Shares owned after transaction: not specified in the provided filing excerpt.
• Filing timeliness: Reported period 2026-03-23; Form filed 2026-03-25 — appears timely.

Context

• This was not a bullish stock purchase: it was a routine tax-withholding sale following RSU vesting. Conversions of RSUs to shares (derivative exercise/conversion) were followed by share withholding and open-market sales to satisfy tax obligations.
• Sales under 10b5-1 plans are commonly automatic and do not, by themselves, indicate insider sentiment about company prospects.