MSFT MICROSOFT CORP Insider Trading

Chief Marketing Officer Takeshi Numoto sold 4,500 shares of MSFT at $402.84 on 2026-06-10 ($1.8M); stock now -29.6% from 52-week high.

Takeshi Numoto sold 4,500 shares (8.7% of pre-transaction holdings) on 2026-06-10 at $402.84, reducing his position from 51,967 to 47,467 shares. The transaction occurs as MSFT trades $390.74, now -29.6% from its 52-week high of $555.45. Examining Numoto's timing history at MSFT specifically, 4 of his 5 prior sells at this ticker were well-timed at the 90-day mark (post-sale declines), including his most recent sale on 2025-12-04 which saw a 90-day decline of -15.4%. His cross-ticker track record shows a 77.78% well-timed rate on 9 prior sells with average 90-day returns of -4.7%. The sale occurs against strong MSFT fundamentals: $82.9B quarterly revenue, $31.8B net income, 14.9% annual revenue growth, and a P/E of 23.18, suggesting the transaction reflects portfolio allocation rather than fundamental deterioration.

EVP CMO Takeshi Numoto sold 2,500 MSFT shares at $412.45; stock now $397.36, down 28.5% from 52-week high.

Takeshi Numoto sold 2,500 shares (4.6% of his pre-transaction holdings) at $412.45, reducing his MSFT stake from 54,467 to 51,967 shares. The stock has declined -28.5% from its 52-week high of $555.45 and currently trades at $397.36, a -3.7% move over the past 30 days. Across his prior trades at MSFT specifically, Numoto has demonstrated a timing pattern: 4 of his 5 prior MSFT sells showed negative 90-day returns, indicating he has historically sold before subsequent declines. His cross-ticker track record shows a 77.78% well-timed rate on sells, suggesting a consistent ability to exit positions ahead of downward moves. Given the stock's current position -28.5% below its 52-week high and Numoto's established pattern of well-timed MSFT sales, this transaction fits a historical precedent of selling into weakness or before further decline.

Judson Althoff, who was CEO Microsoft Commercial, sold 15,500 MSFT shares at $460.99 for $7,145,314.00 on 2026-06-01.

Althoff sold 15,500 shares, reducing his holdings from 125,977 to 110,477 shares (-12.3% vs pre-transaction holdings). The sale price of $460.99 sits between the current price of $441.31 and the 52-week high of $555.45, placing the transaction at -20.6% from the recent peak. His cross-ticker track record across 7 prior sells shows an average 90d return of +2.1% with a 50.00% well-timed rate, while his prior MSFT sales show mixed outcomes: 3 of 5 were well-timed at the 90-day mark. The stock has recovered +6.5% over 30 days and +8.9% over 90 days since the transaction date, and MSFT fundamentals remain robust with $82.9B revenue and $31.8B net income in the latest quarter, supporting a market cap of $3,278.2B.

EVP HR Coleman sells 1,262 shares of MSFT at $411.34 for $519.2K; holds 45.9K shares post-transaction.

Coleman Amy, EVP and Chief Human Resources Officer, sold 1,262 shares of MSFT on 2026-05-14 at $411.34, reducing her holdings from 47.2K to 45.9K shares. The current price of $423.54 is 23.8% below the 52-week high of $555.45, and her prior sell at this ticker on 2025-05-15 generated a 90-day return of +15.2%. Across her full open-market transaction history across all tickers, prior sells have averaged +5.1% 30-day and +15.2% 90-day returns, with a well-timed rate of 0.00% at the 90-day mark. The transaction represents a -2.7% reduction in her MSFT holdings.

EVP Kathleen T Hogan sells 12,320 MSFT shares for $5.0M at $409.52; retains 137,933 shares post-trade.

Kathleen T Hogan, EVP of Strategy, sold 12,320 shares of Microsoft at $409.52 on 2026-03-06, reducing her holdings by 8.2% to 137,933 shares. The sale occurred at a price -24.5% below the 52-week high of $542.07, and the stock has declined 16.8% over the past 90 days. Her prior five sales at Microsoft showed an average 90-day return of +10.4%, meaning the stock generally rose after her previous sales—a pattern of poorly-timed exits at this ticker, with zero of five prior sales well-timed at the 90-day mark. The current trade occurs as Microsoft trades near recent lows within its 52-week range, but her historical selling pattern at this specific company does not suggest prescient market timing.

Director John W. Stanton purchases 5,000 MSFT shares at $397.35; holdings rise to 83,905 shares

Director John W. Stanton purchased 5,000 shares of MSFT at $397.35 on 2026-02-18, increasing his holdings to 83,905 shares from 78,905 shares pre-transaction. The purchase occurred when the stock was trading 26.3% below its 52-week high of $542.07 and has declined 13.1% over the prior 30 days and 16.5% over 90 days. MSFT reported strong recent fundamentals with $81.3B quarterly revenue, $38.5B net income, and 14.9% annual revenue growth, supporting an evaluation of the purchase context. The director's $1,986,750.00 investment in a modestly sized tranche reflects a selective addition to an already substantial position rather than a major portfolio commitment, with the stock trading at a P/E of 24.88 in a $2,967.3B market-cap company.

MSFT VP Bradford Smith bought 3,842 shares at $377.46, then sold all 3,842 shares at $390.57–$438.82 within 12 days, netting $234,277.

Bradford Smith executed a buy-then-sell cycle: purchasing 3,842 shares on April 23 at $377.46, then liquidating the entire position via 2 separate sales on April 30 and May 5 at higher prices ($390.57 and $438.82 respectively). The dual-sale structure closed the position within a 12-day window with a realized gain of $234,277.36 on the cycle. His prior trades at MSFT show 3 prior measurable same-ticker sales with 90-day outcomes: 0 were well-timed (the stock rose 21.0%, 22.3%, and 22.6% post-sale), indicating a pattern of selling before subsequent gains at this ticker. The current stock price of $478.53 is 11.7% below its 52-week high, yet his April 23 purchase price of $377.46 was near the 52-week low of $354.56—a 12-week timing spread that contextualizes the acquisition within a recovery zone.

MSFT: EVP Numoto sold 2,850 shares at $478.72 on 2025-12-04, reducing stake 4.9% to 55.8K shares post-transaction

Numoto Takeshi, EVP and Chief Marketing Officer, sold 2,850 shares of Microsoft at $478.72 on 2025-12-04, with a post-transaction holding of 55.8K shares. This represents a modest reduction of 4.9% from his pre-transaction position. Examining his prior trades at MSFT, four of his five previous sales showed negative 90-day returns, and his cross-ticker track record of eight prior sales achieved a 75.00% well-timed rate at the 90-day mark. The current price of $483.16 is 10.9% below the 52-week high and down 4.7% over 30 days, suggesting recent downward momentum. However, without a scheduled trading plan flag, this transaction cannot be classified as discretionary timing, and the modest share reduction—retaining 55.8K shares post-trade—indicates this is a moderate adjustment rather than a substantial portfolio shift.

CEO Althoff sold 12,750 MSFT shares ($6.3M) at $491.52 on 2025-12-02; stock now $477.73, down 11.9% from 52-week high.

Judson Althoff, Microsoft's CEO of Commercial, sold 12,750 shares for $6,266,829.00, reducing his holdings by 9.0% to 129,348 shares. The sale occurred at $491.52 per share, 3% above the current price of $477.73, and timing appears favorable relative to recent price action: MSFT has declined 7.6% over 30 days and 6.0% over 90 days from the transaction date. Althoff's cross-ticker track record shows a 28.57% well-timed rate on prior sells, with 90-day average returns of +8.1%, suggesting his open-market sales have historically aligned with subsequent price weakness. His same-ticker history at MSFT across 5 prior transactions shows mixed timing outcomes: two sales were well-timed (negative 90-day returns), while three posted positive returns, indicating inconsistent predictive power at this specific security. The stock remains elevated at a P/E of 33.83 and market cap of $3,550.7B against strong fundamentals (revenue $77.7B, net income $27.7B, annual growth +14.9%), so the sale does not signal distress but rather portfolio management by an executive retaining substantial holdings.

Microsoft Vice Chair Smith sells 38.5K shares for $19,967,707.13; prior MSFT sales poorly timed (0 of 5 well-timed at 90d)

Smith Bradford L, Vice Chair and President of Microsoft, executed 2 separate sales totaling 38,500 shares (38.5K shares) for $19,967,707.13 ($20.0M) on 2025-11-03 at a blended average price of $518.64, reducing holdings from 500,096 shares to 461,596 shares (-7.7% vs pre-transaction holdings). His prior 5 sales at Microsoft on 2025-05-05, 2025-05-02, and 2025-04-30 all produced positive 90-day returns (ranging from +19.4% to +31.2%), indicating he consistently sold before subsequent price appreciation; this pattern of 0 of 5 prior sells being well-timed at the 90-day mark continues his tendency to exit before rallies. The current stock price of $514.33 is -5.1% from the 52-week high of $542.07 and trading within a normal range, with modest 30-day (-0.6%) and 90-day (-2.0%) declines providing no obvious depressed valuation context for this sale.