On Monday, November 10, Microsoft (NASDAQ: MSFT ) stock saw its first insider trade in approximately a month.
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Specifically, a filing with the Securities and Exchange Commission (SEC) made on Tuesday revealed that Executive Vice President (EVP) and Chief Financial Officer (CFO) Amy Hood dumped 7,305 MSFT shares at an average price of $544.37 for just under $4 million.
Notably, Microsoft’s CFO is responsible for three of the four most recent trades. Hood also sold 7,305 MSFT on October 13 at a slightly higher $545.42 and dumped 41,674 shares on September 14 for over $20.76 million.
The CEO and EVP has made no other such insider trades since the start of 2026. Lastly, the only notable sale since early September was made by Microsoft’s Chief Executive Officer (CEO) Satya Nadella, who offloaded 86,525 MSFT shares, making more than $43 million.
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Microsoft stock price performance in 2026
Meanwhile, Microsoft stock itself has continued its relatively strong run – especially compared to early 2026 – despite the latest turmoil. While the equity declined 1.99% in the last week and 1.48% in the last month, its latest closing price of $533.16 is, nonetheless, 12.72% higher than the $472.94 recorded on the evening of January 2.
Still, the blue-chip technology giant could face strong bearish pressure later in November. Specifically, Anthropic , the other major artificial intelligence ( AI ) lab, is planning to conduct its initial public offering ( IPO ) at the end of next week in an event that could trigger significant volatility for big tech.
Indeed, the company already triggered a 3% intraday selloff for MSFT on Tuesday, November 10, when it announced its own Sheets , Whiteboards , and Interactive Connectors – arguably a release directly competing with Microsoft.
Why Anthropic IPO could be a bearish catalyst for Microsoft stock
Zooming out, the IPO itself could prove a far greater risk to the entire sector. Specifically, while Anthropic aiming for an approximately $1.5 trillion valuation and the fact it decided to – despite the recent turmoil – go public both appear to be bullish signals, there are multiple concerning elements to the project.
Perhaps the biggest of these is the unorthodox unlock schedule , which led more skeptical observers to conclude the offering is designed to supply senior personnel with ‘exit liquidity’ ahead of the AI bubble bursting and amidst an apparent drought in the private markets.
Anthropic’s biggest competitor, OpenAI, for example, secured $11 billion at a $1.25 trillion valuation in November while its initial goal was a far larger $30 billion at $1.4 trillion .
The second, though far more tangential point of concern was a bout of confusion when the AI lab first sent out and then retracted an update on the details of the IPO.
Lastly, Anthropic’s initial public offering could easily prove a bearish catalyst for Microsoft stock, whether it is a raging success or a failure.
The former would, arguably, further tilt the balance away from OpenAI, of which the blue-chip technology giant is a prominent and early backer. Still, it would probably be only a temporary sell-off since the company also has a large, if less-known, stake in Anthropic.
The latter could, more dangerously, further degrade the reputation of artificial intelligence and increase the odds of the AI bubble bursting.
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