A Hedge Fund Giant Goes All-In on Microsoft’s Autonomous AI Play While Security Woes Linger

Two vastly different investment stories are playing out simultaneously at Microsoft. The Bill & Melinda Gates Foundation has quietly exited its entire stake in the software giant after a quarter-century, while billionaire hedge fund manager Bill Ackman has piled into the stock with a $2.3 billion bet. The conflicting signals reflect a company caught between long-term ambition and short-term headaches.

Ackman’s Pershing Square acquired 5.6 million shares, building the position since February after a post-earnings dip. He points to an attractive price tag: the forward price-to-earnings ratio sits well below Microsoft’s historical average. He also sees hidden value in the company’s 27% stake in OpenAI, which he values at around $200 billion — a figure not fully captured in Microsoft’s current market capitalization.

The Gates Foundation’s departure is purely strategic. It sold its remaining 7.7 million shares in the first quarter of 2026, netting roughly $3.2 billion. The organization needs the cash to fund nearly $9 billion in annual grants, with a plan to exhaust its endowment by 2045. Notably, Bill Gates himself still holds about 103 million Microsoft shares outside the foundation, so the sale is no vote of no confidence.

At the heart of Ackman’s thesis is Microsoft’s accelerating AI business. The company’s artificial intelligence revenue has reached an annualized run rate of $37 billion, up 123% year over year. Cloud unit Azure grew 40% in the same period. To keep up with demand, management has earmarked nearly $190 billion in infrastructure spending for the current fiscal year.

Should investors sell immediately? Or is it worth buying Microsoft?

On the technical front, Microsoft is laying the groundwork for autonomous AI systems. It recently announced the preview of Azure Linux 4.0, an operating system designed to underpin so-called agentic AI — programs that operate independently and handle complex tasks. The company also made Azure Container Linux generally available. Brendan Burns, who heads Microsoft’s cloud unit, unveiled a vision for an open stack for AI agents, including the new Microsoft Agent Framework that lets developers build and orchestrate multi-agent systems.

Yet the present is less rosy. Security experts are warning about a critical vulnerability in Microsoft Exchange that attackers are already exploiting; customers must urgently apply an emergency patch. Meanwhile, the latest Windows 11 security update is failing on some systems, forcing users to rely on a rollback function. On a brighter note, Microsoft Edge now stores passwords in encrypted memory at startup, making data theft significantly harder.

Investors are eyeing the Microsoft Build developer conference in San Francisco starting in early June. The management team is expected to reveal more details on how the new open-source tools will integrate into Azure. A seamless tie-in could cement Microsoft’s position in the market for autonomous AI.

Short term, shareholders have a concrete date on the calendar: May 21, when the stock trades ex-dividend. The quarterly payout is $0.91 per share. Microsoft’s shares were trading around €361, down roughly 10% year to date and far below the 52-week high of over €467. The 200-day moving average of €396 also sits well above the current level, underscoring the gap between operational momentum and market sentiment.