Microsoft just had its worst quarter on Wall Street in nearly two decades — the steepest fall since the Great Recession

“There is concern that the Microsoft 365 Copilot business has not lived up to quite their expectations, and that’s an area that could see new competitors,” Kyle Levins, an analyst at Harding Loevner, which held $219 million in Microsoft shares as of December 2025, told CNBC (1).

What is causing Microsoft’s downturn?

Microsoft has heavily invested in building out AI infrastructure, betting that demand for cloud computing and AI tools will justify the costs. But so far, they aren’t seeing the payoffs some experts expected.

At the center of the concern is Copilot, the AI assistant Microsoft baked into its Office 365 suite. Despite significant fanfare, adoption has been slow. Just 3% of Copilot users pay for it (2). Microsoft claims just 1% of the AI market, compared to ChatGPT’s 65% share and Gemini’s 22% (3).

Despite those flagging numbers, Microsoft is doubling down on AI. The company just announced a $5.5-billion investment in cloud and AI infrastructure in Singapore by the end of 2029 (4).

On the personnel side, the company has seen a string of high-profile departures, including the retirement of gaming chief Phil Spencer (5) and top productivity leader Rajesh Jha (6). Mustafa Suleyman, the DeepMind co-founder who had been leading Copilot’s consumer development, was also reassigned (7).

Analyst Ben Reitzes of Melius Research summed it up bluntly: “Redmond [Microsoft’s headquarters] is in a pickle” (1).

What this means for investors

It’s worth noting that Microsoft isn’t the only tech name taking a beating. A broader sell-off in software-as-a-service (SaaS) stocks, dubbed the “SaaSpocalypse” by some, has dragged major players like Adobe, Atlassian, and ServiceNow down more than 30% this year.

The concern is that traditional software-as-a-service businesses are losing ground to AI-based alternatives. And yet, semiconductor stocks, a key indicator of the demand for AI hardware, have also been volatile due to concerns that the new tech might not deliver the expected returns.

This paradox — that AI appears to be powerful enough to tank entire software companies, but not strong enough to generate returns — is “internally inconsistent,” according to Bank of America senior analyst Vivek Arya (8).

For investors holding tech-heavy portfolios, this shift is worth paying attention to — but there is no clear direction as of yet.

Despite falling stock prices, Microsoft still posted 17% cloud revenue growth in its most recent quarter (4). That disconnect between Microsoft’s strong fundamental performance and its flagging stock price is “the biggest it’s been in decades,” said Gil Luria, an analyst at DA Davidson (1).