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Agnes Heftberger, Managing Director of Microsoft Germany, speaks on stage during the Microsoft AI Tour picture alliance/Getty Images

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

Microsoft just saw its worst quarter on Wall Street in nearly two decades — and investors are paying attention. The tech giant’s stock dropped 23% in the first three months of 2026, the steepest fall since the 2008 financial crisis. For context, the Nasdaq fell just 7% during the same three-month period.

Microsoft, long considered a fairly safe bet by investors, is suddenly looking a lot more risky. Experts say the causes are complex, but may stem from questions about whether Microsoft’s AI investments will pay off.

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“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).

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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).

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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).

He expects the company’s earnings to be strong enough to recommend buying shares. Other experts are more cautious, citing uncertainty around AI returns and rising competition.

So what does all this mean for investors? It depends on your risk profile. If you’re holding Microsoft stock, the case for staying put is reasonable — but so is trimming your position if your tech exposure feels too high. What’s less advisable is making a reactive move to sell based on data from a single quarter.

As with any contraction in any category, there could be a case for buying during the dip. While the market remains volatile, an eventual rebound could earn significant returns — if it happens.

For investors who’d rather not bet on any single company navigating an AI transition, broad-market index funds offer a steadier path. They won’t capture all the upside if Microsoft rebounds sharply, but they also won’t leave you overexposed to a sector that’s still sorting out the impact of AI.

Article Sources

We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.

CNBC (1); The Register (2); Windows Latest (3); Microsoft (4); CNBC (5); CNBC (6); Indian Express (7); Forbes (8)

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Danielle Antosz Contributor

Danielle is a personal finance writer based in Ohio. Her work has appeared in numerous publications including Motley Fool and Business Insider. She believes financial literacy key to helping people build a life they love.

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