Microsoft Stock Heads for Worst Stretch Since 2009 as OpenAI, Copilot Worries Deepen

Microsoft Stock Heads for Worst Stretch Since 2009 as OpenAI, Copilot Worries Deepen

NEW YORK, March 27, 2026, 10:43 EDT

Microsoft slid another 2.1% to $358.38 in early New York trading on Friday, pushing the shares nearly 34% under their October 2025 high of $542.07. That’s put the company on track for its roughest six-month run since 2009, as investors question whether all that AI outlay—and Microsoft’s heavy OpenAI exposure—will deliver returns soon enough.

This isn’t just about Microsoft. The company’s been a flagship AI play for Wall Street, and its drop is forcing investors to reconsider whether Big Tech’s heavy outlays on chips and data centers will keep pulling ahead of profits—especially now that the Nasdaq has slipped into correction. “The market is questioning whether ‘massive capital expenditure hikes will generate sufficient returns,’” said Jesse Cohen, senior analyst at Investing.com. Reuters

New concerns have cropped up over the past few days. The Information said Microsoft has instructed managers across certain cloud and North America sales divisions to put hiring on hold. And according to CNBC, OpenAI flagged to investors that its dependence on Microsoft might represent a business risk, though Reuters was unable to confirm that report right away.

Questions keep running up against solid numbers, though the results haven’t checked every box for investors hungry for concrete proof. Microsoft’s latest quarter showed $81.3 billion in revenue, with Azure up 39%. Cash out the door for property and equipment—$29.9 billion. Total capital expenditures? $37.5 billion, covering data centers, chips, and related infrastructure. The company’s commercial remaining performance obligation climbed to $625 billion, with roughly 45% of that linked to OpenAI.

Copilot just won’t leave the conversation. Back in January, Microsoft noted that Microsoft 365 Copilot—priced at $30 per month for business customers—had picked up 15 million paid seats. But J.P. Gownder, vice president and principal analyst at Forrester, didn’t sound impressed, labeling that figure “disappointing uptake” when stacked against Microsoft’s commercial Microsoft 365 base of 450 million users. Microsoft

Sentiment is shifting, and the division is obvious. UBS lowered its price target to $510 from $600, Barron’s noted this week, citing sluggish Copilot uptake in both Asia and the US after investor meetings. Still, Bank of America jumped back in, reinstating coverage and slapping a Buy on the stock, target set at $500—proof some are sticking to their AI optimism.

Microsoft is scrambling to catch up. The company folded its commercial and consumer Copilot teams together this month, looking to pick up the pace as Google’s Gemini and Anthropic’s Claude Cowork chip away at its lead. Chief Executive Satya Nadella calls this the “beginning phases of AI diffusion,” and he claims Microsoft’s AI business already tops the size of some of its biggest franchises. Reuters

The downside’s right there: Copilot conversions might not pick up, and OpenAI keeps branching out. Microsoft is considering legal action over OpenAI’s $50 billion arrangement with Amazon, the Financial Times has reported, and fresh cloud partnerships aren’t helping clarity. If the tech slide keeps going, Microsoft could find itself squeezed — higher AI costs coming in, but patience for returns is wearing thin. Investors have already signaled less appetite for open-ended AI bets.

Khadija Saeed

Khadija Saeed is a financial markets reporter at TS2.tech. Her coverage ranges from stocks and technology to emerging industries and developments across global markets. She studied economics and finance at the London School of Economics and worked in market research before becoming a financial journalist. Follow Khadija Saeed on Google News.

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