Shares of Oracle are on track for their steepest quarterly decline in more than two decades, as investors question whether the company’s aggressive push into artificial intelligence infrastructure is financially sustainable under its newly appointed leadership.
Oracle stock has fallen about 30 per cent so far this quarter, placing it on pace for its worst performance since the third quarter of 2001, when shares slid nearly 34 per cent during the dot-com bust. The decline comes just three months after Clay Magouyrk and Mike Sicilia were named co-chief executives, marking a turbulent start to their tenure.
Investor sentiment has weakened amid growing skepticism over Oracle’s ability to scale its cloud infrastructure fast enough to support its expanding commitments to OpenAI, the developer behind ChatGPT. In September, Oracle disclosed that OpenAI had agreed to spend more than $300 billion on Oracle infrastructure over time, a deal that initially fueled optimism around the company’s long-term growth prospects.
That enthusiasm has since faded. Earlier this month, Oracle reported weaker-than-expected quarterly revenue and free cash flow, adding pressure to a stock already facing questions about capital intensity. During the earnings call, newly appointed finance chief Doug Kehring outlined plans for $50 billion in capital expenditures in fiscal 2026, a 43 per cent increase from projections made in September and roughly double the level from a year earlier.
In addition to direct spending on data centres, Oracle is planning $248 billion in long-term leases to expand cloud capacity. Analysts say such an expansion will require substantial borrowing. In September, Oracle raised $18 billion through a jumbo bond sale, one of the largest debt issuances ever by a technology company.
While management has pledged to preserve Oracle’s investment-grade credit rating, market indicators suggest rising concern. Prices of Oracle’s credit default swaps have climbed, reflecting investor anxiety about whether the company can absorb its mounting obligations without straining its balance sheet.
Analysts at D.A. Davidson warned earlier this month that Oracle’s financial flexibility could be tested. In a note dated December 12, the firm said it was concerned about Oracle’s ability to meet its commitments without potentially restructuring its OpenAI agreement, citing the company’s already narrow margin above investment-grade status. Oracle declined to comment.
The stock’s reversal marks a sharp contrast from September, when shares surged nearly 36 per cent following news of the OpenAI deal, reaching an intraday record of $345.72. Since then, the stock has lost more than 40 per cent of its value, closing this week below $200. Shares briefly rebounded last week after reports that TikTok had agreed to sell part of its U.S. operations to Oracle and other investors, extending a cloud services relationship that has existed for years.
Some long-term investors remain supportive despite the volatility. Zachary Lountzis, vice president at Lountzis Asset Management, said the recent decline represents a healthy correction following excessive optimism. He said his firm continues to hold Oracle shares, citing confidence in founder Larry Ellison, who remains deeply involved in the company’s strategic direction.
However, others are less convinced. Analysts and investors point out that Oracle’s AI-driven expansion could come at the expense of profitability. The company’s core software business has historically delivered high margins, but large-scale infrastructure investments typically generate lower returns in the early years. Oracle’s gross margin stood at 77 per cent in fiscal 2021, but analysts surveyed by FactSet expect it to fall to around 49 per cent by 2030, with cumulative negative free cash flow projected over the next several years.
Concerns are also emerging around Oracle’s dependence on OpenAI, which continues to burn cash as it invests heavily in global AI infrastructure. Some investors question whether demand from OpenAI will remain strong enough to justify Oracle’s massive capital commitments over the long term.
Despite the risks, some analysts remain optimistic. Earlier this month, Wells Fargo initiated coverage on Oracle with the equivalent of a buy rating and a $280 price target, arguing that successful execution of the OpenAI build-out could significantly reshape market perception. According to Wells Fargo estimates, OpenAI could account for more than one-third of Oracle’s revenue by 2029 if expansion plans proceed as expected.
Oracle’s broader challenge remains competition in cloud infrastructure, where it continues to trail industry leaders Amazon, Microsoft, and Google. While Oracle counts high-profile customers such as Meta, Uber and xAI, several major data platforms, including Databricks and Snowflake, have yet to adopt Oracle’s cloud.
Market watchers say Oracle’s credibility in the AI era will ultimately depend on execution. If the company delivers on its promised infrastructure scale and reliability, analysts believe customers and investors may reassess its position in the cloud market. Until then, Oracle’s stock is likely to remain sensitive to concerns over debt, profitability and the pace of AI-driven growth.
