Oracle's stock suffers worst eight-day stretch in over two decades. Here's why.

By Christine Ji

Hammered by the general software selloff and AI debt concerns, shares of Oracle have shed 25% over eight trading sessions

Oracle issued $25 billion of corporate bonds on Monday as part of its 2026 financing plan.

As the technology selloff deepens, Oracle's stock has been hit by a double whammy of generalized software concerns and jitters around the company's own artificial-intelligence spending.

The threat of new AI tools replacing traditional enterprise software is rippling across Oracle's (ORCL) legacy database business. And as the company aims to transform into an AI cloud business similar to what Microsoft (MSFT), Amazon.com (AMZN) and Alphabet (GOOG) (GOOGL) operate, investors are scrutinizing Oracle's rising debt levels and close relationship to OpenAI.

As a result, Oracle's stock is being punished severely. Thursday marked the eighth consecutive day of losses for shares of Oracle. The stock has shed 25.19% over that stretch, to close Thursday's session at $136.48.

It's been the worst eight-day stretch for Oracle's stock since May 2002, when it fell 25.20%, according to Dow Jones Market Data.

Software stocks could have more room to fall before they bottom out, according to Evercore ISI analyst Kirk Materne, who described the selloff as "unrelenting" in a Thursday note. There's "no relief in sight for software right now as the negative price action persists," he wrote. The iShares Expanded Tech-Software Sector ETF IGV has shed 19.4% over the past eight trading sessions to log its longest losing streak since May 6, 2021, and its worst performance over an eight-day stretch since March 16, 2020, when it dropped 23.6%.

See more: Software ate the world. Now, Wall Street is worried AI will eat software.

Oracle's stock has also been dragged down for months over concerns about the company's rising debt levels as it focuses on building data centers to support its Oracle Cloud Infrastructure division. The stock has fallen 60% from its September peak, which came around the time Oracle announced a $300 billion cloud deal with OpenAI.

On Sunday, the company shared its 2026 funding plan to raise up to $50 billion to meet contracted demand from key cloud customers through a combination of debt and equity. The company also reiterated its commitment to maintaining an investment-grade credit rating.

While the funding plan removed what Deutsche Bank's Brad Zelnick called the "monkey off the back" for Oracle, it hasn't appeased skeptical investors. Questions remain about whether OpenAI will be able to monetize and uphold its cloud commitments and, consequently, if Oracle can convert its future deal pipeline into revenue.

See more: Nvidia and Oracle are flashing similar warning signs about the AI trade

Following Sunday's announcement, Oracle completed a $25 billion bond offering on Monday. The company had previously sold $18 billion of bonds to fund its AI buildout in September. Oracle plans to fund the remainder of the $50 billion through equity issuances.

Credit spreads on Oracle's existing bonds tightened by roughly 30 basis points after Monday's issuance, as bondholders found relief in the company's promise for just a single issuance in 2026, according to data from BondCliQ. However, spreads widened slightly in the following days.

Oracle's latest bond issuance comes as banks are already trying to sell $56 billion in project financing loans associated with Oracle data centers, according to a report from the Financial Times. As a result, banks that are becoming overexposed to Oracle are turning to insurance companies and private credit funds to find buyers for the debt.

-Christine Ji

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02-05-26 1648ET