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Oracle's AI-fueled debt load has investors on edge ahead of quarterly earnings

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It's been a rollercoaster year for Oracle investors, as they try to assess the strength of the software giant's position in the artificial intelligence boom.

The stock is up more than 30% for the year even after a 23% plunge in October, which was its worst month since 2001. It's recovered a bit in November, climbing almost 10% for the month as of Tuesday.

Heading into the company's fiscal second-quarter earnings report on Wednesday, pressure is building on management — and newly installed CEOs Clay Magouyrk and Mike Sicilia — to show that Oracle can continue to finance the company's aggressive infrastructure plans while simultaneously convincing Wall Street that the AI-fueled hypergrowth story remains intact.

In recent months, Oracle has emerged as a more central player in AI, largely due to a $300 billion deal with OpenAI, which came to light in September, an agreement that involves the AI startup buying computing power over about five years, starting in 2027.

Funding Oracle's compute buildout is going to require mounds of debt. In late September, Oracle raised $18 billion in a jumbo bond sale, one of the largest debt issuances on record in the tech industry, and the company is now the biggest issuer of investment grade debt among non-financial firms, according to Citi.

"There is something inherently uncomfortable as a credit investor about the transformation of the sort we're facing that is going to require an enormous amount of capital," Daniel Sorid, head of U.S. investment grade credit strategy at Citi, said on a video call to investors on Friday, a replay of which was provided to reporters.