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Oracle Corp. shares tumbled 6.5% on Monday to their lowest level in 14 months as a fresh escalation between the U.S. and Iran rattled markets in the U.S. and around the world.
Shares edged slightly higher in overnight trading, but the move sparked a wave of commentary on Stocktwits, reigniting the debate over a company that has drifted into risky territory and an increasingly negative sentiment.
Oracle is in a unique position. It has one of the largest remaining performance obligations (RPO) backlogs in the tech industry but is also piling on debt at a rapid pace to build the capacity needed to fulfill those orders.
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Oracle’s future order book is based on business from a handful of companies, chiefly OpenAI, which itself is on shaky footing. Investors are erring on the side of caution in this risk-reward equation, with ORCL shares falling 47% since the start of June.

On Monday, ORCL shares fell below the crucial $134 level that had offered support to the stock this year. By evening, the ticker was trending at the top on Stocktwits, with message volume surging over 2,300% in the last 24 hours.
“$ORCL Oracle is now trading below where it was before landing the OpenAI deal. Wall Street is repricing a $300+ billion OpenAI contract as a liability instead of an asset. In this game, retail investors are the ones absorbing the losses,” a trader wrote.
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OpenAI and Oracle signed a $300 billion, five-year cloud computing contract last September. Beginning in 2027, Oracle will supply OpenAI with the computing power needed to train and run its frontier AI models.
“The market sees the opportunity, but the concern is execution,” said a trader. “Oracle has one of the largest AI backlogs in the industry. The challenge: turning contracts into revenue while funding massive AI infrastructure. $55B+ invested in AI data centers has pressured free cash flow, with more capital needed for expansion.”
The overall sentiment reading for ORCL climbed to ‘extremely bullish’ from ‘bullish’ the previous day, a shift that often follows steep declines in a stock.
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Last month, Oracle reported fourth-quarter results that beat expectations and said its backlog surged 363% to a record $638 billion. But it also forecasts up to $95 billion in capital expenditure for fiscal 2027, following $55.7 billion in spending last fiscal.
To achieve that, Oracle said it would raise $40 billion in debt and equity this fiscal year. In the fiscal year just ended, Oracle raised $43 billion in debt financing and $5 billion in equity.
While raising debt to fund expansion isn’t inherently a negative, Oracle’s reliance on OpenAI and the AI startup’s weakening position have raised concerns around the ORCL investment case.
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Anthropic is now valued above OpenAI and is also reported to have a higher annualized revenue run rate. With reports that OpenAI has pushed its IPO to next year, coupled with Apple’s lawsuit alleging trade secret theft, concerns around the AI startup’s business have intensified in recent months.
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