Oracle Slides After Ellison Scraps Planned $7.5 Billion Sale

Oracle shares fell about 4% on Monday after Larry Ellison abruptly cancelled a prearranged plan to sell as many as 50 million shares, a transaction valued at roughly $7.5 billion at Friday’s closing price. No shares changed hands.

The unusual reversal landed just days after Oracle disclosed the Rule 10b5-1 arrangement in its quarterly filing. Ellison adopted the plan on June 22, and it was scheduled to run through October 24. Oracle said on September 12 that its co-founder, executive chairman and chief technology officer had cancelled the plan and had no other plans to sell Oracle stock. The company gave no reason.

That silence mattered. A planned insider sale of this size would have added a sizable block of potential supply to a stock already under strain, but cancelling it did not erase the market’s broader concern about Oracle’s capital demands. The decision instead became another signal for investors trying to gauge Ellison’s confidence in the company’s valuation and its costly pivot toward AI infrastructure.

Oracle’s latest results show why the stock has become a contest between spectacular demand and heavy financing needs. First-quarter fiscal 2027 revenue rose 30% to $19.3 billion, while cloud revenue climbed 62% to $11.6 billion. Cloud infrastructure revenue more than doubled to $7.4 billion, and remaining performance obligations, a measure of contracted future revenue, reached $664 billion, according to the company.

The buildout is consuming cash at a striking pace. Oracle reported negative free cash flow of $5 billion for the quarter as it added data-center capacity, while its latest filing showed depreciation expense of $3.2 billion, more than double the year-earlier figure. The company also supplemented its restructuring plan by roughly $700 million after August 31, taking expected costs for the program to about $2.8 billion.

Oracle has been cutting costs while expanding aggressively, a combination that leaves shareholders focused on execution rather than demand alone. The backlog promises future revenue, but converting those contracts into profitable cash flow requires servers, power, leases and financing first.

Ellison’s cancelled sale removes one overhang. It does not resolve the balance-sheet debate. For ORCL investors, the next test is whether Oracle can turn its AI order book into operating cash before the infrastructure bill catches up with growth.