Oracle caps new financing at $20B as AI spending tests cash flow

On October 28, 2026, Oracle set a $20 billion cap on new borrowing through fiscal 2030, split between $10 billion in equity and $10 billion in gross debt, excluding refinancing and in addition to a $20 billion share sale completed earlier in fiscal 2027. At its Las Vegas investor day, Oracle sought to ease concerns about its AI buildout, with CFO Hilary Maxson saying free cash flow should turn positive in the second half of fiscal 2028, and Oracle projecting at least $30 billion in cash flow in fiscal 2029. Oracle reported negative free cash flow of $23.7 billion in fiscal 2026 and $125.34 billion in borrowings as of August 31, 2026; shares rose more than 12% that day.