Oracle looks set to burn many more billions in cash at least into the first half of fiscal 2028. That is the less reassuring implication of Reuters' headline that Oracle expects cash flow to turn positive in the second half of that fiscal year, even though the market liked the news. x.com 

The debt behind Oracle's capex is drawing credit-market concern. Its five-year credit-default swap spread has risen past 300 basis points. x.com 

Oracle's $664B contracted backlog justifies holding the stock, but position size should reflect funding risk. Capex was 161% of operating cash flow over the last four quarters, and debt plus leases total about $457B; only about 13% of RPO is expected to become revenue in the next year. Delivery timing, grid approvals and possible further equity issuance matter more than a shortage of demand. x.com 

Oracle is being repriced from a high-margin, low-capex software firm into a capital-heavy cloud infrastructure builder, and the market doubts shareholders will capture the profits. Q4 revenue of $19.18 billion, EPS of $2.11 versus $1.96 expected and $638 billion of RPO all beat, yet shares fell on plans to raise nearly $40 billion of debt and equity in FY2027, including a $20 billion ATM. Mid-chain, Oracle pays Nvidia and Broadcom first while bearing financing and execution risk. x.com 

Oracle's big rally on its RPO jump was fake, and the only data since show OpenAI writing checks its business can't cash. The pop came on an earnings miss and took 57 days to undo; the stock then fell another 46% and has dropped after every report since. Within two weeks, a force majeure dismissed as a nothing burger gave way to word that its cash-incinerating key customer has $20B less revenue than due diligence assumed. Shorting in size is still hard. x.com  x.com  x.com 

Oracle's plan to fund its AI buildout from cash flow makes last week's financing fears look completely overdone. It expects capex to peak in FY27-28, free cash flow to turn positive in H2 FY28 and top $30B in FY29, funding growth from then. Oracle plans at most $20B in further capital raises through FY30, excluding refinancing, after an already completed $20B equity raise. Vendor financing, customer prepayments and customer-supplied hardware should reduce upfront cash needs. x.com  x.com 

Oracle's problem is structural, not just debt: it is building hyperscaler infrastructure without hyperscaler economics. It lacks a full stack and a pricing moat, carries $130B of debt and has -$24B of free cash flow, and a subcontractor does not earn AWS-like margins. That is behind its worst week since the 2001 dot-com bust, per a report by Jordan Novet. x.com 

Oracle's growth is being funded at a staggering cost, making it one to stay away from into Thursday's earnings. FY2026 growth was impressive: revenue $67.4B (+17%), cloud infrastructure $18.1B (+77%), operating cash flow $32B (+54%) and a $638B backlog of remaining performance obligations. But $130B of debt, $27B of lease liabilities, huge data-centre commitments and rising capex left free cash flow at -$23.7B and worsening fast. Not a disaster; the test is capex and backlog turning into cash. … Show more

Oracle looks mispriced because $11 of current consolidated earnings power puts it at 11x earnings without a breakup. It trades below its software business's value despite the highest gross retention in software; separating pre-AI OCI, AI operations and AI development makes it an obvious long. Future funding will cost more, but current leverage is no issue and all contracts are well below spot, leaving nowhere near neocloud risk. Fundamentals may not matter during panics. x.com  x.com  x.com 

Oracle's reliance on OpenAI makes its backlog vulnerable. About $250B of backlog comes from OpenAI, which is not making money; that risk is no longer in Oracle's hands, and the stock is very likely to fall further. x.com  x.com