The AI boom is forcing some of technology's biggest cash machines to behave more like utilities. On July 22, Reuters reported that Microsoft Corporation (NASDAQ:MSFT), Oracle Corporation (NYSE:ORCL), and three other hyperscalers are expected to spend more on capital expenditures than they generate in combined free cash flow by 2027. From 2025 through 2027, their annual operating cash flow is projected to rise by $340 billion, versus a $534 billion increase in capex. Microsoft and Oracle, however, are not carrying the same risk.
Microsoft showed the squeeze in fiscal Q2. Operating cash flow was $35.8 billion, while capex including finance leases reached $37.5 billion. That does not mean the company burned cash: Microsoft reported $5.9 billion of conventional free cash flow because that measure deducts cash property and equipment purchases, not newly originated finance leases.
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Fiscal Q3, however, was stronger. Operating cash flow rose to $46.7 billion and free cash flow reached $15.8 billion, even after $30.9 billion of cash property and equipment spending. Its AI business also passed a $37 billion annual revenue run rate. Microsoft can finance the buildout. The question is whether Azure and Copilot can generate nice returns before expensive GPUs depreciate or become obsolete.
Oracle has a more immediate cash problem. In fiscal 2026, it spent $55.7 billion on capex against $32 billion of operating cash flow, leaving free cash flow at negative $23.7 billion. Demand is real: cloud revenue grew 39% to $34 billion, and remaining performance obligations reached $638 billion. But backlog is not cash. Oracle must construct capacity before much of that revenue arrives, and plans to raise $45 billion to $50 billion through debt and equity.
Insider Monkey's Q1 database counted 282 hedge funds holding Microsoft and 115 holding Oracle, which shows AI spending has not driven away institutional longs. More recent short data are more discriminating, though. By June 30, Microsoft short interest had fallen 6.4% to 1.20% of float, while Oracle's had risen 11.4% to 2.47%. Neither stock is heavily shorted, but bears have become more willing to challenge Oracle.
Microsoft must prove it can preserve software-like returns while building physical infrastructure. Oracle must also prove it can finance that infrastructure without allowing interest costs and dilution to consume the economics. Microsoft faces a return-on-capital test. Oracle faces that test plus a balance-sheet test.
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