Oracle has endured its worst week on Wall Street in a quarter century, following growing investor unease over the software giant’s aggressive borrowing to finance its artificial intelligence ambitions, which raises fresh questions about whether one of the industry’s largest infrastructure bets will generate sufficient returns.

The company’s shares plunged 19% during the week, extending losses in each of the past five trading sessions. The decline marks Oracle’s steepest weekly fall since August 2001, when its stock tumbled 20% during the collapse of the dot-com bubble.

The selloff has erased much of the optimism that surrounded Oracle’s emergence as a major AI infrastructure player. After reaching a market capitalization of about $900 billion in September on expectations that it would become a key supplier of cloud infrastructure for AI developers, the company has now lost roughly 55% of its market value over the past nine months.

At the center of investors’ concerns is Oracle’s rapidly expanding debt burden, which has ballooned as the company races to build AI data centers and fulfill massive cloud commitments, particularly for OpenAI. Unlike larger cloud rivals such as Amazon, Microsoft, and Google, Oracle lacks the broad consumer and enterprise technology ecosystem that allows competitors to spread infrastructure costs across multiple high-margin businesses.

Oracle ended May with approximately $130 billion in debt, while capital expenditures surged 162% year-over-year to nearly $56 billion during fiscal 2026. The spending reflects an unprecedented expansion of the company’s cloud infrastructure as demand for AI computing accelerates worldwide.

The financial strain is becoming increasingly evident in Oracle’s cash flow. The company reported negative free cash flow of nearly $24 billion in its latest fiscal year, highlighting the enormous capital required to compete in the AI infrastructure race.

Rather than slowing investment, Oracle is doubling down.

Earlier this month, the company disclosed plans to raise an additional $40 billion during fiscal 2027 through a combination of debt and equity financing. That fundraising includes a previously announced $20 billion share offering, following $43 billion in debt issuance and $5 billion in equity financing completed during the previous fiscal year.

The scale of Oracle’s financing requirements has become the dominant issue for investors evaluating the company’s AI strategy.

Evercore analysts, who continue to recommend buying Oracle shares, acknowledged that financing concerns are now overshadowing the company’s strong demand outlook.

“We expect financing/leverage and the pace of equity issuance to remain the central investor debate near term, even as demand signals stay strong,” the brokerage said in a research note.

Despite the sharp decline in Oracle’s stock price, Wall Street remains largely optimistic about the company’s long-term prospects. According to FactSet, 71% of analysts currently rate Oracle a Buy, the highest proportion in roughly 15 years, underpinning confidence that AI-related demand will eventually justify the company’s enormous capital investments.

Still, Oracle faces several simultaneous challenges.

Beyond concerns over leverage, the broader software sector has come under pressure as investors worry that generative AI models could replace or diminish demand for many traditional software applications. The iShares Expanded Tech-Software Sector ETF (IGV) has fallen 16% this year, while Oracle has declined 24%, underperforming even the broader software industry.

The company is also reshaping its workforce as it redirects resources toward AI infrastructure. In its annual report released last week, Oracle disclosed that total headcount fell 13% to 141,000 employees during fiscal 2026, equivalent to about 21,000 job cuts. The reductions were notable across sales and marketing functions, pointing to broader restructuring efforts as Oracle prioritizes engineering, cloud infrastructure, and AI-related investments.

Leadership changes have also drawn attention.

Oracle co-founder and Chairman Larry Ellison, who has traditionally played a prominent role during earnings presentations, was absent from this month’s earnings call. Instead, newly appointed finance chief Hilary Maxson joined dual CEOs Clay Magouyrk and Mike Sicilia in addressing analysts’ questions.

Acknowledging the scrutiny surrounding Oracle’s finances, Magouyrk remarked during the call: “Hilary has a tough life.”

The decline in Oracle’s share price has also affected Ellison personally. Once among the world’s wealthiest individuals, he has recently been overtaken in global wealth rankings by Larry Page, Sergey Brin, Jeff Bezos, and Michael Dell, although his net worth still exceeds $200 billion.

Even as investors question the company’s financing strategy, Oracle has shown no indication that it intends to slow its expansion. The company continues developing major AI data center projects across Michigan, New Mexico, and Texas, with facilities expected to come online during 2027.

Management insists that rapid expansion and financial discipline can coexist.

“As we pursue these opportunities, we’ll remain focused on disciplined capital allocation, maintaining a strong balance sheet, and preserving our investment-grade credit rating,” Maxson said during the earnings call.

The coming quarters are likely to determine whether Oracle’s strategy proves visionary or overly ambitious. Analysts note that if demand for AI computing continues to accelerate and large customers generate sustained cloud revenue, Oracle’s heavy investments could position it as a formidable challenger to established hyperscalers.

Airwallex, the global payments platform founded in Australia but now operating from hubs in San Francisco and Singapore, has secured $320 million in a Series H funding round that values the company at $11 billion, a sharp 38% increase from just six months ago, as it aggressively bets on artificial intelligence to redefine how businesses handle money across borders.

The round, led by New York-based venture capital firm Addition, drew participation from a blue-chip group of investors including Baillie Gifford, Hummingbird, QED Investors, T. Rowe Price, Washington University in St. Louis, and Amex Ventures. It comes as Airwallex reports strong momentum: annualized revenue jumped 74% year-over-year to $1.3 billion as of March, while annualized transaction volume more than doubled. Notably, over 90% of its revenue now comes from customers using multiple Airwallex products, indicating deepening integration into clients’ financial operations.

The fresh capital will fuel three priorities: accelerating development in autonomous finance and agentic commerce, expanding its regulatory footprint into new markets, and scaling teams working on next-generation AI-native financial software.

The company already holds more than 85 licenses across North America, Europe, the Middle East, and Asia-Pacific, a significant moat that positions it to support the emerging “agentic economy” where AI systems handle payments and financial decisions with minimal human intervention.

“The licenses, local network integrations, and settlement rails we spent ten years constructing are precisely the kind of infrastructure it needs,” co-founder and CEO Jack Zhang said in a statement. “This new capital lets us move faster into Airwallex’s next chapter.”

Alongside the funding, Airwallex unveiled two new AI-focused products. T:0 is an AI-native platform designed to automate corporate finance functions such as bookkeeping, tax, compliance, and reporting. Currently in private beta, it could roll out more broadly in the coming weeks. Airi, meanwhile, is an agentic consumer wallet that will eventually support delegated agent payments, spending limits, permission controls, and multi-currency balances.

From Payments Infrastructure to AI-Powered Financial Operating System

Airwallex has evolved far beyond its origins as a cross-border payments provider for businesses like McLaren, Qantas, Canva, and Shein. The latest funding and product launches reflect a deliberate shift toward becoming a comprehensive financial operating system powered by AI. In an environment where companies are racing to automate financial workflows, Airwallex is taking a position at the intersection of payments, compliance, and intelligence.

This strategy appears to be paying off commercially. The surge in multi-product usage suggests customers are increasingly embedding Airwallex into core operations rather than treating it as a standalone payments tool. That stickiness could prove crucial as competition intensifies from both traditional fintech players and big tech entrants moving into financial services.

Zhang recently told the Australian Financial Review that the new financing might allow the company to delay a public listing, noting that heavy investment in AI has made margins “too volatile to go public” for now. The decision to stay private gives Airwallex flexibility to double down on long-term bets without the quarterly pressures of public markets.

The funding success comes against a backdrop of growing questions about Airwallex’s ties to China. Founded in Australia in 2015, the company maintains offices in Shanghai, Beijing, and Shenzhen and counts Chinese investors, including Tencent and HongShan Capital (formerly Sequoia China), among its backers. In December, prominent Silicon Valley investor Keith Rabois, a board member at rival U.S. fintech Ramp, publicly accused Airwallex of being a “Chinese backdoor into sensitive American data.”

Zhang has pushed back forcefully, describing the allegations as “wild and totally unfounded conspiracy theories.” He emphasized that American customers’ data is stored in the U.S. and remains inaccessible to staff in China or Hong Kong.

However, the allegation has raised a cloud of scrutiny over Airwallex, making its ability to navigate the geopolitical currents while scaling a key test of its resilience. But its broad regulatory licensing footprint, spanning more than 85 jurisdictions, provides a buffer, allowing it to serve clients with confidence even as scrutiny intensifies.

A Fintech Unicorn Betting on the Agentic Future

At $11 billion, Airwallex joins an elite group of fintech unicorns that have maintained strong valuations amid a more selective funding environment. The company’s focus on AI-powered automation aligns with broader industry trends, where payments are becoming just one part of intelligent financial ecosystems capable of handling complex, multi-currency, and increasingly autonomous transactions.

The move comes as businesses seek greater efficiency and control over their financial operations. This means that platforms that combine global payment rails with AI-driven insights and automation are well-positioned to capture market share. Airwallex’s emphasis on agentic commerce, where AI agents can execute payments within defined parameters, points to a future where financial transactions become more seamless and embedded in broader business workflows.

Investors are believed to see the round as continued confidence in Airwallex’s ability to execute on its ambitious vision despite external headwinds. The participation of sophisticated institutional investors like Baillie Gifford and T. Rowe Price suggests the company’s growth story and technological direction resonate beyond traditional venture capital circles.

Gold’s remarkable bull run has lost significant momentum, with prices falling to around $4,000 an ounce, extending a sharp correction that has forced some of Wall Street’s biggest banks to abandon their once-aggressive bullish forecasts and acknowledge that a rapid return to record highs has become increasingly unlikely.

The precious metal was trading at about $4,025 per troy ounce early Friday, leaving bullion down for the year and roughly 30% below the intraday record of nearly $5,600 an ounce reached in late January. The decline marks a dramatic reversal for an asset that had been one of the world’s strongest-performing investments over the previous two years.

Gold’s retreat follows an extraordinary rally that saw spot prices more than double from around $2,000 an ounce at the start of 2024, fueled by central bank purchases, geopolitical tensions, expectations of lower U.S. interest rates, and heavy investor demand for safe-haven assets.

The mood has since shifted sharply as investors increasingly focus on the prospect of tighter U.S. monetary policy rather than geopolitical uncertainty.

A stronger U.S. dollar and growing expectations that the Federal Reserve will keep interest rates elevated for longer, or even raise borrowing costs further to contain inflation, have significantly reduced gold’s appeal. Because bullion generates no income, higher interest rates increase the attractiveness of interest-bearing assets such as Treasury bonds while also lifting the opportunity cost of holding gold.

The stronger dollar has compounded the pressure by making dollar-denominated bullion more expensive for overseas buyers, weighing on physical demand across key markets.

“The sell-off may appear surprising given ongoing geopolitical uncertainty and continued central bank buying. However, gold’s weakness highlights the extent to which markets have shifted their focus from safe-haven demand towards the implications of higher interest rates and tighter financial conditions,” Ewa Manthey, commodity strategist at ING, wrote on Thursday.

Manthey added that higher bond yields, a firmer dollar, and softer investor demand are likely to keep gold under pressure longer than previously anticipated.

Reflecting that outlook, ING cut its price forecasts, now expecting gold to average $4,300 an ounce in the third quarter of 2026 and $4,600 in the fourth quarter. Those projections are substantially below its earlier forecasts of $4,850 and $5,000, respectively.

ING is not alone in reassessing the outlook. Earlier this week, Deutsche Bank also downgraded its forecasts, reducing its third-quarter estimate by more than 20% to $4,300 an ounce while cutting its fourth-quarter projection by 17% to $4,800, according to analyst Michael Hsueh.

“The usual suspects which might provide support via investment demand are notably absent, for now,” Hsueh wrote, citing weaker inflows into gold-backed exchange-traded funds as well as softer physical buying from China and India.

Those two countries account for the world’s largest consumer demand for physical gold, making any slowdown in purchases a significant headwind for prices.

The downgrade also follows a similar move by Goldman Sachs, which last week reduced its year-end target by $500 to $4,900 an ounce after abandoning its earlier expectation that the Federal Reserve would cut interest rates this year.

Meanwhile, Bank of America, which has maintained one of the most optimistic outlooks on Wall Street with a 12-month target of $6,000 an ounce since January, recently acknowledged that achieving that level now “looks unlikely for now.”

The wave of forecast revisions underscores how quickly sentiment has shifted in the gold market.

Only a few months ago, many analysts expected bullion to continue setting successive record highs as geopolitical conflicts, central bank diversification away from the U.S. dollar, and anticipated Fed easing combined to create what many viewed as a structurally bullish environment.

That optimism has faded as persistent inflation and resilient economic data have prompted markets to reassess the outlook for U.S. monetary policy. Futures markets have significantly reduced expectations for near-term interest-rate cuts, while some investors have even begun pricing in the possibility of further tightening if inflation proves more persistent.

The change in expectations has lifted Treasury yields and strengthened the dollar, two developments that historically create a difficult backdrop for gold.

Even so, analysts caution that the longer-term structural drivers supporting bullion have not disappeared entirely. Central banks continue to diversify reserve holdings, geopolitical tensions remain elevated across several regions, and concerns over government debt levels in major economies could still revive safe-haven demand if financial conditions deteriorate.

For now, however, investors appear to be prioritizing higher real yields over traditional defensive assets, suggesting gold may struggle to regain its record highs until there is clearer evidence that U.S. monetary policy is turning more accommodative or geopolitical risks intensify enough to trigger another sustained flight to safety.