Microsoft Tightens Its AI Command with Leadership Overhaul and $6B OpenAI Deal — But GitHub’s Reliability Woes Loom Large

Microsoft scraps senior leadership for a leaner team to accelerate AI, targets $190B capex, while GitHub suffers 257 outages pushing developers to rivals like Cursor.

Microsoft is tearing up its old playbook. The tech giant has scrapped its traditional Senior Leadership Team in favour of a much smaller governance group that will meet at least once a week, designed to cut through bureaucracy and accelerate AI integration across Windows, Office, and Azure. The new core consists of the CEO, President, CFO, and Chief Human Resources Officer — a tight circle with outsized influence over the company’s strategic direction.

Internally, the restructuring is being driven by a “One Copilot” philosophy. Instead of offering AI tools as standalone features, Microsoft plans to weave intelligence directly into the operating system. By mid-2026, it will roll out “Ask Copilot” in the Windows 11 taskbar, alongside a “Click to Do” tool for quick extractions in Excel. The company is also expanding its commercial marketplace, launching “Multiparty Private Offers” across 30 European countries, allowing channel partners and software publishers to bundle AI agents, software, and services into a single cross-border transaction.

The financial commitment to AI is staggering. Microsoft’s AI-powered revenue has hit an annualised $37 billion, up 123 percent. Capital expenditure for the 2026 fiscal year is expected to reach around $190 billion. That spending is underpinned by a restructured partnership with OpenAI: Microsoft will receive approximately $6 billion from OpenAI in 2026 — $2 billion more than previously forecast — in exchange for ending revenue-sharing arrangements while securing intellectual property rights until 2032. Several analysts have raised their price targets to $575, citing accelerating Azure growth and deeper Copilot adoption in the enterprise.

Yet even as Microsoft doubles down on AI, one of its most important assets is showing serious cracks. GitHub, the code-hosting platform Microsoft acquired in 2018, suffered 257 incidents between May 2025 and April 2026, according to monitoring firm IncidentHub. Forty-eight of those were classed as severe — meaning the platform endured roughly one major outage per week. The worst month was February, with 37 disruptions. GitHub’s CI/CD service Actions alone accounted for 57 outages over the period.

The root cause appears to be a delayed migration to Microsoft’s own Azure cloud. GitHub remains tethered to older data centres, limiting its ability to scale. In October 2025, CTO Vlad Fedorov promised a tenfold increase in capacity. By February, that target was deemed insufficient; the platform would need to handle 30 times its current load. The infrastructure strain has driven frustrated developers to rivals. Cursor, an AI-assisted coding tool, raised $2.3 billion in a Series D round in November 2025 at a $29.3 billion valuation — nearly doubling in six months. Mitchell Hashimoto, co-founder of HashiCorp, posted publicly: “GitHub is no longer a place for serious work if it locks you out for hours every day.”

The operational crisis is compounded by a leadership vacuum. Former GitHub CEO Thomas Dohmke resigned and was not replaced; the remaining leadership team now reports directly to Microsoft’s CoreAI unit. In April, Julia Liuson — a 34-year Microsoft veteran who ran the Developer Division — announced her retirement. Meanwhile, a security breach involving a compromised employee device via a manipulated VS Code extension exposed roughly 3,800 internal code repositories, and a remote code execution vulnerability had to be disclosed.

The rest of Microsoft’s business is humming along. LinkedIn posted 12 percent revenue growth in the quarter ended March 31. Total company revenue reached $82.9 billion. CEO Satya Nadella noted that more than 10,000 customers now use multiple AI models on Azure’s Foundry platform, and the number of clients deploying both Anthropic and OpenAI models doubled quarter over quarter.

Yet the share price tells a different story. Microsoft stock trades at €357.65, 23 percent below its 52-week high of €467.45 and down 11 percent year to date. That slide presented an opportunity for hedge fund manager Bill Ackman. His firm, Pershing Square, began building a stake in February that has grown to $2.09 billion, now representing 15.3 percent of the portfolio. Ackman described the current valuation as a rare chance to buy into the AI story at a discount.

The disconnect is stark. Microsoft is spending aggressively, reorganising at warp speed, and locking in billions from its OpenAI partnership, but GitHub’s recurring outages and leadership exodus threaten to undermine the developer trust that underpins its AI ambitions. For investors, the question is whether Ackman’s bet will be vindicated — or whether the infrastructure cracks and competitive pressure from nimbler rivals will prove too deep to paper over with a fresh org chart.