Microsoft is going all-in on Copilot, its enterprise-focused AI chatbot, but the tech giant is encountering resistance where it matters most: in the hands of users who still prefer ChatGPT.
While both AI tools are powered by OpenAI’s models—including GPT-4 and its successors—Microsoft’s vision of embedding Copilot into its productivity suite has run into stiff headwinds. According to a recent Bloomberg report, Microsoft’s sales team is struggling to convince businesses why they should choose Copilot over ChatGPT, even though the company has a multibillion-dollar stake in OpenAI and exclusive licensing rights to its models.
Microsoft has pitched Copilot as a natural extension of the Microsoft 365 experience. It’s cheaper in some cases, tightly integrated into Word, Excel, Teams, and Outlook, and backed by Microsoft’s long-standing enterprise infrastructure. Yet, many companies are bypassing Copilot for ChatGPT, citing better usability, flexibility, and brand familiarity.
ChatGPT has become the public face of generative AI. It was the first AI tool many employees and developers experimented with. As a result, organizations are seeing internal demand for ChatGPT licenses even when Copilot is technically available.
OpenAI claims to have over 3 million paying enterprise customers, while Microsoft has reported that “multiple dozens” of clients have more than 100,000 Copilot users—translating to a minimum floor of around 2.4 million licenses, but with less transparency.
The Cracks in a $13 Billion Partnership
Beneath the commercial rivalry between Copilot and ChatGPT lies a more serious issue: Microsoft and OpenAI are at odds over the future of their $13 billion partnership.
According to sources familiar with ongoing talks, Microsoft is prepared to walk away from high-stakes negotiations with OpenAI unless new terms meet or exceed existing ones. The tech giant is signaling that it’s content to continue under its current agreement—which guarantees exclusive access to OpenAI’s models until 2030—without committing to additional investments or concessions.
At the heart of the tension is OpenAI’s structural overhaul. The company is trying to formally convert from a nonprofit-capped entity into a for-profit public-benefit corporation. This transformation is critical to its ambitions to raise more capital, potentially go public, and retain investor momentum.
However, Microsoft’s consent is legally required for the restructuring to proceed. And Microsoft, according to insiders, is increasingly skeptical of any deal that would reduce its leverage over OpenAI’s commercial outputs.
One of the biggest sticking points is revenue sharing. Microsoft currently receives 20% of OpenAI’s revenue, capped at $92 billion. But OpenAI is reportedly pushing to reduce that share to as little as 10% by 2030. Reducing Microsoft’s stake could help OpenAI appeal to a broader base of investors, but Microsoft views such a move as eroding its return on a massive financial outlay.
While Microsoft is rumored to have discussed taking up to 49% equity in a restructured OpenAI, no deal has been finalized, and the software giant is wary of trading down its current advantageous licensing rights for uncertain future stakes.
Microsoft insiders argue that public markets and shareholders care less about equity in OpenAI and more about monetized, exclusive access to foundational AI infrastructure—a benefit the company already enjoys.
What’s Next for Copilot?
The fractures in the Microsoft–OpenAI relationship come at a delicate time for both firms. Microsoft is banking on Copilot as its anchor product for AI monetization, having integrated it into Windows 11, GitHub, Azure, and across the Microsoft 365 suite. It’s also bundling Copilot into premium subscription tiers and pushing enterprise clients to adopt it at scale.
Meanwhile, OpenAI continues to expand its reach directly through ChatGPT Enterprise, Team, and API products—positioning itself less like a backend model provider and more like a full-stack software vendor.
This overlapping ambition now threatens to place the two companies on a collision course, even as they remain intertwined through Azure and licensing agreements.
Despite these headwinds, Microsoft’s financials remain robust. Its stock hit an all-time high of $491.76 this week, before closing at $490.40, up 0.85%. Investors are still bullish on Microsoft’s long-term AI positioning, but questions remain about how sustainable the current partnership model with OpenAI truly is.
AI Loyalty vs. AI Delivery
The struggle between Copilot and ChatGPT is not just a product rivalry—it’s a reflection of how quickly AI has become embedded in organizational behavior. Microsoft has deeper enterprise relationships, but OpenAI has captured the imagination of users at scale.
Unless the companies resolve their strategic rift, Microsoft risks investing heavily in an ecosystem that may ultimately compete with its own offerings. Meanwhile, OpenAI must navigate the tension of being both Microsoft’s partner and its biggest competitor in the generative AI space.