It's never been a secret that Microsoft's partnership with OpenAI is less-than-ideal, and things might have just taken a turn for the worse. In a leaked memo exclusively viewed by CNBC, the ChatGPT maker is seemingly getting cozy with Amazon to bolster its enterprise business.
In case you missed it, OpenAI and Amazon have been in discussions over a $50 billion deal that could see the AI firm using its cloud computing services.
A separate report revealed that Microsoft was considering taking legal action against the two companies because the billion-dollar deal could potentially violate a critical clause granting Microsoft exclusive rights as the AI giant’s cloud provider through Azure.
Despite Microsoft's $13 billion (and counting) investment in OpenAI, the company's newly appointed revenue chief, Denise Dresser, indicated that the tie-up with the tech giant has seemingly capped its growth in the enterprise landscape.
“Our Microsoft partnership has been foundational to our success. But it has also limited our ability to meet enterprises where they are — for many that’s Bedrock,” Dresser highlighted in the memo. “Since we announced the partnership at the end of February, inbound demand from our customers for this offering has been frankly staggering.”
Right now, OpenAI is up against Anthropic's massive market share with Claude, not forgetting Google's Gemini, which is also gaining traction and adoption rapidly. As such, its new partnership with Amazon places it in a unique position to compete with its rivals on an even playing field.
Sam Altman just stabbed Microsoft straight in the back.In a new internal memo OpenAI admits their partnership with Microsoft has limited their ability to win major enterprise clients. They are now loudly boasting about their new alliance with Amazon as the better option.… pic.twitter.com/aBiCyNYQfmApril 22, 2026
Dresser called the enterprise market "noisy and volatile" while encouraging staffers to center their focus on customers. She also indicated that Anthropic's business model is built on “fear, restriction, and the idea that a small group of elites should control AI,” but says OpenAI's positive message will stand the test of time.
In the past, OpenAI has complained about Microsoft not meeting its cloud computing needs. But CEO Sam Altman indicated that the company was no longer compute-constrained after announcing the $500 billion Stargate project. However, the AI firm walked away from the project after it was unable to find agreeable terms with Oracle.
This news comes after market analysts and experts began sounding warnings about investor interest in AI after big tech companies invested in the ever-evolving landscape, which failed to establish clear paths to profitability.
Coincidentally, Microsoft has just closed its worst quarter since the 2008 financial crisis, which translates to approximately a quarter of its market value. However, the tech giant isn't giving up on its AI ambitions, as it plans to invest $146 billion in infrastructure in 2026.
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