A leaked internal memo from OpenAI's Chief Revenue Officer suggests growing strains in the company's relationship with Microsoft, even as the creator of ChatGPT deepens its ties with Amazon.com.
In February, Amazon.com invested $50 billion in OpenAI and provided the company with 2 gigawatts of Trainium computing capacity. As OpenAI turns to Amazon.com for growth momentum, its long-standing partnership with Microsoft may be under pressure.
OpenAI Chief Revenue Officer Dennis Desser stated in a Sunday internal memo that the collaboration with Amazon.com is crucial for unlocking commercial AI monetization in the enterprise market. She added that Microsoft has restricted OpenAI's ability to meet existing enterprise client demands. Many of OpenAI's corporate customers are accessing its models through a platform called Bedrock on Amazon Web Services, which Desser described as experiencing "staggering" demand.
The enterprise market has become a key battleground for top AI firms competing for dominance. In the first few months of 2026, Anthropic stunned the market with its rocket-like revenue growth. Desser wrote that Anthropic made a "strategic error by not securing sufficient computing power," adding, "The market will be dominated by us—let's give it our all."
Desser also criticized Anthropic's strategy as being built on "fear, restrictions, and the idea that AI should be controlled by a small elite."
Last October, OpenAI formally transitioned into a public benefit corporation, a move that reduced Microsoft's influence over the AI company and allowed OpenAI to secure more computing power from other cloud service providers. Although Microsoft has been an investor in OpenAI since 2019, having invested a total of $13 billion over the years, the relationship has evolved into a "frenemy" dynamic as Microsoft diverts computing resources to internal projects like Copilot.
As Microsoft's control over OpenAI weakens, OpenAI has been strengthening its relationship with Amazon.com. Last November, OpenAI signed a $38 billion agreement with Amazon.com to use NVIDIA chips for ChatGPT training and inference tasks.
In February, Amazon.com announced plans to invest up to $50 billion in OpenAI and supply 2 gigawatts of Trainium computing power—an AI chip developed by Amazon Web Services. As part of the deal, Amazon Web Services and OpenAI are collaborating to create dedicated "AI agent" environments and features for Bedrock clients.
So far this year, Amazon.com's stock has risen 3.5%, while Microsoft's shares have fallen 21.2%. In comparison, the S&P 500 has remained largely flat through 2026.
To meet growing demand for its products, Anthropic has also been actively securing additional computing agreements. Last week, the company expanded existing partnerships with Broadcom and Alphabet to obtain 3.5 gigawatts of computing capacity. On Friday, Anthropic also reached an agreement with next-generation cloud services firm CoreWeave.
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