A leaked internal note from OpenAI's chief revenue officer shows the company's rift with Microsoft is deepening, just as the creator of ChatGPT is deepening its relationship with Amazon. Amazon invested $50 billion in OpenAI in February and provided the company with 2 gigawatts of Trainium computing power.
As OpenAI turns to Amazon for growth, the company's long-standing relationship with Microsoft may be coming under pressure.
Dennis Dresser, chief revenue officer of OpenAI, said in an internal notice on Sunday that the partnership between OpenAI and Amazon is the key to unlocking the commercialization of AI in the enterprise market. She added that Microsoft has limited OpenAI's ability to meet the existing needs of enterprise customers. Many of OpenAI's enterprise customers are using its models through a platform called Bedrock on Amazon Cloud Technology, and Dresser called the demand "phenomenal."
The enterprise market has become a key battlefield for top AI companies to compete for dominance. In the first few months of 2026, Anthropic shocked the market with its rocket-like revenue growth. Dresser wrote that Anthropic made a "strategic mistake in not acquiring enough computing power," adding: "The market will be dominated by us, let's go all out for this."
Dresser also criticized Anthropic's strategy for being based on "fear, limitations, and the idea that AI should be controlled by a small elite."
In October last year, OpenAI officially transformed into a public welfare company, a move that weakened Microsoft's influence on the AI company and allowed OpenAI to obtain more computing power through other cloud service providers. Although Microsoft has been an investor in OpenAI since 2019 and has invested a total of US$13 billion in the company over the years, as Microsoft invests its computing power in internal projects such as Copilot, the relationship between the two parties has evolved into a "frenemy" situation.
OpenAI has been strengthening its relationship with Amazon as Microsoft's control of OpenAI has waned. In November last year, OpenAI signed a $38 billion agreement with Amazon to use Nvidia's chips for ChatGPT training and inference.
In February this year, Amazon announced plans to invest up to $50 billion in OpenAI and provide OpenAI with 2 gigawatts of Trainium computing power. Trainium is an AI chip developed by Amazon Cloud Technology. As part of the agreement, Amazon Cloud Technologies and OpenAI are collaborating to create exclusive "AI agent" environments and capabilities for Bedrock customers.
Amazon's shares have risen 3.5% this year, while Microsoft's shares have fallen 21.2%. In comparison, the S&P 500 is essentially flat so far in 2026.
To meet the growing demand for its products, Anthropic has also been actively signing more computing power agreements. Last week, the company expanded existing agreements with Broadcom and Google to acquire 3.5 gigawatts of computing power. Last Friday, Anthropic also reached an agreement with CoreWeave, a new generation cloud services company.