For many years, OpenAI and Microsoft were close friends, jumping on the AI bandwagon together and riding the boom. Microsoft initially provided the compute power and funding while OpenAI provided state-of-the-art foundation models. However, it now looks like the AI industry"s most formidable alliance is beginning to fracture.
According to a report by the Financial Times (paywall), Microsoft is planning to pursue legal action against its own golden goose, OpenAI, as well as cloud rival Amazon. The dispute is due to a whopping $50 billion partnership that was signed between Amazon and OpenAI last month, which is something that Microsoft alleges blatantly violates its exclusive cloud computing agreements with the ChatGPT maker.
In late 2025, when Microsoft restructured its historic partnership with OpenAI, it gave up some of its total cloud exclusivity to allow OpenAI to diversify its product hosting. However, Microsoft retained one ironclad clause: all basic, "stateless" application programming interface (API) calls to OpenAI’s models must be routed exclusively through Microsoft Azure.
This was a safety net for Microsoft to ensure that no matter how big OpenAI grew, Azure would be the major platform for its core AI traffic.
However, last month, OpenAI and Amazon signed a massive strategic partnership where Amazon committed $50 billion for AWS to become the exclusive third-party cloud distributor for OpenAI"s new enterprise platform "Frontier". OpenAI and Amazon co-created a "Stateful Runtime Environment" (SRE) hosted on Amazon Bedrock to smartly circumvent Microsoft"s exclusivity clause.
In software terms, a "stateless" model processes each request independently, retaining no memory of past interactions, which is the exact type of API call Microsoft has a monopoly on. A "stateful" environment, however, maintains memory and context over time, allowing AI agents to perform complex, multi-step tasks autonomously. OpenAI and Amazon argue that their new SRE is fundamentally a stateful architecture, and therefore does not violate Microsoft’s monopoly on stateless API calls.
According to the report, the Redmond giant argues that regardless of how Amazon and OpenAI creatively categorize their technical architecture, building a functional enterprise system of this scale without relying on underlying stateless API calls is practically unfeasible.
The dispute also comes at a time when competition between the two cloud providers is already at an all-time high. In fact, AWS currently generates more revenue than Microsoft"s Cloud and Server business combined.
If Amazon successfully courts OpenAI’s enterprise clients through "stateful" loopholes, Microsoft risks losing the very competitive moat it spent tens of billions of dollars trying to build over all these years.
Source: Financial Times (paywall)