OpenAI’s four-page memo to employees has a ‘brutal’ line about Microsoft |
OpenAI chief revenue officer Denise Dresser sent a four-page internal memo to employees on Sunday, and buried inside the enterprise strategy playbook was a line that cut straight at the company’s most important—and increasingly complicated—partner. “Our Microsoft partnership has been foundational to our success. But it has also limited our ability to meet enterprises where they are,” Dresser wrote. It’s a remarkably blunt acknowledgment from a company that still, publicly, calls the relationship “core and strategic.”The memo, viewed by both CNBC and The Verge, was framed around five Q2 enterprise priorities. But it’s that single line about Microsoft that landed hardest—because it didn’t come out of nowhere.
The OpenAI-Microsoft relationship has been quietly unraveling since 2024
The partnership dates back to 2019, when Microsoft invested $1 billion in OpenAI to provide exclusive supercomputing functions to its Azure service. It deepened over the years, but the cracks started showing well before Sunday’s memo.In June 2024, OpenAI cut a $10 billion deal with Oracle for extra compute capacity. Later that year, OpenAI partnered with SoftBank, Thrive, Nvidia, and Oracle on the Stargate AI data center project—which notably omitted Microsoft. Around the same time, Microsoft added OpenAI to the list of competitors in its annual report—a quiet but pointed signal.Then in March 2025, OpenAI executives considered publicly accusing Microsoft of anticompetitive behavior throughout their partnership, and mulled whether to seek a federal regulatory review of their contract. It never got that far. By September 2025, Microsoft and OpenAI signed a non-binding memorandum of understanding, resolving months of tensions while restructuring how enterprises would deploy AI.The peace didn’t last long. On April 2, 2026, Microsoft released three proprietary foundational models under its Microsoft AI brand—signaling the clearest break yet from the partnership. OpenAI now has a rival in the company that helped build it.
Dresser’s memo frames the Amazon deal as the fix to a problem Microsoft created
The line about Microsoft in Sunday’s memo wasn’t just an observation—it was a setup. Dresser immediately pivoted to Amazon, framing the $50 billion AWS partnership announced in late February as the unlock OpenAI needed to reach enterprise customers.“For many [enterprises], that’s Bedrock,” she wrote, referring to Amazon’s cloud AI platform. “Since we announced the partnership at the end of February, inbound demand from our customers for this offering has been frankly staggering.”The Amazon deal is, however, legally fraught. Microsoft is weighing legal action over whether the deal violates a longstanding agreement that requires all access to OpenAI’s models to be routed through Azure. The dispute hinges on a technical workaround—Amazon and OpenAI are building a so-called Stateful Runtime Environment on Bedrock to sidestep the clause. Microsoft’s engineers don’t believe the workaround holds up under the contract’s terms.In a document circulated to investors ahead of its expected IPO, OpenAI itself flagged the Microsoft relationship as a risk factor, writing that its results would depend on its ability to develop relationships with additional partners. The Amazon partnership is, in that light, less a strategic flourish and more an existential necessity.
For OpenAI, loosening the Microsoft relationship isn’t optional—it’s the IPO story
OpenAI generated $13.1 billion in 2025 revenue and was valued at $730 billion by investors. Dresser told CNBC that enterprise accounts for 40% of that revenue and is on track to match its consumer business by year’s end. To make that case credibly to public market investors, OpenAI needs to show it isn’t structurally dependent on a single partner that is now also a competitor.The memo’s Microsoft line is a data point in that narrative. It tells employees—and, now that it’s leaked, the market—that OpenAI sees the relationship clearly: foundational, yes, but also a ceiling it is actively working around.Microsoft declined to comment on the memo.
