MICROSOFT WAS SKEPTICAL OF OPENAI, FEARED AMAZON RIVAL

AI DESK■ 1 MIN READ

FRI, MAY 8, 2026

■ AI-SUMMARIZED FROM 5 SOURCES ▸ TIMELINE

Internal Microsoft emails from 2018 reveal the company harbored doubts about OpenAI's viability, yet hesitated to distance itself for fear of pushing the startup toward Amazon.

Court documents from Elon Musk's lawsuit against OpenAI co-founder Sam Altman expose Microsoft's complicated relationship with the AI company before its eventual partnership. Microsoft executives questioned OpenAI's technical capabilities and business model in communications spanning years. However, the tech giant remained cautious about openly criticizing the startup, worried that doing so might drive OpenAI into Amazon's orbit. The emails demonstrate a strategic calculation: Microsoft valued maintaining influence over OpenAI's direction more than expressing its concerns publicly. This defensive posture ultimately positioned Microsoft to become OpenAI's largest investor when the partnership materialized. The evidence underscores the competitive tensions in AI development, where tech giants balance skepticism with the need to maintain strategic relationships in a rapidly evolving sector.

■ SOURCES

► Wired ► Techmeme ► The Guardian — Technology ► Bleeping Computer ► Bleeping Computer

■ SUMMARY WRITTEN BY AI FROM THE LINKS ABOVE

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MICROSOFT WAS SKEPTICAL OF OPENAI, FEARED AMAZON RIVAL

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