Court documents from Musk v. Altman have unveiled internal Microsoft emails from 2017-2018, revealing skepticism among executives, including CEO Satya Nadella, about OpenAI's potential before their $1 billion investment. Despite initial doubts, Microsoft feared losing OpenAI to Amazon's AWS, prompting a strategic investment to secure the partnership.In 2016, Microsoft offered OpenAI $60 million in discounted Azure services, but usage exceeded expectations. By 2018, internal discussions highlighted concerns over OpenAI's demands and potential, with executives wary of endorsing AI advancements perceived as threatening. Ultimately, Microsoft's investment grew to $13 billion over four years. However, OpenAI recently signed a $138 billion cloud deal with Amazon, marking a significant shift in partnerships.