According to sources familiar with the matter, Microsoft (MSFT.US) has become one of Anthropic's top-tier customers and is recently expected to invest approximately $5 billion annually to utilize Anthropic's artificial intelligence (AI) to power Microsoft products. The company is also intensifying efforts to market Anthropic's AI models to its cloud computing clients, a move that could potentially generate additional revenue for both firms. Sources indicated that Microsoft is incentivizing Azure sales personnel to promote Anthropic's models and has increased spending on Anthropic's AI models for its internal uses and products. These initiatives come at a time when OpenAI, which is backed by Microsoft, is engaging in more business with Microsoft's competitors. According to two Microsoft employees, the company recently informed some sales staff within its Azure cloud division that selling Anthropic AI models to Microsoft cloud clients would count towards their sales quotas just like selling Microsoft's own proprietary software. Microsoft typically does not offer such sales incentives for non-Microsoft products, as these products contribute less to Azure's profitability. The current sales incentives for Anthropic are set to last until the end of June. The company had previously offered identical incentives for selling OpenAI models, which Microsoft also markets through its Azure platform. Functionally, the new quota system means that sales personnel have as much motivation to promote Anthropic models as they do to promote OpenAI models. These actions demonstrate that Microsoft, similar to other established tech giants, is forging close partnerships with several AI developers, representing both significant revenue opportunities and posing potential threats to some of its core business segments. Microsoft is also racing to utilize technologies from both OpenAI and Anthropic to develop its own proprietary AI automation products for enterprise clients, thereby mitigating the risk of ceding such business to emerging AI startups. In November 2025, Microsoft committed to investing up to $5 billion in Anthropic—a company that had previously received backing from Amazon (AMZN.US) and Alphabet's Google (GOOGL.US). Anthropic also stated that it had committed to spending $30 billion on computing capacity from Microsoft Azure and had signed agreements to purchase an additional 1 gigawatt (GW) of computing capacity. Microsoft has invested over $13 billion in OpenAI and holds nearly a 27% stake in the maker of ChatGPT. Anthropic primarily generates revenue by selling AI directly to enterprises, but some sales personnel from both Microsoft and Anthropic are collaborating to market the purchase of Anthropic models via Azure to businesses. Similarly, Anthropic has partnered with both Amazon and Google to jointly sell its models to large clients. As of last July, Microsoft was spending over $40 million per month on Anthropic models, representing an annual run-rate of approximately $500 million. These models power coding agent functionalities within GitHub Copilot, such as the ability to monitor website outages and perform automatic fixes. Subsequently, Microsoft increased its procurement of Anthropic models to drive features in other products like 365 Copilot and Security Copilot, including complex operations such as generating PowerPoint presentations from brief text prompts. The report further added that Anthropic had previously projected its annualized revenue to be between $7.5 billion and $9 billion by the end of 2025. Compared to the startup's public retail pricing, Anthropic offers discounts to Microsoft when the models are used for internal purposes, such as developing prototypes, data analysis, and other research. Microsoft first moved to incorporate Anthropic models into 365 Copilot after its executives expressed disappointment with the underperformance of certain features powered by OpenAI. Microsoft CEO Satya Nadella has recently been pushing product divisions to use Anthropic models to accelerate development. Recently, engineers from Anthropic provided support to Microsoft engineers who were developing Copilot features powered by Anthropic's models.