Microsoft released its fiscal year 2026 fourth-quarter financial results, unexpectedly revealing a stark contrast in returns from its investments in two leading AI companies. Microsoft's investment in Anthropic generated $3.2 billion in revenue during the quarter, while its investment in OpenAI resulted in a $600 million impairment—just Anthropic's quarterly revenue is nearly equivalent to OpenAI's annual revenue.

One investment soars while the other incurs a loss—early signs of diverging outcomes in Microsoft's dual bets

Microsoft invested $5 billion in Anthropic in November 2025, and as part of the agreement, Anthropic also committed to purchasing $30 billion in Azure cloud services. Microsoft's decision to proactively disclose the gains from its investment in Anthropic indicates that this investment has already shown significant book value growth. In contrast, Microsoft currently holds about 27% of OpenAI, and this quarter's $600 million impairment reduced diluted earnings per share by approximately 7 cents.

Looking at the full year, the investment in OpenAI still yielded a positive return for Microsoft—this investment brought in $5 billion in total during the fiscal year 2026, increasing earnings per share by 67 cents for the year. Microsoft's performance in the fourth quarter remained impressive, with revenue of $90 billion and net income of $35.8 billion. For the entire fiscal year 2026, Microsoft achieved revenue of $331.8 billion and net income of $133.7 billion.

The $600 million impairment in a single quarter is indeed not a major issue for Microsoft's scale, but the contrasting financial trends between Anthropic and OpenAI highlight a more concerning trend: Microsoft's carefully laid dual AI investment strategy seems to be quietly shifting toward the newcomer.