Jim Cramer urges Microsoft to take a bold step, pointing to pressure on its software business

Microsoft has come under renewed investor scrutiny as the market debates whether its software-heavy business can justify its valuation alongside its cloud operations. In a segment aired as part of CNBC’s Mad Money, Jim Cramer reviewed recent losses in several large technology names and singled out Microsoft as an example of how quickly sentiment can turn.

Cramer said Microsoft’s stock declined sharply during June, describing it as shedding more than 17% of its value over the month. He also said the drop translated into more than $500 billion in lost market capitalization. His point was not simply that Microsoft fell, but that the decline reflected a broader reassessment of what Wall Street expects from the company’s core products.

The host acknowledged that Microsoft has a “decent cloud business,” but argued that it was not enough to offset concerns tied to the company’s software exposure. Cramer characterized the prevailing narrative as one that is unfavorable to Microsoft’s traditional software franchise, saying the market effectively has “no use for the software right now.”

In response to that assessment, Cramer suggested Microsoft would need to “reverse its fortunes” by doing something “bold.” The most concrete idea he raised was that Microsoft could pursue an acquisition involving OpenAI, depending on whether OpenAI can come public. Cramer framed the scenario conditionally, stating that the move would make sense “if” OpenAI cannot go public because of unspecified constraints related to a process that was described only in partial terms in the segment recap.

Microsoft’s business model sits at the center of the tension Cramer described. The company sells productivity and enterprise software that includes widely used tools such as Office and LinkedIn, while also competing in infrastructure and platform services through Azure. For years, investors have treated the company as both a mature software vendor and a major cloud provider, which can make it difficult for any single segment of the story to explain a stock move.

Cramer’s comments also fit into a broader market theme: as artificial intelligence reshapes enterprise software demand, investors have been forced to decide which incumbents will translate AI momentum into near-term revenue and which will need to invest heavily before results show up in earnings. In that framing, an acquisition or partnership tied directly to AI could be viewed as a way to change expectations faster than organic product timelines.

Still, the segment did not provide details about any Microsoft plan, internal deliberations, or active acquisition talks. Cramer’s remarks were presented as advice or market interpretation rather than as an announcement of corporate action. The idea that Microsoft might acquire OpenAI, and any timing around it, remains speculative based on what was disclosed in the recap rather than on new, confirmable company filings or statements.