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Alphabet's shares dropped about 13% after reporting a negative free cash flow of $9.07 billion, significantly worse than analysts' expectations. The company's advertising revenue also fell short of forecasts, raising concerns about its ability to monetize AI investments. If the decline exceeds 9.77% by market close, it would mark Alphabet's worst stock reaction since its 2004 IPO. In contrast, Microsoft reported a positive free cash flow but lower capital expenditures than expected. Alphabet faces increasing competition from AI assistants like ChatGPT, which could divert users from its search engine. Analysts warn that Alphabet may struggle to maintain its traditional search business while competing in the AI sector.