Microsoft (NASDAQ:MSFT) shares are currently trading at $499.70, nearing their all-time high of $549.20. Analysts suggest that despite strong growth in its Azure cloud services and AI business, a surging 80% increase in capital expenditures to $115.948 billion, which led to a 6.46% decline in free cash flow to $66.987 billion, could be a critical factor determining whether the stock can break new highs. CEO Satya Nadella's sale of $43 million in stock in early September may also impact market sentiment.