What Did It Take To Hold Microsoft Stock?

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Over the last ten years, Microsoft (MSFT) stock turned $10,000 into $92,451 before dividends. That same $10,000 invested in the S&P 500 became $35,968. Looking back makes the strategy seem as simple as buying and waiting, but holding the shares required far more discipline. How many times do you think Microsoft stock fell 20% or more along the way?

How Often Did Microsoft Stock Fall?

Microsoft stock fell 20% or more from a closing high four times. Two of those declines exceeded 30%. All four are listed below.

The deepest drop occurred between November 2021 and November 2022, when the stock fell 37.6% while the S&P 500 lost 20.8%. Investors spent about 19 months below the previous peak until the shares closed above that old high in June 2023. The real question was never just whether to buy Microsoft. It was whether you could sit through falls like these.

What Did Holding Microsoft Through A Fall Feel Like?

The most recent decline began at a closing high on October 28, 2025, and the stock took nearly eight months to reach its low on June 25, 2026, dropping 34.9%. The S&P 500 rose 6.8% over those same months, so shareholders lost ground while the broader market gained.

From that low, the stock took another 3.6 months to close above its old high. All four of Microsoft’s declines eventually ended. Nobody holding shares in the middle of a drop knew that at the time, however, and an investor in the spring of 2026 had no way to know this one would.

Was Something Wrong With Microsoft’s Business?

Microsoft generates revenue from cloud services such as Azure and software such as Microsoft 365. Its two largest segments are Intelligent Cloud, followed by Productivity and Business Processes. During the deepest fall, revenue over twelve months rose 15.2%, and the operating margin stayed close to 42% from the high to the low.

In the latest fall, which was shorter, twelve-month revenue rose 8.3% from the high to the low, and the operating margin edged up from 46.3% to 46.8%.

Sales grew and operating margins held steady during both falls while the stock declined. A drop like that, while the business keeps growing, is the risk of holding the shares.

What Selling Microsoft Stock Would Have Cost

Microsoft stock is up 148.2% since its November 2022 low, and anyone who sold there missed all of it. Today, the stock sits 2.1% below the high it set on October 13, 2026.

Enduring those four falls was the cost of the ten-year gain, and the investors who captured those returns were the ones who sat through every drop. Microsoft’s revenue kept growing during both the deepest decline and the latest one. The next time Microsoft stock falls hard, check whether its revenue is falling with it.

How To Act On MSFT?

Not necessarily on Microsoft alone, if your goal is long-term wealth. Wealth is built by owning the companies that keep outperforming, the leaders of their industries, wherever they are. Here are two companies from Microsoft’s own industry that have beaten it. Over the five years to October 2026, Fortinet stock rose 156% and CommVault Systems stock rose 105%, while Microsoft stock rose 80%.

Finding companies like these takes comparison across industries and sectors, and that is what the Trefis High Quality (HQ) Portfolio does. It holds 30 quality companies in equal weight and, since its inception in September 2020, has returned more than 105%, ahead of a benchmark that combines the S&P 500, S&P Mid-cap and Russell 2000. See how we find the leaders.

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