Have Insiders Sold Microsoft Shares Recently?

We wouldn't blame Microsoft Corporation (NASDAQ:MSFT) shareholders if they were a little worried about the fact that Bradford Smith, the President & Vice Chairman recently netted about US$20m selling shares at an average price of US$519. However, it's crucial to note that they remain very much invested in the stock and that sale only reduced their holding by 8.8%.

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Microsoft Insider Transactions Over The Last Year

In fact, the recent sale by President & Vice Chairman Bradford Smith was not their only sale of Microsoft shares this year. They previously made an even bigger sale of -US$35m worth of shares at a price of US$436 per share. So it's clear an insider wanted to take some cash off the table, even below the current price of US$507. As a general rule we consider it to be discouraging when insiders are selling below the current price, because it suggests they were happy with a lower valuation. However, while insider selling is sometimes discouraging, it's only a weak signal. We note that the biggest single sale was only 16% of Bradford Smith's holding.

In the last year Microsoft insiders didn't buy any company stock. You can see the insider transactions (by companies and individuals) over the last year depicted in the chart below. If you want to know exactly who sold, for how much, and when, simply click on the graph below!

Check out our latest analysis for Microsoft

insider-trading-volume
NasdaqGS:MSFT Insider Trading Volume November 6th 2025

For those who like to find hidden gems this free list of small cap companies with recent insider purchasing, could be just the ticket.

Does Microsoft Boast High Insider Ownership?

I like to look at how many shares insiders own in a company, to help inform my view of how aligned they are with insiders. We usually like to see fairly high levels of insider ownership. It's great to see that Microsoft insiders own 0.03% of the company, worth about US$1.2b. I like to see this level of insider ownership, because it increases the chances that management are thinking about the best interests of shareholders.

So What Do The Microsoft Insider Transactions Indicate?

Insiders sold stock recently, but they haven't been buying. Looking to the last twelve months, our data doesn't show any insider buying. But it is good to see that Microsoft is growing earnings. The company boasts high insider ownership, but we're a little hesitant, given the history of share sales. So while it's helpful to know what insiders are doing in terms of buying or selling, it's also helpful to know the risks that a particular company is facing. To assist with this, we've discovered 1 warning sign that you should run your eye over to get a better picture of Microsoft.

But note: Microsoft may not be the best stock to buy. So take a peek at this free list of interesting companies with high ROE and low debt.

For the purposes of this article, insiders are those individuals who report their transactions to the relevant regulatory body. We currently account for open market transactions and private dispositions of direct interests only, but not derivative transactions or indirect interests.

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Have feedback on this article? Concerned about the content? Get in touch with us directly. Alternatively, email editorial-team (at) simplywallst.com.

This article by Simply Wall St is general in nature. We provide commentary based on historical data and analyst forecasts only using an unbiased methodology and our articles are not intended to be financial advice. It does not constitute a recommendation to buy or sell any stock, and does not take account of your objectives, or your financial situation. We aim to bring you long-term focused analysis driven by fundamental data. Note that our analysis may not factor in the latest price-sensitive company announcements or qualitative material. Simply Wall St has no position in any stocks mentioned.

About NasdaqGS:MSFT

Microsoft

Develops and supports software, services, devices, and solutions worldwide.

Very undervalued with outstanding track record and pays a dividend.

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