Microsoft Stock Hasn't Been This Cheap Since 2019. Now Is the Perfect Time to Buy.

Source Motley_fool

Key Points

  • Microsoft's AI business is crushing it.

  • Its P/E ratio has been skewed recently by one-time effects.

  • 10 stocks we like better than Microsoft ›

Over the past few years, Microsoft (NASDAQ: MSFT) has traded at a premium to the market. However, that's no longer the case. The company didn't do much to lose this premium; instead, it looks like that premium shifted to Alphabet (NASDAQ: GOOG) (NASDAQ: GOOGL). However, I think that has created a potential opportunity for Microsoft stock to rally over the next few months and regain its premium valuation by the time 2026 is over.

On a price-to-earnings basis, Microsoft stock hasn't been this cheap since 2019, and based on the value proposition it's offering investors, there has seldom been a better time to buy.

Will AI create the world's first trillionaire? Our team just released a report on the one little-known company, called an "Indispensable Monopoly" providing the critical technology Nvidia and Intel both need. Continue »

Investor looking at Microsoft's valuation history.

Image source: Getty Images.

Microsoft has reached a rare valuation point

Microsoft does a lot of different things as a business, but none is more important than artificial intelligence. This is the technology that will define the company's future, and Microsoft must get it right. Based solely on its finances, I think it's doing just fine so far.

Microsoft's revenue rose 18% year over year during its latest quarter, but the annual run rate of its AI business rose by 123% to $37 billion. Its cloud computing segment, Azure, grew at a 40% clip, another strong performance compared to its peers.

Yet despite how well Microsoft is doing well from a business standpoint, that hasn't helped its case from a valuation perspective.

MSFT Price to CFO Per Share (TTM) Chart

MSFT Price to CFO Per Share (TTM) data by YCharts.

The two valuation metrics I want to focus on are the price-to-earnings (P/E) ratio and the price-to-operating-cash-flow ratio. The P/E ratio may be more commonly used by retail investors to gauge the value of stocks, but as a metric, it is affected by more items. One of them is changes in the value of the company's portfolio of investments, and over the past few quarters, that factor has been significant for Microsoft. By contrast, operating cash flow only measures how much cash the company actually generates from its businesses. From this standpoint, Microsoft hasn't been this cheap since 2019, although that's also true for the P/E ratio.

Companies rarely sink to relative valuation lows when they're growing rapidly. That's why I think investors have a compelling buying opportunity for Microsoft stock. It offers a rare combination of growth and value right now. With the market currently bullish on other tech stocks, this would be a phenomenal stock to scoop up before a potential rally begins in the second half of 2026.

Should you buy stock in Microsoft right now?

Before you buy stock in Microsoft, consider this:

The Motley Fool Stock Advisor analyst team just identified what they believe are the 10 best stocks for investors to buy now… and Microsoft wasn’t one of them. The 10 stocks that made the cut could produce monster returns in the coming years.

Consider when Netflix made this list on December 17, 2004... if you invested $1,000 at the time of our recommendation, you’d have $472,852!* Or when Nvidia made this list on April 15, 2005... if you invested $1,000 at the time of our recommendation, you’d have $1,317,207!*

Now, it’s worth noting Stock Advisor’s total average return is 984% — a market-crushing outperformance compared to 210% for the S&P 500. Don't miss the latest top 10 list, available with Stock Advisor, and join an investing community built by individual investors for individual investors.

See the 10 stocks »

*Stock Advisor returns as of May 27, 2026.

Keithen Drury has positions in Alphabet and Microsoft. The Motley Fool has positions in and recommends Alphabet and Microsoft. The Motley Fool has a disclosure policy.

Disclaimer: For information purposes only. Past performance is not indicative of future results.
placeholder
Ethereum Staking Record Meets On-Chain Collapse: Analyst Explains What’s Holding ETH PriceEthereum has lost the $2,100 level as selling pressure overwhelms a recovery that has been struggling to find structural support since the mid-May highs. The decline is uncomfortable — but a
Author  NewsBTC
16 hours ago
Ethereum has lost the $2,100 level as selling pressure overwhelms a recovery that has been struggling to find structural support since the mid-May highs. The decline is uncomfortable — but a
placeholder
Bitcoin Price Downtrend Gains Pace, Recovery Hopes Continue To FadeBitcoin price started a downside correction from the $77,800 zone. BTC is showing bearish signs and might continue lower below $75,500. Bitcoin failed to stay above $77,000 and extended losses. The
Author  NewsBTC
16 hours ago
Bitcoin price started a downside correction from the $77,800 zone. BTC is showing bearish signs and might continue lower below $75,500. Bitcoin failed to stay above $77,000 and extended losses. The
placeholder
S&P 500 hit a new intraday record at 7,539.8The S&P 500 hit another record on Tuesday, reaching 7,539.8 during the session and putting the index on pace for a nine-week winning run, its first since 2023. Tech did most of the heavy lifting because, of course, Wall Street went right back to worshiping chips after the long weekend. The Nasdaq Composite also reached...
Author  Cryptopolitan
16 hours ago
The S&P 500 hit another record on Tuesday, reaching 7,539.8 during the session and putting the index on pace for a nine-week winning run, its first since 2023. Tech did most of the heavy lifting because, of course, Wall Street went right back to worshiping chips after the long weekend. The Nasdaq Composite also reached...
placeholder
Is Elon Musk really planning to merge SpaceX with Tesla?Is Elon Musk really planning to put SpaceX and Tesla (TSLA) under one roof? It’s all anyone’s talking about on Wall Street, in executive offices, regarding AI expenditure, rockets, and some strange family tree of businesses. SpaceX is getting ready for a Nasdaq listing in a little over two weeks, after hitting a private value...
Author  Cryptopolitan
16 hours ago
Is Elon Musk really planning to put SpaceX and Tesla (TSLA) under one roof? It’s all anyone’s talking about on Wall Street, in executive offices, regarding AI expenditure, rockets, and some strange family tree of businesses. SpaceX is getting ready for a Nasdaq listing in a little over two weeks, after hitting a private value...
placeholder
SpaceX Wins $2.29 Billion US Space Contract, and 10 Assets Can BenefitSpaceX has received a $2.29 billion contract from the US Space Force to build a major military satellite communications network known as the “Space Data Network Backbone” (SDN Backbone). The project w
Author  Beincrypto
16 hours ago
SpaceX has received a $2.29 billion contract from the US Space Force to build a major military satellite communications network known as the “Space Data Network Backbone” (SDN Backbone). The project w
goTop
quote