How To Get Paid To Buy Microsoft Stock At A 30% Discount

Collect a healthy income stream on Microsoft now that you keep no matter what, while lining up a chance to buy this tech giant at a steep discount if it ever gets there.

Microsoft (MSFT) shares are trading around $391, having underperformed the index significantly over the past year and sitting well off their high. For investors who see a technology leader, not a laggard, that disconnect presents an opportunity to get paid for your patience. Below is a trade that generates immediate income while setting a potential purchase price far below today’s levels.

8.6% annualized yield at a 30% margin of safety, by selling put options.

• Sell a put option on MSFT expiring 6/17/2027, with a strike price of $270.
• Collect roughly $890 in premium per contract (each contract covers 100 shares).
• That works out to about 3.6% annualized on the $27,000 of cash you set aside to secure the trade.
• Park that cash in a money market or savings account earning roughly 5.0%, and your total yield climbs to about 8.6%.
• And if MSFT falls below $270, you buy it at $270, an effective entry near $261.10 a share after the premium, about a 33% discount to today’s $390.99.

Both Outcomes Put Cash In Your Pocket

If MSFT stays above $270 through 6/17/2027, the put expires worthless, and you simply keep the full $890 premium. That is about 3.3% on the $27,000 you set aside over 339 days, cash that might otherwise earn you 5.0% or so. You never buy the stock and keep the income, free to do it again.

If MSFT closes below $270, you are assigned and buy 100 shares at $270. The $890 premium you already pocketed lowers your effective cost to about $261.10 a share, roughly a 33% discount to today’s price, though if the stock has fallen further by then, you would be holding a paper loss.

So what happens if MSFT really does close below $270, and you are the one buying? Then everything rests on a single question.

Would You Be Happy To Own MSFT Down Here?

The trade hinges on your willingness to become an owner at a lower price, so the real question is what kind of business you’d be buying into. On one hand, Microsoft’s growth engine is firing on all cylinders. The company just posted a record third quarter, powered by its Microsoft Cloud division, which saw revenue exceed $54 billion, up 29% year-over-year. Its AI business is exploding, having surpassed a $37 billion annual run rate on 123% growth, while the widely watched Microsoft 365 Copilot now has over 20 million paid seats.

But there’s a hefty price tag attached to that growth, and it’s the single biggest question hanging over the stock. To fuel this AI expansion, management plans to invest roughly $190 billion in capital expenditures in calendar year 2026 alone. That staggering figure has created what an analyst on the company’s earnings call described as a “disconnect that makes investors a bit nervous between how fast they’re seeing CapEx growing and how fast they’re seeing revenue growing.” The risk is that this spending spree doesn’t translate into profit quickly enough, weighing on the stock in the interim.

This is precisely the tension that makes this income-generating trade strong. You are paid a premium to wait and see if the company’s massive bet pays off, with a comfortable margin of safety. Management is confident, guiding for “another year of double-digit revenue and operating income growth” for fiscal ’27. The key thing to watch is whether that capital spending starts delivering on the top line. The CFO stated an expectation for Azure growth to show “modest acceleration in the second half of the calendar year,” and that is the metric that will either validate the spending or vindicate the skeptics.

Wondering whether another stock offers a better yield, or what this same trade would pay on a name you already like? You can screen the latest cash-secured put yields across the market for yourself. And if it is exposure to technology as a whole you want rather than this one name, a technology ETF like VGT covers that single sector. Going broader than any one sector, to a quality-first mix across the whole market, is where the portfolio below comes in.

Getting Paid To Wait Still Leaves You Concentrated

Selling puts can pay you to buy a stock lower – but if that name is already an outsized part of your wealth, adding more is the opposite of what you need. Concentration is the real exposure, and cutting it back the usual way hands a slice to the IRS. There is a way to cap the downside and diversify out without the tax hit.