MSFT Bearish Calendar Put Spread with 307% Upside


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This MSFT Calendar Put Spread Can Net 307%

Bearish play with a target stock price of $365

Strategy has +307% upside potential and 21% undervalued


Strategy: Long MSFT Calendar Put Spread
Sell 16-May-25 365 Put6.55
Buy 20-Jun-25 365 Put9.20
Debit:$2.65


Microsoft has seen its price drop -1.1% today to $386.39. The share price is currently in a downtrend, based on MSFT moving averages. Setting up this calendar spread with strikes at $365 gives you a bearish bias to tap into MSFT stock's weakness.

Option Profit Calculator Results for MSFT Calendar Spread at 16-May-25 Expiration

In this scenario, the optimal stock price for the option strategy would be $365.00 on the date of the first expiration, May 16, 2025. This is equal to the strike price of the options in the spread. Since MSFT is in a technical downtrend currently, and the strikes are below the current stock price of $388.41, the spread is taking advantage of the stock's downward momentum. If the stock price is $365.00 at expiration, we can benefit from the 16-May-25 put, which we sold, expiring worthless, and the option that we are long, the 20-Jun-25 put, will still have time premium built in.

Since we do now know what the exact implied volatility will be on May 16, we can use our historical data to make an educated estimate to help us calculate the value of the 20-Jun-25 option. Applying the median historical implied volatility of 25.0 from similar options, the theoretical value of the put is 10.78 at the date of the 16-May-25 expiration. Using the above assumptions gives us a potential upside of +307% for this calendar spread.

MSFT Calendar Spread Value vs. Market Price

According to Market Chameleon estimated value, MSFT Calendar Spread is trading at a 21% discount to historical benchmark.

If we use historical data to measure how similar spreads in MSFT were priced in the market, the 4-year average price was 3.35, with a high mark of 3.88 and a low of 2.89.

Currently, the calendar put spread is bid at 2.15 and offered at 2.65. The midpoint of the spread is 2.40.

If we use 3.35 as our historical fair value benchmark, the current market ask price is at a 21% discount, while the current market midpoint represents a 28% discount.

Current PriceHistorical Values of Similar Spreads
BidAskMidpointAverageHighLow
2.152.652.403.353.882.89
Market Chameleon captures daily records of market data to calculate historical benchmarks and generate estimated values.

Takeaway

The MSFT calendar put spread we've identified here can be a good way to play a bearish outlook because the option strategy has a +307% upside potential, is 21% underpriced relative to historical measures, and will benefit if the stock continues to trend lower to $365.

See how Market Chameleon can help you make smarter and more efficient trades!



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NOTE: Stock and option trading involves risk that may not be suitable for all investors. Examples contained within this report are simulated And may have limitations. Average returns and occurrences are calculated from snapshots of market mid-point prices And were Not actually executed, so they do not reflect actual trades, fees, or execution costs. This report is for informational purposes only, and is not intended to be a recommendation to buy or sell any security. Neither Market Chameleon nor any other party makes warranties regarding results from its usage. Past performance does not guarantee future results. Please consult a financial advisor before executing any trades. You can read more about option risks and characteristics at theocc.com.


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