Rolling LEAP Options

The practice of extending the trading duration of holding options to the next trading period

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What is Rolling LEAP Options?

Rolling LEAP options refers to extending the trading duration of stock options to the next trading period. Investors rollover options to manage a winning or losing position. In a losing position, they extend the time to hopefully prevent losses before they close the position. However, they must possess sufficient and reliable data to support their decision. Otherwise, they stand to incur larger losses.

Rolling LEAP Options Diagram

If there is a sign of continuous improvement, there is no need to close the position. The prudent action will be to extend the trade. The ideal scenario might be one where the price is quite close to where the investor wants it to be. So, by extending the duration, the investor might make a higher gain or avoid a loss.

LEAP Options vs. Shares

LEAP options are long-term (expiration more than one year ahead) options on stocks. With the introduction of LEAP options, investors can now leverage long-term option opportunities as a buy-and-hold investment. Because of this, investors don’t need to make a large capital outlay. By rolling LEAP options, they can extend their market position further into the future. LEAP stands for “Long-term Equity Anticipation”.

Understanding the Rolling Over Options Process

Rolling LEAP options involves simultaneously closing the existing position and opening a new position at a different strike price, or with a different expiration, or both. One LEAP option contract can replace another LEAP option contract by extending the expiration date. If the option has low volatility, the investor stands to maintain higher leverage with minimal transaction costs.


Let’s say Joe is investing in LEAP option trading. In the stock market, the price of Company X’s stock is $25 per share. Joe decides to purchase at-the-money LEAP options on the stock. Since he is trading options, he pays a premium price of $2.05 per share. He buys 100 LEAP options contracts with a strike price of $25 and a hold period of 1 year. Each contract, in this case, contains 100 shares. So, in total, he has optioned 10,000 shares (100 contracts x 100 shares/contract).

The total value of the shares is $250,000 ($25 per share x 10,000 shares). However, since he is trading option contracts, he only needs to pay a premium fee of $20,500 ($2.05 premium price x 10,000 shares). For Joe to break even, the stock must trade at $27.05 ($25 strike price + $2.05 premium price). Therefore, for him to make a profit, Company X stocks must trade above $27.05.

Let’s say that the stock is trading at $26.50 when the expiration period has just a few weeks to go. He might decide to roll his LEAP options to the next trading period in anticipation of an increase in share price. This is a reasonable decision because the price is near where he wants it to be and has moved in the direction he anticipated. It may only require a little more time to make him a profit.

When is the right time to roll an option?

Rolling LEAP options is entirely a subjective decision. There is no definitive guide regarding the right time to roll them. However, there are a few important considerations to factor into the decision.

1. What were the investor’s initial assumptions?

The investor should consider whether his original assumptions about the investment are still valid. If his viewpoint is now negative, based on either price changes or company news, then he/she might decide to against rolling over his LEAP option.

2. Whether holding the option is the best use of capital

Even if rolling over their LEAP option may be profitable, if the investor speculates they will, at best, enjoy minimal gains, then they might consider closing out their position and using the money elsewhere where there is a better opportunity.

Rolling LEAP options is a simple way for an investor to maintain a low-cost position in a stock over a longer time frame. The rollover may be done in hopes of avoiding a loss or with a view to making a greater profit.

More resources

Thank you for reading CFI’s explanation of rolling LEAP options. CFI is a provider of the Capital Markets & Securities Analyst (CMSA®) certification program and financial analyst training. To keep advancing your career, the additional resources below will be useful:

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