In this example, you trade exposure on 100 shares of stock for exposure on 300 shares, but you avoid or delay exercise as well. At the same time, you net out additional cash profits, which reduces your overall basis in the stock. This makes exercise more acceptable later on. Of course, you can continue to use rolling techniques to avoid exercise. Another important point worth evaluating is the potential tax advantage or consequence. Options are taxed in the year that positions are closed; so when you roll forward, you recognize a loss in the original call transaction, which can be deducted on your current year’s federal income tax return. At the same time, by rolling forward you receive a net payment while deferring profits, perhaps to the following year. However, because the roll forward may involve in-the-money positions, the stock profit may revert to a short-term gain instead of the more favorable long-term gain.



