There are basically two events that would lead an investor to contemplate rolling a position: the option moving into the money and/or the option's imminent expiration. The first item to take into consideration is whether you're dealing with a European-style option or an American-style option. European options can only be exercised at the expiration date, whereas an American-style option can be exercised on any day prior to expiration. Generally speaking, most equity options are American-style, while most index options are European-style. This point is somewhat moot considering that few options get exercised prior to expiration, but be aware that it can happen. Still, what's more important than a possible premature assignment in options is your own decision-making process. Let's use a simple vertical spread as our example. Assume you took a bullish stance in XYZ stock by purchasing the May $50/$55 call spread. If XYZ is trading at $54.50 and the May options expired this weekend, what did you do? There's no absolute right or wrong action. And notice I haven't mentioned when you bought the spread or for what price. Those items should have no bearing on what you want to do now. The facts are that you currently own a certain number of shares of XYZ at $50. You can subtract the sale price of the $55 call to adjust your cost basis, but you get the point.