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Thanks for the replies and worthwhile advice. Although I tried entering a sale of an OTM put option today and apparently it is not allowed through my broker. I am using Scottrade. (It was not a financial stock). Perhaps it is against their policies & I should switch to a better brokerage...

Lets say for example that you decide to sell an OTM call option on a stock. Expiration day rolls around and the option is still OTM. Are you required to buy back to option to close the position?