Everything You Wanted to Know About Options but Were Afraid to Ask
IBKR Podcasts
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How to Trade Short Options
The two parties involved with the initial trade is completely random if one if the one who's long decides to exercise the person who's sold it to them may not be assigned at all from that person but maybe paired up with a different trader. There are some reasons for that and what you need to really think about in that case is if you are long options If you are long especially American style options you always maintain the right to exercise. People have a financial incentive to exercise certain options more than other options.
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