<prompt> Human: So my company does a 15 quarterly match of stock purchased through payroll deductions and once a year lump sum contribution, up to 25,000. My question is if I do a lump sum contribution of 25,000, short my companys stock, then wait a quarter, did I just find a way to get a 15 guaranteed return. What am I missing?  <response>: The holding period is what youre missing. Some such plans have no holding period, some have three years. A friend got burned badly on a three year holding period, even after a 20 discount. 