<prompt> Human: So, my wife works for a large multinational that has the ability to purchase stock at a 15 discount. It gets a little weird here, as the price is on the first or the last day of the offering period, whichever is lower.My wife is a bit nervous, as it deviates from our standard index funds only except bullshit employer 401ks with match strategy, but the way I see it, we are nearly guaranteed a 15 return on whatever we purchase, assume we sell as immediately as we are able to.For what reasons should I think this deal could have negative consequences?Edit: Ninja edit for paragraph formatting.2nd Edit: Just wanted to thank everyone for their comments. uMerakel has it correct on the price we pay, it is the lower of the two offering periods. The most contested comment thread talks about a buy and hold, which I dont think well do, as I dont particularly think the business has anything mind-blowing going on, and we are offered this every six months which means we have to lock up 20k, and sit with 40k unavailable for a limited period on the order of 1-3 weeks. Id prefer to simply liquidate, get the 15 less ordinary income taxes, and push any profits into our Vanguard accounts yes, guarding our vans, etc.. Thanks again PF!  <response>: No major negatives but a new things to keep in mind:-Some plans have restrictions on selling. If you sell immediately you may not be able to participate in the next offering period, or there might be a molding period. If your plan lets you sell immediately with no strings attached thats awesome-There may be a brokerage fee associated with selling shares and transferring money. Something on the order of 30 is what in charged.-Even if you can sell immediately there may be some lag before the shares end up in your account and you can actually sell. You may be subject to price changes during that time.If you plan to sell immediately you really shouldnt think of ESPPs as part of your investment portfolio. They behave more like a medium term savings account, where you can lock money away for a few months and see a nice return. 