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Do investors go long option contracts when they cannot cover the exercise of the options?
I do this often and have never had a problem.  My broker is TD Ameritrade and they sent several emails (and even called and left a message) the week of expiry to remind me I had in the money options that would be expiring soon. Their policy is to automatically exercise all options that are at least $.01 in the money.  One email was vaguely worded, but it implied that they could liquidate other positions to raise money to exercise the options.  I would have called to clarify but I had no intention of exercising and knew I would sell them before expiry. In general though, much like with margin calls, you should avoid being in the position where the broker needs to (or can do) anything with your account. As a quick aside:  I can't think of a scenario where you wouldn't be able to sell your options, but you probably are aware of the huge spreads that exist for many illiquid options.  You'll be able to sell them, but if you're desperate, you may have to sell at the bid price, which can be significantly (25%?) lower than the ask.  I've found this to be common for options of even very liquid underlyings.  So personally, I find myself adjusting my limit price quite often near expiry.  If the quote is, say, 3.00-3.60, I'll try to sell with a limit of 3.40, and hope someone takes my offer.  If the price is not moving up and nobody is biting, move down to 3.30, 3.20, etc. In general you should definitely talk to your broker, like others have suggested.  You may be able to request that they sell the options and not attempt to exercise them at the expense of other positions you have.