As brokerages report it, you can, which is why there are so many people with the problem. If you sold a put option for instance and the underlying security drops below the money and you want to exit the position, you do in fact have to “pay someone to take the stock off your hands” or rather pay someone to exit the position. Hence the negative proceeds entry.
That said, the solution that I found is to correct the brokerage entry manually by doing the following:
If you have a negative proceeds entry, instead put $0 in the proceeds column and a positive offsetting entry in the cost column. As you are techincally "buying to close" the position this does make sense. This seems to have fixed the problem.
Critter 3 is right, albeit likely inadvertently.
