I entered $0 for the sales that did not have a gain and the actual proceeds for those that did have a gain. That's what's not intuitive about the process. It sounds like you're not supposed to enter the sales that didn't have a gain. Why wouldn't you enter ALL transactions, those with a gain and those without? When you do that right now, the application is able to determine that there's a $0 gain for the sales at a loss, but it's unable to correctly match the transaction proceeds with the proceeds reported on the 1099K.
