Appreciate the response and your assumption is correct. It is just a divider between two paths for the software to take - backend auto calcs or a more detailed questionnaire with user driven inputs. However, I hope you can understand that, for someone who's not a tax expert, the majority of the entire process of filing your taxes is about trying not to make a mistake. And for a factual error to be built into the interface is a little jarring. (ie for this step, select what you know NOT to be true) The other problem is that the backend auto calcs are not transparent at all. I only discovered them after the fact when I was checking the forms at the end and noticed the 8949 gains and losses were different than the 1099-B values.
Anyway, for this year I just selected "No" again and didn't bother with indicating that it was employee stock. I guess all I can do is hope that H&R Block comes out with a better competing product sometime soon.
