I would not sweat it so much... It is not on the radar of many people/accountants/investors. My Merrill account gives tax statements that are turned in to the IRS and it says nothing about this. I have filed it and have had no questions. Of course, to this point it has been small change and with a big win, I am sure the IRS would look more at it. But not necessarily. As unclear as this is, a good lawyer would be able to argue any grievance you would have with the IRS, for a lot less than a potential big win gone unnoticed! If you can do it, great, but if it is too late or can't, don't get bummed until you are looking at the 20 buy out. Then argue only if requested and there is a place for "no ill will intention" here. AND....I have always maintained the attitude, the more you are paying in taxes, the more you must be making.... so it is not all bad. Glass half full thinking. Certainly nothing to stress about. $25K potential difference for every $100K in profit. Bummer indeed, but if you have a $400K profit instead of a $500K profit, and you are mad as hell??? then... I suggest a different perspective. Optimization is great if it can be done. Just don't have an ulcer over it.