I have wondered about this exact situation too, and wondered about the exact meaning and scope of the wash rule. The intent of the wash rule was to insure you are "at risk" when selling and buying a stock back. Clearly if you sell for a loss and buy back the next day, the IRS will no let you deduct the loss. But in your case, are you still covered by the rule. You a selling today to report a gain and buying tomorrow, but if you now sell that stock a few months or years from now at a loss, can you take it? Since you once bought and sold withing 30 days, can you now take the loss? Could the IRS say "if you had just held that stock back in 2007, the loss you want to report now would not really have existed, it just would have decreased your gain, so therefore you were not at risk and you can't take your loss now"? I have never asked a certified tax person this question. Surely this board has one that could answer?P.