Your plan is pretty generous compared to mine. I take my measly 5% discount and run. This means placing a market sell order immediately after the shares appear in my brokerage account, which always happens after hours. So you see I am not willing to tolerate much downside risk with this at all. My company does not have a particularly bad outlook, but I figure I have more than enough exposure to its stock price through stock options that I still have. Your situation seems different. There are not too many trading days left in 2007. If you really expect to be in a lower tax bracket next year, I would wait till January.