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I just read Roy's article regarding estimated taxes and was hoping for an answer to my question. Unfortunately, if it was there, I didn't catch it.

In July I plan to sell some stock to diversify my portfolio. Unfortunately, Unca Sam will take his share, and a nice sum, no less. I recently lowered my W-4 exemption to '0' in anticipation of this event, but I'll still be short by $1500 if the current price holds. I'm pretty sure I'll reach the 'safe harbor' that Roy speaks of, but I'm still curious as to whether I can be liable for the underpayment penalty as this is an isolated (unpredictable) event. Could the penalty be avoided by submitting a quarterly voucher in Sept, e.g.?

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