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I could adjust the withhold to cover that which would result in about a 1/3 reduction in take-home. Or I could send a check to the IRS from the proceeds of the stock sales. I do like the safe harbor idea, but given these details is that still the best way to go?

Meeting a safe harbor eliminates underpayment penalty. It is a good option.

If you send a check to the IRS, you will need to do an additional form with your taxes. If you adjust withholding, you don't. The choice is yours.
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