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The thing that hurts more than paying taxes is when you're paying interest and penalties cuz that's just money flushed down in the toilet. And if you can avoid interest and penalties, do it. In the worst case, let's assume you paid estimates where because of tax planning your tax came out less. Worst case scenario, you have an overpayment, which you can either get refunded or apply it to next year. So you don't have to pay the estimates or you pay less estimates next year. You don't lose it, but at least you did not throw Yiddish gelt in interest and penalties to the IRS, for which we don't even know what they do with it.