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Your answer is still confusing but I assume that you are arguing for the pay me now. I do not to expect to have any more Capital Gains the rest of the year.   I took $14,000 of my Capital Gains and bought a 3 month CD which vested last week.  I will use this $14,000  dollars to pay my living expenses for the rest of the year.  My current tax obligation is zero ( although my accountant had me make a $1000 dollar ES to Virginia last month). So I assume your pay me now argument is to do the $100,000 Roth conversion now,  and pay the $17,000 tax now instead of the $23,000 tax, Correct?.