You are in the 35% federal tax bracket, but the federal withholding on your commissions is probably 22%. That means you have about $10,000 too little federal withholding just from that. You need to either make estimated tax payments or increase the withholding on your other income to compensate for the underwithholding on your commissions. (You could ask your payroll department if there's a way to increase withholding on your commissions, but usually there isn't.)