Like the answers to so many other questions – ‘It depends’. To avoid penalty, the taxpayer will want to prepay taxes that are the lower of last year’s tax bill or the current year projected tax bill. We’ll do the math to figure out how you can prepare by prepaying the appropriate amount of tax, knowing what we can about the current year vs the prior year. The trick is to balance prepayment of taxes with considering the best use of your income and cash flows.