You can prepay some taxes early, but there are limits. You can make your Q4 estimated tax payment (due January 15) in December instead — this moves the deduction into the current tax year if you itemize. However, you generally cannot prepay your April tax liability due on an unfiled return. Prepaying state income taxes or property taxes only helps if the payment is actually due and assessed — the IRS disallows deductions for prepaid taxes that weren't yet owed. Due to the $10,000 SALT cap, prepaying state taxes often provides no additional benefit if you've already hit the limit. The strategy requires careful planning to actually generate a tax benefit.