There is no limit on the number of recharacterizations a taxpayer can conduct in a tax year. There is, however, a deadline on when this transaction must be completed. That is the taxpayer’s tax return due date, plus extension. There is a special rule however that if the tax payer files their taxes timely they get the automatic tax extension to recharacterize. In this case, since the tax payer may have filed their tax return already, an amended return will need to be filed.