dmertz
Level 15

Retirement tax questions

Taxes withheld in 2019 apply to your 2019 tax return, not to your 2018 tax return.  To have money from an IRA distribution made in early 2019 apply to your 2018 tax return you would have to have had the IRA distribution paid to you and then used by you to make a 4th quarter estimated tax payment (Form 1040-ES); tax withholding and estimated tax payments are applied differently.

 

Presumably your large amount of tax withholding in January 2019 will cover your tax liability for 2019.  If it won't, though, unless your IRA custodian can process an IRA distribution today, December 31, 2019 (or you don't want the likely increase in your taxable income for 2019), you'll want to have the distribution paid to you in 2020 and by January 15, 2020 use the money to make an an estimated tax payment for the 4th quarter of 2019.  However, estimated tax payments do not reduce the amount of underpayment for earlier quarters of the year, so while the estimated tax payment will reduce or eliminate any further increase in 2019 underpayment penalty, it will not reduce any underpayment penalty for the earlier quarters the way that tax withholding before the end of 2019 would.

 

Regardless with what you do for 2019, you are stuck with the underpayment penalty for 2018 if your tax withholding in 2018 and any estimated tax payments for 2018 where not sufficient or timely to avoid the penalty.