Underpayment penalty

[progree]

9. Yes, you met your tax obligation on a quarterly basis

I don't have any taxes automatically subject to withholding as I don't have earned income.

I calculate my tax liability in early December and then make a withdrawal from my IRA and have a sufficient amount withheld for my federal income tax.

All of my income is "unearned" - dividends, capital gains, Roth conversions, IRA RMD's ... I make my Roth conversions and IRA RMD's in December and so factor in the taxes on that in my 4th quarter estimated tax payment due January 15. And sometimes I check the withholding box too. I forget if Vanguard and Fidelity allow a higher percentage than whatever their default percentage is.

That said, I've filled out many a Form 2210 for underestimating my payments by a small amout. And/or asserting that my IRA RMD "income" and Roth conversion "income" were in December, so that I can pay taxes on those by January 15.

I've been using TurboTax for the last 5 years or so, so I forget the details. But I go through EVERYTHING on the tax return, whether prepared with TurboTax or a CPA, before filing it.