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Hi, about this: "For 2021, you need to pay up to 90% of your 2021 liability, or 110% of your 2020 liability, to avoid an underpayment penalty." For what it is worth, in 2020 I had a tax refund, no liability.

 

And this: "how much more would you have to pay by February 15 to get the total to equal 110% of your 2020 line 24?"  In 2020 I owed nothing.  My tax bill situation is only for 2021 following my May 2021 Roth IRA redemption. 

 

About 7 below: To make a reasonable offer for an OIC, I would have to tap into some portion of my IRA again either way.

 

Here is an interesting question: If I paid $20K by April 18, and then sometime much later IRS approved an OIC for the amount $20K, would I already be in the clear, with no penalties?