@rooksmith to avoid underpayment penalty you need to pay during the year thru withholding or timely (usually quarterly) ES payments, the smaller of 100% of your 2024 (110% if 2024 AGI > 150k or 75k for MFS), or 90% of your 2025 tax - this is your 'safe harbor' amount.
If you had a windfall in 2024 and especially if your AGI was high forcing 110% of prior year tax, then paying ES based on prior year tax is likely to be an overpayment vs. ES based on 90% of current year tax. When you file 2024 TT will generate ES vouchers by default based on 2024 tax since that is known, and assuming your 2025 withholding is the same as 2024; unless you provide 2025 income estimates under Other Tax Situations / Form W4 and Estimated Taxes then TT will do the safe harbor calculation and reset your ES vouchers lower if applicable. If you are using desktop version you can see the calculation under Forms mode, "Est Tax Options". See also lines 1-9 on Form 2210. Ultimately you can just ignore the vouchers from TT if you have a better estimate.
As to skipping payment etc - IRS doesn't know the dates of all your income, by default IRS assumes your income and hence 'safe harbor' amount of tax due, and your withholding, occur evenly thru the year. These are annual totals simply divided by 4. The difference you need to make up in ES by default needs to line up with those even quarters, and the underpayment penalty is assessed on a quarterly basis. By Q1 you need to have paid 25%, 50% by Q2, 75% by Q3, 100% by Q4. So withholding is always considered timely if you are able to increase that to make up some of the difference also.
So you can't just pay it later, or 2-3 installments without incurring a penalty; even if you meet the annual total by the end - or even have a refund - you could still have a penalty for earlier quarters if they were underpaid. This is the "pay as you go" requirement from the IRS, otherwise we'd all ignore taxes until next January. Overpayment later in the year will not eliminate an underpayment for an earlier quarter, but the sooner an underpayment is corrected the sooner the penalty from that quarter will stop accruing.
So if you missed Q1 ES payment you can stop the penalty on that payment from accruing further by paying 50% of your ES total by Q2 deadline (tomorrow 6/16/25).
If you have very uneven income with big windfall especially later in the year then you can adopt the "annualized income" method on Form 2210 where you can show the more precise timing of your income and withholding to line up with one-off ES payments. It can be a lot of additional work and most useful if you have unplanned cap gains or Roth conversion say in Q4. Otherwise in this scenario it may be more beneficial to adopt ES based on prior year tax even if some penalty for missing Q1 as you would defer paying significant tax until April 2026. But the year after you need to revert to paying ES based on 90% of current year tax.
More info on ES - https://www.irs.gov/faqs/estimated-tax
Form 2210 instructions - https://www.irs.gov/pub/irs-pdf/i2210.pdf
