Missed your quarterly estimates this year? You’re not alone. The IRS underpayment charge is nondeductible, compounds daily, and snowballs fast. Writing a big check today will stop new penalty accrual from this point forward, but it won’t erase the penalties tied to the quarters you already missed.
There is, however, a lawful way to make it as if you paid each quarter on time. It relies on how the tax code treats withholding from retirement distributions.
The Core Idea
Tax withheld from certain retirement-plan distributions is treated as if it were paid evenly throughout the tax year, regardless of when you actually withhold. That timing rule lets you retro-allocate withholding to April/June/September/January and eliminate underpayment penalties for earlier quarters.
You can use that rule in two primary ways.