Cracking the Code on Estimated Tax Penalties

Trevor Lawson tackles a timely and often expensive issue for retirees and business owners: the surge in underpayment penalties for estimated taxes. With penalty rates nearly doubling since 2021, Lawson explains how taxpayers with non-withholding income—such as investment gains, self-employment earnings, or Roth IRA conversions—can inadvertently trigger interest-based charges by failing to pay taxes quarterly. The discussion outlines essential "safe harbor" strategies to avoid these costs, including paying 90% of the current year’s tax or 100-110% of the prior year’s tax in equal installments. Lawson shares a pro tip for retirees: using late-year IRA withdrawals with high tax withholding to satisfy annual liabilities, as the IRS treats these withheld amounts as if they were paid evenly throughout the year.Securities and investment advisory services offered through Osaic Wealth, Inc. member FINRA/SIPC. Osaic Wealth is separately owned and other entities and/or marketing names, products or services referenced here are independent of Osaic Wealth. Branch phone: 919-546-0400.