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FedLife Podcast | Ep. 167: Avoiding IRS Estimated Tax Penalties

By STWS
05/12/2026

In this episode, Ed and Dan discuss why many federal employees and retirees may need to make quarterly estimated tax payments and how failing to do so can result in costly IRS underpayment penalties. With more retirees receiving income from pensions, Social Security, investments, rental properties, Roth conversions, and other sources that may not have sufficient tax withholding, understanding estimated tax requirements has become increasingly important. This episode reviews how estimated taxes work, IRS safe harbor rules, and strategies to avoid unexpected penalties.


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FedLife Podcast (Ep. 167): Estimated Tax Payments Explained

Join us as Dan and Ed break down estimated tax payment requirements and share practical guidance for federal employees and retirees looking to avoid IRS underpayment penalties.

In this episode, you’ll learn:

  • Why certain types of income are not subject to mandatory federal tax withholding
  • How the IRS “pay-as-you-earn” system applies to retirees and investors
  • When quarterly estimated tax payments may be required
  • The estimated tax payment schedule and important due dates
  • How Roth IRA and Roth TSP conversions can create estimated tax obligations
  • The IRS safe harbor rules and how they can help avoid penalties
  • How to calculate estimated tax payments using the prior year’s tax return
  • Alternatives to estimated payments, including increasing withholding from wages, annuities, or Social Security benefits

Source Article: https://stwserve.com/some-employees-and-retirees-need-to-pay-federal-estimated-taxes-during-2026-to-avoid-irs-penalties/

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“Securities offered through Raymond James Financial Services, Inc., member FINRA/SIPC.  Investment advisory services offered through Raymond James Financial Services Advisors, Inc. Lee, Sipe & Associates, Inc. is not a registered broker/dealer and is independent of Raymond James.  Content represents the opinions of the speaker and not necessarily those of Raymond James.  Important Disclosure Information:  http://raymondjames.com/smicd.htm 

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