Retired and still surprised by a tax bill you didn’t see coming? In this episode, Ryan Herbert breaks down why many retirees continue writing checks to Uncle Sam and what’s often being overlooked along the way. From first-year retirement income surprises to how extra IRA withdrawals can trigger higher taxes on Social Security, the conversation unpacks common misconceptions about taxation in retirement. You’ll hear real-world examples of how income sources like pensions, TSPs, brokerage accounts, and Roth assets are taxed differently, and why withholding “defaults” can fall short.

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