How to Determine the Best Way to Pay Federal Taxes on Large Roth Conversions

Описание: For many high-net-worth retirees, executing a Roth conversion feels like a home run—a way to reclaim your future from the IRS. But while converting from a Traditional IRA to a Roth is a powerful strategy, the way you pay for that conversion can be the difference between a tax-free legacy and an accidental IRS penalty.

This week, Adam Reed and Garrett Crawford dive into the tactical side of Roth conversions: the critical choice between estimated tax payments and federal tax withholding. They break down why your payment method matters for your long-term growth, the common traps of underpayment penalties in 2026, and how a "set it and forget it" withholding strategy might actually be shrinking your tax-free potential.

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00:00 Intro
01:30 Roth Conversions How To
03:50 Withholding vs Estimated Payment
08:50 59 and a half Penalty
09:45 Utilize the Brokerage Account
17:05 Concerns with Estimated Payments
22:15 Conclusion
24:46 Outro

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