Tax Filing, HSAs, I Bonds, RMDs, Roth Conversions: Q&A #2611

March 14, 2026

Chris is joined by Jake Turner to discuss listener emails on tax filing for mega backdoor Roth contributions, use of HSA funds, I Bonds redemption timing, lowering RMD pressure, and Roth conversions.

(6:30) George asks whether leaving a 1099-R off a return after after-tax 401(k) money was immediately converted to Roth means an amended return is needed or whether the IRS will simply follow up.

(12:15) A listener asks whether HSA funds can be used pre-tax to pay fully self-funded health insurance premiums.

(17:30) The guys are asked how to evaluate redeeming high fixed-rate I Bonds over several years versus waiting until maturity and risking a large one-year tax bill and IRMAA hit.

(30:45) Chris and Jake hear from a widowed listener looking for ways to reduce future RMDs and IRMAA without using Roth conversions or QCDs.

(47:45) Another listener asks whether doing very large Roth conversions over a few years could make more sense than staying within lower tax brackets over a longer period.

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