Tax Filing, Health Insurance, iBonds, RMDs, Roth Conversions: Q&A #2611

Chris is joined by Jake Turner to discuss listener emails on tax filing for mega backdoor Roth contributions, a listener PSA on health insurance premiums, I Bond 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 and requests a listener PSA if that treatment is allowed.

(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) Jim and Chris 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.