IRMAA, Widow Status, Roth Conversions, Annuity RMDs, and Rollovers: Q&A #2538

September 20, 2025

IRMAA, Widow Status, Roth Conversions, Annuity RMDs, and Rollovers: Q&A #2538

Jim and Chris discuss listener questions on IRMAA reductions and Roth-conversion effects, widow filing status and IRMAA, in-kind stock Roth conversions and RMD transfers, annuity RMD interactions, and 60-day rollover mail timing.

(7:45) George asks whether an approved SSA Form 44 that reduced 2025 IRMAA will also govern next year, how a large 2026 Roth conversion will be trued up and affect future IRMAA brackets, and whether that conversion will cause higher IRMAA in multiple subsequent years.

(18:45) A listener wonders if a recently widowed spouse’s IRMAA in 2026 will reflect single status or remain based on the 2024 joint tax return.

(24:45) The guys ask whether in-kind stock Roth conversions change the stock’s tax basis inside a Roth and whether an in-kind RMD transfer to a brokerage establishes a stepped-up basis.

(49:45) Jim and Chris consider a hypothetical where an IRA annuity’s annual payout might be less than the RMD and what happens if the RMD exceeds the annuity payment.

(1:02:15) One listener argues that claiming a mailed check took longer than 60 days to arrive is implausible because USPS optical scans and Informed Delivery images could let the IRS verify delivery dates.

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