Social Security, IRMAA, ACA Planning, IRA to HSA Transfer, Annuities: Q&A #2552

December 27, 2025

Social Security, IRMAA, ACA Planning, IRA to HSA Transfer, Annuities: Q&A #2552

Jim and Chris discuss listener emails on Social Security filing timing and online claiming language, a listener PSA on IRMAA and the online SSA-44, ACA income planning before Medicare, an IRA to HSA transfer, and annuity income needs.

(6:45) The guys address how to word an online Social Security application so the first check is paid for a specific month when claiming at age 70, and whether applying 2–3 months before the 70th birthday is the right approach.

(14:00) A listener shares a PSA on filing SSA-44 online after retirement, including how IRMAA recalculations reflected estimated future-year income and how the resulting tier was communicated in the approval letter.

(25:00) Jim and Chris discuss whether it makes sense, from a planner’s perspective, to stop working and manage income in a way that keeps health insurance affordable until Medicare eligibility.

(38:45) George asks about doing the once-in-a-lifetime tax-free IRA-to-HSA transfer, how the HSA testing period works, and whether it’s worth doing before starting Medicare to reduce future RMDs.

(49:00) A listener asks whether annuity income is still useful for covering a minimum dignity floor gap when assets are high and spending needs are modest, and how to think about guaranteed income given planned retirement timing and gifting goals.

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