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Social Security, IRMAA, ACA Planning, IRA to HSA Transfer, Annuities: Q&A #2552
Friday, 26 December, 2025
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. The post Social Security, IRMAA, ACA Planning, IRA to HSA Transfer, Annuities: Q&A #2552 appeared first on The Retirement and IRA Show.
