HSA Catch-up PSA, Social Security, IRMAA, Roth Conversion, Annuity Timing: QA #2640

October 3, 2026

HSA Catch-up PSA, Social Security, IRMAA, Roth Conversion, Annuity Timing: QA #2640

Jim and Chris discuss listener emails, beginning with a listener PSA on HSA catch-up contributions at age 55, then cover Social Security spousal benefits when claiming before full retirement age, paying IRMAA with HSA funds and the SSA-44 form for IRMAA appeals, whether a Roth conversion counts as a 60-day rollover, and annuity timing as interest rates fall.

(6:45) A listener shares a PSA noting that HSA holders age 55 and older can contribute an extra $1,000 per year until they reach Medicare age, and a spouse can do the same in their own HSA.

(22:00) The guys get a question on whether claiming Social Security at 65 still allows a spousal benefit of half their spouse’s higher benefit, or whether that requires waiting until full retirement age.

(27:15) Georgette asks whether IRMAA surcharges can be paid with HSA funds, following a prior episode’s mention that Medicare Part B and D premiums qualify.

(32:30) A listener seeking IRMAA relief after a spouse’s retirement payout wants to know which year belongs in section 2 of the SSA-44 form.

(45:00) Jim and Chris are asked whether a Roth conversion is treated as a 60-day rollover subject to the once-per-365-days limit.

(1:05:45) A listener who has attended several annuity sales presentations wonders why Jim doesn’t buy his planned annuity now and turn on the income later if payout rates are likely to keep dropping.

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