Social Security, IRMAA Taxation, 529 Rollover, Deferred Annuities: Q&A #2544

November 1, 2025

Social Security, IRMAA Taxation, 529 Rollover, Deferred Annuities: Q&A #2544

Jim and Chris discuss listener questions on Social Security COLA timing, spousal claiming strategy, IRMAA tax treatment, Roth IRA rollovers from 529 plans, and a listener PSA on deferred annuity RMD rules.

(8:00) Georgette asks whether her initial Social Security benefit—approved in September for a December start—will reflect the January COLA increase.


(15:30) A listener with similar PIAs and ages to their spouse asks whether it makes sense for one to claim early and the other to delay until 70.


(30:30) George shares his realization that the IRMAA surcharge appears to be included in the SSA-1099’s taxable benefit amount, and calls it out in a PSA.


(50:30) The guys respond to George’s question about whether a $5,000 rollover from a 529 to a Roth IRA will be treated entirely as contributions for tax-free early withdrawal.


(1:08:00) Jim and Chris address Peter’s PSA about calculating RMDs when comparing DIAs and FIAs with GLWBs for a future income stream starting at age 75.

Podcast: Play in new window | Download (Duration: 1:34:21 — 43.2MB)

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