Social Security, Roth 401k, HSA Reimbursement, Pension Options, Trust Planning: Q&A #2630

July 25, 2026

Social Security, Roth 401k, HSA Reimbursement, Pension Options, Trust Planning: Q&A #2630

Jim and Chris discuss listener emails on Social Security survivor benefit strategies, a Roth 401(k) catch-up rule loophole, HSA reimbursement for Medicare premiums, pension options including a lump sum rollover, and trust titling versus individual beneficiaries.

(13:00) — George asks whether his brother can claim his own Social Security benefit at 62 and switch to the higher survivor benefit at full retirement age.

(22:45) — A listener asks whether starting a new job in 2026 could exempt him from the new mandatory Roth 401(k) catch-up rule.

(28:45) — The guys field a question about using HSA funds to reimburse Medicare Part A premiums paid for a spouse before age 65.

(40:00) — Jim and Chris review a listener’s decision to take a pension lump sum and roll it into an IRA over the annuity options.

(1:13:00) — Georgette asks which accounts should be retitled into her trust versus left as individual beneficiary designations.

Podcast: Play in new window | Download (Duration: 1:26:19 — 39.5MB)

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