Spousal Roth, Backdoor Roth, Social Security, Post-Tax Contributions, HSA Strategy: Q&A #2542

October 18, 2025

Jim and Chris discuss listener questions on spousal Roth IRA eligibility, backdoor Roth contributions using a solo 401k, Social Security timing, post-tax contributions to an IRA and 401k , and an HSA strategy coordinating withdrawals with Roth conversions.
(9:30) George asks whether he can contribute to a spousal Roth IRA after his retirement if his wife continues working and their income meets eligibility thresholds.
(20:00) A listener wonders if switching from a SEP IRA to a solo 401k would allow him to make backdoor Roth contributions and improve tax deductions.
(31:45) The guys address a listener’s plan to claim Social Security at 62 despite having sufficient pension income and IRA savings.
(1:01:30) Jim and Chris respond to a question about making post-tax contributions to a traditional IRA and whether post-tax 401k contributions converted to a Roth 401k right away ever create basis.
(1:05:45) A listener considers paying medical expenses from his HSA instead of IRA withdrawals to allow more room for Roth conversions without increasing taxes.

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