Social Security Filing, Roth 5-Year Rule, HSA Strategy, and Bond Principal: Q&A #2522

May 31, 2025

Social Security Filing, Roth 5-Year Rule, HSA Strategy, and Bond Principal: Q&A #2522

Jim and Chris answer listener questions on Social Security filing, a PSA on SSA’s online application process, the Roth 5-Year Rule, HSA strategy, and bond principal risk.

(8:00) A listener asks whether Social Security’s claim that delayed retirement credits aren’t applied until the end of the following year is accurate, and whether anyone receives them without persistent follow-up.

(29:15) The guys share a listener PSA with their experience applying for Social Security online and highlights the confusing communications around application status and approval timelines.

(18:15) George asks how and when to apply for Social Security if they want benefits to begin at age 70 and their birthday falls on the first of the month.

(35:45) Jim and Chris respond to a question about whether each Roth conversion has its own 5-year clock, even for someone over age 59½ with existing Roth IRAs.

(42:15) Georgette wonders how the Roth 5-Year Rule applies to non-spouse beneficiaries and whether it transfers from the original account holder.

(48:00) A listener shares their HSA strategy as a substitute for long-term care insurance, along with personal experience on how cafeteria plan deductions affected Social Security earnings.

(56:00) The guys explain whether bondholders risk losing principal at maturity when interest rates rise significantly.

Podcast: Play in new window | Download (Duration: 1:16:11 — 34.9MB)

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