Social Security, Milestone Ages, HSAs, Roth Withdrawals, Annuity Providers: Q&A #2641

October 10, 2026

Jim and Chris discuss listener emails on Social Security first check timing at age 70 and child-in-care spousal benefits, additional milestone ages and HSA contribution PSAs, Roth withdrawals under the Rule of 55, and finding annuity providers with good customer service.

(11:30) A listener asks whether Social Security benefits started in the month of a 70th birthday should arrive the following month, or only after the first full month at age 70, as the Social Security Administration explained.

(19:45) The guys field a question on whether a spouse can collect a child-in-care spousal benefit for caring for a stepson who became disabled at 21 and receives Supplemental Security Income.

(27:30) Jim and Chris share a PSA that 120 is a milestone age worth noting, since that is when the life expectancy factor used for most RMDs stops decreasing each year.

(34:30) Georgette notes that each spouse’s $1,000 HSA catch-up contribution must go into their own HSA and wonders whether Roth withdrawals of growth qualify under the Rule of 55 or must wait until 59½.

(43:15) The guys share another PSA pointing out that Rule 72(t), which allows penalty-free IRA withdrawals before 59½, is another milestone worth adding to the recent Retirement Milestone Ages episode.

(49:15) A fellow CFP® clarifies that Medicare enrollment, not age, ends HSA contribution eligibility, so someone working past 65 without Medicare can keep contributing, including the $1,000. catch-up.

(58:15) Jim and Chris address whether any annuity providers offer solid customer service.

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