Social Security, Wash Sales, Taxes: Q&A #2617

April 25, 2026

Social Security, Wash Sales, Taxes: Q&A #2617

Chris is joined by Jake Turner, while Jim is traveling, to discuss listener emails on Social Security spousal benefits, wash sales across brokerage and IRA accounts, estimated tax payments for Roth conversions, and tax withholding strategies in retirement.

(6:45) A listener asks when an ex-spouse can claim a spousal Social Security benefit and if retroactive benefits are available.

(19:20) The guys address if a surviving spouse automatically receives the higher benefit upon their spouse’s death, and why the family maximum benefit is affecting a couple who are each collecting their own individual benefit.

(30:00) A listener wonders how wash sales are tracked across different account types, and if buying back only half the funds results in only half of the sold funds qualifying as a wash sale.

(42:31) Chris and Jake help determine if a Roth conversion requires quarterly estimated tax payments throughout the year or just a single year-end payment.

(55:00) George wants to know if skipping tax withholdings on a pension and part-time job is acceptable when prior over-withholding is expected to cover the year’s tax bill.

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