Social Security, Wash Sales, Taxes: Q&A #2617
The Retirement and IRA Show
Jim Saulnier, CFP® & Chris Stein, CFP®
4.3 • 729 Ratings
🗓️ 25 April 2026
⏱️ 71 minutes
🧾️ Download transcript
Summary
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.
The post Social Security, Wash Sales, Taxes: Q&A #2617 appeared first on The Retirement and IRA Show.
Transcript
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| 0:43.2 | This is the retirement and IRA show coming to you from beautiful Northern Colorado. |
| 0:48.8 | Join us as certified financial planner Jim Sondier, as well as Colorado State University Finance instructor and certified financial planner Chris Stein, teach you about IRAs, 401k's, annuities, |
| 0:56.2 | social security, pension plans, and estate planning in a fun and enjoyable show. |
| 1:01.4 | Whether you are listening live in Colorado or streaming from their website or iTunes podcast, |
| 1:06.8 | Jim and Chris want you to know that they're available to help you plan for your retirement. |
| 1:11.3 | Just visit their website at Jimhelps.com. |
| 1:14.5 | That's Jim H-E-L-P-S dot com. |
| 1:18.0 | And click the Meet the Team button on the homepage. |
| 1:20.7 | Now here's Jim and Chris with today's show. |
| 1:27.2 | Well, hello everybody and welcome to the Retirement and IRA show Q&A edition for this week. |
| 1:32.9 | A small change up. |
| 1:34.8 | Jim will not be joining me today. |
| 1:37.1 | He's traveling. |
| 1:39.1 | He's set for the next couple of weeks to do a bunch of traveling, actually. |
| 1:42.4 | So today he's having some fun at the airport. |
| 1:45.8 | So I recruited Jake from the office, who's been on the show quite a few times at this point, |
| 1:51.3 | and we're going to tackle the Q&A show today. As most of you know, if you're interested in sending |
| 1:57.8 | in a question for the Q&A shows that we do each week, the way to do that is to email Jim directly. |
... |
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