Jim and Chris discuss listener emails on Social Security benefits for a family with a disabled adult child, survivor benefits, ERISA vs. non-ERISA 403(b) protections, a listener PSA on Monte Carlo simulations, special needs trusts, and how a revocable living trust handles a primary home transfer.

(5:00) A listener asks whether her husband’s early Social Security filing while still working would suspend her child-in-care benefits, and whether his benefit would be recalculated to his Full Retirement Age amount once the earnings limit no longer applies.

(20:20) George wonders whether survivor benefits for his wife would be based on his age-70 amount or her Full Retirement Age amount.

(25:15) Jim and Chris take a question about the differences between ERISA and non-ERISA 403(b) protections, and whether state IRA protections offer comparable coverage.

(39:45) The guys share a listener PSA pointing them to a recent Retirement Answer Man episode on Monte Carlo simulations.

(44:00) Georgette enquires which assets belong in a special needs trust and how to structure it tax-efficiently.

(54:45) A listener asks how a primary home transfers to children through a revocable living trust and what the selling process looks like.

The post Social Security, ERISA, Trusts: Q&A #2616 appeared first on The Retirement and IRA Show.

Chris’s Summary
Jim and I are joined by Jake as we discuss tax rules and mistakes through two tax-focused PSAs before moving into listener emails. Jake covers a denied non-cash charitable deduction due to an incomplete Form 8283 and missing contemporaneous documentation, then walks through how estimated tax payments and safe harbor rules are calculated from prior-year tax liability. We then address listener emails on establishing home basis after a spouse’s death, how the senior deduction is reduced for married couples, and comparing IRA versus Roth withdrawal strategies.

Jim’s “Pithy” Summary
Chris and I are joined by Jake as we spend some time on two tax-focused PSAs from Jake before getting into listener emails. Jake walks through a tax court case where a non-cash charitable donation was denied because Form 8283 wasn’t completed correctly and the required documentation wasn’t done at the time—even though the donation itself was valid. This highlights how strict tax rules and mistakes around them can cost you. He also breaks down estimated tax payments—those quarterly amounts that show up on your return after you’ve already paid what you owed—and how they’re calculated off the prior year to get you into the safe harbor.

We then get into a situation involving a home purchased in the early 1970s, no improvements over the years, a spouse passing in a community property state, and now the question of what the basis actually is and how to determine it years later without anything documented at the time, which is more common than you’d think. There’s also a question on the senior deduction where the reduction ends up applying to each spouse, which changes the expected result. Finally, we look at two different withdrawal approaches using traditional IRA and Roth accounts over the next few years, and how those choices shift balances and taxes depending on how the income is sourced and what you’re actually trying to accomplish with it.

The post Tax Rules and Mistakes: EDU #2615 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security claiming strategies, financial education electives for a college student, a listener PSA on podcast word counts, inheritance planning, and SEP IRA conversions.

(11:15) A listener planning to delay Social Security to 70 asks whether proposed benefit caps should change that strategy. He also asks Chris for financial education course recommendations for his son at CSU.

(35:45) The guys address a question from someone who discovered SSA shows zero earnings on their work record for a year they actually worked, following an overpayment dispute, and whether submitting a W-2 can correct the record and trigger retroactive back pay.

(43:45) Jim and Chris share a PSA on podcast word counts, with a speaker-by-speaker breakdown to crown the King and Prince of Word Count.

(49:30) A listener wants to create four separate Roth IRA accounts, each with one of their four adult children named as beneficiary, with the idea that any lifetime gifts to that child come out of their future inherited share. They ask whether this approach is more complicated than it needs to be.

(1:09:30) George asks whether the money his son placed in a traditional SEP IRA can be converted to Roth, and how the IRS would treat it.

The post Social Security, Inheritance Strategy, SEP IRA Conversions: Q&A#2615 appeared first on The Retirement and IRA Show.

Chris’s Summary
Jim and I share retirement lessons learned from a listener’s account of his mother. Her husband’s survivor pension elections, combined with Social Security, left her a unicorn — secure income covering all expenses — yet she died regretting trips never taken despite a $9 million portfolio. The episode also covers why joint account ownership with adult children can create legal exposure, and the importance of funding a living trust while you are still healthy.

Jim’s “Pithy” Summary
Chris and I walk through three retirement lessons learned from a listener whose mother passed at nearly 100 years old — what she did right, what she regretted, and what almost worked but she ran out of time.

Lesson 1: Her husband elected survivor options on his pensions, and combined with Social Security, she had a steady stream of lifetime income long after he was gone. He thought ahead and protected her.

Lesson 2: That income, combined with a modest lifestyle, allowed her to amass millions and become what we call a unicorn — guaranteed income that covered every expense, discretionary and otherwise. But she died with regrets, not because she ran out of money but because she could never bring herself to spend it. Her son urged her repeatedly to spend more on fun, but she was a child of the Depression, and that created a mindset that no amount of counseling could change until it was too late. Her husband, who died at 66 was “the other guy” — he probably expected to live at least into his 80s — so did not get to enjoy the money either. These are exactly the kinds of situations the Fun Number was built for.

Lesson 3: She did do a great deal right with her estate — POA designations in place and proper beneficiary designations so no assets were subject to probate. She even had a living trust in the works – but she ran out of time to fund it, and that distinction — between having a living trust and actually funding it — is a surprisingly common mistake people make when they set one up.

The post Retirement Lessons Learned: EDU #2614 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security claiming strategies, IRMAA income adjustments, a listener PSA on the Roth five-year rule, conduit trusts for minor IRA beneficiaries and I-Bond tax reporting, and an inherited IRA passing through a trust.

(10:30) George asks about the Social Security “January Rule” and whether claiming in December 2027 or January 2028 would capture the most delayed retirement credits after reaching full retirement age in May 2027.

(21:00) A listener who retired early and has been performing Roth conversions asks whether he can also file an SSA-44 based on his wife’s upcoming reduction in work income, even though his conversions have been elevating their household MAGI.

(31:00) The guys review a listener PSA clarifying that the fifth year of the Roth five-year rule must be completed entirely—not merely begun—before the holding period is satisfied.

(39:45) Jim and Chris take a two-part question on how conduit trusts handle IRA distributions inherited by minor children, and whether the annual interest-reporting election used for EE bonds can also apply to I-Bonds.

(1:06:00) A listener whose father-in-law named a trust as the IRA beneficiary — rather than the daughters directly — is getting conflicting advice on whether the IRA funds must be taken immediately or if they can spread the distributions — and the taxes — over five years.

The post Social Security, 5-year Rule, Conduit Trusts, Inherited IRAs: Q&A #2614 appeared first on The Retirement and IRA Show.

If you would like to skip over the guys’ banter this week about Jim’s experience going to a Cincinnati Reds game, you can go to (7:00).

Chris’s Summary
Jim and I are joined by Jacob as we revisit buffered ETF mechanics in light of recent market volatility and explain why 100% and 20% buffers can still show interim losses. We also cover how renewals work, why resets are not taxable events in brokerage accounts, where these products may fit in retirement positioning, and a listener email comparing them with bonds and fixed indexed annuities.

Jim’s “Pithy” Summary
Chris and I are joined by Jacob as we go back into buffered ETF mechanics during a stretch where people are actually seeing movement in these products and questioning what they own. When markets pull back, even modestly, the expectation is that protection means no decline at all. Jacob walks through why that is not how these function in real time, and why a 100% buffered ETF can still show a small loss while a 20% buffered ETF can show more, even when the market decline remains within the stated buffer range. The distinction comes down to how these are priced day to day versus how the protection applies over the defined outcome period.

We also clarify how renewals work, what happens when values reset higher or lower, and how that process functions within a brokerage account. The discussion also covers how these may fit within portfolio positioning depending on how the dollars are being used. Jacob outlines how full principal protection may be used for nearer-term spending needs, including the Minimum Dignity Floor, while partial buffers may apply to longer time horizons where some level of downside can be accepted in exchange for additional upside potential. A listener email introduces the idea of using these as ballast, along with a comparison to bonds and fixed indexed annuities, including differences in liquidity, tax treatment, fee transparency, and how returns are delivered.

The post Buffered ETF Mechanics: EDU #2613 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security timing, whether you can “leave” your Social Security benefit to a spouse who doesn’t independently qualify, having a spendthrift trust purchase an annuity, and using a revocable living trust to manage aging parents’ complex financial affairs.

(13:15) A listener born in November asks what their Social Security benefit would be if they begin claiming now, before full retirement age, while still earning $100,000, and when the earnings penalty would lift.

(25:15) Jim and Chris field a question on whether you can “leave” your Social Security benefit to a spouse who does not independently qualify for Social Security.

(34:00) George asks how to structure his estate so that one child receives an inheritance in installments over 20 years rather than as a lump sum, and whether a trust purchasing an annuity could accomplish that goal.

(1:11:30) The guys hear from a listener who explains how being added as co-trustee on his aging parents’ revocable living trust resolved the recurring problem of financial institutions refusing to honor their power of attorney.

The post Social Security, Spendthrift Trust, Living Trust: Q&A #2613 appeared first on The Retirement and IRA Show.

Note: In this episode some information regarding the 5-year rule was misstated – one must get through the fifth, not just be in the fifth year. Jim and Chris clarify on the April 4, 2026 Q&A #2614 episode.

If you would like to skip over Jim and Chris’s banter on the weather, that manages to touch on Colorado water rights (an issue many east of the Mississippi probably find baffling), then you can start listening at (11:45).

Chris’s Summary
Jim and I continue our look through the Ed Slott IRA quiz, covering IRA recharacterization rules, how a surviving spouse may use a deceased spouse’s five year period following a spousal rollover, which IRA funds can roll into an employer plan, and the timing trap that can unravel the strategy of using an employer plan to separate after-tax basis from pre-tax funds.

Jim’s “Pithy” Summary
Chris and I are continuing our run through the Ed Slott IRA quiz — the questions Ed sends out after his twice-yearly training sessions to make sure advisors know not just the right answer but the reasoning behind it. That reasoning is where most people get tripped up, and this episode has several good examples of exactly that.

We start with IRA recharacterization rules — the deadline, what has to happen at the custodian level, how attributable gains or losses factor into the math, and a conversion planning tool that Congress took away in the 2018 Tax Cuts and Jobs Act. It was a strategy that made conversion timing far more forgiving than it is today, and the fact that it is gone still stings. From there we get into the Roth IRA five-year rules — specifically a spousal rollover scenario with a twist that most people, including Chris, do not see coming. The answer turns on a benefit the tax code extends to surviving spouses that is easy to overlook if you are not specifically looking for it.

We wrap up with which IRA funds can actually be rolled into an employer plan and why that distinction matters if you are sitting on after-tax basis inside a traditional IRA. There is a clean strategy for separating it, but there is also a timing mistake that catches people who think they have successfully pulled it off — when they have not. More people fall into that trap than you would expect, and the consequences are not trivial.

The post Ed Slott IRA Quiz Continued: EDU #2612 appeared first on The Retirement and IRA Show.