Jim and Chris answer listener questions on Social Security filing and its effect on HSA eligibility, Social Security means testing, the timing of annuity purchases in IRAs, the Roth and Roth TSP 5-year rule.
(7:30) Georgette asks whether the six-month Medicare Part A lookback is triggered by her husband’s Social Security application date or benefit eligibility date, and how that affects HSA contributions.
(22:45) A listener worries about possible future Social Security means testing for those who are past full retirement age but not yet claiming.
(36:30) George questions whether buying a Fixed Indexed Annuity inside an IRA is problematic if RMDs begin before maturity and whether turning on a living benefit might help him spend more.
(56:00) Jim and Chris weight in on an office debate on the Roth conversion 5-year rule.
(1:05:55) The guys clarify the Roth TSP 5-year rule and whether the clock resets when transferring to a new Roth IRA.

The post Social Security, Annuities, Roth and Roth TSP 5-Year Rule: Q&A # 2528 appeared first on The Retirement and IRA Show.

Chris’s Summary
I am joined by Jake and Paul to discuss OBBBA tax changes and retiree impacts from the Inflation Reduction Act. We cover changes to brackets, deductions, personal exemptions, and estate limits. Paul explains how new SALT caps, Social Security deductions, and ACA credit rollbacks affect planning opportunities for retirees, especially those near income phaseouts or considering Roth conversions and business deductions.

Jim’s “Pithy” Summary

Chris, Jake, and Paul talk through a range of retiree-focused updates, including several OBBBA tax changes and provisions from the Inflation Reduction Act. These aren’t just technical adjustments—they have real planning implications, especially for people navigating income limits, deductions, and benefits.

They cover updates to itemized deductions, new limitations for higher earners, and what’s changing with the lower tax brackets and standard deduction. Paul walks through how these changes might help—or get phased out—depending on your situation. There’s also a new personal exemption for those over 65 that sounds straightforward but includes some cutoff points retirees need to know about.

The Social Security deduction comes up too, and it’s not what most people think. Paul clears up who qualifies and how it works. They also talk about the rollback of enhanced ACA premium credits and how enrolling in Medicare affects HSA eligibility. Some of the rules people have counted on in the past won’t function the same going forward.

They touch on other updates as well—charitable giving, estate and gift exemptions, even vehicle loan interest. Not all of it applies to everyone, but plenty of retirees could be caught off guard by the fine print.

The post OBBBA Tax Changes Explained: EDU #2528 appeared first on The Retirement and IRA Show.

Jim and Chris answer listener questions on Social Security family maximum rules, spousal and disabled child benefits, defined benefit pension concerns, and 401k managed payout funds.
(7:45) A listener is trying to understand how the Family Maximum Benefit might reduce the amounts paid to his spouse and disabled adult child once he claims his own retirement benefit.
(16:45) Jim and Chris respond to a listener who has a disabled son and is planning to claim a spousal benefit based on his wife’s record. He asks how the family maximum could affect his son’s eligibility for SSDI and future Medicare access.
(30:00) George asks for input on whether to take monthly payments or a lump sum from his pension weighing the potential risks if the company eventually transfers the pension to an insurance company.
(49:00) The guys address a question about a “Managed Payout” fund offered in a 401(k) plan and whether this might be a good way to generate retirement cash flow compared to annuities.

The post Social Security, Pension Buyouts, and Managed Payout Funds: Q&A #2527 appeared first on The Retirement and IRA Show.

Chris’s Summary:
Jim and I examine broker vs advisor sold RILAs using real cap rate comparisons from 2024 to highlight how identical contracts can offer different outcomes. We explain how six-year outcome periods work, what locking in gains actually does, and when fees can reduce returns more than commissions. This episode is less about product bias and more about understanding the trade-offs between access, structure, and transparency in how these annuities are priced and delivered.

Jim’s “Pithy” Summary:

We also dig into the mechanics of locking in gains early. Some RILAs let you reset into a new term right away, while others force you into a cash-style holding account until the original term ends. That difference can make or break your returns. And if you’re thinking “buffered ETFs already do this,” you’re right—we talk about that too.

But the real highlight today is the cap rate comparison between broker vs advisor sold RILAs. Same insurance company. Same date. Same indexes. And yet, in multiple examples, the commission-based version offered meaningfully better cap rates—even after accounting for advisor fees. In one case, the broker version had a 60% cap while the advisor version capped at 30%. So much for the narrative that fee-only automatically means better. It’s a great reminder that both commissions and fees are just compensation structures—and neither tells you whether a product is actually better for the client.

The post Broker vs Advisor Sold RILAs: EDU #2527 appeared first on The Retirement and IRA Show.

Jim and Chris shares listener PSAs on IRMAA and Delayed Retirement Credits, and answer questions on Social Security Spousal Benefits, annuity use cases, and fixed indexed annuity payout concerns.

The post PSAs, Spousal Benefits, Annuity Use Cases, and FIAs: Q&A #2526 appeared first on The Retirement and IRA Show.

Chris’s Summary:
Jim and I explore registered index-linked annuities and compare RILAs vs buffered ETFs across liquidity, taxation, and cap rate dynamics. We walk through how the insurance and investment structures differ, where principal protection varies, and how commission-based and advisory products compare from a fiduciary standpoint. I also explain the tax treatment of qualified versus non-qualified annuities and why IRD status matters when evaluating options for legacy planning.

Jim’s “Pithy” Summary:
Chris and I dig into RILAs—Registered Index-Linked Annuities—and boy, do these things get pushed hard. They’re the lovechild of fixed indexed annuities and variable annuities, designed to sit in the middle of the risk spectrum. I call them the insurance industry’s answer to buffered ETFs and structured notes. The appeal? Some downside protection, some upside potential, and growing popularity with both brokers and RIAs.

But here’s the kicker: the same annuity from the same insurance company can have wildly different cap rates depending on whether it’s sold by a broker (commission-based) or an investment advisor (fee-based). I’ve seen broker-sold versions offer higher cap rates than advisory versions—even after paying a commission! That’s why I harp on this: if you’re considering one, you’ve got to compare both sides of the distribution channel. Otherwise, you might end up paying an advisor 1% a year and getting less upside than if you’d bought it through a broker. It also pays to compare RILAs vs buffered ETFs with regard to taxation, liquidity, and advisor compensation. These all factor into whether these products make sense.

I’m not anti-RILA. They can be compelling—especially in IRAs where the tax downsides of non-qualified annuities don’t bite as hard. But outside retirement accounts, the tax treatment stinks: no step-up in basis, income taxation, IRD status—it’s a mess. So, if you’re going to lock up your money, know exactly what you’re giving up in liquidity and tax flexibility. And for heaven’s sake, check those cap rates side-by-side!

The post RILAs vs Buffered ETFs: EDU #2526 appeared first on The Retirement and IRA Show.

Jim and Chris begin with three PSAs on Social Security experiences, then answer questions on fixed indexed annuities with market value adjustments, SPIA payout options for the Minimum Dignity Floor, and the tax aggregation rule for MYGAs.
(11:30) In this PSA Georgette clarifies that her husband, born February 1, received January benefits at full age 70, with payments starting at the end of January.
(19:45) A listener shares a PSA about their struggle recovering original documents from the SSA after submitting an IRMAA appeal and only getting help after contacting her senator.
(24:15) The guys read a PSA from a listener whose Social Security application was approved, but his first payment was withheld due to how he reported earnings; he later filed an appeal and was paid.
(36:00) George asks why the EDU episode on Fixed Indexed Annuities didn’t mention five-year FIAs with market value adjustments and no surrender fees, noting one issuer allows early access with interest rate risk.
(54:00) Jim and Chris address when they may recommend SPIAs with life-only vs. return of premium options, discussing how payout levels vary based on longevity risk-sharing.
(1:12:15) A listener asks whether a 1035 exchange into a different insurer’s MYGA can avoid the tax aggregation rule; Jim explains how proration works and why the trade-off might not be worth the hassle.

The post Social Security PSAs, FIAs, SPIAs, and MYGAs: Q&A #2525 appeared first on The Retirement and IRA Show.

Chris’s Summary:
Jim and I continue our focus for Annuity Awareness Month by explaining how fixed indexed annuities work and the regulatory nuances that distinguish them from other fixed products. We walk through their structure, common misconceptions, when they can be appropriate, and how to compare them to MYGAs and buffered ETFs. We also highlight the motivations behind annuity recommendations in the financial services industry and the risks of proprietary index products.

Jim’s “Pithy” Summary:
With Annuity Awareness Month continuing through June, Chris and I wade into the world of fixed indexed annuities—what they are, how they work, and why they’re not universally good or bad. I explain how they use options to generate index-like returns, how the “fee is baked in,” and how they compare to MYGAs and the buffered ETFs Wall Street has been offering over the past five or six years. If you’re locking up your money for five or ten years, you need to understand what you’re getting—and what the person recommending it is getting too.

We also break down how advisory platform annuities are changing the landscape. Advisors who used to bash annuities now love them—because they can charge their AUM fee inside the annuity without holding an insurance license. But the one actually recommending the product and earning the commission? That’s the wholesaler, and they’re not a fiduciary. And while some moves might be justified, I’ve seen plenty that just don’t sit right. If someone’s trying to move you from one annuity to another, you’d better ask what you’re giving up—and what they’re getting in return.

I also share what I found digging into one of those so-called “uncapped” proprietary indexes. I used ChatGPT’s deep research tools and spent a good 45 minutes pulling disclosures apart—and what I found didn’t impress me. These indexes often skim returns off the top and bury fees most agents can’t explain. If you’re being sold one of those, do some homework. We’ll get into RILAs next week—because yes, I ran out of time.

The post Fixed Indexed Annuities: EDU #2525 appeared first on The Retirement and IRA Show.

Jim and Chris address questions on Social Security survivor benefits, unreimbursed HSA expenses, SPIA funding from multiple accounts, and Fixed Indexed Annuity details.

(7:45) Georgette asks whether drawing her own reduced Social Security benefit at 62 will affect her ability to switch to her deceased husband’s full survivor benefit at age 67.

The post Social Security, HSA Rules, SPIA Funding, and FIA Details: Q&A #2524 appeared first on The Retirement and IRA Show.

Chris’s Summary:
Jim and I discuss annuity types and features during Annuity Awareness Month, focusing on immediate vs. deferred annuities and fixed vs. variable structures. We cover how each type works, what they offer, and where caution is warranted.

Jim’s “Pithy” Summary:
Chris and I continue our Annuity Awareness Month series by diving into the foundational aspects of annuities—what they are, how they work, and what to watch out for when buying one. We explain the four primary annuity types and features—immediate, deferred, fixed, and variable—and share why understanding the difference between a noun and a verb matters in this world. When you annuitize, that’s the verb; you’re locked in, and there’s no getting out. That’s why we call deferred income annuities a big commitment—once you’re in, there’s no divorce clause!

I share my concerns with the tax deferral hype, especially when annuities are held inside IRAs. Many folks mistakenly believe they’re gaining tax advantage, but in reality, they might just be compounding future tax headaches. We talk about how annuities can offer principal protection and guaranteed lifetime income—but not all annuities do both. And we dive into what happens if you die early or live long, covering things like period-certain options, cash refunds, and installment refunds.

We also walk through the origin of single premium immediate annuities as a modern-day answer to tontines—yes, those ancient, now-outlawed mortality pools where surviving members collected increasingly larger checks. Mortality credits are still alive and well, just repackaged into today’s SPIAs. And if you’ve ever been pitched a variable annuity with enhanced death benefits or living benefits, we explain how those work, what they really cost, and why you need to read the fine print. From mortality and expense fees to revenue-sharing subaccounts, there’s a lot going on behind the scenes.

The post Understanding Annuity Types and Features: EDU #2524 appeared first on The Retirement and IRA Show.