Chris is joined by Jake Turner to discuss listener emails on tax filing for mega backdoor Roth contributions, a listener PSA on health insurance premiums, I Bond redemption timing, lowering RMD pressure, and Roth conversions.

(6:30) George asks whether leaving a 1099-R off a return after after-tax 401(k) money was immediately converted to Roth means an amended return is needed or whether the IRS will simply follow up.

(12:15) A listener asks whether HSA funds can be used pre-tax to pay fully self-funded health insurance premiums and requests a listener PSA if that treatment is allowed.

(17:30) The guys are asked how to evaluate redeeming high fixed-rate I Bonds over several years versus waiting until maturity and risking a large one-year tax bill and IRMAA hit.

(30:45) Jim and Chris hear from a widowed listener looking for ways to reduce future RMDs and IRMAA without using Roth conversions or QCDs.

(47:45) Another listener asks whether doing very large Roth conversions over a few years could make more sense than staying within lower tax brackets over a longer period.

The post Tax Filing, Health Insurance, iBonds, RMDs, Roth Conversions: Q&A #2611 appeared first on The Retirement and IRA Show.

Chris’s Summary

Jim’s “Pithy” Summary

A big part of that nuance is whether the pension is a non-covered one, meaning it replaces Social Security rather than sitting alongside it. That single distinction changes how you benchmark the savings rate entirely, and it’s the kind of thing that gets glossed over when people just throw out rules of thumb without knowing what’s underneath them. Chris and Jake also get into how pension income fits against the Minimum Dignity Floor — and why a pension that looks rock solid at retirement can tell a very different story decades later if there’s no cost-of-living adjustment attached to it.

There’s also a conversation worth hearing about lump sum options — what they’re actually worth, how to think about comparing them to the lifetime income stream, and why the big number isn’t always the better answer. If you have a defined benefit pension and you’ve been wondering how it fits into the bigger retirement picture, or whether you’re ahead or behind where you should be, this episode covers the framework for thinking it through.

The post Retirement Planning With a Defined Benefit Pension: EDU #2610 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on PSAs regarding IRMAA reimbursements, RMD in-kind transfers, and naming a conduit trust as a retirement account beneficiary.

(8:15) A listener shares a PSA that an IRMAA reimbursement was applied as a credit balance drawn down over several months rather than a lump sum.

(17:00) The guys discuss a listener PSA on SSA-44 filing: when income is underestimated and IRMAA is owed, Medicare reconciles the difference the following November or December with no penalties or interest assessed.

(33:45) George asks whether an RMD can be satisfied through an in-kind transfer of mutual funds to a brokerage account, and whether only a portion needs to be sold to cover the tax bill.

(46:00) Jim and Chris take up a listener question about naming a conduit trust as a contingent beneficiary for retirement accounts, kicking off Part 1 of a broader discussion on see-through and conduit trusts — what each structure is, how they differ, and what happens when an IRA names a trust as its beneficiary. They begin exploring the tax implications and planning considerations involved, noting that these arrangements can create both benefits and unintended complications depending on how they’re set up. The conversation will continue on the next week’s Q&A episode, where they’ll complete this listener’s question and address additional questions received on the topic.

The post IRMAA, RMDs, Conduit Trust: Q&A #2610 appeared first on The Retirement and IRA Show.

Chris’s Summary

Jim’s “Pithy” Summary

Tip 32 is one I feel personally right now: if you’re relocating in retirement, rent first. Never move anywhere with a vacation mindset. I’m doing it in Ohio as we speak, and I’d tell anyone thinking about a move to do the same. Tip 74 recommends lifetime gifting — and the way we handle it, that spending belongs in your Fun Number budget. There’s no written rule you have to wait until you’re gone to help the people you care about.

And tip 86 covers financial predators, which is largely solid — but there’s one line in there that made my blood boil when I read it. The implication is that an advisor charging lower fees might be a warning sign. I have never seen any consumer advocate say that. The 99 retirement tips review of this particular point raises a question worth sitting with: who exactly benefits from that framing?

The post Fisher’s 99 Retirement Tips, Part 2: EDU #2609 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security survivor benefits, IRMAA relief and the SSA-44 process, the Social Security earnings test, disclaiming inheritances that are brokerage accounts, and Roth conversion rules for retirees.

(6:00) A listener asks whether his wife’s early Social Security claim at 62 would reduce the survivor benefit she’d receive upon his death.

(14:00) George asks several questions stemming from a successful SSA-44 IRMAA relief request, including whether a retroactive refund is due, whether Step 3 covers the following year, and whether a separate filing is needed for his own income reduction.

(27:30) Jim and Chris respond to a listener who clarifies that benefits withheld under the Social Security earnings test are deferred, not lost, and are returned as a higher benefit at full retirement age.

(31:00) Georgette asks when it makes sense to disclaim an inherited brokerage account and whether passing the assets directly to their children is the right move.

(40:45) The guys are asked about the rules and tax implications of converting brokerage account funds to a Roth IRA, including whether having no earned income in retirement disqualifies someone from doing

The post Social Security, IRMAA, Disclaiming Inheritances, Roth Conversions: Q&A #2609 appeared first on The Retirement and IRA Show.

Chris’s Summary
Jim and I review Fisher Investments’ 99 Retirement Tips and begin working through the list, covering only a handful in this episode. We discuss estate planning basics such as having a will, the importance of reviewing estate documents, and considering living wills and trusts, with emphasis on incapacity planning. We then examine longevity statistics, why life expectancy at birth is often misapplied, and how that connects to retirement income decisions, including Fisher’s warning on annuities.

Jim’s “Pithy” Summary
Chris and I start digging into Fisher Investments’ 99 Retirement Tips and, true to form, we only make it through a few because I may have wandered down a rabbit hole or two. The estate planning stuff is straightforward—have a will, review it, don’t ignore the documents that matter if you’re alive but not fully capable. Death is easy administratively. Incapacity is where things get messy, and that’s where families struggle. And that’s where better planning matters most.

Then we get into longevity. If you’re going to say people might live longer than they think, you better use the right numbers. Not the “life expectancy at birth” headline stat. If a couple makes it to 65, the odds shift. That matters. That changes the runway. That changes how you think about income. It also changes how long that portfolio has to work, and how long decisions have to hold up.

And from there we run into the annuity warning. We’re not pro-annuity and we’re not anti-annuity. Many deserve criticism, but if longevity risk is real—and it can be—then you should evaluate lifetime income options on their merits. Social Security is guaranteed lifetime income. Income annuities are too, so they should belong in the conversation. Whether you use them depends on the situation, but you can’t talk about taking longevity seriously and then issue a blanket warning against annuities.

The post Fisher’s 99 Retirement Tips: EDU # 2608 appeared first on The Retirement and IRA Show.

Jim and Chris are joined by Jake Turner to discuss listener emails in this special tax related episode covering Roth conversions after RMD age, balancing Roth versus Traditional IRA contributions, HSA versus Roth contributions, IRA reporting questions, filing deceased tax returns, and a listener PSA on tax planning software.

(11:30) A listener asks whether converting to a Roth makes sense at age 75 while currently in the 12% bracket and taking RMDs, and whether recent tax law changes create a strategy opportunity.

(20:20) George wonders whether his 30-something children should continue using Roth contributions exclusively or begin balancing with Traditional IRA contributions as their wages increase, and asks what percentage split between Traditional and Roth accounts looks reasonable in retirement.

(48:45) The guys discuss whether covering medical expenses from an HSA and contributing to a Roth IRA, or leaving the HSA intact and paying medical bills out of pocket will result in greater retirement spending flexibility.

(57:00) Jim, Chris, and Jake address whether a spouse who retired during the year is considered covered by a workplace plan, how to answer prior nondeductible IRA contribution questions, and whether Form 8606 is required after making and converting a small IRA contribution in the same year.

(1:10:30) George asks how to handle the direct deposit of a refund on a deceased final 1040, including whether to use the estate bank account with an EIN or the decedent’s existing account, and whether a paper check remains an option.

(1:15:30) A listener PSA introduces Catalyst Tax Insights, a free tool to run “what if” scenarios and estimate taxes owed without using full tax software.

The post Tax Special – Conversions, Contributions, HSAs, Tax Returns, Tax Software PSA: Q&A #2608 appeared first on The Retirement and IRA Show.

If you would rather not listen to the guys’ banter about Jacob’s upcoming move to Iowa, Jim’s garden planning, and a listener correction about the word “imbibe” you can skip ahead to (33:30).

Chris’s Summary
Jim and I are joined by Jacob Vonloh as we discuss using Buffered ETFs prompted by a Morningstar article titled “Buffer ETFs Are Not for Everyone.” We explain how defined outcome ETFs use options to provide an explicit amount of loss protection over a given period while limiting potential gains, and we outline why these products are generally suboptimal for long-term investors. We then connect this to investment positioning, focusing on risk capacity, distribution planning, and why dollars assigned to delay-period Minimum Dignity Floor and Go-Go spending may require a degree of principal protection.

Jim’s “Pithy” Summary
Chris and I are joined by Jacob Vonloh as we take a listener-submitted Morningstar article—“Buffer ETFs are not for Everyone”—and use it to kick off what is going to be a series on principal protection. Morningstar does a very good job in this article laying out what it likes about buffered products, and it also makes some excellent points on where these types of products would fit and where they don’t fit. They’re not for everybody, but they could be of interest in certain cases, in a certain application, and we’re going to share how we use them.

What I want to do in this series is broaden the conversation. Buffered ETFs are just one type of principal protected product. There are multiple tools in that category, and we’re going to walk through where they fit into distribution planning. As you transition from accumulation into what I call the Venn diagram phase, and ultimately into distribution, you have to stop thinking of your portfolio as one big portfolio and start thinking in terms of smaller portfolios—investment positions—based on assigned spending. Dollars earmarked for a legacy position can be invested aggressively. Dollars earmarked for immediate spending—like the Go-Go reserve or the reserve for your MDF—need a degree of principal protection. This ties directly into the Secure Retirement Income Process and the See Through Portfolio and how we navigate asset positioning in retirement.

Show Notes: Morningstar Buffered ETFs article

The post Using Buffered ETFs: EDU #2607 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Medicare Part B decisions for retirees abroad, Social Security survivor benefit surprises, inherited Roth IRA distribution rules, and balancing Treasuries versus annuities when “safety” is more emotional than mathematical.

(6:45) A listener asks about situations where it might make sense to skip Medicare Part B, including retirees living abroad with strong foreign coverage and people who move to the U.S. later in life and must pay for Parts A and B.

(33:30) George asks why some widows and widowers don’t end up receiving the full benefit their spouse was receiving, even when the surviving spouse’s payment increases after the death.

(52:30) The guys respond to a question about whether an inherited Roth IRA requires annual distributions when the original owner was old enough to have RMDs, or whether the beneficiary can wait until year 10.

(1:11:00) Jim and Chris revisit the annuities versus Treasuries discussion through the lens of fear and peace of mind, including why someone might emotionally trust Treasuries more than insurer guarantees even if the math favors SPIAs.

The post Medicare, Social Security, Inherited Roth, Annuities: Q&A #2607 appeared first on The Retirement and IRA Show.

Chris’s Summary
Jim and I are joined by Steve Sansone as we revisit Cash Balance Plans and respond to listener follow-up emails.

(8:30) A CPA asks whether cash balance plans could be a fit for farmers with high income near retirement driven by deferred grain and equipment sales.
(18:30) A listener with two controlled-group businesses asks how a cash balance plan works with divergent profit cycles, whether it can support succession planning, and whether it makes sense if ownership works until death.
(36:45) A financial advisor asks for real-world details on costs, duplication/administration, duration, interest crediting rate risk, investment management, participant inclusion decisions, partner exits, lifetime maximums, and terminate/restart mechanics.

Jim’s “Pithy” Summary
Chris and I are joined by Steve Sansone as we dig back into cash balance plans, but this time we’re doing it by letting listener questions drive the conversation. We take three listener emails that each come at this from a different angle: one from a CPA working with farmers facing lumpy income near retirement, one from a family dealing with two controlled-group businesses that don’t behave the same way financially, and one from an advisor who’s basically saying, “Convince me this isn’t just theoretical.”

Chris and I talk with Steve about what makes these plans work and what makes them a headache—cash flow consistency, the “permanence” expectation, why manufacturers with lots of employees can be a tough fit, and how quickly the math changes when you have to fund meaningful benefits for staff. We also get into the stuff people don’t always hear in the sales pitch: what “interest crediting” really means, where the risk lives if returns don’t cooperate, and why newer market-rate designs change the conversation compared to older fixed-rate versions.

And we cover the messy real-life questions: what happens when partners leave, what it looks like to terminate and restart a plan, and why you can’t treat this like an investment strategy with a neat five-to-ten-year horizon. It’s a tax and retirement-acceleration tool with rules, tradeoffs, and guardrails—and Steve does a solid job laying out when it’s worth the complexity and when it’s just not.

The post Cash Balance Plans Part 2: EDU #2606 appeared first on The Retirement and IRA Show.