John Urban spent his career in enterprise software. He co-founded GT Nexus, a supply-chain network acquired by Infor in 2015. When he retired, he ran into a gap: plenty of tools project your finances out over decades, but almost none help you decide what to actually do this year, with taxes in mind. He built RetireSmartIRA to close that gap, a retirement tax-planning app for people managing Roth conversions, RMDs, IRMAA, and the handful of thresholds that quietly decide how much of their savings they keep. He lives in Northern California with his wife, Kathy. When he isn't modeling tax cliffs, he's usually spending time with old friends, reading, following Bay Area sports, or looking for a good bottle of wine.
Don't Let a Roth Conversion Trigger a Penalty
1 reply
AUTHOR: John Urban on 7/8/2026
FIRST: Michael1 on 7/9 | RECENT: Michael1 on 7/9/2026 at 3:41 AM


Comments
I appreciate your comments Dan and I’m really pleased that article had value for you. Thanks!
Post: A $30,000 Mistake
Link to comment from July 7, 2026
David, the muni-bond point is the one that catches most people off guard. Tax-exempt at the federal level, but it still counts toward IRMAA MAGI, so a portfolio heavy in munis can push someone into a higher tier without a single dollar of taxable income. Your $2,200/month Bronze experience is exactly the kind of real-world data point that makes the abstract thresholds feel concrete. And your closing line is the right frame. Better to be paying IRMAA than nowhere near it. Appreciate you sharing it.
Post: A $30,000 Mistake
Link to comment from July 5, 2026
Steve, I think that's a fair challenge. For many well-prepared retirees, especially those who are going to remain comfortably above the key thresholds no matter what, the Roth conversion decision may not move the needle as much as people hope. Where I think the issue still matters is income sequencing. Even if someone can't avoid higher income altogether, they may still be able to control which year income lands in: whether a capital gain is realized before or after Medicare, whether a QCD replaces a taxable withdrawal, whether a conversion crowds an IRMAA or NIIT tier. Those choices may not matter for everyone, but when they do, the dollar impact can be surprisingly large. So I agree with your larger point: this is not universal advice. For some households it is noise. For others, especially those near ACA, IRMAA, NIIT, or RMD-driven thresholds, it is worth modeling before acting. Appreciate the thoughtful comment.
Post: A $30,000 Mistake
Link to comment from July 5, 2026
Doug, this is one of the least-discussed cliffs out there, and you've described it exactly. The moment one spouse ages into Medicare, the ACA household drops from two people to one, and the income threshold that governs the under-65 spouse's subsidy compresses hard. Same dollars of income, much lower bar to clear. It's also a preview of something none of us really want to think about, but all of us eventually face. When one spouse dies, the survivor moves to single brackets and the single IRMAA tiers, and income that was comfortable for a couple can suddenly sit two or three tiers higher. The split-Medicare years are the first quiet rehearsal of that shift, while both spouses are still here to plan around it together. If you're already modeling the split-household ACA years, you're most of the way to modeling the survivor transition too. Same lever, same thresholds, just triggered by a harder event.
Post: A $30,000 Mistake
Link to comment from July 4, 2026
David, that's a sound approach, and running it through a few scenarios is the get to a plan that's right for you. One subtlety worth checking as you model it: the ACA hit and the IRMAA hit don't land on the same clock. ACA subsidy loss is same-year, based on this year's MAGI. IRMAA runs on a two-year lookback, so a conversion in 2026 doesn't surface as a surcharge until 2028. In the pre-Medicare conversion years, that means you can be absorbing an ACA clawback and pre-loading a future IRMAA surcharge from the same dollar, in the same year. It doesn't change your overall plan, but it can change the sequencing: how much to convert in which year, and where the bracket-fill line sits, so you're not stacking both hits harder than you need to in any single year. It's worth watching the two timelines separately as you run it.
Post: A $30,000 Mistake
Link to comment from July 4, 2026
William, thank you for reading, and for sharing this. You're describing exactly why the conversion math changes with age. Once RMDs are large and there's no long runway left for the lower rates to pay off, converting often just pulls the tax forward without a real payback. Paying as you go can be the best answer at that point. The one lever still worth a look at 80, if you give to charity is the QCD. It comes straight out of the IRA, counts toward your RMD, but never lands in your income. So it's the rare move that lowers the RMD dollars hitting your MAGI without a conversion. Even a modest QCD can be enough to keep you off the next bracket or IRMAA tier in a close year like the one you just had. You may already be doing this. If not, it might be worth a look before next year's RMD.
Post: A $30,000 Mistake
Link to comment from July 4, 2026
Andrew, you're not missing anything. You're right, and my wording was sloppy there. The 2029 gain does land in the 2031 IRMAA lookback, so it isn't avoided. It's paid, just later. What the deferral actually buys is narrower than "sidesteps both." In a pre-Medicare year, a large realization can hit twice at once: the ACA subsidy clawback and the setup for a future IRMAA surcharge, stacked in the same income. Moving it to 2029 clears the ACA cliff entirely (you're on Medicare) and turns the IRMAA piece into a single, known, budgeted surcharge year in 2031, rather than one hit compounding on top of another. So the benefit is separating and planning the two events, not escaping IRMAA. I should have said that. Your November routine is exactly right. Sizing the QCD each year to hold MAGI under the next threshold is the right move. It counts toward your RMD but stays out of MAGI, which is what makes it such a clean IRMAA lever once RMDs begin. Sounds like you're already on it.
Post: A $30,000 Mistake
Link to comment from July 4, 2026