IRA Rollover Mistakes and Exceptions: EDU #2542

The Retirement and IRA Show

Jim Saulnier, CFP® & Chris Stein, CFP®

Business, Investing

4.3 • 730 Ratings

🗓️ 15 October 2025

⏱️ 81 minutes

🔗️ Recording | iTunes | RSS

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Summary

To skip over Jim and Chris chatting about the government shutdown delaying Social Security and Medicare announcements, and Jim’s upcoming travel plans—including concerns about flight delays and his upcoming elk hunt in Utah you can skip ahead to (8:15).

Chris’s Summary
Jim and I walk through common IRA rollover mistakes and clarify the once-per-year rollover rule, including exceptions for Roth conversions and employer plan transfers. We explain the differences between direct and indirect rollovers, how constructive receipt is determined, and when a spousal rollover might cause unexpected tax penalties. We also outline when 60-day rollovers can still be useful, especially with maturing MYGAs, and share practical tips to avoid triggering unexpected distributions.

Jim’s “Pithy” Summary
Chris and I cover IRA rollover mistakes—especially the ones that crop up with 60‑day rollovers. We’re talking the kind of errors that can cost you taxes, penalties, and your sanity. This all started with some emails about the 60‑day rollover strategy for Roth conversions, but it quickly turned into a full‑blown EDU on how rollovers go sideways—fast.

We explain the difference between a direct and indirect rollover (hint: if you’re frolicking in dollar bills on your living room floor, it’s indirect), why you can’t do more than one IRA‑to‑IRA rollover per 365 days, and how the IRS finally shut down the old rollover shuffle thanks to the poor guy in the Bobrow case—who won one fight and lost the big one in the same ruling.

Then we take it further. Surviving spouses? You’ve got options. But if you’re under 59½ and roll inherited IRA money into your own account too soon, you just triggered the 10% penalty. Only a spouse can do that kind of rollover, by the way. Chris and I get into a whole scenario with a dead husband, a widow, and a girlfriend who didn’t get the memo on common‑law marriage. No joke.

And if you’re sitting on a MYGA in an IRA, you better pay attention when that thing matures. Insurance companies love to auto‑renew on day 31, and we explain how a 60‑day rollover can give you breathing room—if you haven’t already used your one for the year. Our go‑to move with IRA‑based MYGAs? You guessed it: the 60‑day rollover. Just don’t mess it up or you’ll blow your chance at penalty‑free flexibility—and that includes protecting your Minimum Dignity Floor.

The post IRA Rollover Mistakes and Exceptions: EDU #2542 appeared first on The Retirement and IRA Show.

Transcript

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0:00.0	The retirement and IRA show represents the words and views of the show hosts exclusively and should not be construed as investment legal or tax advice. All information is believed to be from reliable sources. However, we make no representation as to its completeness or accuracy. All economic and performance information is historical in nature and is not indicative of any future results. Any indices mentioned on the show are unmanaged and cannot be invested indirectly. Diversityiversification and asset allocation strategies do not assure profit or protect against loss.
0:23.7	Never make any investment or financial decisions based on information offered on this show
0:26.8	without first consulting your financial legal or tax advisor.
0:29.6	Financial planning services offered through Jim Solnier and Associates LLC, a registered investment advisor. This is the retirement and IRA show coming to you from beautiful Northern Colorado.
0:47.8	Join us as certified financial planner Jim Sonier, as well as Colorado State University
0:52.8	Finance instructor and certified financial planner Chris Stein teach you about IRAs for Jim Sondier, as well as Colorado State University Finance Instructor and Certified Financial
0:55.1	Planner Chris Stein teach you about IRAs, borough in case, annuities, Social Security,
1:01.1	pension plans, and estate planning in a fun and enjoyable show. Whether you are listening live in
1:06.8	Colorado or streaming from their website or iTunes podcast, Jim and Chris want you to know that
1:12.4	they're available to help you plan for your retirement.
1:15.3	Just visit their website at JimHelps.com.
1:18.4	That's Jim H-E-L-P-S dot com and click the Meet the Team button on the homepage.
1:24.7	Now here's Jim and Chris with today's show.
1:30.3	Good day, everybody. Welcome to the retirement and R-R-R-A show, EDU edition this week.
1:38.0	On today's show, we're, was kind of prompted by several emails we've gotten recently asking us about IRA rollovers
1:49.8	and we had recently discussed a rollover technique where by utilizing 60-day rollovers you could
1:58.9	that could assist you in your ability to optimize a Roth conversion.
2:05.0	I'm not going to go into the whole strategy here, but it prompted some questions about
2:09.6	rollovers, which led us to today deciding we're going to talk a little bit about common
2:15.2	rollover mistakes that people make.
2:17.1	And we're going to share these mistakes with you all so that hopefully you will not make
2:20.8	those same mistakes when doing a rollover from one IRA to another IRA.
	...

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