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.

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