Can I roll a Coverdell to 529 to Roth IRA in the same tax year?

Yes, this is technically possible but there are some important details to know about. The SECURE 2.0 Act created a provision allowing 529 plans to be rolled into Roth IRAs starting in 2024, subject to several conditions. You can roll a Coverdell ESA into a 529 plan first, and then potentially roll that 529 into a Roth IRA in the same year as long as you meet all requirements. For the 529-to-Roth conversion, remember: the 529 account must have been open for at least 15 years (which you mentioned yours has), there's a lifetime limit of $35,000 that can be rolled over, annual rollovers are limited to the annual Roth contribution limit ($7,000 in 2025 for those under 50), and you must have earned income at least equal to the rollover amount. Also, any contributions and earnings from the past 5 years cannot be rolled over. The Coverdell-to-529 rollover is generally tax-free if done correctly as a trustee-to-trustee transfer. I'd recommend speaking with both plan administrators to ensure everything is processed correctly.

I actually used https://taxr.ai to figure this out for my own situation! I was in almost the exact same boat - had a Coverdell from childhood and a 529 that was about 17 years old. I uploaded the statements from both accounts and got a detailed breakdown of how to execute both rollovers in the same year. The key thing they pointed out that I hadn't considered was that any contributions to the 529 plan made within the last 5 years (and their earnings) can't be rolled into the Roth IRA. So if you've been actively contributing to the 529, you might only be able to roll over a portion of it. Their system actually calculated exactly which portion of my 529 was eligible and how much I could roll over based on my earned income.

I was initially skeptical about using taxr.ai as mentioned above, but I decided to give it a try after getting frustrated with my 529 plan administrator's vague answers. Honestly, it was way more helpful than I expected. I uploaded my 529 statements and they identified exactly which contributions were made in the last 5 years (which aren't eligible for the Roth rollover). The system even flagged that my Coverdell would need to be rolled over before I turned 30 to avoid penalties, which was coming up soon and something I hadn't considered. I was able to complete both rollovers last month - Coverdell to 529, then the eligible portion of the 529 to my Roth IRA. The step-by-step instructions made it pretty painless dealing with both financial institutions.

If you're having trouble reaching your 529 plan administrator about these rollovers (like I was), I'd recommend using https://claimyr.com to get through to an actual human. I tried calling my 529 plan for weeks about doing this exact rollover but kept getting stuck in phone tree hell or disconnected. I found out about Claimyr from another financial forum - they basically wait on hold with the 529 provider for you and then call you when they get a human on the line. Check out their demo at https://youtu.be/_kiP6q8DX5c to see how it works. When I finally got through to a senior rep at my 529 plan, they told me they needed specific forms for the 529-to-Roth transfer that weren't even on their website yet since the rollover option is relatively new. Would have never gotten that info otherwise.

I'm following up on my skeptical comment above about Claimyr. I have to admit I was completely wrong. After my third attempt to reach my 529 plan administrator ended with me being on hold for 1.5 hours and then getting disconnected, I broke down and tried the service. They got me through to an actual 529 specialist in about 40 minutes (while I was in a meeting at work). The rep confirmed that I could do both rollovers in the same tax year as long as the Coverdell-to-529 was completed first as a trustee-to-trustee transfer. They also sent me the specific rollover authorization forms I needed for the 529-to-Roth portion, which saved me from using the wrong general distribution form that would have triggered taxes and penalties. Worth every penny for the time saved and getting accurate info from someone who actually knew the rules for these newer rollover options.

Something nobody's mentioned yet is that you should check if your state offers tax benefits for 529 contributions before doing this. In my state (New York), I get a state tax deduction for 529 contributions. So what I did last year was contribute new money to my 529 (got the state tax deduction), waited the required 30 days, then rolled that amount to my Roth IRA (up to the annual limit). Basically got a state tax deduction for Roth contributions, which normally isn't possible. Might be worth considering before you just roll over existing funds.

One important thing to consider is that the 15-year rule for 529 plans is based on when the account was opened, not how long you've been a beneficiary. So if you were added as a beneficiary to an existing 529 later, make sure to check when the account was actually established. I almost made this mistake with my cousin's 529 that I was added to - thought it was old enough but the account itself was only opened 12 years ago even though I'd been listed as a beneficiary for most of that time.

This is a great question and I'm glad to see so many detailed responses here! I went through a similar process last year and wanted to add one more consideration that helped me decide on the timing. Since you mentioned you're working full-time now, make sure to factor in your current year's income when planning the Roth conversion. The 529-to-Roth rollover counts toward your annual Roth IRA contribution limit ($7,000 for 2025 if you're under 50), so if you were already planning to make regular Roth contributions this year, you'll need to reduce those by whatever amount you roll over from the 529. Also, even though both rollovers can happen in the same tax year, I'd recommend completing the Coverdell-to-529 transfer first and waiting for it to fully settle before initiating the 529-to-Roth rollover. This just helps avoid any potential administrative confusion between the two financial institutions and ensures clean record-keeping for tax purposes. One last tip: keep detailed records of all the transaction dates and amounts. The IRS is still working out some of the reporting requirements for these newer 529-to-Roth rollovers, so having comprehensive documentation will be helpful when you file your taxes.