From the inbox:

Jeremy, I remember that you aren’t a big fan of 529s. But now that you can move excess 529 funds into a Roth IRA (thanks to Secure Act 2.0) … now, surely, you must LOVE them! Right?

Actually…. no.

Why I Still Don’t Love 529s

Way back in the day I chose not to contribute to 529 plans for our kids because there was minimal benefit.
See: Why GCCJr has no 529

tldr: I already get tax-deferred / tax-free gains, have full access to all funds, and don’t risk penalties or converting my nice 0% capital gains into more heavily taxed ordinary income

But, with the Secure Act 2.0, a new option was created: the option to rollover unused 529 funds into a Roth IRA in the future.

At face value, that seems like a nice option. But does it mean contributing to a 529 is now a MUST?

I think the answer is no. The rules on the 529-to-Roth rollovers are too limiting… max $35k lifetime, account must be 15+ years old, must have earned income (the 529-to-Roth rollover is just a source of contribution funds), etc… For deeper analysis, read Kitces: 529-To-Roth IRA Rollovers: Taking Advantage Of The New Option To Move Education Savings To Retirement Savings

Full disclosure: I have opened 529s for both of our kids. They each have a few hundred dollars. I did this because I got an immediate benefit of a $50 Target gift card with each account (pdf.) In the coming years I will also be moving long-term holdings of I-bonds into 529s to avoid ~$30k of taxable income. Mayhaps these funds will end up in a Roth IRA way down the road.

Making the Most of 529-to-Roth rollover

Let’s say we wanted to make the most of a future 529-to-Roth rollover. A (delayed) mega backdoor Roth, if you will.

One idea proposed in email by a GCC reader was this:

Contribute $100/month for 15 years at 9% apr –> $35k+. Start 529-to-Roth rollover in 15 years and continue each year until 529 is empty (or $35k limit reached.) Assuming no tax law changes between now and then, you now have $35k in a Roth (about $22k in today’s dollars.)

This assumes a high-income household, else there are better uses for that $1,200 per year (first contribute directly to IRA / 401k / HSA.)

You can put this on auto-pilot today and set a calendar reminder for 2025 + 15 = 2040.

Be sure to highlight that you (or the 529 beneficiary) need earned income in 2040 / 2041 / 2042 / 2043(?) to get the full $35k into the Roth

Worth doing? Maybe.

(Delayed) Mega Backdoor Roth Analysis

Because future earned income is required to pull off a 529-to-Roth rollover, the benefit (if any) of making these 529 contributions is in the form of tax-deferral and future tax-avoidance (on unrealized gains.)

Whereas if that money was instead invested in a taxable brokerage account..

In year 1, if $1,200 is invested in an SP500 type index fund on Jan 1, maybe it earns 1.5% in qualified dividends for total income of $18.

A high-income household might pay tax of 20%+ or ~$3.60. This will grow each year.

In 15 years we would have made ~$18,000 in total contributions. The remaining $17k would be capital gains. If we realized all of those gains in one year and paid 20% tax on them (because still working / high-income household), that would cost $3,400 ($2,150 in today’s dollars.)

Worth it?

Whether or not intentionally contributing funds to a 529 with the sole purpose of a future 529-to-Roth rollover is worth it is likely a matter of personal preference.

Personally… what to do with $1,200 per year is below my radar of things on which to spend mental energy. You probably have your own threshold.

I would already pay 0% tax on the annual dividends and on the long-term capital gains a decade and a half from now, so there is no need to complicate things with a new separate account.

For somebody in a high-income household aggressively saving for retirement, what you do with $1,200/year also doesn’t matter too much. For simple math, let’s say income exceeds $120,000. Whether you put 1% of income in a 529 or a brokerage account doesn’t significantly change the outcome.

If I want to put $35k into a Roth account in 35 years and have the earned income to do so, I can just do it at that time (again, no need to complicate things.) Moving $35k between our pre-tax / post-tax / taxable buckets also doesn’t much change the ratio between those accounts. In terms of a 25x / 4% rule value, it is less than 1 year of target spending ($1kk * 4% = $40k.)

[ But Jeremy, don’t you often talk about how you get $1,200 in credit card bonuses?! Why the hypocrisy?]

Option A – invest $1,200 I already have in a tax-deferred account that I can’t touch for 15 years without penalty. In year 1 I can save $3.60.

Option B – open a new credit card and get $1,200 in tax-free income, now, today

By my math, $1,200 >> $3.60 (and also $3.60 << $50 Target gift card.)

(But you can do both if you want.)

Summary

Since passage of the Secure Act 2.0, there is a new escape valve that allows somebody to move unused 529 funds into a Roth IRA.

The value of intentionally making 529 contributions in order to maximize this 529-to-Roth rollover is not significant, imho, but I fully support anybody who chooses to go through the effort.

What do you think of 529-to-Roth rollovers?