Your own Roth contributions come out any time, at any age, with no tax and no penalty. You already paid tax on that money and the IRS has no further claim on it. The growth on top is where the rules live, and there are two separate five-year clocks that people run together when they shouldn't.
The first clock decides whether earnings come out tax free. It starts on January 1 of the year you made your first contribution to any Roth IRA, and it never restarts. Open a Roth in December 2020 with $500 and the clock started January 1, 2020. Open a second Roth at a different company in 2026 and it rides on the original clock. One clock per person, not one per account.
Clearing five years isn't enough by itself. You also need a triggering event, and there are four: you're 59 and a half or older, you're disabled, the money is going to your beneficiary after your death, or you're taking up to $10,000 lifetime for a first home. Five years plus a trigger makes it a qualified distribution, which means the earnings come out with no income tax at all. Five years without a trigger, or a trigger without five years, and the earnings are taxable and usually carry a 10% penalty on top.
The second clock is about conversions, and it exists to keep people from using a conversion as a back door around the early withdrawal penalty. Every Roth conversion starts its own five-year clock. If you're under 59 and a half and you pull converted money out before that batch's five years are up, you owe the 10% penalty on it even though you already paid income tax when you converted. Convert in 2026 and that batch is penalty free in 2031. Convert again in 2027 and that batch has its own date. Past 59 and a half, this clock stops mattering.
The order money comes out in is fixed and it's set up in your favor. Contributions first. Then conversions, oldest batch first. Earnings last. So somebody who has put in $40,000 over the years and has $60,000 in the account can take $40,000 out whenever they want with nothing owed, because the IRS treats those dollars as leaving before anything else. That ordering is why a Roth doubles as a backup reserve for a lot of households even when the plan is to leave it alone.
Keep your own records. The number that matters is total contributions across every Roth you've ever had, and nobody tracks that for you. Your custodian reports contributions on Form 5498 each year and doesn't add them up across companies or across decades. Keep a running total somewhere, along with the year of your first contribution and the year and amount of every conversion. If you inherit a Roth, the original owner's five-year clock carries over to you.
I'm a licensed insurance broker and not a CPA. These rules interact with the ten-year inheritance rules and with state tax in ways specific to your situation. But the one thing to write down today is the year you opened your first Roth. If that year is more than five back and you're past 59 and a half, both clocks are behind you and the whole account is available. And if you're setting one up for a kid with a summer job, starting the clock early is most of the reason to do it at all, which a Roth IRA for the kid with a summer job gets into.