The pitch for a Roth IRA is simple enough that most people stop listening after it. You pay tax now, the money grows, and you owe nothing later. That is close to true, and the part that gets left off is the part that costs people money. A Roth withdrawal is only tax free if it counts as a qualified distribution, and qualifying takes two things at once. You have to be 59 and a half, and the account has to be at least five years old. Miss the second one and the growth in a perfectly funded Roth comes out taxable.
Start with what is never at risk. Your own direct contributions can come out at any time, at any age, with no tax and no penalty, because that money was already taxed the year you earned it. There is no waiting period on contributions and no form to file to get at them. The rules only bite when you reach past the contributions into the earnings, meaning the interest, dividends, and gains stacked on top. That distinction matters more than any other in this account. Most people who think they broke a rule actually only touched contributions and owed nothing at all.
The first five year clock covers earnings. It starts on January 1 of the tax year of your first contribution to any Roth IRA, and it runs once for you, not once per account. Open a second or third Roth later and it inherits the original start date. Once it starts it never resets, even if you drain the account to zero and fund a new one years later. So the clock is not really about the account. It is about the first time you ever put a dollar into a Roth IRA, which is why the single most useful move here is starting one early with a small amount.
That start date has a quirk worth knowing. Contributions can be made up until the tax filing deadline and counted toward the prior tax year. Fund a Roth in April of one year and label it for the year before, and the five year clock backdates to January 1 of that earlier year. You just bought yourself roughly fifteen months of credit on a five year requirement for no extra cost. For someone opening a first Roth in the spring, that one checkbox on the funding screen can decide whether a withdrawal four years out is qualified. Custodians ask which tax year you want, and people click through it without reading.
The second clock covers conversions, and it works differently. When you move money from a traditional IRA into a Roth, that converted amount gets its own five year period, and each conversion has a separate one. The purpose is to stop people under 59 and a half from using conversion as a way around the early withdrawal penalty. Pull a converted amount out before its five years are up and you can owe the 10 percent penalty on it, even though you already paid income tax at conversion. Once you are past 59 and a half, this conversion clock no longer applies for penalty purposes. Someone doing a backdoor Roth in their thirties needs this on a calendar.
Order matters when money leaves. The IRS applies a fixed sequence, described in Publication 590-B, rather than letting you pick which dollars come out. Contributions come out first, then conversions on a first in first out basis, then earnings last. That ordering is quietly generous, because it means a withdrawal has to clear every safer layer before it can touch the taxable one. Someone who has contributed for a decade may have a large cushion before any of this applies to them. Knowing the order also tells you exactly how much you can take without a tax question, which is the sum of contributions plus seasoned conversions.
Two edge cases catch people. A Roth 401(k) at work runs its own five year clock tied to that plan, and it does not carry over when you leave. Roll it into a Roth IRA and the money adopts the IRA clock, which helps if your IRA is old and hurts if you are opening the IRA that day. On the inherited side, a beneficiary gets tax free earnings only if the original owner had already cleared five years, and the beneficiary picks up the deceased owner's start date rather than starting fresh. Both cases turn on a date nobody writes down. Ask your custodian for the year of your first Roth contribution and save the answer somewhere you will find it in twenty years.
