Roth IRAs have the most flexible withdrawal rules of any retirement account — but the rules have important nuances that, if misunderstood, can trigger unexpected taxes and penalties.
The fundamental distinction: contributions vs earnings
- Contributions (money you put in): Can be withdrawn anytime, at any age, with no taxes or penalties. This is money you already paid tax on.
- Earnings (investment growth): More complex — withdrawal rules depend on age and account age.
The 5-year rule (two separate rules)
Rule 1 (for qualified distributions): Your Roth IRA must be at least 5 years old before earnings can be withdrawn tax-free — even after age 59½. The clock starts January 1 of the year you make your first Roth IRA contribution. Open a Roth IRA with $1 today, and the 5-year clock starts this calendar year.
Rule 2 (for conversions): Each conversion has its own 5-year seasoning period for penalty-free withdrawal of converted funds (before age 59½). This is the clock that matters for the Roth conversion ladder.
The withdrawal ordering rules
The IRS defines a specific order for Roth IRA withdrawals:
- Regular contributions (first out — no tax, no penalty)
- Conversions (second — no income tax, 10% penalty if under 59½ and within 5 years of conversion)
- Earnings (last — taxable and 10% penalty if not a qualified distribution)
Exceptions to the 10% early withdrawal penalty
- First-time home purchase (up to $10,000 lifetime)
- Disability
- Substantially equal periodic payments (72t SEPP)
- Higher education expenses
- Health insurance premiums during unemployment
- Qualified reservist distributions
- Death of account owner
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About the author

Enrique 'Kike' Faúndez is an Information Systems and Management Control Engineer from Universidad de Chile, with master’s degrees in Finance from Universidad de Chile and Industrial Engineering from Pontificia Universidad Católica de Chile. He has 15+ years of experience in regulated financial services across finance, operations, and digital product development. He founded CashControlly in Santiago, Chile, with the conviction that personal financial control should not be a privilege, but an accessible and well-designed tool.
- Master's in Finance, Universidad de Chile
- Master's in Industrial Engineering, Pontificia Universidad Católica de Chile
- Information Systems and Management Control Engineer, Universidad de Chile
- AI and ITIL certifications
- 15+ years in regulated financial services
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