Compared to your tax bracket today, where do you expect to land in retirement?

Lower — once I stop working, my taxable income drops a lot; About the same; Higher — RMDs, a pension, Social Security, or rising rates will push me up

How would you actually pay the income tax on the conversion?

From a taxable brokerage account or savings — the IRA stays whole; A mix — partly from outside, partly withheld from the conversion; I'd have to withhold it from the converted amount itself

When would you most likely need to start tapping this money?

Within the next 5 years; 5 to 15 years from now; More than 15 years from now, or maybe never — it's mostly for heirs

What does your taxable income look like THIS year specifically?

Unusually low — gap year, sabbatical, layoff, or retired but pre-Social-Security; Pretty typical for me; Higher than usual — bonus year, RSUs vesting, or peak earnings

How close are you to Medicare age (65)?

Already 63 or older — Medicare is right around the corner; Between 50 and 62 — Medicare is on the horizon but a few years off; Under 50 — Medicare is decades away

Are you currently covered by an ACA Marketplace plan with a subsidy?

Yes — the premium tax credit meaningfully lowers what I pay; I'm on a Marketplace plan, but my subsidy is small or doesn't apply; No — I'm on employer coverage, Medicare, or pay full freight already

What's the long-term purpose of this money?

I plan to spend most of it down in retirement; A mix — I'll spend some, leave the rest; Mostly for heirs — I want to leave a tax-free inheritance

Where are you in the Required Minimum Distribution timeline?

I'm already taking RMDs (age 73 or older); I'm within 10 years of RMD age — the window is closing; RMDs are more than 10 years away

Are you planning a state move that would change your income tax situation?

Yes — moving to a state with NO income tax (FL, TX, TN, NV, etc.); Staying put, or moving somewhere with similar state taxes; Yes — moving to a state with HIGHER income tax than where I am now

Should I Convert My Traditional IRA to a Roth IRA?

Answer a few honest questions about your tax situation, age, and time horizon, and our Decision Guide will tell you whether a Roth conversion is worth it for you this year.

Published April 25, 2026

Questions in this guide:

Compared to your tax bracket today, where do you expect to land in retirement?
- Lower — once I stop working, my taxable income drops a lot
- About the same
- Higher — RMDs, a pension, Social Security, or rising rates will push me up
How would you actually pay the income tax on the conversion?
- From a taxable brokerage account or savings — the IRA stays whole
- A mix — partly from outside, partly withheld from the conversion
- I'd have to withhold it from the converted amount itself
When would you most likely need to start tapping this money?
- Within the next 5 years
- 5 to 15 years from now
- More than 15 years from now, or maybe never — it's mostly for heirs
What does your taxable income look like THIS year specifically?
- Unusually low — gap year, sabbatical, layoff, or retired but pre-Social-Security
- Pretty typical for me
- Higher than usual — bonus year, RSUs vesting, or peak earnings
How close are you to Medicare age (65)?
- Already 63 or older — Medicare is right around the corner
- Between 50 and 62 — Medicare is on the horizon but a few years off
- Under 50 — Medicare is decades away
Are you currently covered by an ACA Marketplace plan with a subsidy?
- Yes — the premium tax credit meaningfully lowers what I pay
- I'm on a Marketplace plan, but my subsidy is small or doesn't apply
- No — I'm on employer coverage, Medicare, or pay full freight already
What's the long-term purpose of this money?
- I plan to spend most of it down in retirement
- A mix — I'll spend some, leave the rest
- Mostly for heirs — I want to leave a tax-free inheritance
Where are you in the Required Minimum Distribution timeline?
- I'm already taking RMDs (age 73 or older)
- I'm within 10 years of RMD age — the window is closing
- RMDs are more than 10 years away
Are you planning a state move that would change your income tax situation?
- Yes — moving to a state with NO income tax (FL, TX, TN, NV, etc.)
- Staying put, or moving somewhere with similar state taxes
- Yes — moving to a state with HIGHER income tax than where I am now

A Roth conversion is worth doing when you can pay the tax bill from outside the IRA, you have at least 10 years for the converted dollars to grow, and you're confident you're in a lower tax bracket today than you'll be in retirement — most often during a low-income gap year, the years between retirement and Required Minimum Distributions, or in your 20s and 30s when bracket headroom is enormous. It's a bad idea if you'd have to withhold the tax from the converted amount, you'll need the money within five years (the conversion clock matters), or you're already in a high bracket and expect to retire into a lower one. Two specific traps catch people: if you're 63 or older, conversions spike your MAGI and trigger Medicare IRMAA surcharges two years later; and if you rely on an ACA marketplace subsidy, a conversion can blow past the income cliff and cost you $10,000+ in lost premium tax credits. For most people the right answer isn't 'all of it' — it's a partial conversion sized to fill the rest of your current tax bracket, repeated over several years.

Sources

Retirement plans FAQs regarding IRAs — Internal Revenue Service
Is a Roth IRA conversion right for you? — Vanguard
Convert to a Roth IRA: Roth Conversion Rules & Deadlines — Fidelity
Roth IRA Conversion: Rules, What to Know — NerdWallet
How to Dodge the 'Medicare Tax' Before You Retire — Kiplinger
Pro rata rule on Roth IRA conversions: What to know & how to avoid — Thrivent

Should I Convert My Traditional IRA to a Roth IRA?

Sources

Related Decision Guides