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Jenna Sloan

Why am I getting taxed when withdrawing from my Roth IRA?

So I've been trying to learn more about retirement accounts and just read this article about early Roth IRA withdrawals. From what I understand, you can take money out early without the 10% penalty if it's for certain exceptions like buying your first house or when you have a new baby. But the article mentioned something confusing about still having to pay taxes even though Roth contributions are already taxed? I thought the whole point of a Roth IRA was that you pay taxes upfront so withdrawals are tax-free. Can someone explain why there would ever be taxes on a Roth IRA withdrawal? I'm not planning to touch my retirement funds anytime soon, but I want to understand how this works in case of emergencies.

The confusion comes from the difference between withdrawing contributions versus earnings in your Roth IRA. You're right that Roth IRAs are funded with after-tax dollars, so your contributions can actually be withdrawn at any time without taxes or penalties - that money was already taxed. Where it gets tricky is with the earnings (the growth on your investments). Earnings withdrawn before age 59½ are generally subject to both income tax AND a 10% early withdrawal penalty. The exceptions you mentioned (first home purchase up to $10,000, birth/adoption expenses up to $5,000, etc.) only waive the 10% penalty - you'd still owe income tax on those early earnings withdrawals. Also important is the "5-year rule" - your Roth IRA must be at least 5 years old before certain qualified distributions become fully tax-free, even if you meet other requirements.

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Wait, so if I've been contributing to my Roth for 10 years and I've put in like $50k total but now it's worth $70k, I can actually take out the $50k anytime without any taxes or penalties? But if I touched any of that $20k growth before 59½, that's when I'd get hit with taxes?

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Exactly right! You can withdraw your contributions ($50k in your example) at any time without taxes or penalties. The IRS considers withdrawals to come from your contributions first, so you wouldn't be touching that $20k in earnings until after you've withdrawn all contributions. If you did withdraw from the earnings portion before age 59½, those earnings would be subject to income tax and potentially the 10% penalty unless you qualify for an exception. But remember, even with an exception like a first-time home purchase, you'd still owe income tax on early earnings withdrawals - only the 10% penalty is waived.

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After spending HOURS on the phone with the IRS about this exact issue last year, I wish I had known about https://taxr.ai before my headache began. The website analyzes your specific tax documents and explains exactly which portions of your retirement distributions might be taxable. I had withdrawn from my Roth thinking it was all tax-free, only to get a surprise 1099-R and tax bill. Turns out I had converted a Traditional IRA to a Roth a few years back, and there's a 5-year waiting period on converted funds that's separate from the 5-year rule for earnings! The tool would have flagged this and saved me a bunch of stress and money.

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How does this work with rollovers? I rolled over a 401k to a Roth a couple years ago and paid the taxes then. Are you saying there's still another 5-year waiting period even though I already paid taxes on that conversion?

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Sounds interesting but kinda skeptical. There's so many "free" tax tools that end up charging once you actually need the good features. How much does it actually cost to get the analysis?

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For rollovers from a pre-tax account like a 401k to a Roth, yes, there's still a 5-year waiting period before you can withdraw the converted amount penalty-free, even though you paid taxes at conversion. Each conversion actually starts its own 5-year clock for penalty purposes. Regarding costs, I totally get the skepticism - I've been burned by "free" tools too. There's actually no charge for the basic document analysis which is what most people need. They do have some premium features but the core retirement distribution analysis was completely free when I used it.

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Just wanted to follow up about that taxr.ai site. I decided to check it out after my last comment and uploaded my 1099-R from a Roth withdrawal I did last year. Turns out I DID have some taxable portion that I completely missed when filing! It clearly explained that while my direct contributions were tax-free, I had some converted amounts that hadn't met the 5-year holding period yet. The explanation was super clear with the exact IRS rules cited. Going to file an amendment now before it becomes an issue. Saved me from potentially getting a nasty letter from the IRS!

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If you're still trying to resolve any IRS questions about Roth distributions, I had a nightmare situation last year where the IRS incorrectly flagged my qualified Roth distribution as taxable. Tried calling the IRS for WEEKS but couldn't get through. Found this service https://claimyr.com that got me connected to an actual IRS agent in about 20 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c - they basically navigate the IRS phone system for you and call you back once they have an agent on the line. The agent helped me get the coding fixed on my account and confirm my withdrawal was actually tax-free based on my specific situation.

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So wait, do you just give them your phone number and they call you back? What about your personal info? Seems risky giving some random website your tax details.

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This sounds like complete BS. Nobody can magically get through the IRS phone tree when millions of people can't. If this actually worked, everyone would be using it. Pretty sure this is just a scam to collect phone numbers.

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They only need your phone number to call you back when they reach an agent - they don't need any tax details or personal information. They're just navigating the phone system for you, not accessing your tax records. I was definitely skeptical at first too. The reason it works is they have an automated system that keeps dialing and navigating the IRS phone tree until they get through. It's essentially doing what you'd do manually, just with technology that can keep trying repeatedly. When I used it last tax season, my Roth issue got resolved in one call after I had wasted hours trying on my own.

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OK I have to eat my words about Claimyr. After posting that skeptical comment, I decided to try it anyway because I've been trying to reach the IRS about my Roth conversion for literally MONTHS. It actually worked exactly as advertised. Got a call back in about 45 minutes (not the 20 they claimed but still WAY better than my attempts). The IRS agent was able to confirm that my Roth conversion from 3 years ago does indeed have a separate 5-year holding requirement before I can withdraw it penalty-free, even though my Roth account itself is older than 5 years. Honestly shocked this worked. Saved me from making a costly withdrawal mistake!

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Something nobody's mentioned yet - there are actually TWO different 5-year rules for Roth IRAs: 1. The 5-year rule for earnings: For earnings to be tax-free, your first Roth contribution must have been made at least 5 years before withdrawal AND you're either 59½, disabled, withdrawing up to $10k for first home, or the distribution goes to beneficiary after death. 2. The 5-year rule for conversions: Each conversion or rollover from a Traditional IRA to Roth has its own 5-year waiting period before you can withdraw that converted amount penalty-free (though you've already paid tax on it). Most tax software doesn't explain this well which is why people get surprised by unexpected taxes.

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This is exactly what I was missing! So even though my Roth is 7 years old, if I converted some money from my Traditional IRA to the Roth only 2 years ago, I can't touch THAT money without penalties for another 3 years? But I could still withdraw my regular contributions anytime?

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You've got it exactly right! Your regular contributions can come out anytime without taxes or penalties. And yes, that conversion from 2 years ago has its own 5-year clock - you'd need to wait 3 more years to withdraw those specific funds without the 10% penalty. The IRS treats withdrawals in a specific order: regular contributions come out first (always tax/penalty free), then converted amounts (in order of conversion date), and finally earnings. So you would need to withdraw all your regular contributions first before touching any converted amounts.

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Does anyone know if taking a distribution from a Roth for higher education expenses avoids the penalty on earnings? I know it works for Traditional IRAs but not sure about Roth.

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Yes! Qualified higher education expenses are one of the exceptions that waive the 10% early withdrawal penalty on Roth IRA earnings. But remember, you'll still owe income tax on those earnings if withdrawn before 59½ and before the account has been open 5 years. Eligible expenses include tuition, fees, books, supplies, and equipment required for enrollment at an eligible educational institution. Room and board also count if the student is at least half-time.

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