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Andre Dupont

Help understanding 1099-R with blank Box 2a and checked Box 2b (taxable amount not determined)

Title: Help understanding 1099-R with blank Box 2a and checked Box 2b (taxable amount not determined) 1 My daughter recently cashed out her small Roth IRA and now I'm trying to help her with the tax filing mess. The distribution was only about $650 and she had some federal tax withheld at the time. The problem is when she's trying to file her taxes in TurboTax, it keeps flagging an error because Box 2a (taxable amount) is completely blank on her 1099-R form. Box 2b (taxable amount not determined) is checked, and we're not sure what to put in the software. We've gone through all the questions in the tax software multiple times but it still keeps giving us an error message. I'm wondering if we need to calculate something ourselves or if we're missing something obvious here. Has anyone dealt with this particular 1099-R situation before? Any advice would be greatly appreciated!

14 For a Roth IRA distribution, the taxable amount depends on whether it's a qualified distribution or not. Since Box 2b is checked (taxable amount not determined), the payer is basically saying "we don't know if this is taxable or not" - they're leaving it to you to figure out. Here's what matters: If your daughter has had the Roth IRA for less than 5 years OR she's under 59½ and doesn't qualify for an exception, then the earnings portion (not the contributions) would be taxable. If it's a qualified distribution (5+ years AND she's 59½ or meets an exception), then nothing is taxable. For Box 2a, you need to determine what portion, if any, is taxable. Since it's a small amount ($650 or so), it's very possible that it's mostly contributions which aren't taxable. You'll need to enter the amount that represents earnings only, which could be very small or zero.

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8 Thanks for the info. My daughter is definitely under 59½ (she's 24), and she only had the account for about 3 years. Does this mean the whole $650 is taxable or just part of it? And how do we figure out what part is the "earnings"?

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14 Since she's 24 and had the account less than 5 years, the distribution is non-qualified, so only the earnings portion would be taxable, not her original contributions. To determine the earnings, she needs to check her Roth IRA statements or contact the financial institution. The basic formula is: Earnings = Total Distribution - Total Contributions. If she put in $500 and withdrew $650, then $150 would be taxable. The tax software should walk you through this calculation with specific questions about contributions versus total distribution.

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5 I went through something similar last year with my own Roth IRA withdrawal. After hours of frustration, I found this tool called taxr.ai (https://taxr.ai) that really helped me sort it out. It basically analyzed my 1099-R and showed me exactly what was taxable. For your daughter's situation, it sounds like the payer didn't calculate the taxable amount (which is why Box 2b is checked). The tool walks you through figuring out what portion is contributions vs. earnings. Since it's a Roth, her contributions came in post-tax and wouldn't be taxable again, but any earnings might be if she's under 59½ and hasn't had the account for 5 years.

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12 How exactly does taxr.ai figure this out? Does it just ask you questions or does it actually look at the form somehow? I'm having a similar issue with my husband's old 401k that he rolled over.

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19 Does this work for other tax documents too? I've got a stack of forms I'm staring at and honestly have no idea what half of them mean or if I'm filling everything out right.

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5 The tool actually analyzes your tax documents directly - you upload your 1099-R and it uses AI to interpret the information on the form. It then explains what each box means and helps calculate what portion is taxable based on your specific situation. For your rollover situation, it would be super helpful because it can distinguish between taxable distributions and non-taxable rollovers, which often get confused on tax forms.

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12 I just wanted to update that I tried taxr.ai after seeing it mentioned here. It was actually pretty impressive! Uploaded my husband's confusing 1099-R and it immediately identified that our rollover was non-taxable but had been reported incorrectly. Saved us from potentially paying taxes on money that shouldn't have been taxed. The tool explained that for direct rollovers, Box 2a should be zero even though our form had an amount listed. Would never have caught that on my own. It even generated the explanation to include with our return if we get questioned.

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7 If your daughter is still having issues figuring out the taxable portion, you might want to try calling the IRS directly. I know that sounds painful, but I used this service called Claimyr (https://claimyr.com) when I had a similar issue with a retirement distribution. Instead of waiting on hold for hours, they had me connected to an IRS agent in like 15 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent I talked to was actually super helpful and walked me through exactly how to report a distribution where Box 2b was checked. They explained that I needed to determine the taxable portion myself based on my contribution basis.

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3 Wait, does this service actually work? I tried calling the IRS last year and literally gave up after being on hold for 2+ hours. How does Claimyr get you through when the IRS phone lines are always jammed?

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22 Sounds like BS to me. The IRS is impossible to reach. And even if you do get through, they give different answers depending on who you talk to. I've had better luck just googling my tax questions.

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7 It absolutely works! The service basically holds your place in line and calls you when an agent is about to pick up. I was skeptical too at first, but it's actually a pretty clever system - they use an automated process to navigate the IRS phone tree and wait through the hold times for you. Once you connect with an IRS agent, they're usually quite knowledgeable about specific tax situations like this. In my experience, they're much more reliable than random internet advice when it comes to something as specific as how to handle a 1099-R with Box 2b checked.

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22 I need to eat my words here. After my skeptical comment, I decided to try Claimyr out of pure frustration with my own tax situation. I couldn't believe it, but I was talking to an actual IRS representative within 20 minutes. The agent explained that for my Roth distribution (similar to OP's daughter), I needed to use Form 8606 to calculate the taxable portion properly. Turns out I've been doing it wrong for years! They walked me through how to determine what portion of my distribution was contributions versus earnings. Definitely worth it instead of guessing and potentially getting audited later.

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16 My advice: Make sure to fill out Form 8606! That's the form for nondeductible IRAs and Roth distributions. It'll help calculate exactly what portion of the distribution is taxable. The general rule is that Roth contributions come out first (tax-free), then any converted amounts (potentially taxable), and finally earnings (taxable for non-qualified distributions). Since your daughter's distribution is small and the account was only open a few years, it's very possible that it's mostly contributions and very little earnings.

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11 Is Form 8606 something you have to file separately or does TurboTax automatically include it if you enter the 1099-R info correctly?

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16 TurboTax should automatically generate Form 8606 if you enter all the information correctly. The key is making sure you answer all the questions about the Roth IRA history accurately - how long it's been open, how much was contributed, etc. If the software keeps flagging an error, it might be because you haven't provided all the historical contribution information it needs to calculate the taxable portion. Sometimes you need to enter prior year contribution amounts so it can track the basis correctly.

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9 I had exactly this issue! The solution is actually pretty simple. Since it's a Roth IRA and Box 2b is checked, you need to determine what portion of the distribution is earnings vs contributions. In TurboTax, there should be a question asking "Do you know your basis in this Roth IRA?" For a Roth that's only been open a few years with a small amount, it's likely very little is actually taxable. Just make sure to enter the total contributions your daughter made to the account (her basis).

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2 This is the correct answer! I'm a tax preparer and deal with this all the time. For Roth IRAs, contributions come out first tax-free, then conversions, then earnings. Since most young people haven't had much growth in their accounts, it's common for distributions to be almost entirely return of contributions, which means zero tax.

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This is a really common issue that trips up a lot of people! When Box 2a is blank and Box 2b is checked on a 1099-R for a Roth IRA, it means the financial institution is leaving it up to you to determine what's taxable. The key thing to remember is that with Roth IRAs, you get your contributions back first, tax-free. Since your daughter is 24 and only had the account for 3 years, and it was a small distribution of $650, there's a good chance most or all of it was just her original contributions coming back out. Here's what you need to do: Figure out how much she contributed to the Roth IRA over the years vs. how much it grew. If she put in $600 and it grew to $650, then only $50 would be taxable earnings. If she put in the full $650 or more, then nothing is taxable. Check with the financial institution for her contribution history, or look at old tax documents if she claimed the Saver's Credit for Roth contributions. Once you have that number, TurboTax should be able to handle the rest and generate Form 8606 automatically.

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