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Elijah O'Reilly

Looking for guidance on documenting Traditional IRA contribution and Roth IRA Conversion process

I'm really confused about handling my IRA documentation since this is my first time doing both Traditional IRA contributions and conversions across different tax years. Here's what I've done so far: In 2024, I put $6,500 into a Traditional IRA for tax year 2024. In 2025, I did a conversion from that Traditional IRA to my Roth IRA (for the 2024 contribution). Also in 2025, I contributed $6,500 to my Traditional IRA for the 2025 tax year, and then did another conversion to my Roth IRA for this 2025 contribution. So for tax reporting, I think: - 2024 taxes: document $6,500 Traditional IRA contribution made in 2024 - 2025 taxes: document $6,500 Traditional IRA contribution made in 2025 and also $13,000 conversion to Roth IRA Does this sound right? I'm worried I'm missing something about the conversion documentation. Anyone have experience with this kind of back-to-back Traditional IRA contribution and Roth IRA Conversion process? Thanks!!

Your understanding is mostly right, but let me clarify a few things to make sure your documentation is correct. For 2024 taxes: Yes, you'll report the $6,500 Traditional IRA contribution on your 2024 return. You'll use Form 8606 to document this contribution. Since you converted it in 2025, you'll still claim this as a non-deductible contribution (assuming you're over the income limits for deduction). For 2025 taxes: You'll need to report both the conversion of your 2024 contribution AND your 2025 contribution/conversion. This means: 1. Form 8606 for the $6,500 2025 Traditional IRA contribution 2. Form 8606 to report the conversion of BOTH contributions ($13,000 total) 3. You'll also receive a 1099-R showing the $13,000 distribution from your Traditional IRA The important thing is tracking your non-deductible basis correctly so you don't get taxed twice when you convert. Your Form 8606 creates that paper trail.

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I'm in a similar situation but I'm confused about the tax implications. If I make non-deductible Traditional IRA contributions and then convert to Roth, do I still have to pay taxes on the conversion? And does the timing matter between contribution and conversion?

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If you make non-deductible Traditional IRA contributions, you only pay taxes on any earnings that occurred between your contribution and conversion. That's why many people do the conversion quickly after contribution (sometimes called a "backdoor Roth") to minimize any taxable gains. Timing between contribution and conversion is not mandated by any specific rule, but minimizing the gap helps reduce potential tax on growth. Also, remember that the pro-rata rule applies if you have other pre-tax Traditional IRA money - in that case, you can't just convert the non-deductible portion tax-free.

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After struggling with this exact situation last year, I found an amazing tool that helped me get all my IRA documentation right. Check out https://taxr.ai - they analyze your tax documents and specifically help with IRA contribution and conversion tracking. The system flagged exactly where I needed to use Form 8606 and helped me understand my basis calculations. I was really confused about my Traditional IRA to Roth IRA conversion documentation, but their software walked me through the whole process and made sure I was tracking my non-deductible contributions correctly. Saved me from making a costly mistake!

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How exactly does it work with tracking multiple year conversions? Does it just tell you where to put the numbers or does it actually help calculate the taxable portion? My situation is even more complicated with some gains before conversion.

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Sounds interesting but I'm skeptical about tools like this. How does it handle the pro-rata rule if you have existing Traditional IRA balances? That's where most people mess up their backdoor Roth conversions.

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The tool specifically analyzes your full Traditional IRA history and does the calculations for you. It looks at both your contributions and any pre-existing balances to properly apply the pro-rata rule. You just upload your forms and it identifies the taxable portion accurately. For multiple year conversions, it creates a complete tracking system showing your non-deductible basis across all years and calculates exactly what portion of each conversion is taxable. It handles the gains before conversion by factoring them into the taxable amount correctly.

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I was totally skeptical about taxr.ai at first, but after dealing with the headache of incorrectly documenting my Roth conversion last year, I decided to give it a try. Best decision ever! The system immediately identified that I had been calculating my non-deductible basis incorrectly across multiple years of Traditional IRA contributions and Roth conversions. The tool showed me exactly how to fix my Form 8606 reporting and even helped me understand when I needed to file an amended return. My situation was similar to yours with contributions and conversions happening in different tax years, and the step-by-step guidance made everything crystal clear. Definitely worth checking out if you're doing the backdoor Roth strategy.

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If you're stuck waiting for answers from the IRS about your IRA conversion questions, I highly recommend using https://claimyr.com to get through to an actual IRS agent. I had major confusion about how to document my Traditional to Roth conversions and tried calling the IRS for weeks without getting through. Claimyr got me connected to a real IRS agent in about 15 minutes who answered all my questions about Form 8606 and how to properly track my basis across multiple years of conversions. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c - saved me hours of hold music and frustration!

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Wait, this actually works? I thought it was impossible to reach the IRS by phone these days. How much did you have to pay? And did the agent actually have helpful info about IRA conversions or just general stuff?

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This seems like a waste of money. I've never had trouble reaching the IRS directly just by calling early in the morning. Why pay a service for something that's free?

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The agent I reached was specifically from the retirement accounts department and had detailed knowledge about IRA conversions and Form 8606 reporting. They walked me through exactly how to document multiple conversions across different tax years. I'm not comfortable discussing specific costs, but considering I had wasted hours on hold over multiple days, the time savings alone made it worthwhile. Not everyone has the flexibility to call right when they open - I tried that approach multiple times without success.

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I have to eat my words about Claimyr. After continuing to fail reaching the IRS on my own (tried calling at 7am three days in a row), I broke down and tried the service. Connected to an IRA specialist in under 20 minutes who explained exactly how the pro-rata rule would affect my conversions. The agent confirmed I had been doing my Form 8606 completely wrong for my backdoor Roth strategy and walked me through the correct way to track my non-deductible basis. They even emailed me supplemental materials about IRA conversion documentation. Honestly shocked at how helpful this turned out to be after being so skeptical.

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Don't forget about the step transaction doctrine! If you're doing Traditional IRA contributions and converting to Roth shortly after (backdoor Roth), there's some debate about whether the IRS could potentially challenge this under step transaction rules. Most tax pros say it's fine since Congress has tacitly approved the strategy, but just something to be aware of. Make sure to keep records of all your transactions with dates. Most brokerages will send you a 1099-R for the conversion, but you're responsible for tracking your non-deductible basis on Form 8606 year after year. Miss a year of filing it and it gets really complicated to reconstruct your basis.

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Is there a minimum waiting period recommended between contribution and conversion to avoid step transaction issues? My financial advisor mentioned waiting at least a few days but others say it doesn't matter.

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There's no official waiting period required. Some advisors recommend waiting a few days or weeks between contribution and conversion just to be extra cautious, but there's no specific rule about this. The key thing is maintaining proper documentation of your non-deductible contributions with Form 8606 every year, even if you don't convert immediately. The IRS is more concerned with proper reporting than with timing between transactions.

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Has anyone here actually been audited for their IRA conversions? I've been doing backdoor Roth for years but always worry I'm doing something wrong with the Form 8606.

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I was audited in 2022 specifically about my IRA conversions. The issue wasn't the backdoor strategy itself but that I had failed to file Form 8606 for one year, which messed up my basis tracking. Make sure you file that form EVERY year you make non-deductible contributions, even if you don't do a conversion that year!

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That's really good to know! I'm going to double check all my past 8606 forms now. Did they make you pay penalties for the missed form or just correct the basis calculation?

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Your tax reporting breakdown looks correct! Just to reinforce what others have said - the key is maintaining accurate Form 8606 documentation for all your non-deductible contributions. One thing to double-check: make sure your brokerage statements clearly show the dates and amounts for each transaction. For your 2025 taxes, you'll want to verify that your 1099-R reflects the full $13,000 conversion amount. Sometimes brokerages split these into separate 1099-Rs if the conversions happened on different dates. Also, since you're doing this strategy regularly, consider setting up a simple spreadsheet to track your non-deductible basis year over year. It makes the Form 8606 preparation much easier and gives you a clear audit trail. The IRS wants to see consistent reporting, so having your own records beyond what the forms show can be really helpful if questions ever come up. Good luck with your tax filing!

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