How to properly complete Form 8606 for multiple Roth conversions? Filing confusion

I'm pulling my hair out trying to figure out these Form 8606s for our Roth conversions. My tax software doesn't support this form so I have to do them manually, and now I'm completely lost. For context, we're married filing jointly and did several IRA movements in 2023-2024: - I converted about $2,700 from my traditional IRA to my Roth (money that had been sitting in the traditional for a few years) - My wife contributed $6,500 to her traditional IRA for 2023 and then converted it to her Roth. By conversion time it had grown to $6,503. All this happened in 2023. - I made a $6,500 contribution for 2023 directly to my Roth, then recharacterized it to my traditional IRA, and then converted it back to my Roth. However, all this happened in early 2024. I'm completely confused about: 1. How many Form 8606s do we need to fill out total for our 2023 tax return? 2. For my wife's conversion, where do I report the $6,503 instead of $6,500? I think it's Part I line 8, but the wording is confusing me. 3. For my 2023 contribution that I recharacterized and converted in 2024, what parts of that (if any) need to be included on our 2023 return? Any help would be so appreciated because I'm about to lose my mind over this!

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18 comments

Anderson Prospero

•8M

You're dealing with a few different scenarios here, so let me break this down for you: 1. You'll need to file two Form 8606s for 2023 - one for you and one for your wife. Each person with an IRA transaction needs their own form. 2. For your wife's conversion where the amount grew to $6,503, you're right that it goes on Part I, line 8. This line is asking for the value of the traditional IRA at the time of conversion. The $3 of earnings will be taxable income. 3. For your 2023 contribution that you recharacterized and then converted in 2024, you won't report the conversion on your 2023 return. The recharacterization means it's as if you originally contributed to the traditional IRA, but the conversion is a 2024 event that will be reported on your 2024 return. Your Form 8606 for 2023 should report the $2,700 conversion from your existing traditional IRA. Your wife's Form 8606 should report her $6,500 contribution and $6,503 conversion.

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Anderson Prospero

•8M

For the 2023 contribution you made in 2024, you don't report the conversion on your 2023 return, but you do need to report the contribution itself on your 2023 Form 8606 (since it's a 2023 contribution). The recharacterization makes it as if you originally contributed to the traditional IRA, so you'd complete Part I to establish your basis. For your $2,700 conversion of old money, you'll need to complete both Part I and Part II of Form 8606. Part I tracks your basis in nondeductible contributions (if any), and Part II reports the conversion. If this money was all from deductible contributions or earnings, then Part I will show zero basis and the full $2,700 will be taxable on Part II.

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Tyrone Hill

•8M

Hey there, I went through a similar nightmare last year! I wasted days trying to figure this out until I finally found taxr.ai (https://taxr.ai) that helped me understand how to properly handle my Roth conversions. I had done a backdoor Roth and some regular conversions across different years, and their AI analyzed all my documents and explained exactly which forms I needed. It spelled out line-by-line how to complete Form 8606 for each scenario, which saved me from making some expensive mistakes. The tool even caught that I had basis in my traditional IRA that I didn't know about, which reduced my tax bill by over $800! It's amazing for complicated situations like yours where multiple transactions are happening across different tax years.

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Tyrone Hill

•8M

It actually analyzes your specific documents - you can upload prior year returns, 1099-Rs, and other statements, and it builds a personalized analysis. It's not just generic advice. The pro-rata calculation is exactly what it helped me with most. I had multiple IRAs with different basis amounts, and it correctly calculated my taxable portion across multiple years. It tracked my non-deductible contributions over time and showed exactly how to report them on Form 8606. Even my CPA friend was impressed with how it handled the calculations.

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Toot-n-Mighty

•8M

Just wanted to update that I tried taxr.ai after seeing this thread. I was completely lost on my Form 8606 situation with multiple rollovers and conversions over the past few years. I uploaded my last two returns and my 1099-Rs, and it created a complete guide for filling out my forms. It explained which lines to use for my specific situation and caught a mistake I made in 2022 that would have caused issues this year. Super grateful I found this - saved me from potentially paying taxes twice on the same money! And it explained everything in plain English instead of IRS jargon.

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DeShawn Washington

•8M

Have you tried calling the IRS directly? I spent THREE WEEKS trying to get through to ask about my Form 8606 question. Always "high call volume" and disconnects. I finally used Claimyr (https://claimyr.com) and got through to an IRS agent in about 20 minutes! They have this system that navigates the IRS phone tree and holds your place in line, then calls you when an agent is about to answer. You can watch how it works here: https://youtu.be/_kiP6q8DX5c The agent walked me through exactly how to fill out my 8606 for multiple conversions. Honestly worth every penny not to spend hours on hold or getting disconnected.

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DeShawn Washington

•8M

The agent was surprisingly helpful! She didn't just read instructions - she actually worked through my specific scenario and told me exactly which lines to use for my conversion and how to handle the basis calculations. As far as the service itself, I don't remember the exact cost but it was reasonable considering I had already wasted hours trying to get through myself. And yes, I'm confident the advice was correct - I cross-referenced it with my tax software and everything matched up. The peace of mind alone was worth it. No more stressing about whether I was doing the form correctly.

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Sofía Rodríguez

•8M

I was really skeptical about Claimyr after seeing it mentioned here, but I was desperate after spending literal days trying to get through to the IRS about my Form 8606 questions. I decided to try it yesterday, and I'm honestly shocked - it actually worked! I got connected to an IRS rep within 30 minutes. The agent walked me through exactly how to handle my Roth conversion that had similar timing issues to yours. For anyone else struggling with these forms and complex IRA situations, being able to actually talk to someone at the IRS who can address your specific scenario is game-changing. I've never been able to get through on my own despite trying for years.

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Aiden O'Connor

•8M

Just to add some clarity on the Form 8606 sequencing for your situation: For your wife: - Form 8606 Part I: Report $6,500 contribution (line 1), then report $6,503 on line 8 - The $3 earnings will flow to line 18 and be taxable For you: - One Form 8606 for the $2,700 old money conversion (Parts I and II) - For the 2023 contribution made in 2024 that was recharacterized and converted, you'll report the contribution on your 2023 Form 8606 but the conversion goes on 2024 The most common mistake people make is not filing Form 8606 in the year they make nondeductible contributions, even if they don't convert until later. This causes all kinds of basis tracking problems down the road.

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Aiden O'Connor

•8M

Yes, it's absolutely necessary to file Form 8606 even if you contribute and convert in the same year. This formally establishes your basis in the IRA, which is critical for proper tax treatment. Without filing Form 8606, you have no official record of making a non-deductible contribution. This could lead to double taxation later because the IRS would have no way to know that you already paid tax on that money. Think of Form 8606 as your receipt proving you've already been taxed on those funds. Even if the entire process happens in one year, the documentation is still required to keep everything clear and proper.

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Jamal Brown

•8M

Honestly, the backdoor Roth process is unnecessarily complicated. I've been doing them for years and here's my simplified approach: For each person: 1. Contribute to traditional IRA 2. Convert to Roth 3. File Form 8606 for each person who did a conversion The key thing that messes people up is when the value changes between contribution and conversion. If you convert quickly there's minimal growth (or loss). Make sure you track your "basis" (non-deductible contributions) correctly or you could end up paying tax twice on the same money!

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