Two years of backdoor Roth IRA contributions showing on single 1099-R form - how to properly file?

This is a common situation with backdoor Roth IRA contributions. The 1099-R form is showing the total distributions from your traditional IRA, not your taxable income. Here's how to handle it in TurboTax: When you enter the 1099-R information, TurboTax will ask you about the purpose of the distribution. You'll need to indicate that these were conversions to a Roth IRA. Then TurboTax should prompt you with questions about your basis (non-deductible contributions). This is where you'll enter your Form 8606 information for both tax years. Make sure you have your 2020 Form 8606 information available, as you'll need to reference your non-deductible contribution amount from that year. Each year's contribution should have its own Form 8606, even though they're showing up on one 1099-R. The key is properly documenting your basis so you're only taxed on any earnings between contribution and conversion, not on the contribution amounts themselves.

I was in the exact same boat last year and found a great solution with taxr.ai (https://taxr.ai). I also had multiple backdoor Roth conversions show up on a single 1099-R and was completely confused about how to report it properly in my tax software. What I really liked about taxr.ai is that they analyzed my 1099-R and previous 8606 forms, then explained exactly which numbers needed to go where in TurboTax. They showed me how to properly document my basis so I wasn't double-taxed on those contributions. Their system specifically recognized my backdoor Roth situation and walked me through the exact screens in TurboTax I needed to navigate. The guidance was super specific to backdoor Roth reporting issues, which regular tax software help sections just don't cover well.

I just wanted to follow up and say I tried taxr.ai after seeing the recommendation here. It was exactly what I needed! I had almost the same situation with backdoor Roth contributions from multiple years on a single 1099-R, and their analysis showed me exactly how to handle it in TurboTax. They identified that I needed to reference my previous year's Form 8606 and showed me which screens in TurboTax to navigate to properly document my basis. The step-by-step guidance was really clear, and I'm confident I reported everything correctly now. Much better than the generic advice I was finding elsewhere! Really glad I gave it a try instead of potentially misreporting my backdoor Roth conversions.

I had a similar issue and spent HOURS trying to get through to the IRS for clarification. After being on hold forever and getting disconnected multiple times, I found Claimyr (https://claimyr.com). They got me connected to an actual IRS agent in about 15 minutes who walked me through how to properly report multiple year backdoor Roth contributions on a single 1099-R. The IRS agent explained exactly how Form 8606 handles this situation and confirmed I wouldn't be double-taxed as long as I documented everything correctly. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c Before using Claimyr, I was going in circles trying to get clear answers about backdoor Roth reporting. Getting direct confirmation from the IRS gave me peace of mind that I was handling this correctly.

I need to apologize and update everyone. After being skeptical about Claimyr, I decided to try it anyway out of desperation (been trying to resolve my Roth conversion issues for weeks). It actually worked! I got connected to an IRS agent in about 20 minutes who was knowledgeable about backdoor Roth contributions. The agent confirmed I needed to reference my previous year's Form 8606 and explained exactly how to report the basis correctly when multiple years appear on one 1099-R. What impressed me most was how much time it saved - I had previously spent over 4 hours on multiple calls trying to get through. The agent even looked up my previous year's filing to make sure everything would match up correctly. Completely worth it for the peace of mind alone.

Just to add another approach - I had this exact issue last year and ended up consulting with a CPA who specializes in retirement accounts. He said the key document is Form 8606, which tracks your non-deductible contributions. For TurboTax specifically, when you enter the 1099-R, make sure to select that this was a conversion to a Roth IRA. Then, when it asks about your basis, you'll need to reference both your 2020 and 2021 Form 8606 information. The CPA emphasized that keeping good records of your Form 8606 from each year is crucial for backdoor Roth strategies. Also, don't panic if TurboTax initially shows tax due on the full amount - once you complete the Form 8606 section properly, it should adjust to show the correct taxable amount (which should be minimal or zero if you did direct conversions without much time for earnings).

Has anyone actually gotten audited over backdoor Roth contributions? I'm in the same boat with multiple years showing on one 1099-R and now I'm worried. Should I be concerned about red flags if I report this as described above?

I went through this exact same situation last year and want to share what worked for me. The key thing to understand is that the 1099-R is just reporting the total distribution amount - it's not determining your taxable income. Here's what I did in TurboTax step by step: 1. Enter the 1099-R as a Roth conversion (not a regular distribution) 2. When TurboTax asks about your basis, you'll need your Form 8606 from 2020 AND the one you'll file for 2021 3. The 2021 Form 8606 will show your total basis from both years ($15k in your case) 4. This should result in zero or minimal taxable income since you're converting non-deductible contributions The critical part is making sure you filed Form 8606 for 2020 when you made that contribution. If you didn't file it, you might need to amend your 2020 return first. Also, keep excellent records - bank statements showing the contributions, conversion confirmations, and all your Form 8606s. The IRS wants to see a clear paper trail that these were legitimate backdoor Roth strategies, not attempts to avoid taxes on deductible IRA contributions. Don't stress too much about the single 1099-R - this is actually pretty common when conversions happen across calendar years but get processed together.