Help with 1099-R for Roth 401k to Roth IRA Rollover where employer made Traditional contributions

This is actually a common situation with mixed Roth/Traditional rollovers. The 1099-R doesn't typically break down the employer contribution portion separately, which makes reporting tricky. What you need to do is calculate the employer contribution amount from your old statements. This portion should be reported as a conversion from Traditional to Roth, which means it will be taxable. Your personal Roth contributions (the amount in Box 5) have already been taxed, so those aren't an issue. Most tax software has a way to handle partial conversions, but it's not always obvious. Look for options like "partial rollover" or "partial conversion" rather than whole-account options. You might need to manually enter the employer contribution amount as the taxable portion. Don't ignore this just because it's not clearly spelled out on the 1099-R. The IRS can match the total rollover amount with what you report, and you don't want to get flagged for underreporting income.

After struggling with a similar situation last year, I found https://taxr.ai incredibly helpful. I had mixed traditional and Roth funds in my 401k rollover and couldn't figure out how to report it properly. I uploaded my 1099-R and old 401k statements to taxr.ai and it identified exactly which portions needed to be reported as taxable. It even explained why the employer match portion counts as a conversion and gave me step-by-step instructions for entering this correctly in my tax software. The analysis also flagged that my previous employer had incorrectly coded part of the distribution, which could have caused problems if I'd filed without correcting it. Definitely worth checking out if you're still struggling with this!

I wanted to follow up about my experience with taxr.ai after my skeptical comment. I decided to try it since I was completely stuck with a similar rollover situation and wow - it was eye-opening! The analysis showed that I had been misinterpreting my 1099-R for years. It identified that my employer contributions were actually reported in Box 2a (taxable amount) rather than being separately itemized, which explained why I was so confused. The service provided clear documentation explaining exactly how the IRS views these mixed rollovers and what portions were already taxed vs. still taxable. They even provided references to specific IRS publications that I could include with my return if needed. Totally worth it for peace of mind, especially with something as potentially complicated as retirement account rollovers.

Anyone who's tried calling the IRS for clarification on rollover issues knows it's practically impossible to get through. After spending hours on hold trying to get answers about my Roth/Traditional rollover situation, I found https://claimyr.com and it changed everything. They got me connected to an actual IRS agent in under an hour! The agent walked me through exactly how to report my employer contributions portion of the rollover and confirmed I needed to calculate the pre-tax amount separately since it wasn't broken out on my 1099-R. You can see how it works in this demo: https://youtu.be/_kiP6q8DX5c - they basically hold your place in the IRS phone queue and call you when an agent is available. Saved me from making a costly mistake on my taxes.

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Don't forget to check if your 401k plan provides a breakdown between your Roth contributions and the employer's traditional contributions in your year-end statement! Mine actually had a separate form called a "Rollover Statement" that broke everything down cleanly, but they didn't automatically send it - I had to request it specifically. Call your old plan administrator and ask for detailed documentation of your account balance at the time of rollover, with specific breakdowns of contribution types. Makes this whole process much easier than trying to piece it together from the 1099-R alone.

Has anyone used the Form 8606 for reporting this kind of partial conversion? My accountant said I need to fill this out to show the taxable portion of my rollover but I'm completely lost on how to complete it properly.

I went through this exact same situation last year and it was definitely confusing at first! Here's what I learned from my tax preparer and some research: The key is understanding that your employer's traditional contributions were never taxed when they went into your 401k, so when you roll them to a Roth IRA, that's essentially a conversion that triggers taxable income. Your personal Roth contributions that show in Box 5 are fine since you already paid taxes on those. What helped me was creating a simple spreadsheet tracking my contribution history. I went back through my pay stubs and 401k statements to identify exactly how much my employer contributed as traditional (pre-tax) money versus my own Roth contributions. This gave me the exact amount I needed to report as taxable conversion income. Most tax software will handle this once you know the amounts - look for the section on "partial rollovers" or "mixed traditional/Roth distributions." You'll enter the total rollover amount, then specify how much was already taxed (your Roth portion) versus how much needs to be taxed now (employer traditional portion). Don't skip this step - the IRS will eventually catch discrepancies between what your 1099-R shows and what you report, and it's much easier to get it right the first time than deal with notices later!