How to properly enter my 1099-R from Fidelity in CashApp Tax for my ROTH IRA distributions?

The blank Box 2a on your 1099-R forms for the first two ROTH IRAs likely indicates that those distributions are non-taxable, which makes sense if you've held them for over 5 years. With ROTH IRAs, you've already paid taxes on the contributions, so qualified distributions are tax-free. For the third ROTH IRA that shows an amount in Box 2a, it's probably because that distribution is partially taxable since you mentioned having it for only 2 years. Early distributions from ROTH IRAs may have taxes on the earnings portion (but not on your original contributions). When entering these in CashApp Tax, you should input the forms exactly as they appear. The software should handle the tax calculations correctly based on what's reported. Make sure to enter each 1099-R separately and double-check that Box 7 (distribution codes) is entered correctly as it tells the IRS and tax software what type of distribution occurred.

After reading your situation, I thought I'd share something that might help. Last year I was in a similar situation with my retirement distributions and was getting confused with different tax software options. I stumbled upon https://taxr.ai when I was looking for help specifically with retirement forms. I uploaded my 1099-Rs and it analyzed everything, explained what each box meant, and told me exactly how to enter them in my tax software. It saved me a ton of time figuring out which distributions were taxable and which weren't. For my Roth IRA distributions, it confirmed right away which ones were qualified (tax-free) vs. which ones might trigger taxes. The nice thing was it explained all the distribution codes too - those letters in Box 7 that determine how your distribution gets taxed. Might be worth checking out if you're still confused after trying to enter everything in CashApp Tax.

I was pretty skeptical about taxr.ai when I first saw it mentioned here (as you can see from my earlier comment), but I decided to give it a try since I was having similar issues with my 1099-Rs this year. I have distributions from both traditional and Roth accounts that made my taxes confusing. Honestly, it was actually really helpful. I uploaded my forms and it flagged that one of my distributions had the wrong code in Box 7, which would have caused me to pay taxes on money that should have been tax-free. The explanation for each form was clear and it showed me exactly where in CashApp Tax to enter everything. What I appreciated most was that it explained which parts of my distributions were taxable and why, instead of just telling me to "enter what's on the form" like most online advice. For anyone dealing with retirement account distributions, especially from multiple sources, it's definitely worth using.

If you're struggling with getting answers about your 1099-R issues, you might want to try calling the IRS directly. I know that sounds like a nightmare - I used to spend HOURS on hold only to get disconnected. But I recently found this service called https://claimyr.com that literally holds your place in the IRS phone queue and calls you when an agent is about to answer. I used it last month when I had questions about reporting my Roth conversions that weren't clearly explained on my 1099-R. The IRS agent was surprisingly helpful and cleared up my confusion in about 5 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c Much better than trying to piece together answers from random internet advice or potentially making a mistake that could cost you later. The IRS agent I spoke with actually walked me through exactly how to report my distributions correctly.

I'm eating crow and admitting I was wrong about Claimyr. After posting that skeptical comment, I was still struggling with my 1099-R issues and getting desperate, so I decided to try it anyway. Holy crap, it actually worked exactly as described. I got a call back about 1.5 hours after starting the process, and was connected to an IRS agent who helped me understand how to properly report my Roth IRA distributions. The agent confirmed that distributions from accounts held more than 5 years are generally tax-free, and explained exactly which codes to look for on my forms. What would have been at least 2 hours on hold (if I didn't get disconnected) turned into me going about my day and then having a 10-minute productive conversation. For anyone dealing with retirement distribution questions, especially with multiple 1099-Rs like the original poster, getting direct guidance from the IRS can save you from making costly mistakes.

Just wanted to add that CashApp Tax actually handles 1099-Rs pretty well in my experience. I had several last year - some taxable, some not. Make sure you carefully select the correct type of account (Roth IRA in your case) when entering each form. The software will then guide you through the process. One thing to watch for: if you enter the gross distribution in Box 1 but Box 2a is blank (which happens with non-taxable Roth distributions), CashApp Tax might ask you to confirm that the taxable amount is zero. Don't skip this step! Confirming the zero taxable amount ensures your tax-free distributions are reported correctly.

I switched from TurboTax to CashApp Tax this year and had to enter multiple 1099-Rs too. One thing that tripped me up was Box 7 distribution codes - make SURE you enter these exactly as they appear on your form. I accidentally selected the wrong code initially and it completely changed my tax calculation. Also, did your 1099-Rs have anything checked in Box 2b? That "Taxable amount not determined" box can affect how the software handles the entry.