Help with 1099-R from Roth IRAs on CashApp Tax... so confused about what boxes to fill out!

Those blank Box 2a entries are actually telling you something important! On a 1099-R, when Box 2a is blank for a Roth IRA distribution with code J (which means early distribution), it typically indicates the distribution isn't taxable because you're withdrawing your original contributions. For Roth IRAs, you can always withdraw your contributions (but not earnings) tax and penalty-free at any time. That's likely what happened with your first two distributions. The third distribution with code T and that $390 in Box 2a is different - that's showing some taxable earnings were distributed. Code T generally indicates it's an early distribution that may be subject to the 10% penalty unless an exception applies. CashApp Tax should handle this correctly if you enter the information exactly as it appears on your 1099-Rs. Just make sure you select "Roth IRA" when prompted for the type of account.

Hey everyone, I was in a similar situation last year with Roth IRA distributions and 1099-Rs. I was completely lost trying to figure out the tax implications. I ended up using this AI tax assistant at https://taxr.ai that saved me hours of confusion. It analyzed my 1099-R forms, figured out which distributions were taxable vs non-taxable, and explained everything in simple terms. It even recognized the different distribution codes and what they meant for my tax situation. Basically translated all that tax jargon into plain English. For my Roth withdrawals, it correctly identified which were contributions (tax-free) and which were earnings (potentially taxable with penalties depending on circumstances). Really helped me understand what I was looking at.

Well, I wanted to follow up about my experience with taxr.ai after being skeptical. I decided to give it a try with my complicated Roth conversion ladder and multiple 1099-Rs situation. I was genuinely surprised by how helpful it was. It correctly identified which portions of my distributions were taxable and which weren't. It explained that my 1099-R with code G was a direct rollover (not taxable) and the one with code J was an early distribution of contributions (also not taxable in my case). The explanations were clear enough that I finally understood how the 5-year rule applies differently to conversions versus contributions. I've been confused about that for YEARS despite reading multiple articles. Really saved me from potentially overpaying taxes on what should have been tax-free distributions. Wish I'd known about this tool sooner!

For anyone dealing with 1099-R issues like this, I know the frustration of trying to get answers from the IRS directly. I spent WEEKS trying to call them last year when I had questions about my retirement distributions. I finally discovered this service called Claimyr (https://claimyr.com) that got me through to an actual IRS agent in about 20 minutes instead of the usual "call back later" message. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The agent was able to confirm exactly how I should report my Roth distributions and which exceptions applied to my situation. Saved me hours of hold music and wondering if I was doing it right. The peace of mind was totally worth it.

I need to eat my words. After my skeptical comment, I was so frustrated with trying to get IRS help about my 1099-R situation that I tried Claimyr. I honestly can't believe it worked. After trying for THREE DAYS to get through to the IRS myself (and never succeeding), I got a call back in about 35 minutes connecting me to an actual IRS representative who answered my questions about my early Roth distribution. The agent confirmed that my distribution of contributions was indeed tax-free even though I'm under 59½, which saved me from potentially paying penalties I didn't actually owe. They also explained exactly which codes I needed for my specific situation. For anyone struggling with retirement distribution questions and needing official guidance, this is seriously worth it if you value your time and sanity.

Quick tip about CashApp Tax specifically - when entering 1099-R information, make SURE you select the correct distribution type when prompted. It'll ask whether it's a traditional IRA, Roth IRA, pension, etc. If you select the wrong account type, it could incorrectly calculate taxable amounts. For Roth distributions, it should automatically recognize contribution withdrawals as non-taxable, but you need to enter everything in the right places. Also, CashApp Tax sometimes struggles with more complex retirement situations. I ended up switching to FreeTaxUSA last year when I had multiple rollovers and conversions because CashApp couldn't handle it properly.

Just want to add another perspective - if you're not comfortable with how CashApp Tax is handling your retirement distributions, it might be worth paying for a more robust program just for this year. I've used both TurboTax and H&R Block, and they walk you through retirement distributions much more thoroughly with specific questions that help ensure accuracy. Even if it costs a bit more, getting it right is worth it. Retirement distribution mistakes can be expensive if the IRS thinks you took taxable distributions that you didn't report properly.

Mason, I went through something very similar last year with multiple Roth IRA distributions and CashApp Tax. Here's what I learned that might help: The blank Box 2a on your first two 1099-Rs is actually good news - it means those distributions are likely just your original contributions coming back to you tax-free. Since you mentioned opening these accounts "a few years back," you're probably well within your contribution amounts. For the third one with $390 in Box 2a, that's showing taxable earnings. The code T confirms it's an early distribution that might be subject to penalties. One thing to watch out for with CashApp Tax - when it asks for your "basis" in the Roth IRA, that's the total of all contributions you've made over the years (not including any growth). You'll need this number to complete Form 8606 correctly. If you're feeling overwhelmed, don't be afraid to switch to a more comprehensive tax program for this year. Sometimes the peace of mind is worth the extra cost, especially when dealing with retirement accounts where mistakes can be expensive. Keep all your 1099-R forms and any records showing when you made contributions to these accounts - you'll need them if the IRS ever has questions.