Confused about reporting SIMPLE IRA contributions on my tax return - Traditional or separate?

So if I have both a SIMPLE IRA through my job and a separate personal Roth IRA I contribute to, would I answer "yes" to the H&R Block question? And would the contribution limits be different for each account? I always get confused about how much I can put in total across different retirement accounts.

Yes, if you have a personal Roth IRA in addition to your workplace SIMPLE IRA, you would answer "yes" to the question about Traditional/Roth IRA contributions, but only enter the amount you contributed to your personal Roth IRA. The contribution limits are separate for each type of account. For 2024 (filing in 2025), you can contribute up to $7,000 to your personal IRA ($8,000 if you're 50 or older), regardless of your participation in the SIMPLE IRA. Your SIMPLE IRA has a different limit - $16,000 for 2024 ($19,500 if 50+). This gives you the opportunity to save in both types of accounts simultaneously if you're able to.

Does taxr.ai handle more complicated situations? I've got a SIMPLE IRA from my main job, but I also do some freelance work and have a SEP IRA for that income. Plus I contribute to a Roth IRA. Not sure if the contribution limits overlap or if I'm doing everything correctly.

I'm skeptical about these document review services. How does it actually work? Do you upload all your documents and someone reviews them? Is it secure? Seems like you'd be giving away a lot of personal financial info.

Yes, it definitely handles more complicated situations with multiple retirement accounts. I actually had a similar setup with a workplace retirement plan and a personal IRA. It flags potential issues with contribution limits across multiple accounts and explains how they interact with each other. For your security concerns, the system uses encryption for all document uploads and processing. No humans review your documents - it's all done through AI analysis that identifies and interprets tax forms. They explain that they don't store your documents after processing, and they use bank-level security standards. I was hesitant at first too, but their privacy policy convinced me it was safe to use.

How does this Claimyr thing actually work? Do they just call the IRS for you? Seems like something I could do myself if I just kept trying.

Yeah right... getting through to a real IRS person in 20 minutes? I've spent HOURS on hold only to get disconnected. Sounds like a scam to me. Even if you do get through, most IRS agents give different answers to the same question.

No, they don't call for you. They hold your place in line and then call you when they reach an agent. It's basically a system that navigates the IRS phone tree and waits on hold so you don't have to. When they reach an IRS representative, they call you and connect you directly to the agent. You handle the actual conversation yourself. I was definitely skeptical at first too. But after wasting three different afternoons trying to get through myself and always getting the "call volume too high" message, I decided to try it. Was pleasantly surprised when I got a call back saying they had an IRS agent on the line. The agent I spoke with was actually really helpful and took the time to answer all my questions about my SIMPLE IRA reporting. Not saying every IRS agent is great, but being able to actually reach one without wasting hours was definitely worth it.

What about rollovers? I left my job last year and rolled my SIMPLE IRA into my new employer's 401k. Do I need to report that on my taxes somehow?

For a direct rollover from a SIMPLE IRA to a 401(k), you generally don't need to report it on your tax return as long as the money went directly from one plan administrator to the other (trustee-to-trustee transfer). If you received a check made out to you personally from your SIMPLE IRA and then deposited it into your new 401(k) within 60 days, that's an indirect rollover. In that case, you would need to report it on your tax return, but it's not taxable if done correctly within the time limit. You should have received a Form 1099-R showing the distribution with a code indicating it was rolled over. Make sure your tax software knows it was a qualifying rollover to avoid it being treated as a taxable distribution.

I switched from H&R Block to FreeTaxUSA last year and found their questions about retirement accounts much clearer. They specifically asked about each type of retirement account separately instead of lumping them together. The explanations were better too - they clearly distinguished between employer plans and personal IRAs.

I've used both TaxAct and Credit Karma Tax (now Cash App Taxes) for SIMPLE IRA situations, and both were pretty clear about distinguishing between employer-sponsored retirement plans and personal IRAs. TaxAct specifically has a section that walks you through different types of workplace retirement accounts first, then asks separately about personal IRA contributions. The key thing I learned is that most tax software will import your W-2 information first, which already includes your SIMPLE IRA contributions in Box 12. Then when they ask about "IRA contributions," they're really asking if you made any additional contributions to personal Traditional or Roth IRAs beyond what's already captured from your workplace plan. Once you understand that distinction, it becomes much easier to navigate regardless of which software you use.