TurboTax vs FreeTaxUSA - Program Not Correctly Handling BackDoor Roth IRA Conversion

Thanks for replying! I looked under Deductions & Credits and found the IRA Contributions section, but I'm still confused. When I indicate the Traditional IRA contribution was non-deductible, it asks for the "basis" amount. Is that just the total amount I contributed before conversion? And should I be entering anything in the "amount converted to Roth IRA" field that appears later? Also, when I search for Form 8606, nothing comes up in FreeTaxUSA's search. Is it possible the form is generated behind the scenes and I just can't see it until I preview my full return?

The basis amount is indeed the total you contributed to your Traditional IRA before converting it. This establishes that you've already paid taxes on this money, which is crucial for the backdoor strategy. The "amount converted to Roth IRA" field should match the amount on your 1099-R form, typically in Box 1. After completing both sections correctly, I recommend previewing your full tax return to verify Form 8606 is there. FreeTaxUSA does generate some forms automatically in the background, but you should be able to see it in the final preview. If your refund amount still doesn't correct itself after completing both the non-deductible contribution and conversion sections, you might need to contact FreeTaxUSA support directly as there could be a software glitch.

Wait, so this taxr.ai thing actually works? I've been having nightmares with my backdoor Roth conversion too, but I'm using TurboTax. Would it work with different tax software or is it only for FreeTaxUSA users? My situation is similar but I also have some old Traditional IRA funds with a mix of deductible and non-deductible contributions which makes it even more confusing.

I'm skeptical about using another service when I'm already paying for tax software. How exactly does this taxr.ai analyze your "tax transcript"? Sounds like you'd have to upload sensitive financial documents to some random website. Is it secure? And do they just tell you what to fix or do they actually file for you?

It works regardless of what tax software you're using - I've seen people use it with TurboTax, H&R Block, and even when filing manually. The AI is trained on tax forms and rules rather than specific software interfaces. For complex situations with mixed deductible/non-deductible contributions, it's actually even more helpful because it can distinguish between the different types of basis calculations. Regarding security concerns, you don't actually upload your entire return or sensitive documents. You can just share the specific form or section screenshot where you're having issues. They use bank-level encryption, and they don't file for you or access your accounts - they just analyze what you share and provide guidance on how to correct issues yourself. I was hesitant too but found it much more helpful than spending hours on hold with tax software support.

How does Claimyr actually work? I'm confused about how they get you connected faster than just calling FreeTaxUSA yourself. Do they have some special priority line or something? And does FreeTaxUSA even have phone support? I thought they were mainly email-based.

This sounds like BS honestly. If FreeTaxUSA has a phone queue, how does some random third-party service magically get you to the front? They probably just automate the call and hold process which you could do yourself. Plus, I bet they charge a fortune for this "service." Just email FreeTaxUSA support directly and save your money.

Claimyr works by using an automated system that navigates through phone trees and waits on hold for you. When a representative finally answers, you get a call connecting you directly to them. FreeTaxUSA does have phone support, but it's notoriously difficult to get through during tax season. They charge a small fee, but considering I was spending hours trying to get through and getting nowhere, it was absolutely worth it to me. The time I saved was valuable, especially with the filing deadline approaching. Plus, resolving this backdoor Roth issue saved me from potentially overpaying by thousands of dollars, so the service fee was minimal in comparison.

I used H&R Block last year for my backdoor Roth and it was actually pretty straightforward. They have a specific interview question that asks if you're doing a backdoor Roth, and then it walks you through both the non-deductible contribution and conversion steps in the right order. Their Form 8606 generation worked correctly for me without any issues. It's a bit more expensive than FreeTaxUSA but worth it for the clearer guidance on more complex tax situations.

Thanks for sharing your experience! That's really helpful to know. I think I'll give H&R Block a try this year since I'd rather pay a bit more for a smoother experience, especially with something like backdoor Roth where the tax implications can be significant if reported incorrectly. Did you use their Deluxe or Premium version? I'm trying to figure out which tier I need.

I used their Premium version because I also had some investment income and rental property to report. For just the backdoor Roth, I believe their Deluxe version would be sufficient as it covers IRA contributions and Form 8606. Their website has a comparison chart that can help you determine exactly which features you need. The interface is pretty intuitive, with a dedicated section for IRA contributions where you specifically mark them as non-deductible. Then when you enter the 1099-R for the conversion, it connects the dots automatically. Just make sure you complete both sections for everything to calculate correctly.

This is such an important point that often gets overlooked! I nearly made this mistake myself. For anyone confused: with a backdoor Roth, you should NOT be deducting your Traditional IRA contribution at any point. The whole strategy only works tax-efficiently if you use after-tax dollars for the initial contribution. Otherwise, you'll end up paying taxes during the conversion step.

Thank you for bringing this up! I didn't deduct my Traditional IRA contribution on last year's taxes, so I should be okay on that front. But it's a really good reminder about ensuring consistency between tax years. I feel like there are so many gotchas with this strategy that the software doesn't really warn you about. Do you know if FreeTaxUSA has any special review checks for these kinds of issues?