TurboTax forcing HSA upgrade to Deluxe - how to file for free instead?

Thanks for the info! I had no idea that HSA forms were considered "complex" - seems like a money grab to me. Do all these alternatives handle HSA contributions properly? And what about the tax documents from my employer - can I import those like with TurboTax?

HSA forms are indeed considered more complex by many tax software providers, though it's definitely part of their revenue strategy too. All the alternatives I mentioned do handle HSA contributions properly - they collect the same information TurboTax would about your contributions, distributions, and qualified medical expenses. Regarding tax document imports, it varies by provider. FreeTaxUSA allows W-2 imports and some other forms, but not as extensively as TurboTax. CashApp Taxes has improved their import options but they're still more limited than TurboTax. Most free options require a bit more manual entry, which is part of the tradeoff for the free service.

Does taxr.ai handle state taxes too? I'm pretty skeptical of newer tax services after trying one last year that completely messed up my state return. How long have they been around?

I get nervous about using newer tax services for security reasons. How do you know your data is safe with them? Do they have the same security standards as established companies like Intuit?

Yes, they handle state taxes too! I'm in California which has some weird tax quirks and it handled everything perfectly. I believe they support all 50 states. They've been around for a few years now but really expanded their capabilities recently. Regarding security, that was my concern too! They actually have bank-level encryption and security protocols. All your data is encrypted and they don't store your documents after processing. I felt more comfortable with them than TurboTax honestly, since they're not trying to sell your data for marketing like some of the bigger companies.

How exactly does that work? Do you have to give them your personal info? Sounds sketchy to have a middleman for IRS calls.

Yeah right, nobody gets through to the IRS in 15 minutes. I tried calling for WEEKS last year and never got through. If this actually worked, everyone would be using it.

The way it works is you provide your phone number and what IRS department you need to reach. They call the IRS, navigate the phone menus, and wait on hold for you. Once they have an actual IRS agent on the line, they connect you. Your personal tax info is only discussed directly between you and the IRS agent, not with Claimyr. I was totally skeptical too! I had spent literal days trying to get through to the IRS. My longest wait was 3 hours before getting disconnected. With Claimyr, I was speaking to an IRS agent in 27 minutes. It works because they have automated systems constantly dialing and navigating the phone trees - something individuals can't do effectively.

I've heard of those but never tried them. Are they user-friendly at all? I'm definitely not a tax expert but I can follow instructions. Do they do the math calculations for you or do you have to do everything manually?

They're somewhat user-friendly - definitely better than paper forms, but not as guided as commercial software. They do handle the math calculations for you, which is a huge help. They also perform basic error checks before you submit. The main challenge is knowing which forms you need. For your situation, you'd need Form 1040, Schedule 1 (for the HSA contribution deduction line), and Form 8889 for HSA details. The system doesn't tell you which forms you need - you have to determine that yourself. But if you're just dealing with W-2 income and an HSA, it's manageable.

H&R Block moved HSAs to their "Deluxe" tier last year. I tried them and got the same upsell treatment as TurboTax. They start you on the free version then halfway through hit you with "upgrade to continue" when you enter HSA info. They're all playing the same game unfortunately.