Getting charged for filing 1099-NEC on supposedly free tax service

Does the IRS Free File still have income limits? I thought I made too much last year to qualify (around $78k)? Also, do these other services you mentioned handle multiple state filings without charging extra?

Yes, the IRS Free File program does have income limits - currently it's $73,000 for 2023 tax returns (filing in 2024). If you're at $78k, you might be just above that threshold. Cash App Taxes (formerly Credit Karma Tax) offers completely free federal and state filing with no income limitations, and they handle 1099-NEC/self-employment income. They support one state filing for free, but if you need multiple states, FreeTaxUSA might be better - they offer free federal filing including self-employment and charge about $15 per state.

How accurate is their document scanning? I have terrible handwriting on some of my records and previous software has messed up the numbers badly.

I'm intrigued but skeptical. Does it actually handle more complex situations? Like if I have rental income plus a small business plus W2 employment? Most "free" services fail as soon as you have multiple income streams.

Their document scanning is surprisingly good - much better than what I've experienced with other tax software. It even handled my wife's messy expense receipts with decent accuracy, though I still double-checked everything. The AI seems to be trained specifically for tax documents. For complex situations with multiple income streams, that's actually where I found it most helpful. I have a W-2 job plus some freelance work, and my wife does Uber Eats. The system organized everything by income type and walked us through each section without getting confused. I believe rental income is definitely covered too - there was a specific section for it that I noticed but didn't need to use.

Wait, how does this actually work? Do you have to give them personal information? Sounds kinda weird to have a third party connecting you to the IRS.

This sounds like BS honestly. Why would I pay someone else to wait on hold when I can just do it myself? And the IRS agents usually don't even give good advice. Last time I called they gave me completely wrong information about my self-employment taxes.

They don't need any sensitive personal information - just your phone number to call you back when an IRS agent is on the line. You enter what department you're trying to reach and they handle the waiting. When they connect you, it's a direct line to the IRS agent, just like if you'd waited on hold yourself. I was skeptical too but it's simply a hold service. You don't discuss your tax details with Claimyr at all - only with the actual IRS agent once you're connected. For me, it saved about 2 hours of hold time when I was trying to sort out exactly what forms I needed for my wife's 1099-NEC income.

I haven't tried FreeTaxUSA yet! Does it have a good interface? My biggest frustration with some of the smaller tax services is that the UI feels like it was designed in 1997 lol.

The interface isn't as fancy as TurboTax or H&R Block, but it's definitely not from the 90s! It's clean and straightforward, just without all the animations and excessive hand-holding. Everything is organized logically and I actually find it faster to use than the big name services. They're especially good with 1099-NEC and other self-employment forms since you don't get routed into "upgrade now!" pages halfway through. Their help content is also surprisingly detailed if you get stuck on something.

I found a workaround last year! If you go through the IRS Free File portal instead of directly to the tax service website, some of them are required to give you the free version even with 1099-NEC forms. There's an income limit though.