I Used Claude to File My Taxes for Free(kachess.dev)
kachess.dev
I Used Claude to File My Taxes for Free
https://kachess.dev/taxes/ai/personal-finance/2026/02/27/breaking-up-with-turbotax.html
33 comments
Claude also wrote the blog post, which means I'm not interested in reading it even though I'd love to hear directly from the author about the topic.
How do we know that Claude wrote the blog post?
The aesethetic tells are excessive headings for small sections, many of which are largely just a list. There's the numbered list but then the sections that are a sequence of "Bold Text: Single sentence." Plenty of em-dash too, but I don't really look at that much.
It's basically a long list of factual statements all with the same weight, very little opinion expressed about the experience. I don't actually mind an infodump from a human, you usually can still work out some of what they care about, and you also can be reasonably sure they didn't fill in the gaps. Most likely I would have enjoyed whatever the author fed into the LLM.
It's basically a long list of factual statements all with the same weight, very little opinion expressed about the experience. I don't actually mind an infodump from a human, you usually can still work out some of what they care about, and you also can be reasonably sure they didn't fill in the gaps. Most likely I would have enjoyed whatever the author fed into the LLM.
Speaking as someone who has used em-dashes and semicolons for years, it’s a shame what the AI companies have done with punctuation.
Yeah we’re in a weird place where the prompt would still have to contain most of the content and then be “prettied up”. Since generic AI “prettied up” style is so same-y and dry it would be refreshing to just see whatever the original was, warts and all. Just blog-post the prompt!
FreeTaxUsa [1] exists and is much cheaper than Turbo Tax.
That being said, this is not free - you are paying for Claude to do this in both tokens and data. I personally think it is insane to hand over your private financial data to an AI company, but I also recognize not everyone has the same concerns.
[1]: https://www.freetaxusa.com/
That being said, this is not free - you are paying for Claude to do this in both tokens and data. I personally think it is insane to hand over your private financial data to an AI company, but I also recognize not everyone has the same concerns.
[1]: https://www.freetaxusa.com/
How is giving the info to an AI company worse than giving it to FreeTaxUSA or Quickbooks/Intuit?
The former businesses don’t run technology stacks that might, inherently by design, regurgitate any given piece of information that they encounter.
They’re also purpose built to do tax/accounting work, and can’t go “off script” with filling in your tax return.
They’re also purpose built to do tax/accounting work, and can’t go “off script” with filling in your tax return.
https://github.com/calef/us-federal-tax-assistant-skill is the link to the skill that came out of this work.
Sounds like a much better use of LLMs: use them to replace jobs that should never have existed in the first place. Use them to replace parasitic systems.
Even so, you should never trust their calculations. Don't have it file your taxes, have it explain to you how to file your taxes. Use it to dig through all the bureaucratic forms and let it help you find your way. Don't let it do it for you, because you have no idea where it might end up, and filing your taxes incorrectly can have severe consequences.
Even so, you should never trust their calculations. Don't have it file your taxes, have it explain to you how to file your taxes. Use it to dig through all the bureaucratic forms and let it help you find your way. Don't let it do it for you, because you have no idea where it might end up, and filing your taxes incorrectly can have severe consequences.
I used Claude to successfully argue with a fraudulent supplier, by threatening to sue.
They had sent me a detailed quote for their service. Upon cancellation they sent me a "final" bill with some bogus final fees inflating the quote by about 50%. Their claim, correct, was that the fee was present in T&C, buried somewhere in para 70. But under UK law, there are various protections against it - not to mention, if you send someone a quote, you don't then say "surprise"!
I fed Claude all the materials, their T&C's, the emails etc. It gave me a legal basis for suing them in small claims court. One of the 4 was hallucinated, but easy to validé, and the remaining 3 were solid. It then wrote me the sharp refusal to pay with a threat to sue for fraudulent business practice.
I'm sure any real lawyer would look at this and laugh, but it did the trick. No way would I ever do all this on my own.
They had sent me a detailed quote for their service. Upon cancellation they sent me a "final" bill with some bogus final fees inflating the quote by about 50%. Their claim, correct, was that the fee was present in T&C, buried somewhere in para 70. But under UK law, there are various protections against it - not to mention, if you send someone a quote, you don't then say "surprise"!
I fed Claude all the materials, their T&C's, the emails etc. It gave me a legal basis for suing them in small claims court. One of the 4 was hallucinated, but easy to validé, and the remaining 3 were solid. It then wrote me the sharp refusal to pay with a threat to sue for fraudulent business practice.
I'm sure any real lawyer would look at this and laugh, but it did the trick. No way would I ever do all this on my own.
I did something similar with OpenClaw (using claude) and my SO's old work. They were going to deduct money off her final check without written consent, after she quit, and were also late on paying her at all. I told OpenClaw the basic situation, and I told it to research applicable laws and cite it's sources.
Once I verified what it found was good, I had it write a demand letter specifying all the statutes that were being violated, and what remedies we would be entitled to if we had to chase it up.
She got a phone call within an hour of delivery saying her pay is being sent to payroll with every penny intact.
Also: I don't give openclaw access to any of my personal info, I literally just tell it to research stuff for me and take advantage of it's ability to store stuff in files.
Once I verified what it found was good, I had it write a demand letter specifying all the statutes that were being violated, and what remedies we would be entitled to if we had to chase it up.
She got a phone call within an hour of delivery saying her pay is being sent to payroll with every penny intact.
Also: I don't give openclaw access to any of my personal info, I literally just tell it to research stuff for me and take advantage of it's ability to store stuff in files.
>1099-Rs from multiple inherited IRAs
There is nothing complicated about these, a 1099-R is one of the more straightforward info forms and any tax software can handle the input numbers and distribution code. Whether the IRA is inherited or not does not add complexity to the 1099-R, so not sure why this attribute gets multiple mentions.
The only other thing that might be considered complicated is the Form 1116 foreign tax credit. MFJ filers don't need it if total is $600 or less, so this might have added needless complexity.
Interesting that there is no Schedule A here, because that is one form (of many) that gives the lie to those who claim "oh the government already knows everything about your tax filing and could generate your return for you".
In short, this exercise didn't really involve any "intelligence" beyond what every tax software already does.
>E-filing isn’t available for trust returns
False.
There is nothing complicated about these, a 1099-R is one of the more straightforward info forms and any tax software can handle the input numbers and distribution code. Whether the IRA is inherited or not does not add complexity to the 1099-R, so not sure why this attribute gets multiple mentions.
The only other thing that might be considered complicated is the Form 1116 foreign tax credit. MFJ filers don't need it if total is $600 or less, so this might have added needless complexity.
Interesting that there is no Schedule A here, because that is one form (of many) that gives the lie to those who claim "oh the government already knows everything about your tax filing and could generate your return for you".
In short, this exercise didn't really involve any "intelligence" beyond what every tax software already does.
>E-filing isn’t available for trust returns
False.
If you're going to do this, you should also use well-respected tax filing software for free to create your return. They usually only charge you to file it. Prepare it in their system, see if you get different results then Claude, figure out the discrepancy.
I use Free File Fillable Forms to prepare my taxes. It can be a bit tricky to make sure all the correct forms are completed and the calculations are correct, so that is the exact approach I take. It's a pain in the butt to essentially do my taxes twice, but I'm willing to go through that if it means I'm not giving money to the tax prep industry.
https://www.irs.gov/e-file-providers/free-file-fillable-form...
https://www.irs.gov/e-file-providers/free-file-fillable-form...
He checked the work with a LLM too? Does this guy want to get audited by the IRS? I'm also not sure I'd feel comfortable giving my tax details to an AI company to train on.
How does Anthropic pricing work exactly? Were the 150k tokens really free or would you need to pay a subscription and/or overage for that?
How does Anthropic pricing work exactly? Were the 150k tokens really free or would you need to pay a subscription and/or overage for that?
> I'm also not sure I'd feel comfortable giving my tax details to an AI company to train on.
I'm pretty sure grok already has them after DOGE scraped all the data the IRS and the treasury department’s bureau of fiscal service had on the American public.
I'm pretty sure grok already has them after DOGE scraped all the data the IRS and the treasury department’s bureau of fiscal service had on the American public.
Can you use Claude to figure out how to elect people who will bring back the free filing program?
I can't imagine doing something like this anytime soon, but I will probably follow the advice around having AI check the return against all my forms and previous years return before submitting.
If you do this, make sure you use a local only LLM. I would be cautious in uploading SSNs and other highly personal information.
I wonder how well this does on a German tax declaration, might be a good alternative to touring test judging by complexity
oh man... I am not sure I am ready to trust CC at that level. Though, this year I did vibe an expense tracker and heavily used CC to look at and categorize entries and apply appropriate Schedule C categories to my business expenses.
It might not have been faster this year... but I expect it will be next year.
It might not have been faster this year... but I expect it will be next year.
it can actually look across conversations, i would make sure to tell it not to. (one fun thing to do is to ask it to look across the past year and generate a claude wrapped where it roasts you.)
i also probably wouldn't use it for anything i don't know how to verify myself.
i also probably wouldn't use it for anything i don't know how to verify myself.
This is a terrible idea. You shouldn’t trust LLMs to handle this level of complexity well for anything you can’t verify yourself. And far from saving money, it certainly isn’t “free” to use Claude at this scale. There’s no way this cost less than using TurboTax.
If you have simple taxes, you can probably figure out how to file yourself, as it’s mostly just copying from a box on one form into another. If you have complex taxes, you should have a CPA prepare them.
If you have simple taxes, you can probably figure out how to file yourself, as it’s mostly just copying from a box on one form into another. If you have complex taxes, you should have a CPA prepare them.
The picture on the page had me thinking maybe this was a joke.
This is very brave.
> The IRS already has your W-2s, your 1099s, your brokerage statements. It knows the tax rules. For most Americans, the government could calculate their tax bill, send them a pre-filled return, and let them approve or dispute the result. This is how it works in the UK, Japan, Germany, and dozens of other countries. The reason it doesn’t work that way here is that Intuit and H&R Block have spent decades and hundreds of millions of dollars ensuring it doesn’t.
This is crony capitalism and both the political parties are fine with it
This is crony capitalism and both the political parties are fine with it
One political party created the free IRS Direct File program, a popular new technology that allowed anyone to file their taxes directly with the IRS. The other political party dismantled IRS Direct File immediately upon taking power.
Imho, the fact that you can probably guess which party is which is some evidence that the cliche that both parties are the same isn't really true anymore.
Imho, the fact that you can probably guess which party is which is some evidence that the cliche that both parties are the same isn't really true anymore.
Direct File is a bandaid. What they should be doing is what other developed countries are already doing - sending the tax invoice to taxpayers.
That doesn't give an opportunity to correct errors that exist in forms. Forms often give erroneous information or leave out details. Some forms or deductions may get skipped altogether. For these reasons, people can't just be sent an invoice. Direct File was appropriate.
Our effective system of government basically is crony capitalism. Those who contribute the most to bringing the political party and administration in power reap the most rewards.
I've already started loading all of my incoming tax forms into a folder so that I can attempt the same, so it's helpful to see someone do it and the tips.
I understand the risks with it but I don't care. I cannot fucking wait for the SaaSpocalypse to hit these companies.
I understand the risks with it but I don't care. I cannot fucking wait for the SaaSpocalypse to hit these companies.