The picture on the page had me thinking maybe this was a joke.

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.

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.

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.

> 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

https://github.com/calef/us-federal-tax-assistant-skill is the link to the skill that came out of this work.

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.

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?

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.

>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.

Can you use Claude to figure out how to elect people who will bring back the free filing program?

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.

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.

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.

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/

This is very brave.

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.