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I Used Claude to File My Taxes for Free

kachess.dev

21–30 of 34 posts

Re: I Used Claude to File My Taxes for Free

#21
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/

Re: I Used Claude to File My Taxes for Free

#23
post #13
post #6

> 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 o…

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.

Direct File is a bandaid. What they should be doing is what other developed countries are already doing - sending the tax invoice to taxpayers.

Re: I Used Claude to File My Taxes for Free

#24

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/

How is giving the info to an AI company worse than giving it to FreeTaxUSA or Quickbooks/Intuit?

Re: I Used Claude to File My Taxes for Free

#26
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.

Re: I Used Claude to File My Taxes for Free

#27

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.

Re: I Used Claude to File My Taxes for Free

#29

Earlier quoted context omitted.

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 inf…

Speaking as someone who has used em-dashes and semicolons for years, it’s a shame what the AI companies have done with punctuation.

Re: I Used Claude to File My Taxes for Free

#30
post #24

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/

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.

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