I was one of the human book-keepers for this benchmark (the preparer; my co-founder verified the VAT submission once ready), and given that at the time of doing this I knew I was eventually going to use this data for evaluating the models, I was super careful. So I guess this is a "good book-keeper". In the previous company our book-keepers made lots of mistakes; some serious enough that we had to restate our company's accounts.
Interesting write-up. Having been a bookkeeper a long time ago, I'm not too surprised at this being susceptible to automation by an LLM backed system.
It seems also that the classes of error they encountered could be handled by improved skills/knowledge base access on the fine points of relevant tax legislation.
The important part for their software ofc is, will they take responsibility for the output if HMRC come calling? Without that users are adopting the risk which they may not be keen to do (dealing with HMRC is not fun), with that it could be a very nice saving for a lot of small companies (and bad for the employees of a lot of accountancy firms)
Parses emails or other sources, extracts numbers, correlates different transactions, web search, asks questions, stores notes (regex based, very simple).
The hard part is getting good data, I'm sure that lexus nexus or whoever can get API access to my bank account and all my credit cards, but I can't. Email turned out to be the best way for most of my providers. Managed to avoid 2factor auth so far, but it will suck when I need it.
We've got integrations with major UK banks. Curious if you'd like to use a polished product or be more interested in bank-feed-as-an-API type of use case? What banks do you use?
Credit union atlantic. The possibility of you being able to profitably support small regional credit unions is pretty much 0. Maybe with a general browser use AI and an SMS portal. Also you'd need to bypass anti-bot protections, maybe solve captchas.
In my opinion that is the thing holding back almost all of these accounting products that make consumers lives better. I've solved it because all my cards and bills happen to support email, so I can use that as my source of truth for all my credit cards.
The token is stored on a LUKS encrypted drive on kwallet. You'd have just as much luck getting my password from my firefox installs sqlite DB.
I think if you were to send me an email, and the bot was to parse it, the only data exfiltration attack you could do would have to route through the tavily question asking API. Maybe you could do something like ask "what does <the password string> mean on <some host you control>. The data exfiltration surface is pretty low. I want say 100% impossible, but very hard to do reliably.
Also this isn't really an agent. At least not a long lived one. Each email or transaction gets it's own session, the llm can make a few tool calls but must emit json as the final result. Very very short context lengths.
Oh, I'm actively doing this at the moment. FreeAgent grabs my transactions from Wise already, and then I give it [Claude Code, in fact] a folder of PDFs to attach to my invoices, including figuring out VAT, and it's uploading what it found using the FreeAgent API. My accountant hasn't complained yet, and it seems considerably more accurate than when my wife was doing it.
They're not going to unless it's obviously and egregiously wrong - the risk on quality of input remains yours. It's the tax version of garbage in, garbage out. They're just guaranteeing the processing step.
The problem with LLM's is that they could work correctly for months and years and then do something egregious which will will go unnoticed because of the misplaced trust one develops on a system that "just seems to work." Get flagged for an expensive audit and there go all the savings and then some.
Humans are more likely to make small mistakes but the internal consistency check is pretty good at catching large errors. On top of that, fudging numbers to make everything add up is not something humans do (not unintentionally at least)
I'd be scared shitless to even try something like this. There is no just a pretty website, a video, and a blog post. No info on the founders, I can't find anything on LinkedIn and a company Vineyard Finance LTD that was incorporated last year.
We're all unhinged about the data we're giving LLMs but here I'd draw the line. I'd rather keep paying for the small amount I pay to have my accounts done.
The company I work for, Digits, has been regularly updating our AI-vs-human bookkeeper benchmark. Look at page 8 -- many models are nearly as accurate as a human bookkeeper
I just have a folder on my computer where I keep things in beancount. Then I have mercury CLI access with a read token to my business bank account, and I have my emails fully synced in there as well via IMAP. Claude Code with Opus just seamlessly hooks everything up so my accounts are up to date. At the end of the year, I used that information to prepare my tax returns for the business and then later the part that flowed to me as the owner.
I had a fairly complicated tax return in 2025 involving a couple of change of business tax consideration and some money that was accidentally sent to me as a 1099 instead of to the business and I did everything with tax software with Claude Code advising.
The end result was pretty damned good. I was unsurprisingly audited and the only error was in some way where I allocated a small amount of my wife's tax-free disability payments (disability is the mechanism that California uses to provide maternal benefits pay protection; she's not actually disabled). The IRS told me about it, I paid that bit (it was meant to be claimed back from the employer, not the US government) and everything was hunky dory. To be honest, the sum was so small I did not investigate (and haven't yet followed up with getting reimbursed by her employer).
Honestly, almost all of it could have been avoided if I'd paid an accountant and a tax lawyer and they'd told me things and I'd done as they did, but in the end the combination of the fact that the IRS is very reasonable when you explain things and a modern agent means that the entire process was quite simple. In the end, I preferred the interactive mechanism of working with software because most accountants and lawyers will prefer to get all of your documentation all at once and then work on it rather than do it incrementally. In my case, I was able to work on the return incrementally and then have everything plugged in. I could ask a bunch of questions and get clarification.
I think I will probably do all this the same way this year (though of course my taxes will be simpler).
As in, "what makes you think you were audited?". They sent me paperwork saying they were reviewing my return and that they found a discrepancy (the disability thing) and it took many months after the usual time for it to process.
If you mean "for what reason could you have been audited?" it was because a client I had previously worked for accidentally reported paying me as an individual instead of my LLC.
I don't know how much a tax lawyer/ account would quote for this in California, but I saved 3000 EUR/ tax year on a German Steuerberater in a similar way.
This is a prime example of a problem space where accuracy matters, but it also matters who ultimately goes to prison. I'm going to go out on a limb and guess it's not the LLM.
If you're acting in good faith and your accountant does something crazy or evil, your liability is limited to some extent. You may get a tax bill but you're probably not gonna end up behind bars. But if your LLM decides to do a little bit of tax fraud, you're in uncharted waters. In the end, the gun did it, but you were the one holding the gun.
A lot of jobs are like that. You're not as much buying the service as you're buying not having to worry about the service.
> This is a prime example of a problem space where accuracy matters, but it also matters who ultimately goes to prison.
I don't disagree that tax fraud is bad but accuracy really doesn't matter 1/10th what people think it does.
Something to keep in mind in the EU with VAT is that there are approximations, errors and then huge frauds like the infamous "carousel fraud". Sadly the carousel fraud is all too common in the EU: this one gets people really sent to jail. But it's not an error a LLM shall make that could lead to a carousel fraud taking place: it's an elaborate scheme.
Now... If you're self-employed and have to pay the VAT (which may or may not be the case depending of the type of self-employment work you do) or if you're a SME and you've got approximations and errors well it's really not a big deal.
Because the public servants in charge of collecting the VAT and verifying that you filled your stuff correctly... Do make shitload of errors too. And then, depending on the country, these public servants have a special privilege: they can decide an amount of VAT+fine (if there's a fine) that you agree with and if you agree with it, their number is the number.
It's everything but a correct number. It's a number they ended up on that is "close enough" (for some definition of "close"). Sometimes by hammering number after number on a little calculator and then ending up saying:
"We ask you to pay 3500 EUR of additional VAT. If you sign here and accept, the IRS (equivalent of the IRS) won't be able to bother you ever again for that year/years".
This notion that, somehow, there's "one" correct number and that public servants paid something like 2 K EUR net per month (which may be the reason why so many are so prompt to ask for bribes btw) can determine it in a few minutes is ridiculous.
It's simply not happening. Usually the accountant doesn't know the exact number. The SME owner doesn't know the real amount of VAT due. And the public servant(s) in charge of a VAT audit, if any takes place, certainly as zero clue as to what the exact VAT number should be.
The rules are way too complicated, there are way too many special cases, and some things are simply extremely hard to take into account (for example during one audit the person told me he disagree with the 90% of 21% VAT deducted for my ISDN line --yup it was a long time ago-- but then I told him it was during a previous TVA audit, a few years before, that the VAT auditor, seen my job, fixed at 90%).
For some stuff you can opt for a fixed number: say a car, there are rules, depending on the country, where you can, say, get back 75% of 50% of the VAT. But people can also, depending on the country, opt-in for the "real usage": you do 12 387 km during the years, how many were really for work? 6 287 km ? Or may 6 275 km?
What if one day while going to work, you took a detour because you want to drop a gift for your grandma's birthday? How were these kilometers accounted for?
Restaurant bills? What if one of the person wasn't work related (your nephew happened to be in town and you had to take car of him and you knew the clients well so they didn't mind: how does the accountant account for that)?
Gifts to client. You got a discount buying 6 packs of bottle of champagne, but not five (no discount if only five), so you bought a sixth one. But that sixth one you kept for you.
Nobody computes those amounts correctly. Nobody.
And don't get me started on the public servants who'll give, during an audit, an unfair advantage to people from their community (whatever that community may be) or those, literally, banging underneath the table while talking about their next vacations: they're telling you an "arrangement" can be made. Basically you give that one person some money (cash bills of course) and, boom, the 20 K EUR of VA...
1 Just as with traditional non-ai ways of doing things, there is a deterministic layer that can trigger when things are off. This can range from letting the ai know to stopping before a human confirms.
2 Usually, specially for SMBs, nobody goes to prison over accounting errors. That's because SMB owners make mistakes all the time and, because of that, authorities are fairly practiced in understanding how mistakes look, and how fraud looks.
> If you're acting in good faith and your accountant does something crazy or evil, your liability is limited to some extent.
From my understanding, you are the person signing off on the paperwork that is submitted to the IRS.
There is this cache 22 with taxes.
You are responsible, but you outsource it to a accountant. Because you are not knowledgeable about the taxes. But you are expected to be knowledgeable to understand the tax documents that you submit to the IRS. That is why the accountant always ask you to review the documents and sign them like 20 times.
The same applies when you run a company, depending on the country, you need to prove yourself knowledgeable in accounting, before you are allowed to run a company. Normally that is included in a university degree, but if you have a middle school diploma, you need to do a official examen to get that degree.
Whatever you submit for your company, you are again responsible. Even if you hired a accountant.
So while technically, if a accountant makes gross mistakes, the bill will always fall in your lap, because you are expected to understand the reports you submit to the IRS. And catch any errors before doing so.
With the IRS, the burden of proving your innocents is often put you. Its because the good faith argument can be misused easily. That is why the buck stops at you.
So using a LLM or a accountant, really does not matter. Sure, a accountant can go to jail if there has been major issues (its not going to be with one client issue).
But you can lose your house / company, have your life ruined by whatever you submitted.
This is also something where how you interact with the IRS really really depends on your initial interactions.
If the IRS comes to you and says "your taxes are wrong you owe X amount" and you immediately turn around and prepare to fight them then they are going to be merciless with you.
But if they come to you and you turn around and show the auditor your methodology and what you thought you were supposed to be doing, etc and focus on fixing the issue and settling your debt then they are going to hook you up with IRS staff dedicated to helping fix this kind of stuff.
And most importantly they'll connect you with someone who can set up a payment plan out over whatever period of time to pay back what you owe without killing your business or taking your assets.
But again if you get audited and immediately become adversarial then they'll assume you were doing it intentionally and will take anything not bolted down.
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The rationale is basically that the IRS staff are mostly there to help you get your taxes in order and ensure that those taxes are paid but as soon as it starts to look like you are intentionally avoiding paying your taxes you get kicked over to the enforcement divisions and eventually the criminal divisions.
So good faith is absolutely something the IRS will honor but that stops the moment it looks like you are trying to hide stuff from them.
I don't think that's actually the case. If you get an tax attorney to document your treatment and indicate that they believe it's legal (e.g. a tax opinion letter), then you're off the hook for penalties and criminal liability (assuming the tax attorney did everything properly). You still have to pay the difference though.
An accountant may not save you from financial penalties but I believe that they are liable for them so you can recover it from their insurance.
> Whatever you submit for your company, you are again responsible. Even if you hired a accountant.
> So while technically, if a accountant makes gross mistakes, the bill will always fall in your lap, because you are expected to understand the reports you submit to the IRS. And catch any errors before doing so.
I've had a tiny accounting firm take on more and more accounting debt over years just to get the accounts (lots of journal entries into contra accounts; this was before I took over the company), that I was mostly rolling my eyes at how horrible they've become when I tried enlisting Claude's help to untangle them and hopefully move away from using that firm.
I know bookkeeping is tough, especially for newer businesses that haven't set up the processes, but a lot of the professional services industry feels like outsourcing a website to a freelancer on Upwork.
The job performed by the humans was broader than what was requested of the model in this benchmark: humans also had to find the relevant invoices (searching through mailboxes, or requesting them from providers) and reason through any circumstances which cannot be inferred from the bank feed and invoices/receipts on their own. In the benchmark these circumstances are presented to the model as “user notes."
This is precisely the kind of fine print on white-collar AI capability that companies keep running into: pretty much any non-entry office job worth having involves a lot of undocumented (even undocumentable) problems requiring judgment and experience.
And I would be pretty nervous about asking any of the frontier LLMs to retrieve invoices: "cool, Claude logged that it found the May 6th bill from the paper supplier, I am sure it didn't just make something up arbitrary, then compound on the error by agentically iterating over the made-up invoice lurking in its reasoning traces. I checked the first 30 times and there were no problems!"
> And I would be pretty nervous about asking any of the frontier LLMs to retrieve invoices:
I watched an accountant YouTuber reviewing a new AI-driven personal finance app the other day (I really need to touch grass), and it started out just fine. He had seeded the account with a bunch of his data and was able to ask questions about which categories had the most spend, etc.
About half a dozen questions in, he asked it to calculate a certain segment of his spend (and being an accountant, he had his numbers memorized), and he immediately got back a calculation that he did not expect. So he asked for an itemized response and it hallucinated line items that never appeared in his account data, which he pointed out to viewers. He followed up with the chatbot with "where did line item X come from?" and the bot acknowledged that it wasn't legit. He immediately noped out after that, and who could blame him?
AI helps automate things that didn't already have rigorous formatting and structures available as input... and that's really all it does (99% of the time).
Doesn't matter how many more nines you add, rigorous formatting is still required. In some cases, it has teeth with compliance standards. Those standards cannot be compromised because there are already a lot of other layers contributing inaccuracy. It all adds up.
In most situations, you could just hire a junior dev (or an intern! remember those?) write some CSV scripts and call it a day. Cheaper and auditable too. Those scripts can't change anyway until standards are revised.
I'm still not seeing the benefit outside of solopreneur efforts and shady businesses wanting to launder blame.
If and when a large number of companies blindly turn over their accounts payable workflow to some AI agent system, it'll be very interesting to see the "social engineer the LLM" methods that fraud people use to get money sent to them. Basically the same idea as the ancient "send a fax with a bill for an unsolicited delivery of copier toner to 30,000 businesses" but taken into the modern era.
That's why we have purchase orders that can only be entered by buyers. Product is received and approved by buyer. Invoice goes to accounting, who can't approve it unless there's a matching purchase order and receiver.
Yes, letting agents do whatever they want leads to disaster. But humans are gullible stochastic token generators as well. And that's why the problem is already solved.
I run a team that includes people that do this kind of work using ocr software that matches invoices to po's. No AI needed. This is a solved problem. Why are there people involved? Because sometimes the invoice and po don't match. For instance, price on invoice is higher than po, refer to buyer. Buyer is sick, supplier puts you on hold, no parts for your factory, lose millions... Would you trust an AI to choose what to do next? This might get referred to me to resolve and make a decision, not just on the facts available, but on other facts I can discover, and years of experience. I might end up making an unauthorised payment, would you give an AI that power?
With AI you can scale the protection against social engineering. Where with humans you have to start from scratch each time and they are more likely to mess up.
i specialize in invoice related analytics and business processes. AI can be useful for data extraction and saves me some typing time. even so, i dont blindl trust it because it sometimes makes very reasonable mistakes because invoices, quotes, and POs are sometimes structured in very informal ways. people misuse the lines, sublines, totals, and other data fields. they are often technically incorrect but when you look at them you know what they mean. i am not sure how to hand that off to something that has plausible deniability to guess even if it doesnt know
sometimes details are just in notes at the bottom and are applied to selectively applied to line items. sometimes the charge doesnt exist anywhere on the bill but there is an understanding (due to a separate agreement) of additional charges to be paid as a result of the invoice.
taxes sometimes are or are not explicitly stated
tariffs sometimes are or are not explicitly stated
when things are not explicitly stated or line item'd, they will usually still appear in the invoice total. so you have item 1 - $500, item 2 $500. total: $1300
At the end of the day invoices are often part of an ongoing communication / conversation between two organizations and they are created with an assumption that a rational and reasonable human who is in the loop with that conversation is going to read it.
I think it would be absolutely insane to hand over a serious-sized company's books to an LLM.
As a small consultancy though, looking forward to my next filing, and having just moved to a new and better-specced jurisdiction, I'm sorely tempted to outsource to Claude.
I've had mixed experience with accountants in the past. No horror stories, but I often feel I'm not getting everything laid out clearly, and that I don't fully understand the process.
I've got plenty of reasons to dislike LLMs in my own work, but when dealing with well-scoped but professionally gatekept things like tax or property transactions, they're an absolute godsend.
Ha even if this was true (it’s not) you’re basically saying “humans will make some mistakes so let’s throw caution to the wind” which is probably the worst application of AI that I’ve heard yet.
If there is an acceptable margin of error for humans, we should be able to measure it for AI, and once AI is within those margins then it should be feasible to replace the human.
Accountant here. It suprised me when I joined the field, but profit is calculated using a range of accounting estimates. Each accountant will make different decisions. Not least about which accounting period something belongs. Imagine a factory with freight inwards. It is month end and I have a sheaf of bills from various freight companies, but which ones are missing, not received yet? I can't wait, I have 2 days to report, so I make an estimate...now imagine that I have perhaps 100 such things. I may have to justify my estimates, but how should I estimate it? Same as last month? Perhaps I know there is a lot of shipments so I make it at the higher end.
Now I have a product failure at a major customer that I may have to send free replacements for. Should I recognise that cost now, or not? The accounting standards say if I know about it, and I can measure it and there is a high degree of certainty then I should. But the method of choosing is up to me. £10m or 1m cost, and this year or next...
and I get to decide.
We bought a £6m dollar machine to be depreciated over time, but how long. The machine lasts 10 years, but will we still be using it then? Do I capitalise the internal R&D work as well?
All of which is audited, but the auditor often only has the information I give them.
Accounting is not deterministic, within certain bounds it is very subjective.
My wife (head of accounting for a small business) has been working on automating large parts of her job using AI.
It's not completely reliable and the human cannot be taken out of the loop, but the number of menial tasks she's been able to automate has been really cool. A lot of processing data that arrives in non-standard formats, generating documents based on that data, etc.
She still has to review everything, but her workload is way down, and when her assistant quit she automated away his whole position.
Unrelated, but I feel it's unfair to rob the word "bookkeeper" of its peculiarity of having three subsequent double letters by inserting a space in the middle.
That "nearly" is doing an awful lot of heavy lifting. It doesn't matter if your AI model is 99% or 99.99% accurate. For a tax return it has to be perfect every time or someone is at best getting a fine or at worst going to prison.
Sure, human error happens too, but humans take accountability. That's why accountants are a regulated profession. Until an AI company CEO is willing to go prison if the output of their model is wrong, these tools are worthless.
Toot uses automated and AI systems to generate classifications and reconciliation suggestions. Output may be incomplete or wrong and must be reviewed by you.
Toot is a software tool. It does not provide accounting, tax, legal, audit, or financial advice, and nothing it produces is a substitute for a qualified accountant or tax adviser. You are responsible for checking Output before approving it or relying on it, and for any decision you make based on it. To the extent permitted by law, we are not responsible for outcomes arising from automated Output you approve without review.
Comparing this to a human book keeper is farcical.
That "nearly" is doing an awful lot of heavy lifting. It doesn't matter if your AI model is 99% or 99.99% accurate. For a tax return it has to be perfect every time or someone is at best getting a fine or at worst going to prison.
This is wildly out of touch with reality, at least in the US. The IRS barely audits anyone anymore, and if you make a mistake and they catch it, they often just correct it and send you a letter. You might pay a little in penalties, but it’s not that big of a deal. And I know literally dozens of small business owners who pretty blatantly dodge taxes in a hundred different ways and none of them have ever gotten so much as a slap on the wrist. And some of them have been audited!
This literally has nothing to do with AI? I’m pointing out that taxes aren’t some magical area where you must be exact to the penny or hellfire will rain down on you. Hundreds of millions of Americans file their taxes and many have mistakes major and minor, intentional and not. The world somehow keeps turning.
"The VAT return prepared by the model was essentially correct: the most important number in the return, which is how much VAT the company was owed by the tax agency, was off by only 7 pence relative to the human-prepared return."
I don't know how taxes work in Europe, but in the US being "essentially" correct is not good enough for the IRS.
The paragraph after this one goes on to explain other mistakes the LLM made? Yikes
Ask most people in the US how they file their taxes, most will probably tell you they clicked around turbotax until the biggest return number showed up. Is that indicating correct tax filing? I'm not sure. I would guess not.
This is interesting to see, but surely any non-trivial business [edit: who needs to file a VAT return] is already entering its invoices into a finance system which can automatically generate a VAT return in a deterministic way.
I'm not so interested in having an LLM do my bookkeeping for me. But I'm very interested in whether LLM's can unravel the accounting obfuscations that billionaires use to avoid paying taxes on their wealth.
One idea I've had for reform is to ban central banks from inventing new currency except to pay every citizen a UBI debt free, and only tax limited liability entities (not humans). This would give citizens, instead of borrowers, first spend on new money and orient limited liability entities to serving citizens in the market to get their taxed revenues. It would also be a boon for financial privacy and reduce the burden on the average man.
thats not true. maybe for simple 1040s yes, but depending on what you have you could take aggressive positions bc they could be subject to valuation differences.
I wouldn't be surprised if it were more accurate based on the errors I've seen. I always eyeball the books and was confused when a £15k building popped up on our asset sheet. It turns out a "workshop" had been categorised as a building we had purchased, rather than the training session it actually was.
This is the importance of having layers and multiple sets of eyes on things, though. Even if it had got past me, my accountant would have surely queried it at year end, but that could be true of an LLM mistake too.
I was wondering what a book keeper is, thinking it would be some kind of librarian. Isn't the accounting sense written as a single word, i.e. bookkeeper?
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[ 2.6 ms ] story [ 39.0 ms ] threadAnything to avoid using the metric system.
Though seriously, what is this metric? Why would I care if an LLM is accurate as a human bookkeeper? Humans aren't exactly known for perfect recall.
I was one of the human book-keepers for this benchmark (the preparer; my co-founder verified the VAT submission once ready), and given that at the time of doing this I knew I was eventually going to use this data for evaluating the models, I was super careful. So I guess this is a "good book-keeper". In the previous company our book-keepers made lots of mistakes; some serious enough that we had to restate our company's accounts.
It seems also that the classes of error they encountered could be handled by improved skills/knowledge base access on the fine points of relevant tax legislation.
The important part for their software ofc is, will they take responsibility for the output if HMRC come calling? Without that users are adopting the risk which they may not be keen to do (dealing with HMRC is not fun), with that it could be a very nice saving for a lot of small companies (and bad for the employees of a lot of accountancy firms)
I've gotten very good results with some vibe-coded deepseek book keeping. https://github.com/traverseda/beansync
Parses emails or other sources, extracts numbers, correlates different transactions, web search, asks questions, stores notes (regex based, very simple).
The hard part is getting good data, I'm sure that lexus nexus or whoever can get API access to my bank account and all my credit cards, but I can't. Email turned out to be the best way for most of my providers. Managed to avoid 2factor auth so far, but it will suck when I need it.
In my opinion that is the thing holding back almost all of these accounting products that make consumers lives better. I've solved it because all my cards and bills happen to support email, so I can use that as my source of truth for all my credit cards.
I think if you were to send me an email, and the bot was to parse it, the only data exfiltration attack you could do would have to route through the tavily question asking API. Maybe you could do something like ask "what does <the password string> mean on <some host you control>. The data exfiltration surface is pretty low. I want say 100% impossible, but very hard to do reliably.
Also this isn't really an agent. At least not a long lived one. Each email or transaction gets it's own session, the llm can make a few tool calls but must emit json as the final result. Very very short context lengths.
Quiet plug for https://github.com/pjlsergeant/byre which I use for all my little projects like this.
They're not going to unless it's obviously and egregiously wrong - the risk on quality of input remains yours. It's the tax version of garbage in, garbage out. They're just guaranteeing the processing step.
We're all unhinged about the data we're giving LLMs but here I'd draw the line. I'd rather keep paying for the small amount I pay to have my accounts done.
For slightly out of date founder bios (both Adam and Iva) were also co-founders here:
https://www.biomage.net/our-team
https://digits.com/downloads/beyond-the-hype-evaluating-llms...
It's also not hard to imagine tax authorities using AI to audit everyone's tax returns every year.
We sure live in interesting times.
I had a fairly complicated tax return in 2025 involving a couple of change of business tax consideration and some money that was accidentally sent to me as a 1099 instead of to the business and I did everything with tax software with Claude Code advising.
The end result was pretty damned good. I was unsurprisingly audited and the only error was in some way where I allocated a small amount of my wife's tax-free disability payments (disability is the mechanism that California uses to provide maternal benefits pay protection; she's not actually disabled). The IRS told me about it, I paid that bit (it was meant to be claimed back from the employer, not the US government) and everything was hunky dory. To be honest, the sum was so small I did not investigate (and haven't yet followed up with getting reimbursed by her employer).
Honestly, almost all of it could have been avoided if I'd paid an accountant and a tax lawyer and they'd told me things and I'd done as they did, but in the end the combination of the fact that the IRS is very reasonable when you explain things and a modern agent means that the entire process was quite simple. In the end, I preferred the interactive mechanism of working with software because most accountants and lawyers will prefer to get all of your documentation all at once and then work on it rather than do it incrementally. In my case, I was able to work on the return incrementally and then have everything plugged in. I could ask a bunch of questions and get clarification.
I think I will probably do all this the same way this year (though of course my taxes will be simpler).
If you mean "for what reason could you have been audited?" it was because a client I had previously worked for accidentally reported paying me as an individual instead of my LLC.
If you're acting in good faith and your accountant does something crazy or evil, your liability is limited to some extent. You may get a tax bill but you're probably not gonna end up behind bars. But if your LLM decides to do a little bit of tax fraud, you're in uncharted waters. In the end, the gun did it, but you were the one holding the gun.
A lot of jobs are like that. You're not as much buying the service as you're buying not having to worry about the service.
– IBM Training Manual, 1979
https://simonwillison.net/2025/Feb/3/a-computer-can-never-be...
I don't disagree that tax fraud is bad but accuracy really doesn't matter 1/10th what people think it does.
Something to keep in mind in the EU with VAT is that there are approximations, errors and then huge frauds like the infamous "carousel fraud". Sadly the carousel fraud is all too common in the EU: this one gets people really sent to jail. But it's not an error a LLM shall make that could lead to a carousel fraud taking place: it's an elaborate scheme.
Now... If you're self-employed and have to pay the VAT (which may or may not be the case depending of the type of self-employment work you do) or if you're a SME and you've got approximations and errors well it's really not a big deal.
Because the public servants in charge of collecting the VAT and verifying that you filled your stuff correctly... Do make shitload of errors too. And then, depending on the country, these public servants have a special privilege: they can decide an amount of VAT+fine (if there's a fine) that you agree with and if you agree with it, their number is the number.
It's everything but a correct number. It's a number they ended up on that is "close enough" (for some definition of "close"). Sometimes by hammering number after number on a little calculator and then ending up saying:
"We ask you to pay 3500 EUR of additional VAT. If you sign here and accept, the IRS (equivalent of the IRS) won't be able to bother you ever again for that year/years".
This notion that, somehow, there's "one" correct number and that public servants paid something like 2 K EUR net per month (which may be the reason why so many are so prompt to ask for bribes btw) can determine it in a few minutes is ridiculous.
It's simply not happening. Usually the accountant doesn't know the exact number. The SME owner doesn't know the real amount of VAT due. And the public servant(s) in charge of a VAT audit, if any takes place, certainly as zero clue as to what the exact VAT number should be.
The rules are way too complicated, there are way too many special cases, and some things are simply extremely hard to take into account (for example during one audit the person told me he disagree with the 90% of 21% VAT deducted for my ISDN line --yup it was a long time ago-- but then I told him it was during a previous TVA audit, a few years before, that the VAT auditor, seen my job, fixed at 90%).
For some stuff you can opt for a fixed number: say a car, there are rules, depending on the country, where you can, say, get back 75% of 50% of the VAT. But people can also, depending on the country, opt-in for the "real usage": you do 12 387 km during the years, how many were really for work? 6 287 km ? Or may 6 275 km?
What if one day while going to work, you took a detour because you want to drop a gift for your grandma's birthday? How were these kilometers accounted for?
Restaurant bills? What if one of the person wasn't work related (your nephew happened to be in town and you had to take car of him and you knew the clients well so they didn't mind: how does the accountant account for that)?
Gifts to client. You got a discount buying 6 packs of bottle of champagne, but not five (no discount if only five), so you bought a sixth one. But that sixth one you kept for you.
Nobody computes those amounts correctly. Nobody.
And don't get me started on the public servants who'll give, during an audit, an unfair advantage to people from their community (whatever that community may be) or those, literally, banging underneath the table while talking about their next vacations: they're telling you an "arrangement" can be made. Basically you give that one person some money (cash bills of course) and, boom, the 20 K EUR of VA...
2 Usually, specially for SMBs, nobody goes to prison over accounting errors. That's because SMB owners make mistakes all the time and, because of that, authorities are fairly practiced in understanding how mistakes look, and how fraud looks.
From my understanding, you are the person signing off on the paperwork that is submitted to the IRS.
There is this cache 22 with taxes.
You are responsible, but you outsource it to a accountant. Because you are not knowledgeable about the taxes. But you are expected to be knowledgeable to understand the tax documents that you submit to the IRS. That is why the accountant always ask you to review the documents and sign them like 20 times.
The same applies when you run a company, depending on the country, you need to prove yourself knowledgeable in accounting, before you are allowed to run a company. Normally that is included in a university degree, but if you have a middle school diploma, you need to do a official examen to get that degree.
Whatever you submit for your company, you are again responsible. Even if you hired a accountant.
So while technically, if a accountant makes gross mistakes, the bill will always fall in your lap, because you are expected to understand the reports you submit to the IRS. And catch any errors before doing so.
With the IRS, the burden of proving your innocents is often put you. Its because the good faith argument can be misused easily. That is why the buck stops at you.
So using a LLM or a accountant, really does not matter. Sure, a accountant can go to jail if there has been major issues (its not going to be with one client issue).
But you can lose your house / company, have your life ruined by whatever you submitted.
If the IRS comes to you and says "your taxes are wrong you owe X amount" and you immediately turn around and prepare to fight them then they are going to be merciless with you.
But if they come to you and you turn around and show the auditor your methodology and what you thought you were supposed to be doing, etc and focus on fixing the issue and settling your debt then they are going to hook you up with IRS staff dedicated to helping fix this kind of stuff.
And most importantly they'll connect you with someone who can set up a payment plan out over whatever period of time to pay back what you owe without killing your business or taking your assets.
But again if you get audited and immediately become adversarial then they'll assume you were doing it intentionally and will take anything not bolted down.
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The rationale is basically that the IRS staff are mostly there to help you get your taxes in order and ensure that those taxes are paid but as soon as it starts to look like you are intentionally avoiding paying your taxes you get kicked over to the enforcement divisions and eventually the criminal divisions.
So good faith is absolutely something the IRS will honor but that stops the moment it looks like you are trying to hide stuff from them.
An accountant may not save you from financial penalties but I believe that they are liable for them so you can recover it from their insurance.
> So while technically, if a accountant makes gross mistakes, the bill will always fall in your lap, because you are expected to understand the reports you submit to the IRS. And catch any errors before doing so.
I've had a tiny accounting firm take on more and more accounting debt over years just to get the accounts (lots of journal entries into contra accounts; this was before I took over the company), that I was mostly rolling my eyes at how horrible they've become when I tried enlisting Claude's help to untangle them and hopefully move away from using that firm.
I know bookkeeping is tough, especially for newer businesses that haven't set up the processes, but a lot of the professional services industry feels like outsourcing a website to a freelancer on Upwork.
And I would be pretty nervous about asking any of the frontier LLMs to retrieve invoices: "cool, Claude logged that it found the May 6th bill from the paper supplier, I am sure it didn't just make something up arbitrary, then compound on the error by agentically iterating over the made-up invoice lurking in its reasoning traces. I checked the first 30 times and there were no problems!"
I watched an accountant YouTuber reviewing a new AI-driven personal finance app the other day (I really need to touch grass), and it started out just fine. He had seeded the account with a bunch of his data and was able to ask questions about which categories had the most spend, etc.
About half a dozen questions in, he asked it to calculate a certain segment of his spend (and being an accountant, he had his numbers memorized), and he immediately got back a calculation that he did not expect. So he asked for an itemized response and it hallucinated line items that never appeared in his account data, which he pointed out to viewers. He followed up with the chatbot with "where did line item X come from?" and the bot acknowledged that it wasn't legit. He immediately noped out after that, and who could blame him?
Doesn't matter how many more nines you add, rigorous formatting is still required. In some cases, it has teeth with compliance standards. Those standards cannot be compromised because there are already a lot of other layers contributing inaccuracy. It all adds up.
In most situations, you could just hire a junior dev (or an intern! remember those?) write some CSV scripts and call it a day. Cheaper and auditable too. Those scripts can't change anyway until standards are revised.
I'm still not seeing the benefit outside of solopreneur efforts and shady businesses wanting to launder blame.
I don't get this argument. People say the same about autonomous driving.
But humans also have some number of nines. If you can get it better than humans, that's better!
I don't get your argument either. I hear yours often enough and so much louder that I feel it's a deliberate muddying of waters.
What cannot be obsoleted becomes bureaucracy. To my ears, it sounds like you're afraid of ending the wild west.
That's why we have purchase orders that can only be entered by buyers. Product is received and approved by buyer. Invoice goes to accounting, who can't approve it unless there's a matching purchase order and receiver.
Yes, letting agents do whatever they want leads to disaster. But humans are gullible stochastic token generators as well. And that's why the problem is already solved.
sometimes details are just in notes at the bottom and are applied to selectively applied to line items. sometimes the charge doesnt exist anywhere on the bill but there is an understanding (due to a separate agreement) of additional charges to be paid as a result of the invoice.
taxes sometimes are or are not explicitly stated
tariffs sometimes are or are not explicitly stated
when things are not explicitly stated or line item'd, they will usually still appear in the invoice total. so you have item 1 - $500, item 2 $500. total: $1300
At the end of the day invoices are often part of an ongoing communication / conversation between two organizations and they are created with an assumption that a rational and reasonable human who is in the loop with that conversation is going to read it.
As a small consultancy though, looking forward to my next filing, and having just moved to a new and better-specced jurisdiction, I'm sorely tempted to outsource to Claude.
I've had mixed experience with accountants in the past. No horror stories, but I often feel I'm not getting everything laid out clearly, and that I don't fully understand the process.
I've got plenty of reasons to dislike LLMs in my own work, but when dealing with well-scoped but professionally gatekept things like tax or property transactions, they're an absolute godsend.
Get a large enough org and watch your accounting grow an error margin.
You haven't met many accountants i see.
Regardless that's not what he is saying.
If there is an acceptable margin of error for humans, we should be able to measure it for AI, and once AI is within those margins then it should be feasible to replace the human.
This was my CPA wife’s response btw.
The entire field is based on balance sheets and context that informs compliance.
Let me put it this way: it’s such a bad idea that even Intuit doesn’t let their AI replace a human.
Now I have a product failure at a major customer that I may have to send free replacements for. Should I recognise that cost now, or not? The accounting standards say if I know about it, and I can measure it and there is a high degree of certainty then I should. But the method of choosing is up to me. £10m or 1m cost, and this year or next... and I get to decide.
We bought a £6m dollar machine to be depreciated over time, but how long. The machine lasts 10 years, but will we still be using it then? Do I capitalise the internal R&D work as well?
All of which is audited, but the auditor often only has the information I give them.
Accounting is not deterministic, within certain bounds it is very subjective.
It's not completely reliable and the human cannot be taken out of the loop, but the number of menial tasks she's been able to automate has been really cool. A lot of processing data that arrives in non-standard formats, generating documents based on that data, etc.
She still has to review everything, but her workload is way down, and when her assistant quit she automated away his whole position.
Sure, human error happens too, but humans take accountability. That's why accountants are a regulated profession. Until an AI company CEO is willing to go prison if the output of their model is wrong, these tools are worthless.
But don't take my word for it, head on over to Toot's own terms of service https://toot-books.pages.dev/terms#ai-not-advice
Comparing this to a human book keeper is farcical.This is wildly out of touch with reality, at least in the US. The IRS barely audits anyone anymore, and if you make a mistake and they catch it, they often just correct it and send you a letter. You might pay a little in penalties, but it’s not that big of a deal. And I know literally dozens of small business owners who pretty blatantly dodge taxes in a hundred different ways and none of them have ever gotten so much as a slap on the wrist. And some of them have been audited!
I don't know how taxes work in Europe, but in the US being "essentially" correct is not good enough for the IRS.
The paragraph after this one goes on to explain other mistakes the LLM made? Yikes
We should use money issued by the most trustworthy entity around, whatever it may be at the time, and the state should have to compete for that spot.
This is the importance of having layers and multiple sets of eyes on things, though. Even if it had got past me, my accountant would have surely queried it at year end, but that could be true of an LLM mistake too.
Don't get me wrong, I'm all for open-weight models, but you still need to be careful what you use LLMs for.