Tax season starts early this year. Or at least it should for you, because this one is a doozy. Thanks to the One Big Beautiful Bill Act (OBBBA), which Congress passed in 2025, there are some significant and potentially confusing changes coming to your tax return. Don’t be afraid to ask for help, even if you’re asking an artificially intelligent chatbot.
Tech
Trump made tax day more complicated. ChatGPT and Claude can make it easier.
Whenever a friend asks me about using AI, I say the same thing: Treat it like a capable coworker who never gets tired and sometimes gets things wrong. You can ask a chatbot a thousand questions, and with the latest frontier models — ChatGPT 5.2 Thinking and Claude Opus 4.6 — you’re going to get better answers than you might have last year, presumably with fewer hallucinations. They’re even getting better at doing math, which has historically been a weak spot for LLMs. Still, you wouldn’t let your energetic but slightly dishonest coworker file the final draft of an important report.
Treat ChatGPT and Claude the same way, especially when it comes to tax season. These tools aren’t designed to file your taxes for you, and you shouldn’t be uploading your forms for proofreading before submitting to the IRS. Your tax documents — namely your W2 and any 1099s — include sensitive personal information like your social security number and address. It’s generally a good rule not to upload those anywhere, unless you’re sure the site is private and secure. (The consumer versions of ChatGPT and Claude, by default, are not.)
Even if you are using an accountant, ChatGPT and Claude can help you get up to speed on all the tax code changes this year. Think of them as tax prep tools, a way to learn what kinds of questions to ask and which deductions to seek out. (The two big tax filing software companies offer their own chatbots — Turbotax has its Intuit Assist assistant and H&R Block has its AI Tax Assistant — that promise to make navigating the accounting labyrinth easier. In my experience, their functionality is limited and the sites tend to steer you toward paying for other financial products, like loans and banking services.) You can ask ChatGPT and Claude to explain particular rules based on your situation, a task that’s much harder if you’re just Googling or reading FAQs.
Before I go any further, however, I want to make something super clear: There’s a difference between using AI for tax research and using AI for financial advice. The former is a helpful information-gathering exercise. The latter is a great way to lose money. Chatbots sound smart but they are ultimately text generation machines, not certified financial planners or certified public accountants.
You certainly don’t have to use AI on your taxes this year. But much in the same way you might have Googled something like the child tax credit in the past, you might try chatting with the bots, asking them questions, and double-checking all their answers. Here’s how to get the most out of them this tax season.
One Big Beautiful Bucket of Confusion
Regardless of your political leanings, it’s important to know that the changes to the tax code ushered in by the OBBBA are pretty major: There are a lot of them, and they are quite specific. If you’re used to doing your taxes a certain way, you should know that your tax return this year will not just look like an updated version of last year’s tax return. There will be meaningful changes to the types of deductions and credits you can claim, and if you don’t take advantage of them, you could miss out on some free money. Here’s a breakdown, although I very much encourage you to check out the IRS page on the subject as well as the surprisingly helpful guides put together by Turbotax and H&R Block.
Some of the changes from the bill took effect in 2025 and will apply to the tax returns you’re filing now. They include deductions for taxes on tips and taxes on overtime, which don’t actually amount to no taxes on these streams of income as Trump has argued, but will save some people money. If you have kids, you’ll want to note that there’s a slight bump to the Child Tax Credit (from $2,000 to $2,200), and an expansion of 529 plans for education expenses. This year is also when you can claim your Trump Child Savings Accounts, also known as Trump Accounts. If you’re eligible, your tax filing software or account might prompt you to set them up by filling out the proper IRS form, but you can also fill it out here.
One other significant change: The IRS Direct File, which allowed people in 25 states to file their taxes online for free, is now gone. There are still a couple options to file for free through the IRS, but suffice it to say many more people will be using tools like Turbotax and H&R Block this year.
Again, those are just a few of the many changes ushered in the OBBBA. Learning about how new rules apply to your specific situation is difficult, especially if you, like me, feel like you’re allergic to accounting. This is where the chatbots come into play.
ChatGPT: good at chatting, bad at math
When it comes to your taxes, chatbots like ChatGPT and Claude are great for talking through questions and scenarios. If you’re a W-2 employee and your spouse is a freelancer, you’ve got two kids and a house, and your Jeep doubles as a delivery vehicle for your smoked meats side hustle, where you make a killing on tips, there’s a lot ChatGPT can tell you about the tax rules that apply to you — especially the new rules. Think of this less as advice and more as information that can help you get better organized for your actual tax preparation experience, whether that’s on Turbotax or in a conversation with a human accountant.
To be honest, when it comes to saving money, I don’t think you can ask enough questions. Start by telling your chatbot about your family’s situation, your ages, what you do for work, how you invest your money, and even what kind of car you drive, then ask what you should do differently on your taxes this year.
You could also keep a chatbot open in a window while you’re filing your taxes and ask it about the steps you don’t understand. The AI tools from H&R Block and Turbotax are designed to assist here, but in my experience, they don’t tailor the explanation to your situation, which makes them less helpful. If you’re working with an accountant, they’re probably using AI to make their jobs easier and save time. Being at least more familiar with the technology could improve those interactions, too.
Let me put it another way: You could use all the help you can get this year. There are enough new rules and changes to the tax code that not totally understanding how they apply to you could lead to mistakes or, worse, missed opportunities.
Everyone in this process could use all the help ,in fact; the Internal Revenue Service lost 25 percent of its workforce in the months after Trump took office, and it’s apparently chaos there now. Like I said, this year’s a doozy.