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<\/a> coming to your tax return. Don\u2019t be afraid to ask for help, even if you\u2019re asking an artificially intelligent chatbot.<\/p>\n<\/div>\n 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 \u2014 ChatGPT 5.2 Thinking<\/a> and Claude Opus 4.6<\/a> \u2014 you\u2019re going to get better answers than you might have last year, presumably with fewer hallucinations. They\u2019re even getting better<\/a> at doing math, which has historically been a weak spot for LLMs. Still, you wouldn\u2019t let your energetic but slightly dishonest coworker file the final draft of an important report.<\/p>\n<\/div>\n Treat ChatGPT and Claude the same way, especially when it comes to tax season. These tools aren\u2019t designed to file your taxes for you, and you shouldn\u2019t be uploading your forms for proofreading before submitting to the IRS. Your tax documents \u2014 namely your W2 and any 1099s \u2014 include sensitive personal information like your social security number and address. It\u2019s generally a good rule not to upload those anywhere, unless you\u2019re sure the site is private and secure. (The consumer versions of ChatGPT and Claude, by default, are not.)<\/p>\n<\/div>\n 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 \u2014 Turbotax has its Intuit Assist<\/a> assistant and H&R Block has its AI Tax Assistant<\/a> \u2014 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\u2019s much harder if you\u2019re just Googling or reading FAQs.<\/p>\n<\/div>\n Before I go any further, however, I want to make something super clear: There\u2019s 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.<\/p>\n<\/div>\n You certainly don\u2019t 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\u2019s how to get the most out of them this tax season.<\/p>\n<\/div>\n Regardless of your political leanings, it\u2019s 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\u2019re 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\u2019s tax return. There will be meaningful changes to the types of deductions and credits you can claim, and if you don\u2019t take advantage of them, you could miss out on some free money. Here\u2019s a breakdown, although I very much encourage you to check out the IRS page<\/a> on the subject as well as the surprisingly helpful guides put together by Turbotax<\/a> and H&R Block<\/a>.<\/p>\n<\/div>\n Some of the changes from the bill took effect in 2025 and will apply to the tax returns you\u2019re filing now. They include deductions for taxes on tips and taxes on overtime, which don\u2019t actually amount to no taxes on these streams of income as Trump has argued<\/a>, but will save some people money. If you have kids, you\u2019ll want to note that there\u2019s a slight bump to the Child Tax Credit<\/a> (from $2,000 to $2,200), and an expansion of 529 plans<\/a> for education expenses. This year is also when you can claim your Trump Child Savings Accounts, also known as Trump Accounts<\/a>. If you\u2019re 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<\/a>.<\/p>\n<\/div>\n 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<\/a> options<\/a> 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.<\/p>\n<\/div>\n 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\u2019re allergic to accounting. This is where the chatbots come into play.<\/p>\n<\/div>\n When it comes to your taxes, chatbots like ChatGPT and Claude are great for talking through questions and scenarios. If you\u2019re a W-2 employee and your spouse is a freelancer, you\u2019ve 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\u2019s a lot ChatGPT can tell you about the tax rules that apply to you \u2014 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\u2019s on Turbotax or in a conversation with a human accountant.<\/p>\n<\/div>\n To be honest, when it comes to saving money, I don\u2019t think you can ask enough questions. Start by telling your chatbot about your family\u2019s 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.<\/p>\n<\/div>\n You could also keep a chatbot open in a window while you\u2019re filing your taxes and ask it about the steps you don\u2019t understand. The AI tools from H&R Block and Turbotax are designed to assist here, but in my experience, they don\u2019t tailor the explanation to your situation, which makes them less helpful. If you\u2019re working with an accountant, they\u2019re probably using AI<\/a> to make their jobs easier and save time. Being at least more familiar with the technology could improve those interactions, too.<\/p>\n<\/div>\n 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.<\/p>\n<\/div>\n Everyone in this process could use all the help ,in fact; the Internal Revenue Service lost 25 percent of its workforce<\/a> in the months after Trump took office, and it\u2019s apparently chaos<\/a> there now. Like I said, this year\u2019s a doozy.<\/p>\n<\/div>\n<\/div>\nOne Big Beautiful Bucket of Confusion<\/strong><\/h2>\n<\/p>\n<\/div>\n
ChatGPT: good at chatting, bad at math<\/strong><\/h2>\n<\/p>\n<\/div>\n