Tax Season 2025: AI, New Rules & What You Need to Know
Tax season starts early this year, or at least it should for taxpayers preparing for a particularly complex filing cycle. Thanks to the One Big Beautiful Bill Act (OBBBA), passed by Congress 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 that means turning to an artificially intelligent chatbot.
Whenever someone asks about using AI, the advice is consistent: treat it like a capable coworker who never gets tired and sometimes gets things wrong. With the latest AI models – ChatGPT 5.2 Thinking and Claude Opus 4.6 – you’re likely to get better answers than in previous years and they’re even getting better at math, historically a weak spot for large language models. Still, you wouldn’t let an 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 taxes. 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 – W2s and 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. Tax filing software companies offer their own chatbots – TurboTax has Intuit Assist and H&R Block has its AI Tax Assistant – that promise to make navigating the accounting labyrinth easier. However, their functionality is often limited, and the sites tend to steer users toward paying for other financial products, like loans and banking services.
Before proceeding, it’s important to understand the 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 way to lose money. Chatbots sound smart, but they are ultimately text generation machines, not certified financial planners or certified public accountants.
You don’t have to use AI on your taxes this year. But, much like Googling the child tax credit in the past, you might try chatting with the bots, asking questions, and double-checking their answers.
One Big Beautiful Bucket of Confusion
Regardless of political leanings, the changes to the tax code ushered in by the OBBBA are 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 be an updated version of last year’s. 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 savings.
For 2025, the standard deduction has been raised to $15,750 for single filers, up from $15,000. For married couples filing jointly, It’s increased to $31,500, up from $30,000. And for heads of households, their standard deduction will be $23,625, up from $22,500. Most filers take the standard deduction because it is higher than the total of itemized deductions they are eligible to claim.
Anyone born before January 2, 1961, and who has a valid Social Security number may now take a $6,000 deduction (or $12,000 if married filing jointly and each spouse qualifies). This new deduction is taken on top of your standard deduction or itemized deductions.
There are also changes to tax credits and other provisions. 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.
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 a couple of options to file for free through the IRS, but 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 by the OBBBA. Learning how these new rules apply to your specific situation is difficult, especially if you find accounting challenging. 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 have two kids and a house, and your vehicle is used for a side hustle, 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.
Tell 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 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 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.
The Internal Revenue Service lost 25 percent of its workforce in the months after 2025, and it’s reportedly chaotic there now. This year’s filing season is a doozy.