Tax season kicks off this year, or at least it should for everyone. It’s a bit of a mess, honestly. Thanks to the One Big Beautiful Bill Act (OBBBA) passed in Congress back in 2025, there are some important, and maybe a bit confusing, updates to your tax return. Don’t hesitate to seek help, even if it’s from an AI chatbot.
Whenever friends ask me about using AI, my response is usually the same. Think of AI as a diligent co-worker who might get things a bit wrong now and then. You can throw a ton of questions at your chatbot, particularly with the new models out there—perhaps they’re a bit better and a bit more reliable than what we had last year. Still, it’s not wise to rely completely on an overzealous, albeit friendly, colleague for a crucial report. Math has always been a soft spot for large language models, and… well, you get the idea.
Consider ChatGPT and Claude similarly, especially around tax time. They weren’t designed to file taxes, so avoid uploading your documents for edits before sending them to the IRS. Forms like W2s and 1099s contain sensitive info, like Social Security numbers. It’s generally better not to share those unless you’re very sure about your site’s privacy. (Just a heads up: consumer versions of ChatGPT and Claude aren’t necessarily secure.)
Even if you have an accountant, ChatGPT and Claude can be handy for keeping up with this year’s tax law changes. Think of them as learning aids—great for figuring out what questions to ask and which deductions might be applicable. Major tax prep companies have their own chatbots, too. TurboTax and H&R Block offer assistants that promise to make navigating through taxes a bit simpler. However, in my experience, those tools have limited functionality and often try to upsell you on financial products. It’s a lot to sift through, really, and asking the AI direct questions can be a bit more straightforward than scrolling through FAQs.
That being said, let’s clarify something: there’s a big difference between using AI for tax audits and for financial advice. While AI can offer good information for audits, it’s not the best idea to rely on it for advice—it could end up costing you money. At the end of the day, these chatbots are just text generators; they aren’t financial planners or CPAs.
You definitely don’t have to rely on AI for your taxes this year. But similar to how you’ve probably Googled tax credits before, chatting with a bot could help clarify things and confirm any suspicions. Here’s how to navigate these tools this tax season.
big beautiful bucket of mess
No matter your political views, the changes brought about by OBBBA are pretty substantial. There are quite a few specifics involved. If you’ve been filing taxes a certain way, this year’s return won’t just be an altered version of last year’s. There will be notable changes in deductions and credits available, and if you don’t take advantage of them, you could miss out on some money. For details, refer to the IRS page. We also have some really useful guides here and one more there.
Some changes in this bill will start in 2025, but they’ll apply to tax returns you’re filing now, including deductions for tips and overtime, which, just so you know, are not tax-free—contrary to what some might claim. Still, these adjustments could mean some savings for certain individuals. If you have kids, be aware of adjustments to the child tax credit (increased from $2,000 to $2,200) and new rules for 529 Plans for education expenses. This year, you can also claim a Trump Child Savings Account if you qualify. Tax software might guide you to complete the necessary IRS forms, or you can fill them in here.
Another key shift: the IRS Direct File option that used to let people in 25 states file their taxes online for free has been removed. There are still ways to file for free through the IRS, but expect more people to turn to tools like TurboTax and H&R Block this year.
These are just a few highlights among the numerous changes introduced by the OBBBA. Figuring out how the new rules apply to you can be tough, especially if math isn’t your strong suit. That’s where chatbots might come in handy.
ChatGPT: Good at chat, bad at math
When it comes to taxes, chatbots like ChatGPT and Claude can be helpful for discussing questions and scenarios. If you’re a W-2 employee, your spouse is freelancing, you’ve got kids and a home, and your Jeep is your delivery truck for smoked meats, there’s a lot ChatGPT can share about applicable tax rules, especially the new ones. It’s less about advice and more about gathering info for your actual tax prep—whether that’s with TurboTax or with an accountant.
Honestly, I think there’s no such thing as asking too many questions when it comes to saving money. Start by sharing your family situation, your age, your job, how you invest, and even your car type, then ask what changes you might need to consider for your taxes this year.
You could also keep the chatbot open while filing your taxes and ask about any unclear steps. Sure, H&R Block and TurboTax’s AI tools aim to assist, but in my experience, they can be a bit vague and not tailored to individual situations. If you’re working with an accountant, they might be using AI to streamline their work and save time. But overall, improving tech savviness is a plus.
To sum it up, utilize all the help available this year. With so many new tax laws and changes, not grasping how they apply could lead to mistakes or, worse, missed opportunities.
In fact, it seems everyone involved could use some assistance. The IRS has lost about 25% of its workforce since President Trump’s inauguration, leading to notable challenges. As mentioned, it’s a chaotic time this year.
