Tax season is starting early this year, or at least it should be, because this one is particularly challenging. Thanks to the One Big Beautiful Bill Act (OBBBA), passed by Congress in 2025, there are 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.
One Big Beautiful Bucket of Confusion
Regardless of your political leanings, the changes to the tax code brought about by the OBBBA are major. There are many changes, and they are quite specific. If you’re used to filing your taxes a certain way, this year’s return will not simply be an updated version of last year’s. There will be meaningful changes to the types of deductions and credits you can claim, and failing to take advantage of them could indicate missing out on potential savings.
Some of the changes from the bill took effect in 2025 and apply to the returns being filed now. These include deductions for taxes on tips and taxes on overtime, which, while not eliminating those taxes entirely, will save some people money. For families with children, there’s a slight increase to the Child Tax Credit (from $2,000 to $2,200), and an expansion of 529 plans for education expenses. This year also marks the first time taxpayers can claim Trump Child Savings Accounts, also known as Trump Accounts.
Another significant change is the elimination of IRS Direct File, which previously allowed people in 25 states to file their taxes online for free. While a couple of free filing options remain through the IRS, more people will likely be using tools like Turbotax and H&. R Block this year.
Navigating these changes can be difficult, especially if you find accounting challenging. Here’s where chatbots can be helpful.
ChatGPT: good at chatting, bad at math
Chatbots like ChatGPT and Claude can be useful for discussing tax questions and scenarios. For example, if you’re a W-2 employee with a freelancing spouse, two children, a house, and a vehicle used for a side hustle generating significant tips, ChatGPT can help explain the tax rules that apply to your situation—especially the new rules. Think of this as information gathering to better prepare for filing, whether using tax software or working with an accountant.
You can ask chatbots about your specific family situation, ages, employment, investments, and even your vehicle to understand what you should do differently this year. You can also use them to clarify steps while filing your taxes. While H&R Block and Turbotax offer their own AI assistants, they may not tailor explanations to your specific situation and may steer you toward other financial products.
It’s crucial to remember that chatbots are not designed to file your taxes and you should not upload sensitive documents like W2s and 1099s to them, as these contain personal information like your social security number and address.
Frequently Asked Questions
What is the One Big Beautiful Bill Act?
The One Big Beautiful Bill Act (OBBBA) is legislation passed by Congress in 2025 that has brought about significant changes to the tax code.
Can I use AI to file my taxes?
No, chatbots are not designed to file your taxes for you, and you should not upload your tax documents to them.
What kind of help can AI offer with my taxes?
AI chatbots like ChatGPT and Claude can help you understand the new tax rules and what questions to ask an accountant or when using tax filing software.
Given the complexity of this year’s tax season, will you consider utilizing AI tools to help navigate the changes and ensure you’re claiming all eligible deductions?
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