Taxes in the Agentic Age

Foolishly, I do my own taxes every year.
I always leave it until the last moment, and it is incredibly stressful. Part of that is like anything you do once a year - that feeling that you used to know how to do this, but have forgotten. By about a quarter of the way into it, I find my groove, and, for the most part, Turbotax and I become good friends.

This year was different. It was a love triangle. Me, Turbotax, ChatGPT.
I was shocked and frustrated to find that, as of April 12 2026, Turbotax does not have an integrated agent. After all, Turbotax is really a guided romp through answering questions and inputting data. It has lots of prompts suggesting questions you might have, and so many “learn more” buttons. But you can’t ask it anything. You can’t talk to it.

So, whenever I had a question, I just asked ChatGPT.

I did a bit of that for 2024 taxes, but not to nearly the extent of this year. Part of the change was me, since I am way more comfortable with, and conversant in, what these frontier model chatbots can do. But a big part was the exponential improvement of ChatGPT itself.

To itemize deductions for my consulting business, I was able to take .csv downloads of my bank and credit card transactions and have ChatGPT collate totals, and prep the notes that I’ll keep to justify the math behind those totals. By doing this, I could “talk to” my accounts. Questions that flummoxed me last year and sent me delving into the inadequate filtering and searching capabilities of my banks’ web portals, were easily answered by ChatGPT.

The agent also told me how to input things in the right place in Turbotax, more accurately, more quickly, and more completely than Turbotax’s own help system. This just goes to underscore my assertion that all user facing apps need to incorporate their own agents, or, the chatbots will eat their lunch.

By next year, no one will put up with tax prep software that doesn’t do this for you.
As a matter of fact, I suspect that by next year, there will be custom agents that just do it all for you.