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Key takeaways:

• • • The AI tools demonstrated at the 2026 TEI Tax Technology Seminar were genuinely capable — These included agentic systems running live, nine-year-olds building software by voice, and automation pipelines deployed by major tax departments. The question of Does this work? is effectively settled.

    • That progress shifted the conversation to harder problems — Some of these problems are hallucinations that fail silently, governance vacuums in which tax rarely owns AI implementation, training rollouts that collapse when people aren’t ready, and rising token costs that could entirely change the economic case for automation.

    • The community’s defining posture wasn’t skepticism or hype — Instead, it was honest reckoning. Tax leaders believe in the tools and were actively deploying them but also are refused to treat capability as a substitute for the institutional work of process, ownership, and oversight.

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“I think you are a very bad man,” said Dorothy.

“Oh, no, my dear; I’m really a very good man, but I’m a very bad Wizard, I must admit.”

— The Wonderful Wizard of Oz, L. Frank Baum

LAS VEGAS — I arrived in Las Vegas a day early for the , which gave me one free evening before three days of packed sessions. Little question as to what I was going to do: The Wizard of Oz show at the Sphere.

It’s spectacular. The Sphere wraps you in imagery at a scale so vast if feels like you’re going to fall into it. The tornado shakes you like it’s going to rip the entire building apart and fling you to Oz right alongside Dorothy. The technology is genuinely, thrillingly good… and that’s what makes the fissures so disorienting when you spot them. A munchkin’s head rendered as a 2D .png with a visible gap where the neck should be. A bad CGI effect. Dorthy flickering at the edges like a bad cutout on a green screen. You don’t catch the tech glitches when the spectacle is unconvincing; rather, you catch them precisely because it’s so good that the gaps have nowhere left to hide.

The next morning, I walked into the TEI Tax Technoloy Seminar and found three days of panels that played out the exact same dynamic — except the stakes were far more real.

A very good man

TEI organizers opened with the obvious joke: “We’re careful to limit the number of AI sessions,” they noted, before audibly pondering whether it was time to just rename the whole thing. Fair question, given how much has changed over eight annual iterations of this get-together. Indeed, if you’d been dropped into this event from its first meeting nearly a decade ago, you’d think you’d been dropped into Oz.

One presenter described her elementary-school-aged children building video games by dictating instructions to a coding tool, then showing the games running. That alone would have been science fiction five years ago. However, the room was full of it. OpenAI sent four members of its own tax department to demonstrate live automation pipelines. Google and Microsoft walked attendees through building AI agents with nothing more than a mouse and keyboard, making it look so easy my grandmother could have made it work.

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One presenter described her elementary-school-aged children building video games by dictating instructions to a coding tool, then showing the games running. That alone would have been science fiction five years ago.

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Down the hall, the advanced tax systems that many industry visionaries were dreaming about just two years ago weren’t theoretical anymore — they were running live. Tax directors from Amazon, Walmart, and a dozen other household names sat alongside Big Four advisors and every major tax software provider through three days of sessions, all of it sold out.

We were definitely not in Kansas anymore. Nor was this the AI of two years ago, the one that could draft a passable email or a poem but couldn’t so much as parse a spreadsheet. This was something materially different. The tools had crossed a threshold. They worked, and everything the profession had been promising for years was alive and functioning in the room.

And that changed the conversation entirely.

A very bad wizard

When the technology was half-baked, the debate was simple: Is this even possible? Skeptics said no, enthusiasts said give it time, and everyone argued about capability.

The 2026 TEI Tax Technology Seminar was the place where that argument effectively ended — not because the skeptics lost, but because the question became irrelevant. The tools were plainly, demonstrably good — indeed, a nine-year-old could use them and was.

The new question that arose was harder and less comfortable to discuss: What can’t AI do?

The room answered honestly and brutally. Someone described uploading a tax schedule to an AI agent and getting numbers that didn’t look right. When challenged, the AI confessed: I couldn’t open your file, so I was just telling you what you wanted to hear.

That anecdote landed differently than it would have two years ago. Back then, it would have been evidence that AI wasn’t ready. At the 2026 TEI Tax Technology Seminar, in a room in which people had just watched live agentic demos and were actively deploying these tools, it was evidence of something more unsettling: AI doesn’t fail loudly anymore. It fails quietly and even politely.

AI performs competence it doesn’t have, at a level of sophistication that’s just good enough because it is genuinely smarter than it was a few years ago, and it will get away with it unless a human knows enough to push back. Like its counterpart in Oz, this makes an AI tool is a very good man — genuinely useful, genuinely capable — and sometimes a very bad wizard. It can’t do the thing you actually need it to do on its own, but it may try to trick you into thinking it did.

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AI performs competence it doesn’t have, at a level of sophistication that’s just good enough because it is genuinely smarter than it was a few years ago, and it will get away with it unless a human knows enough to push back.

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That theme echoed across three days of honest, sometimes uncomfortable conversations that went beyond just the technology itself. A transformation director confessed to deploying a training program across dozens of global clients and failing spectacularly. A tool designed to save two hours of work suddenly consumed an entire day because the people who’d actually had to use it hadn’t been consulted. Others described Alteryx workflows nobody could explain because the person who built them had left the company without documenting the logic.

And, more concerning, when the room was polled on whether the tax function actually owns AI implementation at their company, two hands went up out of more than 50. Human-in-the-loop was a constant refrain, of course, but attendees confessed to grappling with how to review an ever-increasing volume of work when the errors were increasingly polite, quiet, and technical.

Of course, the professionals at the seminar weren’t dismissing the technology, which is what made the honesty remarkable. As one senior director said flatly: “You will not survive in this field if you don’t have a change mindset.” They believed in the tools, and they were buying them, deploying them, building around them. They just refused to pretend the tools alone would be enough.

Going home

Overall, the 2026 TEI Tax Technology Seminar was the place that the tax technology community stopped debating whether the Wizard was real and started grappling with the fact that he couldn’t get them home.

That’s not disillusionment; indeed, it’s the opposite. Dorothy doesn’t have her crisis when Oz looks fake, she has it after she meets the Wizard and discovers he’s real but insufficient — that his balloon won’t get her home. And unlike Baum’s Wizard, the magic isn’t a fraud — which is precisely what makes the problem harder. A humbug you can dismiss, but real capability that still can’t get you home? That’s the problem you actually have to solve.

Like Dorothy, today’s tax leaders will have to click their ruby slippers themselves.

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