Challenging the IRS with AI: How I Used Tech to Make Sense of a Tax Dispute

How I used AI tools like Claude to make sense of IRS chaos -nine documents, one clear appeal, zero tax attorneys.

When your new tax advisor runs on algorithms, not caffeine.

Continuing my series on unconventional AI adventures, here’s what happened when I went head-to-head with the IRS. Spoiler: it didn’t solve everything, but it made tackling an overwhelming challenge a lot easier.

The IRS Letter Nobody Wants

When my mother received an unexpected letter from the IRS about taxes on a 529 plan disbursement, she did what most people would do - she paid it. Because, well, it’s the IRS.

Months later, while packing up her home for a move into assisted living, I found a 1099-Q in her files. I realized we had grounds to fight the penalty. The kicker? I had done her taxes that year using TurboTax. Cue the guilt.

Unsure how to proceed, I sought AI IRS Assistance.

How I used AI as My Tax Appeal Attorney

I opened Claude and gave it this prompt:

“Act as an experienced tax attorney specializing in IRS disputes. Review nine documents, including IRS letters, 1099-Qs, and payment receipts. Craft a compelling argument for why my client deserves a refund, outline a strategy for engaging with the IRS, and suggest any additional documentation to strengthen the case.”

What Worked

AI wasn’t just helpful, it was strategic. Here’s what made a difference:

• Crafted a professional, lawyer-level tone and logical narrative.

• Organized the paperwork in a way that made sense to both humans and bureaucracies.

• Provided step-by-step instructions for mailing, follow-up, and escalation.

It turned a chaotic pile of forms into a clear, confident submission.

What Didn't Work

AI can’t speed up government response times. It’s been four months, and counting. The IRS is still reviewing the case.

And no, AI didn’t magically get me a refund. But it gave me something equally valuable: structure, confidence, and a clear argument grounded in logic.

Meanwhile at the IRS: hundreds of humans reviewing one AI-generated letter.

Why This Matters

AI isn’t just for content creation, analytics, or automation. It can be your expert in unfamiliar territory — the kind of silent partner that helps you think like a professional, even when you’re completely out of your depth.

It didn’t replace a tax attorney. It just made me sound like one.

AI isn’t just for creating content or analyzing data. It can be your expert in unfamiliar territory, helping you navigate complex challenges like IRS disputes.

The Takeaway

AI can’t fix slow systems, but it can make navigating them less painful. Whether you’re appealing an IRS decision, disputing a bill, or writing to a government agency, a good prompt can turn confusion into clarity.