Investor Says ChatGPT Astra Found $308,533 Tax Error
Bill D'Alessandro says he received a draft 2025 tax return showing $117,360 owed, then asked ChatGPT Astra to review it against source documents. He reports the 90-minute review produced a report showing a $191,173 refund, which his accountant agreed was correct, and recommends pairing frontier LLMs with past tax returns.
Original post · 1 min read
Oof.
But it didn't feel right to me.
I asked ChatGPT Astra to do a secondary review, ticking and tying every number to source documents. Max effort. It ran for 90 minutes.
Output - a 15 page report. It says I'm actually due a $191,173 REFUND.
I reviewed Astra's work line by line with my accountant. He agreed, the LLM is correct.
I was about to send Uncle Sam $117,360. Instead, I'm getting back $191,173.
That's a swing of $308,533 (!!!!!!)
The LLM couldn't have done my tax return from scratch - I still need my accountant. But for massively complex detail oriented work, and LLM is the best thought partner you can have.
Connect a frontier LLM to your email and file storage, then ask it to review your past tax returns. You never know what it might find. My prompt is in the next tweet.



