Using AI to Categorize 1,500+ Bookkeeping Transactions: Claude Leads

Past_Replacement_815 · reddit · 2026-10-31

A bookkeeper handling 1,500–2,000 bank and credit card transactions tried using AI to auto-categorize them into bookkeeping categories like travel, motor expenses, and subscriptions. Testing ChatGPT, Gemini, and Claude, he found ChatGPT and Gemini occasionally made mistakes or invented information, while Claude performed noticeably better — though he hasn't verified accuracy line by line.

His goal is for AI to handle 80–90% of categorization, flag uncertain entries for manual review instead of guessing, and output an Excel sheet with suggested categories plus confidence levels. He's asking for tool recommendations (Copilot, specialist software), prompting tips to reduce hallucination, and real-world experiences from others doing AI-assisted accounting.

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