Bookkeeping categorization: how to do it with AI
Last checked 2026-10-15
IntermediateBot with human review 🏪 Small business
Categorize transactions from a bank export.
1. Bot automation level
Bot with human review The bot does the work, but facts, numbers or code should be checked.
2. Before you hand it to the bot
- Gather inputs: files, data samples, links and any templates.
- Access: make sure you can use the chosen bot/plan (see limits below).
- Context: tell the bot audience, purpose, constraints and examples of good output.
- Privacy check: remove personal, confidential or regulated data unless your plan/workspace is approved for it.
- Success criteria: write down what 'done' looks like (length, format, tests passing, fields filled).
3. Copy-paste prompts
Main prompt
Categorize these transactions into my chart of accounts.
Beginner-friendly
Categorize these transactions into my chart of accounts. I'm new to this: explain each step in plain words and ask me for anything you need before starting.
Check-your-work
Categorize these transactions into my chart of accounts. When you finish, list any assumptions you made, anything you're unsure about, and what I should double-check before using the result.
Free tiers that can handle this (verified): ChatGPT (incl. Work & Codex), Claude (incl. Claude Code), Google Gemini. Others: check plan.
4. Step-by-step
- Export transactions (CSV) and your chart of accounts.
- Remove account numbers.
- Ask the bot to categorise each row and flag uncertain ones.
- Review flagged rows and a sample of the rest.
- Import into your accounting tool and reconcile.
5. Which bots and plans can do it
| Tool | What's different here | Plan limits | Source |
|---|---|---|---|
| ChatGPT (incl. Work & Codex) | Runs code on uploaded files. | Free tier has limited deep research, Codex and Work; scheduled tasks need Go or higher (per chatgpt.com/pricing). | help.openai.com/en/articles/20001275-chatgpt-work-and-codex |
| Claude (incl. Claude Code) | Code execution creates edited files. | Claude Code and Research need Pro or higher; computer use is Pro/Max only (research preview). | code.claude.com/docs/en/desktop |
| Google Gemini | File analysis. | Free tier includes Deep Research, Canvas, Gems; video generation needs AI Plus or higher. | gemini.google/overview/deep-research/ |
| Microsoft Copilot | Excel with Microsoft 365. | Copilot in Word/Excel/PowerPoint/Outlook needs an eligible Microsoft 365 plan. | www.microsoft.com/en-us/microsoft-copilot/for-individuals/features |
Free or paid?
- ChatGPT (incl. Work & Codex): Free plan: yes. unlimited text chats; limited uploads, images, voice, deep research and Codex. Paid: price not verified, so check the official site. Its free tier can handle this task.
- Claude (incl. Claude Code): Free plan: yes. chat, web search, files & code execution, Artifacts, connectors. Claude Code and Research need Pro. Paid: the lowest price we could verify on the official pricing page is $20/month (other plans may exist). Its free tier can handle this task.
- Google Gemini: Free plan: yes. Flash-Lite model, image generation, Deep Research, Live, Canvas, Gems. Video needs AI Plus or higher. Paid: the lowest price we could verify on the official pricing page is $99.99/month (other plans may exist). Its free tier can handle this task.
- Microsoft Copilot: Free: not verified, so check the official site. Paid: the lowest price we could verify on the official pricing page is $23.5/month (other plans may exist). For this task, check the plan.
6. Risks and what to double-check
- Wrong categories affect taxes — review with your accountant.
- Don't upload full bank statements to unapproved tools.
- Read the output carefully; AI can be confidently wrong.
- AI can hallucinate facts — verify anything that matters.
- Don't share secrets or other people's personal data.
Professions that use this
Accountant · Small business owner