14 ChatGPT Prompts for UK Tax Planning and Self-Assessment

I'm going to paste a list of business expenses in no particular order. Group them into categories that match typical Self-Assessment expense categories (e.g. office costs, travel, professional fees, subsistence). Flag anything that looks like it might not be a straightforward allowable expense with "(check this one)". EXPENSES: [paste your list]

I am [employment status, e.g. "self-employed as a freelance designer" / "employed plus a small side business" / "a landlord with one rental property"]. Build me a checklist of the documents and figures I should gather before starting my Self-Assessment return, in the order I'd realistically need them.

Explain [term, e.g. "payments on account" / "the trading allowance" / "Class 2 vs Class 4 National Insurance"] as if to someone doing their first tax return, with a short concrete example using round numbers. Tell me if this is something I should confirm with gov.uk since rules change.

I'm going to paste transaction descriptions from my bank statement. Group them into likely categories (income, business expense, personal, unclear) so I can review them faster. Don't guess amounts, just group what I give you. TRANSACTIONS: [paste a list of transaction descriptions]

I need to ask [HMRC / my accountant] about [describe your situation and question]. Write a clear, specific message that gives them enough context to answer without me having to go back and forth. Keep it factual, not apologetic.

I've received a notice about [a late filing penalty / interest on unpaid tax]. Explain what typically causes this kind of notice, and what the general process is for appealing if someone believes there's a reasonable excuse -- and remind me to verify the current appeal process on gov.uk since it can change.

I expect to owe roughly [amount] in tax by [date]. I get paid [frequency, e.g. "monthly", "irregularly"]. Suggest a savings approach -- like a fixed percentage set aside per payment -- so the bill doesn't come as a shock. Keep the maths simple and show your working.

I'm trying to understand, at a conceptual level, the general differences between operating as a sole trader versus a limited company in the UK -- not specific numbers, just the shape of the tradeoffs (admin burden, how profit is taxed, flexibility). Remind me this needs confirming with an accountant before I decide anything.

I have a vague worry about [describe the worry, e.g. "whether I should be VAT registered"]. Help me turn this into 3 specific, well-formed questions I could take to an accountant, so the conversation is efficient rather than me trying to explain a feeling.

Here's a rough summary of my income and expenses for the year: [paste a summary] Write this up as a short year-end review I can read before my accountant meeting: what changed versus a typical year, what looks unusual, and what questions I should be ready to answer.

I currently keep track of business income and expenses by [describe your current, probably messy, method]. Suggest a simple, low-effort system I could realistically stick to, given that I [describe your constraints, e.g. "am not good with spreadsheets" / "am often on the move"].

Write me a short quarterly reminder message to myself about tax admin tasks I should be doing (saving receipts, setting aside tax, checking mileage), written in a tone that will actually make me act rather than skim past it.

I'm going to describe what's on a receipt in my own words. Turn each one into a single structured log line: Date | Amount | Category | Note. Ask me if any required field is missing rather than guessing. RECEIPT DESCRIPTIONS: [describe your receipts one by one]

No. These prompts help you organise information and understand it in plain English, but filing has to go through HMRC's own systems or an accountant. Treat AI output here as a first draft of your understanding, not a final answer.

Because tax rules, thresholds, and allowances change, sometimes mid-year, and a language model's knowledge has a cutoff date. The prompts are genuinely useful for organising and explaining -- they're not reliable for "is this number correct right now," and treating them that way is the single most common mistake people make with AI and tax.

Strip out your National Insurance number, Unique Taxpayer Reference, full bank account numbers, and full address before pasting anything from a real letter or statement. None of it is needed for the prompt to work.