Could AI Assistants Like ChatGPT Support Self Assessment Tax Questions?

Could AI Assistants Like ChatGPT Support Self Assessment Tax Questions?
Charlotte Baroukh

Charlotte Baroukh

Tax Expert @ Pie

3 min read

Updated: 16 Feb 2026

3 min read

Updated: 16 Feb 2026

Must know things

AI assistants are changing how we handle self assessment tax returns, making the process less daunting for everyone. These clever tools interpret complex tax rules, suggest allowable expenses you might have missed, and highlight potential savings.


They offer round-the-clock support during the busiest tax season without the hefty hourly fees that traditional accountants charge. Many can even spot common errors before you submit, reducing your chances of facing an HMRC enquiry.


Pie tax, the UK's first personal tax app, can save you hours of frustrating tax research with instant, accurate answers. Or if you're just here to get to grips with it all, let's break it down!

What are AI tax assistants and how do they help with self assessment?

AI tax assistants are smart digital tools that use artificial intelligence to answer your specific tax questions in plain English. They can understand what you're asking even when you don't use technical tax terminology. These assistants scan through thousands of pages of tax legislation, HMRC guidance and case law in seconds. This gives you tailored answers without the headache of sifting through complex documents yourself.

 

They're like having a tax expert in your pocket, available whenever you need them. Unlike static guidance pages, AI assistants can follow up on your questions and ask for clarification.

 

They adjust their answers based on your specific circumstances and remember your previous questions. This creates a more personalised experience than generic tax advice websites. For self-employed people especially, these tools can be a game-changer during self assessment season. They help you understand which expenses you can legitimately claim and which might trigger an HMRC red flag.

What are AI tax assistants and how do they help with self assessment?

Common tax questions AI can answer for your self assessment

"Can I claim my home office as an expense?" This is one of the most frequent questions for remote workers. AI assistants can explain exactly how the simplified and actual cost methods work for your situation. "Do I need to report my cryptocurrency sales?" AI can clarify when crypto transactions count as taxable events. It can also guide you through calculating your gains correctly for your tax return.

 

"How should I handle my side hustle income?" AI assistants can explain whether your activity counts as a hobby or a business. This distinction makes a significant difference to your tax obligations."What receipts do I need to keep?" Your AI assistant can outline HMRC's record-keeping requirements. It can suggest simple systems to stay compliant without drowning in paperwork.

 

"Am I paying too much tax?" By analysing your income sources and deductions, AI can spot potential areas where you might be overpaying. It can suggest legitimate ways to reduce your bill through available reliefs and allowances.

Benefits of using AI for your tax questions

Speed is perhaps the biggest advantage you get answers in seconds rather than waiting days. This contrasts sharply with waiting for an accountant to respond or spending hours searching through HMRC's website. Accessibility matters too. You can ask questions in everyday language without needing to know tax jargon or specific legislation references.

 

Cost savings are significant for many people. While professional tax advice might cost £150+ per hour, many AI tax assistants offer subscription models that work out much cheaper. Privacy can be a plus some people feel embarrassed asking "basic" tax questions.


With AI, there's no judgement, so you can ask anything without feeling silly. Learning as you go happens naturally with AI assistants. The more you interact with them, the more you understand about your tax situation, potentially making you more tax-efficient in the future.

Benefits of using AI for your tax questions

Limitations you should know about

AI tax assistants aren't perfect. They can sometimes misunderstand complex questions or miss important context that a human accountant would catch. They're only as good as their training data. If tax laws have changed very recently, some AI systems might not have the latest updates unless they're specifically designed to stay current with HMRC rules.

 

Personal judgement still matters. AI can tell you what's generally allowed, but determining if an expense is "wholly and exclusively" for business sometimes requires human discretion.


Complex situations like international income or unusual business structures might be beyond what current AI can reliably handle. These cases often benefit from human oversight.


The final responsibility always rests with you. Even if an AI gave you incorrect advice, HMRC will still hold you accountable for errors on your tax return.

How to get the best results from your AI tax assistant

Be specific with your questions. Instead of asking "What can I claim?", try "As a freelance graphic designer working from home, what expenses can I claim for my self assessment?" Provide relevant context upfront. Mention your employment status, income sources, and any unusual circumstances that might affect the answer to your question.

 

Ask follow-up questions if something isn't clear. Good AI assistants can explain their reasoning or simplify complex concepts when asked. Double-check important advice, especially for decisions involving large sums of money. You might use the AI to understand the basics, then verify with HMRC guidance for critical matters.

 

Keep records of the advice you receive and act on. If HMRC ever questions your tax position, it helps to show you made decisions based on reasonable guidance. I learned this lesson the hard way last year when I claimed my entire internet bill as a business expense. My AI assistant flagged this as risky and suggested a fairer apportionment, potentially saving me from an enquiry.

How to get the best results from your AI tax assistant

Final Thoughts

AI tax assistants are making self assessment more approachable for millions of people who previously found tax confusing or intimidating. They bridge the gap between doing everything yourself and paying for full accountancy services.

While they can't completely replace professional advice for complex situations, they're ideal for answering day-to-day tax questions. They help you understand your tax position better without overwhelming you with technical details.

 

As these tools continue to improve, they'll likely become an essential part of how most people manage their tax affairs. They save time, reduce stress, and potentially help you pay exactly what you owe, no more and no less.

Pie tax: Simplifying AI Tax Assistance

Tackling self assessment doesn't need to fill you with dread. Pie tax, the UK's first personal tax app, makes the whole process surprisingly straightforward with our intelligent AI assistant.


Our system learns about your specific situation and provides guidance tailored to your needs. Whether you're juggling employment, self-employment, property income or investments, we've got you covered.

 

You'll see your tax calculation update in real-time as you add information. This gives you a clear picture of what you owe and why, eliminating nasty surprises at the end of the process.


The app connects directly to HMRC, so when you're ready, you can submit your return with a single tap. No more rushing to meet the January deadline at the last minute.

 

Curious to see how it works? Take a look at Pie tax and discover how we're making tax less taxing for people just like you.

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