10 Things You Can Ask Penny via Messaging

Penny is not just a chatbot that gives canned responses. She is an AI bookkeeper who understands your finances, learns your business, and can handle a remarkable range of tasks — all through WhatsApp. Many Accounted users start by scanning a few receipts and gradually discover just how much Penny can do.

In this article, we share ten of the most useful things you can ask Penny on WhatsApp. Whether you are a brand new user or you have been using Accounted for months, there is probably something here you have not tried yet.

1. Scan and Categorise a Receipt

This is where most people start. Take a photo of any receipt — paper or screen — and send it to Penny on WhatsApp. Within seconds, she extracts the date, amount, supplier name, and VAT, categorises the expense, and adds it to your records.

You can also forward digital receipts. If you receive an email receipt from Amazon or a subscription service, screenshot it and send it to Penny. She handles digital receipts the same way as paper ones.

What makes this powerful is the categorisation. Penny does not just store the receipt — she understands it. A purchase from Screwfix goes under tools and equipment. A payment to your phone provider goes under telecoms. Over time, she learns your specific suppliers and gets even more accurate.

For more on how this works, read our guide to receipt scanning on WhatsApp.

2. Check Your Estimated Tax Bill

Send Penny a message like "How much tax do I owe?" and she will respond with your current estimated income tax and National Insurance liability, based on your year-to-date income and expenses.

This is not a rough guess. Penny calculates your liability using the current tax year's rates and thresholds, factoring in your personal allowance, basic and higher rate bands, Class 2 and Class 4 National Insurance, and any other relevant considerations.

The value of this feature cannot be overstated. Many sole traders have no idea what they owe until January. Penny gives you this information at any time, updated in real time as your financial position changes. Knowing in September that you will owe £6,000 in January gives you months to plan and save.

3. Log a Business Trip

Mileage claims are one of the most commonly missed tax deductions. Penny makes logging them trivial. Just message her: "Drove 30 miles to a client meeting in Manchester today."

Penny records the trip, calculates the claim at HMRC's approved rates (45p per mile for the first 10,000 miles, 25p thereafter), and adds it to your expenses. She also tracks your total mileage for the year, so she knows when to apply the reduced rate.

If you have regular trips — the same client every Tuesday, for example — you can set up recurring trips so Penny logs them automatically.

4. Ask a Tax Question

Penny is remarkably good at answering everyday tax questions in plain language. Try questions like:

• "Can I claim my phone bill as a business expense?"
• "What is the VAT threshold?"
• "How does the trading allowance work?"
• "Do I need to register for self-assessment?"
• "What is the deadline for filing my tax return?"

Penny answers based on current UK tax rules and regulations. She explains concepts in straightforward language, avoiding jargon. If a question is outside her confidence level, she will tell you honestly and suggest consulting a human accountant.

This is not generic information from a search engine. Penny's answers are contextualised to your situation. When you ask about claiming expenses, she considers your business type, your income level, and your existing claims.

5. Categorise a Bank Transaction

When Penny is not sure about a transaction, she asks you. But you can also proactively tell her about transactions. If you see a payment in your bank that Penny has not yet categorised, message her: "The £200 payment to ABC Supplies was for office furniture."

Penny will find the matching transaction, categorise it as office equipment, and note the description. Next time a payment to ABC Supplies appears, she will know how to handle it automatically.

This conversational approach to categorisation is faster and more natural than clicking through dropdown menus in traditional accounting software. You are having a conversation, not operating a database.

6. Get a Profit Summary

Message Penny: "What is my profit this month?" or "How am I doing this year?" She will respond with a clear summary of your income, expenses, and net profit for the period you asked about.

You can ask about any time period: this week, this month, this quarter, this tax year, or even a custom date range. Penny breaks down the numbers in a way that makes sense, highlighting your biggest income sources and largest expense categories.

For sole traders who have never felt comfortable reading a profit and loss statement, this conversational format is transformative. You get the information you need without the accounting jargon.

7. Set a Reminder for a Tax Deadline

Tell Penny: "Remind me about my self-assessment deadline" or "When is my next VAT return due?" She maintains a calendar of all your relevant tax deadlines and can send you reminders at whatever frequency you prefer.

Penny does not just know the standard deadlines. She tracks your specific obligations based on your registration status, income level, and filing history. If you are registered for MTD, she knows your quarterly submission dates. If you are VAT-registered, she knows your VAT quarter dates.

According to HMRC's self-assessment deadline guidance, the deadline for online filing is 31 January following the end of the tax year. Late filing incurs automatic penalties starting at £100.

8. Record a CIS Payment

If you work in construction, Penny understands the Construction Industry Scheme. Message her: "Received £1,600 from BuildCo today, they deducted £400 CIS."

Penny records the gross payment, the CIS deduction, and the net amount received. She tracks your total CIS deductions for the year and factors them into your self-assessment calculation, ensuring you reclaim everything you are owed.

She will also ask about materials when recording CIS payments, because materials are excluded from CIS deductions. This attention to detail prevents errors that could affect your tax return.

9. Check If You Are Near the VAT Threshold

Ask Penny: "Am I close to the VAT threshold?" She will tell you your current rolling 12-month taxable turnover and how close you are to the £90,000 registration threshold.

This is important because VAT registration is mandatory once you exceed the threshold, and failing to register on time can result in backdated VAT charges. Penny monitors this continuously and will proactively alert you if you are approaching the limit, even if you do not ask.

10. Prepare for Your Self-Assessment Filing

When it is time to file your self-assessment return, message Penny: "I am ready to file my tax return."

Because Penny has been tracking your income, expenses, and deductions throughout the year, your return is largely prepared already. She walks you through any remaining items, confirms the figures, and submits your return to HMRC directly — all from the WhatsApp conversation.

No logging into HMRC's website. No deciphering form fields. No January panic. Penny handles the filing and confirms when HMRC has accepted your return.

For a full walkthrough of how self-assessment works with Accounted, see our guide to meeting Penny.

Bonus: Things Penny Cannot Do (Yet)

Penny is impressive, but she has boundaries. She cannot:

• Provide formal legal or tax advice (she always recommends professional advice for complex matters)
• Access systems outside Accounted (she cannot check your HMRC account directly)
• Make payments on your behalf (she tracks finances but does not move money)
• Handle company accounts for limited companies with multiple directors (she is optimised for sole traders)

These boundaries exist deliberately. Penny is designed to be helpful within her capabilities and honest about her limitations. You will never get a wrong answer from Penny because she guessed rather than admitting uncertainty.

Getting Started with Penny

If you are already an Accounted user, you can start using all of these features right now — just send Penny a message on WhatsApp. If you are not yet using Accounted, now is the time to start.

As FSB research shows, UK sole traders spend an average of 15 hours per month on administrative tasks. Penny can reduce this to minutes per day, giving you time back to focus on earning, growing your business, or simply living your life.

Visit our pricing page to find the right plan, learn more about all our features, or sign up today to start using Penny.