The problem
Since April 2026, sole traders whose qualifying income was over $66,500£50,000€59,500A$96,000C$94,000 in 2024 to 2025 must keep digital records and send HMRC an update every quarter, by 7 August, 7 November, 7 February and 7 May. A one-person round of 300 cleans a month at $24£18€21A$35C$34 takes about $86,184£64,800€77,112A$124,416C$121,824 a year (300 × $24£18€21A$35C$34 × 12), well over that line. Typing 300 payments a month into a spreadsheet at 30 seconds each is 150 minutes, plus 40 receipts at a minute each and about 2 hours a quarter adding it all up: about 230 minutes a month (150 + 40 + 40).
What the AI does
Squeegee lists Income Quarterly Updates on every plan, including Core: it keeps track of income and spending and submits quarterly updates to HMRC from inside the app. The round's jobs, invoices and payments already live in Squeegee, so income is recorded as each payment comes in. You add expenses such as fuel, insurance and pole parts as you pay them, broken down into HMRC's expense categories. Squeegee says it is HMRC-recognized; check it on GOV.UK's software finder before you rely on it. You check each update before it goes, and the deadlines live first in your own diary.
A worked example
A one-person window cleaner in Kettering has about 300 customers on 4-weekly rounds at an average of $24£18€21A$35C$34 all in Squeegee Core ($25£19€23A$36C$36 a month excluding VAT, or $21.05£15.83€18.84A$30.39C$29.76 billed yearly). HMRC has written to say they must use Making Tax Digital, and they decide to file from Squeegee rather than keep a spreadsheet and buy separate software.
Before
About 230 minutes a month typing 300 payments and 40 receipts into a spreadsheet and adding up each quarter
After
About 50 minutes a month: 40 receipts logged as they're paid, plus a 30-minute check before each quarterly update
What it's worth
About $100£75€89A$144C$141 a month of time saved, at no extra cost if the round already runs in Squeegee. That is 3 hours a month (230 minutes down to 50) at $33£25€30A$48C$47 an hour. Core is $25£19€23A$36C$36 a user a month excluding VAT, or $21.05£15.83€18.84A$30.39C$29.76 billed yearly; matching bank transactions to customers and invoices needs Advanced at $33£25€30A$48C$47.
How to set it up
- Check on GOV.UK whether you must use Making Tax Digital now (qualifying income over $66,500£50,000€59,500A$96,000C$94,000 in 2024 to 2025) or from April 2027 (over $39,900£30,000€35,700A$57,600C$56,400 in 2025 to 2026), and sign up with HMRC.
- Write the four quarterly deadlines (7 August, 7 November, 7 February, 7 May) and the 31 January tax return deadline in your main diary, with a reminder two weeks before each, and check the diary on the first of every month. The diary is the primary record, not the app.
- Check Squeegee is listed on GOV.UK's software finder for Making Tax Digital for Income Tax, then link it to HMRC following Squeegee's own guide.
- Log every business expense in Squeegee as you pay it, such as fuel, van costs, insurance and pole parts, in the right HMRC category, and keep the receipts.
- Record cash and bank transfer payments against invoices on the day, so the income in Squeegee matches the bank.
- A week before each deadline, check the quarter's totals against your bank statements, with your accountant if you have one, then send the update and check your HMRC online account says it was sent.
What goes wrong
- Automations and connections can fail silently: an expired link to HMRC or an update left unsent won't file itself. The diary check on the first of each month is the control, along with the confirmation in your HMRC online account.
- Only what's in Squeegee goes into the update. Cash that wasn't recorded, or expenses paid from a personal card, will be missing unless you add them.
- Squeegee's MTD page says it helps with the information for the year-end tax return but doesn't say it submits it. Ask Squeegee, or plan for your accountant's software to file it by 31 January.
- GOV.UK says HMRC won't apply penalty points for late quarterly updates in the 2026 to 2027 tax year; after that, late updates build up points towards a $266£200€238A$384C$376 penalty. Don't let the first year teach you to file late.