IRAS 2027 Prep: Use AI to Organise Your Taxes Early

Tax season in Singapore arrives every March to April, and every year the same thing happens: people dig through twelve months of receipts, guess their reliefs, and file late at night. The 2027 filing season covers income you earn in 2026, so you can avoid that scramble entirely by setting up a small system now.

IRAS pre-fills most of your return on myTax Portal from your employer, bank and CPF records. What it does not pre-fill are the reliefs and deductions you have to claim yourself. That is where organising early pays off. This guide shows you how to use AI to sort your documents, build a reliefs checklist, and file with confidence. If prompts are new to you, our guide to writing AI prompts that work is a good start.

You do not need a perfect system, just one place where every deductible item lands. Keep a folder, physical or digital, for: medical receipts, course fees, donations, insurance and work-related expenses. Once a month, let AI sort the pile:

🧾 Receipt sorter

Here are my 2026 expense notes: [paste items with amounts and dates, no personal data]. Categorise each one: donations to approved IPCs, medical, course fees, insurance, work expenses, or not deductible. For anything uncertain, say "check with IRAS" instead of guessing.

Keep the categorised list in a spreadsheet or notes app. Five minutes a month beats five hours in March.

Reliefs are the difference between a S$500 tax bill and a S$2,000 one. The common ones for salaried workers: earned income relief (S$1,000, higher once you pass 55), CPF relief, course fees relief (up to S$5,500), NSman relief, parent relief and working mother's child relief. SRS contributions and CPF cash top-ups also qualify within limits. Let AI turn your situation into a checklist:

📋 Reliefs checklist

I am a Singapore tax resident employee. My situation: age [X], NSman [yes/no], children [yes/no], parents living with me [yes/no], SRS contribution this year S$[X], CPF cash top-up S$[X], course fees S$[X], donations to an approved IPC S$[X]. List every tax relief I may be eligible for in YA 2027, with the current amount and any cap. Where you are unsure, tell me to verify on iras.gov.sg.

Check each item against the IRAS reliefs page before filing. The chatbot cannot see your full situation, so treat its list as a starting point, not the final answer.

Some deductions must be acted on before 31 December 2026 to count for YA 2027. Three big ones: top up your Supplementary Retirement Scheme account (the cap is currently S$15,300 a year for Singaporeans and PRs), make a CPF cash top-up under the Retirement Sum Topping-Up scheme (up to S$8,000 relief for yourself and another S$8,000 for eligible family members), and donate to an approved IPC, which earns a 250% tax deduction while the current extension runs to 31 December 2026.

📅 Year-end action plan

Today is [date]. My expected 2026 chargeable income is about S$[X] and I have S$[X] of spare cash. List the actions I can still take before 31 December 2026 to reduce my YA 2027 tax, in order of impact: SRS top-up, CPF cash top-up, donations. Show the estimated tax saving for each and any limits. Do not invent rules; where unsure, say "verify on iras.gov.sg".

When the filing window opens, typically 1 March to 18 April 2027, log in to myTax Portal with Singpass, review the pre-filled income, and add your reliefs. Exact dates are confirmed on iras.gov.sg closer to the season. Before submitting, let AI review the whole picture:

🔍 Pre-fill review

Here is my pre-filled YA 2027 return: [paste the income and relief sections, no NRIC or personal identifiers]. My situation: [brief]. What should I double-check, and which reliefs am I likely missing? If unsure about any item, say "verify on iras.gov.sg".

Keep your receipts for at least five years. IRAS can ask to see them, and a tidy folder makes the answer easy.

AI is a great organiser but it is not a licensed tax advisor. It can misremember a relief amount or invent a deduction, and an incorrect return is ultimately your responsibility. Always confirm numbers on iras.gov.sg, and for anything complicated, a call to IRAS is free and surprisingly helpful. Never paste your NRIC, full name or bank details into a chatbot. Start the folder this week, and next March you will be the person who files in ten minutes. CPF top-ups are a big part of tax planning, so our CPF planning guide covers them in detail, and GST for SMEs helps if you also run a business.