Hiring your first employee in Singapore looks straightforward until you hit CPF contribution forms, probation notice periods, and IRAS reporting deadlines. Most founders assume payroll is payroll—it isn't. Singapore's Ministry of Manpower (MOM) rules are strict, IRAS expects accuracy, and a single compliance misstep can trigger fines and back-pay liability that wipes out months of margin. This guide walks you through the actual mechanics: what probation legally requires, how much CPF you're legally obligated to contribute (and from what salary ceiling), which benefits are mandatory, tax withholding math, and when outsourcing payroll stops being a luxury and becomes the only sane choice. Probation period: what MOM actually requires Singapore allows probation, but it's not a free-pass termination period. The rules are specific: Duration: 3 months minimum, up to 6 months maximum. You can extend once if the initial period is under 3 months (e.g., 2-month initial + 2-month extension), but the total cannot exceed 6 months. Notice period during probation: Both employer and employee must give written notice. The contract can specify shorter notice during probation (e.g., 3 days instead of 1 month), but it must be in the employment agreement signed before work begins. What probation doesn't protect: You still cannot terminate for pregnancy, union membership, jury duty, or injury. Probation makes termination easier, not consequence-free. Probation documentation: Keep signed contracts and performance notes. If a dispute reaches the Ministry of Manpower, MOM will ask why probation ended—vague 'cultural fit' won't hold up. Set probation in writing before the first day. Verbal agreements or letters count, but the contract must clearly state the probation period, notice requirements, and conditions for termination. CPF contributions: the numbers and your ceiling Central Provident Fund (CPF) is not optional in Singapore. Any resident employee earning more than SGD 50 per month must be enrolled. Here's the breakdown: Contribution rates (as of 2025): Employee contributes 8% of monthly gross salary (capped at SGD 6,800 gross = SGD 544/month max contribution). Employer contributes 17% of monthly gross salary (same SGD 6,800 ceiling = SGD 1,156/month max contribution). For employees aged 55–60: rates vary; consult your accountant for exact percentages. For employees over 60: rates are lower; some may be partially exempt. What salary counts toward CPF? Gross salary including basic pay, allowances, bonus, and overtime. Exclude: meals, transport reimbursements, and one-off termination payments. Your obligation: You deduct the employee's 8% from their paycheck and remit both your 17% contribution and their 8% to the CPF Board by the 4th of the following month. Late payment incurs interest and penalties. Missing CPF is one of the fastest ways to trigger MOM audits. Track this carefully. If you use spreadsheets, you'll need a second person to audit; one typo (like including reimbursement in gross) cascades into under-contribution and back-pay liability. Most founders find payroll-integrated invoicing tools or dedicated payroll software cheaper than the tax hit and audit cost of errors. IRAS withholding tax and income tax registration Singapore residents pay personal income tax. You must register as an employer with the Inland Revenue Authority of Singapore (IRAS) within 7 days of hiring. Failure to register is itself a breach. Tax withholding: IRAS publishes tax tables; you withhold tax based on the employee's salary and filing status. You remit withheld tax monthly to IRAS by the 7th of the following month. The employee does not pay IRAS directly; you do it on their behalf. At year-end, IRAS reconciles against the employee's actual tax liability; over-withholding triggers a refund, under-withholding triggers an adjustment notice to you. Registration and returns: File an Employer's Return of Remuneration (EROR) annually with IRAS. You'll need the employee's:— Full name and NRIC (National Registration Identity Card). Date of birth and tax residence status. Annual gross salary and tax withheld. IRAS operates online via myTax Portal. If you're unsure about tax tables or filing thresholds, a Singapore accountant (SGD 500–1,500 per year for one employee) is cheaper than an audit adjustment. Medical benefits and mandatory coverage Singapore does not mandate employer-provided health insurance for private-sector employees. However, hospitalization insurance (typically covering A/B ward, day surgery) is strongly recommended and often expected at SGD 30–60 per month per employee. What is mandatory: Work injury compensation: You must buy work injury compensation insurance (WICI) via an NTUC Income or private insurer. Cost: ~SGD 20–50/month depending on role and industry risk rating. Group Personal Accident Insurance (GPA): Not mandatory but common; covers off-site accidents. Usually bundled with WICI. COVID-era note: The government ended most C