CSLB Law & Business ExamBusiness FinancesMedium

A sole proprietor contractor expects to owe more than $1,000 in federal income tax for the year after subtracting withholding and credits. According to IRS rules, what should the contractor do to avoid an underpayment penalty?

  1. APay the full amount owed when filing the annual return
  2. BFile a tax extension request in April
  3. CMake quarterly estimated tax payments throughout the year
  4. DIncrease W-2 withholding from an employer job only
Show answer & explanation

Correct answer: C. Make quarterly estimated tax payments throughout the year

Self-employed individuals expecting to owe $1,000 or more in tax must make quarterly estimated tax payments (Form 1040-ES) to avoid underpayment penalties, since no employer withholds tax on their behalf.

Why the other options are wrong

  • A. Paying only at filing time results in underpayment penalties for the earlier quarters.
  • B. An extension only extends time to file, not to pay, and doesn't prevent underpayment penalties.
  • D. A sole proprietor typically has no employer W-2 withholding to adjust.

Estimated Quarterly Taxes

Payments self-employed individuals make four times per year to cover income and self-employment tax obligations, avoiding IRS underpayment penalties.

  • Required if expected tax owed is $1,000 or more
  • Paid via IRS Form 1040-ES
  • Due dates roughly mid-April, June, September, and January

Memory trick: No boss withholding? Pay the IRS quarterly yourself.

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