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Key September 2025 Tax Deadlines for Individuals

As September 2025 approaches, it’s crucial for individuals to stay on top of important tax deadlines, such as tip reporting and estimated tax payments. This article will guide you through the intricacies of safe harbor rules, penalty avoidance, and strategic tax planning for 2026.

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2025 Fall and 2026 Tax Planning

Consider scheduling a consultation with our office to effectively plan for the upcoming tax years.

September 10 - Report Tips to Employer

Employees who receive tips exceeding $20 in August must report them to their employer by September 10 using IRS Form 4070. Employers will withhold FICA taxes and income tax from regular wages for these tips. If regular wages are insufficient, the uncollected withholding amount will be noted in box 8 of your W-2, requiring payment when filing your annual return.

September 15 - Estimated Tax Payment Due

The third installment of 2025 individual estimated taxes is due. The U.S. utilizes a “pay-as-you-earn” taxation system, facilitated through mechanisms such as:

  • Payroll withholding for employees;
  • Pension withholding for retirees; and
  • Estimated tax payments for self-employed individuals and those with other income sources not covered by withholding.

Failing to prepay a safe harbor amount may result in underpayment penalties, calculated as the federal short-term rate plus three percentage points, applied quarterly.

Federal law offers solutions to avoid these penalties:

  • Underpaying below $1,000 incurs no penalty;
  • Two safe harbor prepayment options: 90% of current year’s tax liability or 100-110% of prior year’s tax liability depending on Adjusted Gross Income (AGI).

Example: If your tax is $10,000 with prepayments of $5,600, and 90% of $10,000 equals $9,000, you've underpaid. However, if the previous year’s tax was $5,000 and prepayments are $5,600, you meet the 110% prior year safe harbor, avoiding penalties.

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It is vital that prepayments match anticipated income, especially during large cash influx events like asset sales or retirement. Timely installment payments are essential for safe harbor qualification. For assistance with your safe harbor estimates, reach out to our office.

CAUTION: be aware that state de minimis and safe harbor rules can differ from federal guidelines. Contact us for state-specific information.

Weekends & Holidays:

If a deadline falls on a weekend or legal holiday, it automatically extends to the next business day.

Disaster Area Extensions:

Tax deadlines are extended for regions labeled as disaster areas. For more information, visit:

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