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Essential September 2025 Tax Deadlines and Planning Tips

As we approach September 2025, several key tax deadlines are drawing near, crucial for both individual and business taxpayers. This month serves as an important reminder of tax obligations including tip reporting, estimated tax payments, and strategic planning for the upcoming tax year. Our firm in Maitland, Florida, serving communities like Winter Park and Altamonte Springs, is here to help you navigate these crucial dates with expertise and precision.

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Ready to proactively manage your taxes? Contact our office to schedule a consultation and discuss your 2025 fall and 2026 tax planning. Let's optimize your tax situation together.

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September 10 - Reporting Tips to Your Employer
If you earned over $20 in tips during August 2025, it’s mandatory to report these to your employer using IRS Form 4070 by September 10. Employers will account for FICA taxes and income tax withholding, taking these sums from your regular wages. In cases where wages fall short, the uncollected amount will appear in box 8 of your W-2, requiring you to settle this when you file your annual return.

September 15 - Estimated Tax Payments Due
The U.S. tax system operates on a “pay-as-you-earn” basis. On September 15, the third installment for 2025 individual estimated taxes is due, a critical date particularly for self-employed individuals and those with non-withholding income. Our services in Lake Nona and Davenport guide clients in setting up payroll and pension withholdings effectively.

Avoiding the Underpayment Penalty
To avoid penalties, it’s vital to meet specified “safe harbor” prepayment thresholds. Penalties accrue based on the federal short-term interest rate plus three percentage points on underpayments exceeding safe harbor amounts. The law offers two main safe harbors:

  • Payments equal to or above 90% of current year taxes.
  • 100% of last year’s tax liabilities, 110% for higher AGI clients.

For further clarity, if your additional owed amounts exceed prepayments, you may face penalties unless safe harbor or de minimis rules apply. For example, if last year’s tax was $5,000, and this year your prepayments are $5,600, surpassing 110% of the prior year’s ($5,500), you’re within safe harbor and avoid penalties.

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State-Specific Rules and Extensions
Be aware, state rules might differ. Additionally, any due date falling on weekends or holidays extends to the next business day. In designated disaster areas, extensions may apply. For current designations, refer to FEMA and IRS disaster relief resources.

Maximize your tax efficiency this fall by staying informed and proactive. For tailored advice on estimated taxes and preparation for 2026, reach out to our expert team today. Let's ensure you meet obligations while leveraging tax opportunities tailored to your financial situation.

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