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Navigating September 2025 Tax Deadlines: Tips & Strategies

As we approach September 2025, it's crucial to stay informed about key tax deadlines. Understanding the landscape of tip reporting and estimated tax obligations not only helps prevent penalties but also prepares you for strategic tax planning for 2026.

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2025 Fall and 2026 Tax Planning

Our team at TaxxGuy LLC is ready to guide you through these requirements and offer personalized tax planning sessions. Let's start by marking the following critical dates on your calendar:

September 10 - Tip Reporting Deadline

If you earned over $20 in tips in August as an employee, you must report them to your employer on IRS Form 4070 by September 10. Employers are tasked with withholding FICA and income taxes from these tips. Should your regular wages fall short to cover these withholdings, expect to see the uncollected amount reported in Box 8 of your W-2, requiring settlement upon filing your year's return.

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September 15 - Estimated Tax Payment Due

The third installment of your 2025 estimated taxes is due. Given the "pay-as-you-earn" nature of our tax system, ensuring adequate prepayment through payroll or pension withholding remains vital. If these aren't applicable, you'll need to make estimated tax payments, especially if you're self-employed or have additional income streams.

Falling short of the necessary prepayment can incur an underpayment penalty—calculated as the federal short-term rate plus 3%. However, the IRS provides you with means to avoid this through two "safe harbor" provisions:

  • Pay at least 90% of the current year's tax liability.
  • Alternatively, cover 100% (or 110% for higher income earners) of the previous year's liability.

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Example: If your current year's tax is $10,000 and prepayments amount to $5,600, the balance due is $4,400. To check penalty exposure, compare your prepayments against 90% of the current year's tax ($9,000) and 110% of the prior year's tax ($5,500 if total last year was $5,000). The latter qualifies under the "safe harbor" provision.

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This highlights the necessity of accurate prepayments, especially with sudden income hikes through stock sales or significant bonuses. Ensure timeliness in each estimated tax installment to utilize safe harbor shields effectively.

Additional Considerations

Be mindful of differences in state and federal rules regarding de minimis amounts and safe harbor estimates. Our team is well-prepared to assist with these nuances.

Weekends & Holidays

Note that deadlines falling on weekends or public holidays extend to the next business day, free from penalty concerns.

Disaster Area Extensions

In disasters, filing extensions may apply. Check FEMA’s disaster declarations and IRS’ tax relief updates for current extensions.

Contact TaxxGuy LLC for any customized support with these tax challenges. Our goal remains to provide clarity and ensure seamless compliance with less stress, through bespoke strategies tailored to your financial landscape.

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129 Underhill Lane
Peekskill, New York 10566