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Key September 2025 Tax Deadlines and Preparations

September 2025 is a crucial month for staying tax-compliant, especially for those in the trades and construction industries. As seasoned tax advisors serving both the Central Texas area and clients nationwide, we want to ensure that you’re up-to-date with key tax deadlines such as tip reporting and estimated tax payments, while also preparing you for a smooth 2026 tax season.

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For personalized tax planning that aligns with your business goals, contact ChesebroCPA to schedule a consultation.

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September 10 - Deadline for Reporting Tips
If you are in a tip-based job and have earned over $20 in tips for August, you must report these tips to your employer using IRS Form 4070 by September 10. Employers then handle the necessary FICA and income tax withholdings. Should your regular wages be insufficient to cover these withholdings, any uncollected amounts will be noted in box 8 of your W-2 form, requiring you to settle these when you file your tax return for the year.

September 15 - Estimated Tax Payment Due
This date marks the deadline for the third installment of your 2025 individual estimated taxes. The U.S. tax system operates on a “pay-as-you-earn” basis, and meeting this requirement could involve payroll withholdings for employees, pension withholdings for retirees, or estimated tax payments for self-employed individuals. Underpaying throughout the year may result in penalties, calculated as the federal short-term rate plus three percentage points.

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Safe Harbor Rules to Avoid Penalties
Federal laws offer mechanisms to avoid these penalties, the most common being "safe harbor" payments. Make sure your prepayments are sufficient:

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  • If your annual payments meet or exceed 90% of the current year’s tax obligation, you are covered under the first safe harbor.
  • The second safe harbor involves meeting 100% of your prior year’s tax liability, which is increased to 110% for taxpayers with an AGI above $150,000 ($75,000 if married but filing separately).

Example: If your current year’s tax is $10,000 and prepayments total $5,600, you owe $4,400. You don't satisfy the first safe harbor, but if your previous year’s tax was $5,000, your $5,600 prepayment surpasses 110% of that, keeping you within the second safe harbor.

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This highlights the importance of adequate prepayments, especially during high-income events like asset sales or retirement. Prompt payment of each required installment also ensures you remain penalty-free. Contact ChesebroCPA for tailored support in setting up your safe harbor estimates.

State Specifics and Caution
Keep in mind that state-specific safe harbor and de minimis rules may differ from federal ones. For nuanced guidance, reach out to our office.

Important Considerations

  • Weekends & Holidays: If a due date falls on a weekend or holiday, it automatically extends to the next business day.
  • Disaster Area Extensions: Extensions apply if your area is designated as a disaster zone. Stay updated via FEMA and the IRS websites.

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