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Key Tax Dates for September 2025: Stay Compliant

As we navigate through the third fiscal quarter, it’s crucial to align your financial management tasks with the September 2025 tax deadlines. Key responsibilities this month include reporting tips and making estimated tax payments. Staying informed can help you take advantage of safe harbor rules, minimize penalties, and lay the groundwork for efficient tax planning as we head into 2026 and beyond.

2025 Tax Strategies and Planning for Fall 2026

At Michael Dolezal & Co, we pride ourselves on offering comprehensive tax and business services tailored to your needs. Don’t hesitate to contact us to schedule your consultation and develop your personalized tax mitigation strategy.

September 10: Ensure Proper Tip Reporting to Employers

If you earned over $20 in tips during August, reporting them to your employer by September 10 using IRS Form 4070 is mandatory. Employers are tasked with withholding FICA taxes and applicable income tax from these reported tips. Should your paycheck be insufficient to cover these withholdings, the shortfall will be detailed in box 8 of your W-2, rendering you responsible for payment upon filing your annual return.

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September 15: Deadline for Third Quarter Estimated Tax Payments

The "pay-as-you-earn" system necessitates that taxpayers remain proactive in meeting their tax liabilities through various mechanisms:

  • Employees contribute via payroll withholdings.
  • Retirees manage withholding through pensions.
  • Self-employed individuals, and those with other forms of income, comply by making estimated payments.

Failing to meet the minimum prepayment requirement invites underpayment penalties, calculated quarterly at the federal short-term rate plus three percent. Fortunately, two safe harbor options exist to mitigate this risk:

  • The first requires payments to equal or surpass 90% of current year tax liabilities.
  • The second, typically at 100% of the previous year’s taxes, increases to 110% if the taxpayer’s AGI exceeds $150,000 ($75,000 if filed separately).

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Example:

Consider your annual tax liability is $10,000, but you’ve only pre-paid $5,600. Falling short of the $9,000 threshold (90% of $10,000), you’d incur a penalty. However, if the prior year’s tax was $5,000, and you prepaid $5,600 (exceeding the 110% requirement), the second safe harbor safeguards you from penalties.

Always ensure your prepayments are adequate—especially after a significant income increase—common with assets sales, bonuses, or retirement. Late payments can disqualify safe harbor protections. For guidance on your specific circumstances, reach out to our office for tailored advice.

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Caution: It's noteworthy that state-specific de minimis amounts and safe harbor regulations may differ from federal guidelines. For detailed state-specific details, reach out to our experts at (216) 485-2028.

Accommodations for Weekends, Holidays, and Disaster Zones

Should a due date fall on a Saturday, Sunday, or recognized holiday, it extends to the subsequent business day. Additionally, disaster declarations can influence these timelines, possibly granting further extensions. To determine if your area qualifies, visit the latest updates through FEMA’s Disaster Declarations and the IRS Tax Relief page.

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