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Essential September 2025 Tax Deadlines for Individuals

September brings crucial tax deadlines that individuals must not overlook, particularly in the area of tip reporting and estimated tax payments. Delve into safe harbor rules, learn how to avoid penalties, and explore key strategies for your 2026 tax planning.

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2025 Fall and 2026 Tax Strategies

Ensure you're set for a successful tax year by contacting our office to schedule your personal tax planning consultation.

September 10 - Reporting Tips to Employers

Employees who earn tips exceeding $20 in August must report them to their employer using IRS Form 4070 by September 10. Employers are then responsible for withholding FICA and income taxes from your regular wages. Failure to cover all withholding through regular wages will result in uncollected amounts being noted in box 8 of your W-2, which you'll need to pay when filing your tax return.

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September 15 - Estimated Tax Payment Deadline

The third individual estimated tax installment for 2025 is due now. Our tax system operates on a “pay-as-you-earn” principle. To support this, taxpayers have methods such as:

  • Payroll withholding for employees;
  • Pension withholding for retirees; and 
  • Estimated tax payments for the self-employed and those with untaxed income sources.

Failing to meet prepayment safe harbors can lead to underpayment penalties. Determined quarterly, these penalties comprise the federal short-term rate plus 3%. To avoid penalties, your underpayment should stay under $1,000 or meet either of the safe harbor prepayment guidelines:

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  • 90% of the current year’s tax obligation;
  • 100% of the prior year’s tax, or 110% for higher income brackets (over $150,000 AGI; $75,000 if filing separately).

Example: If you owe $10,000 in taxes this year and prepaid $5,600, you fall short of the first safe harbor, as it requires $9,000 (90%) in prepayments. However, if last year’s tax was $5,000, your $5,600 prepayment surpasses 110% of that amount, invoking the second safe harbor ensuring no penalty.

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Maintaining sufficient prepayments is particularly crucial for those experiencing income surges, like from substantial stock sales, property sales, bonuses, or retirement. For detailed safe harbor estimate guidance, connect with our office promptly.

Warning: State-specific de minimis thresholds and safe harbor rules may differ from federal standards. Consult our office for state-specific advice.

Special Situations:

Dates landing on weekends or holidays automatically extend to the next business day. For areas designated as disaster zones, extensions may apply. For details, visit:

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