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LEARNING CENTER

Key September 2025 Tax Deadlines for Individuals

As we move into the heart of tax planning season, September 2025 brings critical deadlines for individuals, including tip reporting and estimated tax payments. This guide explores the intricacies of safe harbor rules, penalty avoidance strategies, and forward-planning techniques to ensure a smoother 2026 tax year.

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2025 Fall and 2026 Tax Planning

Tax Planning: To navigate these responsibilities effectively, consider scheduling a consultation with our office. Our expertise in maximizing tax credits, deductions, and strategic loopholes ensures you remain ahead in financial planning.

September 10 - Reporting Tips to Your Employer

Employees receiving over $20 in tips during August must file IRS Form 4070 by September 10. Employers are tasked with withholding FICA and income tax, reflecting any uncollected amount in box 8 of your annual W-2, to be reconciled during tax filing.

September 15 - Estimated Tax Payment Due

The third installment of 2025 estimated taxes is due. Our "pay-as-you-earn" system is supported by payroll and pension withholding, and quarterly estimations for individuals with additional income streams. Failure to prepay a safe harbor amount triggers an underpayment penalty, calculated quarterly at the federal short-term rate plus 3 percentage points.

To prevent penalties, taxpayers can leverage two safe harbor options:

  • Current Year Safe Harbor: Paying at least 90% of the current tax year's liability.
  • Previous Year Safe Harbor: Covering 100% of last year's tax (110% for individuals with AGI above $150,000 or $75,000 if married filing separately).

Consider an illustrative scenario: If your anticipated tax stands at $10,000 and your prepayments total $5,600, your remaining liability is $4,400. While this falls short for the current year safe harbor (90% = $9,000), if last year's tax was $5,000, a prepayment of $5,600 exceeds 110% of the previous year's liability, waiving the penalty.

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Adequate prepayments are crucial, particularly amidst income spikes from investments or life events like bonuses and retirement. Timeliness in each installment is vital for safe harbor qualification. Queries on your estimates? Reach out to our office for guidance.

Caution: State Discrepancies

Be mindful that state de minimis thresholds and safe harbor norms may diverge from federal stipulations. Contact us for state-specific advisories.

Timing Extensions

Weekends & Holidays: Deadline extensions apply if the due date coincides with weekends or legal holidays. Disaster Area Extensions: Designated disaster regions receive deadline extensions. For confirmation, consult FEMA (fema.gov/disaster/declarations) and IRS (irs.gov/newsroom/tax-relief-in-disaster-situations).

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