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Navigating September 2025 Tax Deadlines: Tips and Strategies

As September approaches, it's crucial to stay informed about key tax deadlines that can impact your financial planning for the year. This month, particular attention should be given to tip reporting and the third installment of estimated tax payments. Understanding these obligations and the associated "safe harbor" rules can help you avoid penalties and strategically prepare for 2026.

Your Guide to Fall 2025 and 2026 Tax Planning

It’s wise to consult with a tax professional to optimize your financial strategy. At our firm, we offer personalized consultations to assess how the current tax landscape affects your unique situation and offer tailored advice to enhance your financial outcomes.

September 10 - Tip Reporting Deadline

If you earn more than $20 in tips during August, the IRS mandates that you report these earnings to your employer by September 10 using IRS Form 4070. Your employer will account for these tips when withholding FICA and income taxes from your regular wages. Should your wages not suffice to cover these withholdings, the shortfall will be recorded in box 8 of your W-2, which you will need to address upon filing your annual tax return.
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September 15 - Third Estimated Tax Payment

The deadline for the third estimated tax payment of 2025 approaches on September 15. Our pay-as-you-go tax system incorporates various methods, such as payroll and pension withholdings, as well as quarterly estimated payments for individuals with income not subject to withholding, such as self-employed individuals.

Failure to meet the "safe harbor" prepayment can result in an underpayment penalty, which is calculated using the federal short-term rate plus 3%. This can be avoided if the shortfall is under $1,000, or by making safe harbor prepayments, either covering 90% of your current tax liability or 100% (110% for high earners) of the previous year’s tax.

Illustrative Scenario:

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Imagine your annual tax bill stands at $10,000, with prepayments totaling $5,600. According to the first safe harbor rule, a penalty might be incurred since 90% of $10,000 is $9,000, which exceeds your prepayments. However, should the prior year's tax be $5,000 and your prepayments exceed $5,500 (110% of the previous year's tax), you would meet the safe harbor condition and avoid penalties.

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This underscores why ensuring sufficient prepayments is essential—particularly if you anticipate a significant income boost from events like major asset sales or bonuses. Always ensure timely payments and enquire if you're unsure about your estimated tax obligations.

State Variations: Note that state-specific rules may differ. For precise details, reach out to our office.

Holidays & Disasters

Due dates extending over weekends or holidays automatically shift to the next business day. Furthermore, areas marked as disaster zones by FEMA might receive deadline extensions. More details can be found at: FEMA and IRS.

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