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Key Tax Deadlines and Planning for September 2025

As we navigate the critical tax deadlines in September 2025, it's essential for individuals and businesses to plan strategically to ensure compliance and maximize savings. In this guide, we’ll explore important due dates such as tip reporting and estimated tax payments, offering insights on safe harbor rules, penalty avoidance, and preparatory strategies for 2026. 

Tax Planning for Autumn 2025 and Beyond

At TaxDrx, located in Cranford, NJ, our dedicated team is here to guide you through this season with personalized advice. Schedule a consultation to harness our proactive tax strategies. 

September 10 - Reporting Tips

By September 10, employees receiving over $20 in tips during August must report them to their employers using IRS Form 4070. Employers are responsible for withholding applicable FICA and income taxes from regular wages. If regular wages are not sufficient, the uncollected amount will appear in box 8 of the employee’s W-2, requiring payment upon filing taxes.

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September 15 - Estimated Tax Payments

The third installment for 2025 individual estimated taxes is due on September 15. Our “pay-as-you-earn” tax system necessitates understanding and meeting this requirement to avoid penalties. Here’s how to manage your tax obligations effectively:

  • Employees should ensure payroll withholding is adequate.

  • Retirees can arrange for pension withholding.

  • Self-employed individuals and those with additional income sources should make estimated tax payments.

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Failure to meet safe harbor prepayments could result in an underpayment penalty, calculated quarterly, at the federal short-term rate plus 3 percentage points.

Two safe harbors help avoid penalties:

  • The first is based on your current year’s tax: payments must be at least 90% of this amount.
  • The second is based on the previous year’s tax: usually 100% of that liability, or 110% for those with an AGI above $150,000 (or $75,000 if married filing separately).
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Quick Example: If your tax for the year is $10,000, with prepayments of $5,600, you’ll owe an additional $4,400. To avoid penalties, your prepayments should have been $9,000 (90% of $10,000) or possibly the $5,600 (111% of last year’s $5,000 tax, given that exceeds the latter safe harbor requirement).

When income surges occur, such as from windfalls or bonuses, it’s crucial to reassess your prepayments to avoid penalties.

Be Aware: State-specific safe harbor rules may differ, so reach out to TaxDrx for precise guidance.

Adjustments for Special Dates:
If a due date lands on a weekend or holiday, it extends to the next business day. Additionally, special extensions apply for disaster-designated areas, as detailed on the FEMA and IRS websites.

Schedule a Complimentary Consultation
Choose from our locations and meet with one of our qualified staff members. If you prefer to secure a Virtual Meeting via Zoom or Phone, please contact our offices at 877.908.1040
Schedule Here
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TAX DRx at a Glance

Our expertise is widespread and we have multiple office locations to make it convenient for you to get help. You can find us at:

TAX DRx Corporate Headquarters

502 Centennial Ave
Cranford, NJ 07016
(Grd St Pkwy - Ext 136)
(877) 263-1041

NYC - Harlem Franchise Office

2123 Frederick Douglass Blvd
New York, NY 10026
(8th Ave & 115th St.)
(Subway B, C, Bus M3)
(877) 263-1041

TAX DRx - Hillside

*Charles Dort, Managing Partner*
1568 Maple Ave, Store #1
Hillside, NJ 07205
(Corner of Conklin Ave)
(877) 408-1048

TAX DRx, dba/ TaxJohn

TaxJohn Tax Services
121 Park Ave
Plainfield, NJ 07060