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June 2025 Tax Deadlines: Critical Compliance Dates for Individuals and High-Income Filers

Staying proactive about your tax obligations is essential—not only to minimize unnecessary penalties but also to optimize your overall tax position. For physicians, high-income executives, business owners, and individuals navigating significant asset sales, a clear understanding of upcoming due dates in June 2025 is foundational to smart tax mitigation and financial stewardship.

Key June 2025 Individual Tax Due Dates: What to Know and How to Prepare

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June 2 – Final Due Date for IRA Trustees to Issue Form 5498

If you hold an Individual Retirement Arrangement (IRA), your trustee must provide you with Form 5498 by June 2, detailing the Fair Market Value (FMV) of your accounts as of December 31, 2024. The FMV impacts your Required Minimum Distribution (RMD) calculation, crucial for those age 73 and older in 2025. Timely reporting here not only ensures compliance but enables you to factor RMDs into your retirement cash flow and tax projections.

June 10 – Tips Reporting for Employees

For professionals or their household members working in tip-based roles: If you received more than $20 in tips during May, you’re required to report them to your employer by June 10 using IRS Form 4070. This requirement ensures proper tax withholdings for FICA and income taxes. If withholding from regular wages is insufficient, the uncollected amount will appear in Box 8 of your W-2, triggering payment due when you file your tax return. Staying on top of this reporting prevents surprises and potential enforcement actions come filing season.

June 16 – Second Quarter Estimated Tax Payments

For high earners, self-employed professionals, or those realizing capital gains (think sales of appreciated land, businesses, or other assets), the second quarter estimated tax payment is due June 16. The U.S. tax system operates on a pay-as-you-earn basis, mainly via:

  • Payroll withholding for employees
  • Pension withholding for retirees
  • Quarterly estimated tax payments for those with significant income not subject to withholding

Failing to prepay a safe harbor amount exposes you to underpayment penalties—specifically, the federal short-term rate plus 3%. To avoid this:

  • If you owe less than $1,000 after withholdings and credits for the year, no penalty applies.
  • Prepay at least 90% of your current year’s tax, or 100% of your prior year’s liability (110% if your AGI exceeds $150,000; $75,000 MFS).

Example: Let’s say your 2025 tax is projected at $10,000. If you’ve prepaid $5,600 in estimates and withholdings, you owe $4,400 at filing. 90% of $10,000 is $9,000—your prepayments are insufficient for the current-year safe harbor. But, if your 2024 tax was $5,000, then prepaying $5,600 (which exceeds 110% of $5,000) shields you from underpayment penalties under the prior-year safe harbor.

Major asset sales, business wind-downs, or large bonuses can dramatically increase your tax liability, so regularly review and adjust prepayments as needed for peace of mind and penalty avoidance.

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State Tax Nuances

Keep in mind: State estimated tax deadlines, safe harbor percentages, and de minimis thresholds may differ from federal rules. If you have multi-state or complex income, connect with our office for specifics tailored to your state(s).

June 16 – Tax Filing Deadline for U.S. Taxpayers Abroad

If you are a U.S. citizen or resident alien living and working or serving in the military outside the U.S. or Puerto Rico, June 16 is your filing deadline for your 2024 individual return and payment. If you need additional time, filing Form 4868 gives a four-month extension—but not an extension to pay. Any additional tax owed after June 16 will be subject to interest and late payment penalties.

Extensions for Military Personnel in Combat Zones

Special filing extensions apply for service members in qualified combat zones or participating in contingency operations. You have 180 days after your last day in the qualifying area, or after qualified hospitalization, to take most IRS actions. The extension also includes any unexpired time you had left at the time of deployment. Maximize these provisions but remember: the IRS may not know who is deployed without notification—reach out for assistance if needed.

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Additional Reminders

  • Weekends & Holidays: If a tax due date lands on a Saturday, Sunday or legal holiday, your deadline extends to the next business day. Stay vigilant as state rules may vary.
  • Disaster Area Extensions: Certain federally declared disaster zones may qualify for additional deadline relief. For real-time updates, consult FEMA’s Disaster Declarations and the IRS’s Tax Relief in Disaster Situations pages:

Your Trusted Partner for June Tax Deadlines

Tax compliance is a year-round effort, especially for physicians, entrepreneurs, and high-net-worth individuals juggling multiple revenue streams and assets. As your mentor in tax mitigation, my commitment is to keep your planning proactive, educational, and stress-free whenever possible. If you have questions about safe harbor rules, need help recalibrating your estimates, or want insight into state-specific requirements, don’t wait until the last minute.

Click on the button to schedule a 15-minute discovery call and gain clarity and confidence for June 2025 and beyond.

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