As we approach the midway point of the year, June brings several critical tax and financial deadlines that require careful attention. For our high-net-worth clients, fiduciaries, and family offices in Burlingame and beyond, staying ahead of these dates is essential for preserving wealth and avoiding unnecessary penalties. Let us explore the key obligations you need to mark on your June 2026 calendar, from estimated tax payments to specific reporting requirements for IRA owners and taxpayers living abroad.

IRA Valuation Reporting: The June 1 Deadline

By June 1, 2026, IRA trustees must issue Form 5498, providing IRA owners with the fair market value (FMV) of their accounts as of December 31, 2025. In our estate and gift valuation practice, accurate FMV reporting is a foundational element. For individuals who are age 73 or older during 2026, this December 31 valuation determines your Required Minimum Distribution (RMD) for the current year. Proper tracking ensures compliance and supports comprehensive wealth planning.

Mastering Q2 Estimated Tax Payments by June 15

The United States operates on a “pay-as-you-earn” tax system, making June 15 a vital deadline for timely second-quarter estimated tax payments. For investors or those managing complex estates, missing this deadline triggers an underpayment penalty, computed quarterly based on the federal short-term rate plus three percentage points.

To avoid penalties, taxpayers must meet “safe harbor” prepayments. If your underpayment is less than $1,000, no penalty applies. Otherwise, you must prepay 90% of your current year’s tax liability or 100% of your prior year’s liability. For high-net-worth individuals with an Adjusted Gross Income (AGI) over $150,000 ($75,000 if married filing separately), the prior-year safe harbor threshold increases to 110%.

Consider this scenario: Your 2026 tax liability is $10,000 and your prepayments total $5,600, falling short of the 90% current-year rule. However, if your prior-year tax was $5,000, your $5,600 prepayment exceeds the 110% safe harbor ($5,500), successfully shielding you from penalties. We frequently see safe harbor miscalculations when clients experience sudden liquidity events, like selling property. Keep in mind that California state safe harbor rules differ from federal guidelines, so proactive planning is highly recommended.

Filing Requirements for Taxpayers Living Abroad

If you are a U.S. citizen or resident alien living and working outside the United States and Puerto Rico, June 15 is the deadline to file your 2025 income tax return and pay any tax due.

The IRS provides extended relief for specific circumstances. Taxpayers impacted by the terrorist attacks in Israel throughout 2024 and 2025 have until September 30, 2026, to file and pay taxes otherwise due between September 30, 2025, and September 30, 2026. Furthermore, military personnel deployed in combat zones receive an automatic 180-day extension upon leaving the area, plus any remaining days from their normal filing period.

If you need more time to prepare your return, you can file Form 4868 to secure a four-month extension to October 15. However, this only extends the time to file, not the time to pay. If you expect to owe, include payment with the extension to avoid late payment penalties and interest.

Navigating Tip Reporting and Disaster Relief

Employees receiving more than $20 in tips during May must report those earnings to their employers by June 10 using IRS Form 4070 or a detailed written statement. Your employer will then withhold the necessary FICA and income taxes from your regular wages.

Additionally, it is crucial to monitor natural disaster designations. When a geographic area is declared a federal disaster area, standard deadlines are extended to provide relief. If you believe your location might qualify, verify declarations and filing extensions through these official resources:

• FEMA: https://www.fema.gov/disaster/declarations
• IRS: https://www.irs.gov/newsroom/tax-relief-in-disaster-situations

Lastly, remember that if any due date falls on a Saturday, Sunday, or legal holiday, it automatically shifts to the next business day.

Align Your June Tax Obligations With Your Legacy Goals

Whether you are calculating safe harbor estimates for a recent liquidity event, managing foreign tax filings, or verifying IRA valuations for a trust, these June deadlines require precision. At Sullivan & Company CPA Inc. in Burlingame, we specialize in translating complex tax and valuation requirements into clear, defensible strategies. If you need assistance structuring your estimated payments, extending your returns, or addressing a forensic accounting concern, our team is ready to help. Contact our office today to secure your financial legacy and reduce compliance stress.