June 2025: The Small Business Owner’s HR, Benefits, Payroll, and Tax Compliance Deadlines

June 2025: The Small Business Owner’s HR, Benefits, Payroll, and Tax Compliance Deadlines

Paige Smith | Published May 20, 2025 7 Min

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The commercial summer season has officially begun! Depending on your industry, you might be knee-deep in summer promotions (or even fall production cycles) or bracing for a slower few months ahead. 

Whatever your situation, make sure you stay up to date on your compliance deadlines. Here are all the dates you should know about in June. 

Federal holidays

June 19, 2025

Juneteenth

Juneteenth commemorates the day Union Army Major General Gordon Granger rode into Galveston, Texas, and issued an order proclaiming that the enslaved African Americans living there were free.

Today, many businesses observe Juneteenth by shutting down for the day or encouraging employees to participate in local events and celebrations. 

Tax and payroll compliance deadlines

Payroll tax deposits (for semi-weekly depositors)

The Internal Revenue Service (IRS) requires employers who file Forms 940 and 941 to deposit payroll taxes at different frequencies throughout the year. 

If you report more than $50,000 in payroll taxes during the lookback period of July 1, 2023, to June 30, 2024, you’re considered a semi-weekly depositor, which means you follow the schedule below:

If payday for your employees is on…Deposit employment taxes by…
WednesdayThe following Wednesday
ThursdayThe following Wednesday
FridayThe following Wednesday
SaturdayThe following Friday
SundayThe following Friday
MondayThe following Friday
TuesdayThe following Friday

There’s one exception: If you accumulate $100,000 or more of tax liability in a single day, you have to deposit the amount by the following business day, regardless of your usual deposit schedule. 

To learn more about federal payroll tax deposits, read Publication 15

It’s also a good idea to contact your state and local tax agencies to find out if you owe deposits for local payroll taxes. 

June 2, 2025

Form 730 filing deadline for April wagers

Because the last day of May fell on a weekend, Form 730 is due June 2 if you meet the following criteria below and accepted wagers during April 2025:

  • You are in the business of accepting wagers
  • You conduct a wagering pool or lottery
  • You are required to be registered and receive wagers for or on behalf of another person, but did not report that person’s name and address

Learn more about Form 730 here.

Form 2290 filing deadline for vehicles first used in April

If you’ve registered a heavy highway motor vehicle (with a taxable gross weight of 55,000 pounds or more) that was first used in April 2025, you have to file Form 2290 by June 2. 

To learn more about Form 2290, review the IRS’s instructions and information

June 10, 2025

Employee tip reporting deadline for May 

Employees who earned tips of $20 or more during May have to report those tips to you by June 10. You can learn more about tip withholding and reporting requirements here

June 16, 2025

Payroll tax deposits for monthly depositors

If you follow the monthly payroll tax deposit schedule (meaning that you reported less than $50,000 in payroll taxes during the lookback period), your tax deposit for May payrolls is due on Monday, June 16. 

Estimated tax payment for Q2 due 

If you make quarterly estimated tax payments, your second payment of the year is due June 16. You will likely make quarterly estimated tax payments if you fall into one of the following categories:

  • C corporations
  • S corporation shareholders
  • Partners
  • Sole proprietors 
  • Independent contractors
  • Freelancers 
  • Gig workers

You can pay online, over the phone, or via mail using Form 1040-ES. For more information on estimated taxes, review Publication 505.

Form 8813 quarterly payment voucher due for partnerships 

If you operate a partnership, you need to file Form 8813 by June 16 and pay any tax due. You can file the form at this address:

Internal Revenue Service Center
P.O. Box 409101
Ogden, UT 84409

For more information on Form 8813, see the IRS instructions here

Estimated tax payment due for Q2 for tax-exempt organizations

If you own a nonprofit and owe more than $500 in taxes for the year, you need to pay any estimated tax on unrelated business income by June 16. You can use Form 990-W to calculate the amount of estimated tax required. 

Forms 8804 and 8805 due for partnerships with accounts outside the US and Puerto Rico

If you run a calendar-year partnership, and you maintain business accounts and records outside of the US and Puerto Rico, you have to file Forms 8804 and 8805 to report your total tax liability by June 16. 

Tax returns due for military personnel and US taxpayers living and working abroad

Business and personal income tax returns (plus tax payments) for the following groups are due by June 16:

  • On-duty military personnel abroad who don’t qualify for the longer combat zone extension
  • US citizens and resident aliens who live and work outside of the US and Puerto Rico

If you fall into one of these categories, make sure to include a statement along with your return explaining which of the above situations apply to you. Individuals living outside the US need to file Form 1040 or Form 1040-SR (for seniors).  

If you need more time to file your tax return, you have to file Form 4868 by June 16 to get an automatic four-month tax extension. Keep in mind this extension doesn’t apply to your payments; you still need to make tax payments by June 16 to avoid penalties.  

For details on the special rules that apply for US taxpayers living and working abroad, read Publication 54

June 30, 2025

End of Q2 for companies following the calendar year

If you follow a calendar year, the second quarter ends on June 30. 

Form 730 filing deadline for May wagers

Form 730 for May wagers is due on June 30. 

Form 2290 filing deadline for vehicles first used in May

If you registered a heavy highway motor vehicle that you used for the first time in May, you have to file Form 2290 by June 30. 

HR compliance deadlines

June 30, 2025

Deadline for retirement plans with publicly traded employer securities to file their annual report 

The Securities and Exchange Commission (SEC) requires all publicly traded companies to file SEC Form 11-K every year. This annual report includes information about employee stock purchases and any plans that own interests in securities. 

If you have a retirement plan with publicly traded employer securities, you need to file Form 11-K by June 30.

Deadline for processing Employee Stock Ownership Plan (ESOP) diversification elections for calendar year plans

If you have an Employee Stock Ownership Plan (ESOP), you have to process your employees’ diversification elections by June 29, 180 days after the end of the plan year. 

ESOP holders can diversify their stock accounts once they become qualified participants, when they reach the age of 55 and have participated in the plan for 10 years. 

Reaching this status triggers the six-year qualified election period for these participants. Some plans give participants even more time to diversify their accounts, so it’s a good idea to check your plan document or reach out to your plan provider if you have questions.

Mid-year benefits review for employees

Six months into the calendar year is a perfect time to remind your employees to take advantage of their employee benefits, whether it’s a health savings account or flexible paid time off. Send your employees an email listing their available benefits, or schedule a meeting to answer questions. 

Deadline for issuing corrective distributions due to failed nondiscrimination test for EACAs

When your eligible automatic contribution arrangement (EACA) doesn’t have Safe Harbor status, you’re required to conduct nondiscrimination testing on these plans on a regular basis.

These tests—also known as the Actual Deferral Percentage (ADP) and Actual Contribution Percentage (ACP) tests—determine whether accounts belonging to rank-and-file employees and those belonging to managers, owners, and other higher-compensated employees (HCEs) receive a proportional amount of contributions. 

If these tests reveal that there is a discrepancy that benefits high-income earners, you’re required to contribute more funds to your rank-and-file plan participants, correct excessive distributions made to HCE plans, or both. 

Plan sponsors for EACAs that failed the ADP or ACP tests during the prior plan year and choose to make corrective distributions to HCE plans must process these refunds by June 30 to avoid a 10% excise tax. 

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Paige Smith

Paige Smith

Paige is a content marketing writer specializing in business, finance, and tech. She regularly writes for a number of B2B industry leaders, including fintech companies and small business lenders. See more of her work here: