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

September is the start of the last stretch to the end of the year. Whether you’re making the most of the final few weeks of summer, capitalizing on back-to-school season, or prepping for holiday campaigns, it’s important to stay on top of your compliance deadlines. Here are the dates to mark for payroll, HR, benefits, and taxes. 

Federal holidays

September 2, 2025

Labor Day

Some businesses take the day off completely, and others take advantage of Labor Day weekend promos and sales. Whatever your plans are, make sure you’re prepared. 

September 11, 2025

National Day of Service and Remembrance 

The National Day of Service and Remembrance honors the people who lost their lives on September 11, 2001. It’s not an official federal holiday, but many individuals and businesses take time off to volunteer or participate in community events. 

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Tax and payroll compliance deadlines

Payroll tax deposits (for semi-weekly depositors)

Employers who file Forms 940 and 941 have to deposit payroll taxes on different schedules 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…

Wednesday

The following Wednesday

Thursday

The following Wednesday

Friday

The following Wednesday

Saturday

The following Friday

Sunday

The following Friday

Monday

The following Friday

Tuesday

The following Friday

There’s one exception: if you accumulate $100,000 or more in tax liability on a single day, you must 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. 

September 2, 2025

Form 2290 filing deadline for vehicles first used in July 

If you registered a heavy highway motor vehicle (with a taxable gross weight of 55,000 pounds or more) that was first used in July, you have to file Form 2290 by September 2. This form is usually due at the end of the month after the vehicle’s first use, but since the last day of August fell on a weekend, the deadline is September 2. 

Keep in mind that this is Labor Day, so plan to send your form ahead of time if possible. 

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

Form 730 filing deadline for wagers in July

You have to file Form 730, the monthly tax return for wagers, if you accepted wagers during July and meet the following criteria:

  • are in the business of accepting wagers

  • conduct a wagering pool or lottery

  • are required to be registered and received wagers for or on behalf of another person, but did not report that person’s name and address

Form 730 is normally due on the last day of the month after you accept wagers, but because August 31 fell on a weekend, you have until September 2. Learn more about Form 730 here.

September 10, 2025

Employee tip reporting deadline for August 

If your employees earn tips, they need to report any tips of $20 or more that they earned in August by September 10. Learn more about tip withholding and reporting requirements here

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September 15, 2025

Payroll tax deposits for monthly depositors

If you’re on the monthly schedule for payroll, your tax deposit for August payrolls is due on September 15. 

Estimated tax payment for Q3 due 

If you make quarterly estimated tax payments, your third payment of the year is due September 15. You have to 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’re a partnership, you need to file Form 8813 by September 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

Form 1120-S extended filing deadlines for S-corps

If you own an S corporation (or if your LLC is taxed as an S corp), you have to use Form 1120-S to report your income, losses, and dividends as a shareholder of the company. This form was due March 17. 

However, if you filed Form 7004 in March to request an automatic six-month extension, your deadline is now September 15. You also have to pay any tax, interest, or penalties at this time, and give each partner a copy of their final Schedule K-1 or Schedule K-3 (Form 1120-S). 

Form 1065 extended filing deadlines for partnerships

If you own a partnership (or an LLC set up as a partnership), you have to use Form 1065 to report the gains, losses, deductions, and credits of your operation. Keep in mind that each partner is responsible for paying their share of income from the business on their personal tax returns (Form 1040).

If you filed Form 7004 in March to request an automatic six-month extension, your deadline to file this form—and pay any tax, interest, or penalties due—is now September 15. 

Make sure you also give each partner a copy of their final Schedule K-1 or Schedule K-3 (Form 1065), if applicable. 

Estimated tax payment due for Q3 for tax-exempt organizations

When you own a tax-exempt organization like a nonprofit, you need to pay estimated tax on unrelated business income by September 15. Keep in mind that this is only if you expect your tax liability to be more than $500. 

You can use Form 990-W to calculate the amount of estimated tax required. 

Form 1042 extended filing deadline 

If you withhold taxes for international employees, you’re required to submit Form 1042 on an annual basis to report those withholdings. If you requested a six-month filing extension, the form is due September 15. 

Learn more about Form 1042 from the IRS here

September 30, 2025

End of Q3 for companies following the calendar year

If you operate on a calendar year, the third quarter ends at the end of the month on September 30. 

Form 2290 filing deadline for vehicles first used in August 

If your business’s newly registered heavy highway motor vehicle was first used in August, you have to file Form 2290 by September 30. 

Form 730 filing deadline for wagers in August

If you’re in the business of accepting wagers and you accepted some during August, you have to file Form 730 by September 30. Learn more about Form 730 here.

HR compliance deadlines

September 15, 2025

Deadline to make retirement plan employer contributions for partnerships and S corporations

If you run a partnership or S corporation, and you filed an extension for your 2024 tax returns, the deadline to make any tax-deductible retirement plan employer contributions is September 15, the same day as the extended filing deadline.

Minimum funding contributions due for defined benefit plans

If your business has a defined benefit, money purchase, or target benefit plan that follows the calendar year, you must meet your minimum funding requirement for the 2024 plan year by September 15, eight and a half months after the end of the plan year in question. 

Form 5500 due for certain plans

If your business offers pension or welfare benefit plans covered by The Employee Retirement Income Security Act of 1974 (ERISA), you’re required to file Form 5500 with the Employee Benefits Security Administration (EBSA). This form reports information about these plans, including its qualification, financial condition, operation, and investments. 

Although Form 5500 is typically due on July 31, plan sponsors who qualify for an automatic corporate tax extension have until September 15. 

Pension Benefit Guaranty Corporation premiums due

The Pension Benefit Guaranty Corporation (PBGC) collects flat-rate and variable-rate insurance premiums from plan sponsors every year. Your business has to pay a premium for every one of your plan participants in case the pension plans are terminated. 

For single-employer plans that began in 2025, the per participant flat rate is $106; for multiemployer plans that began in 2025, the per participant flat rate is $39. These premiums are due by September 15. You can see the full rate sheet here

September 30, 2025

Deadline to furnish the Summary Annual Report for calendar-year plans

A Summary Annual Report (SAR) is a summary of the information you submit in your Form 5500, including the total value of your company’s benefit plan during the previous plan year and other details. 

If you operate on a calendar year, your deadline to give the SAR to your employees is September 30 (within nine months of the end of the plan year). 

If you’ve successfully filed for an extension with Form 5558, your deadline for furnishing SARs to your employees will be December 15.

Remind employees to use their benefits

With Q4 around the corner, it’s a perfect time to encourage employees to take advantage of their full employee benefits, especially any that expire at the end of the calendar year. 

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: