Running a business means staying on top of more than just sales and expenses. One of the most common issues business owners face every year is missing payroll and contractor tax deadlines. Filing W-2s and 1099s late can lead to penalties, IRS notices, and unnecessary stress.
This guide breaks down what W-2s and 1099s are, who needs them, and the key deadlines business owners should never miss.
What Is a W-2?
A Form W-2 reports wages paid to employees and the taxes withheld from their pay during the year.
You must issue a W-2 if:
- You paid an employee wages or salary
- You withheld federal, state, or local taxes
- You paid Social Security or Medicare taxes on their behalf
Who Receives a W-2?
- Employees
- The Social Security Administration (SSA), which shares the data with the IRS
W-2 Filing Deadline
January 31
- Provide W-2s to employees
- File W-2s and Form W-3 with the SSA
This deadline applies whether you file electronically or by paper.
Missing this deadline can result in IRS penalties that increase the longer the delay continues.
What Is a 1099?
A Form 1099 reports payments made to non-employees, such as independent contractors or vendors.
The most common types are:
- 1099-NEC: For payments to independent contractors
- 1099-MISC: For rent, legal payments, prizes, or other income
You generally must issue a 1099 if:
- You paid $600 or more during the year
- The recipient is not your employee
- The payment was for business purposes
1099 Filing Deadlines
1099-NEC
January 31
- Provide to contractors
- File with the IRS
This deadline applies to both paper and electronic filing.
1099-MISC
January 31
- Provide to recipients
February 28 (paper filing with IRS)
March 31 (electronic filing with IRS)
Why These Deadlines Matter
Missing W-2 or 1099 deadlines can lead to:
- IRS penalties per form
- Notices and follow-up letters
- Delays in employee or contractor tax filings
- Extra work correcting mistakes later
Penalties can range from $60 to $310 per form, depending on how late the filing is. Intentional failure to file can result in even higher fines.
Common Mistakes Business Owners Make
- Misclassifying workers as contractors instead of employees
- Forgetting to collect W-9s from contractors
- Filing the wrong 1099 type
- Missing the January 31 deadline
- Using incorrect names or Social Security numbers
These errors are common, but they are also avoidable with proper bookkeeping support.
How to Stay Compliant and Stress-Free
To stay on track:
- Collect W-9s before paying contractors
- Keep payroll and contractor records updated monthly
- Review worker classifications regularly
- File early, not at the deadline
- Work with a professional bookkeeping team
How Accredited Bookkeeping Can Support Your Business
At Accredited Bookkeeping, we understand the challenges small businesses face when it comes to managing finances. We’re here to help you streamline your bookkeeping processes, avoid unnecessary financial errors, and gain greater clarity about your financial health. Our services are designed to fit the specific needs of your business, giving you peace of mind while you focus on growth.
Contact us today for a free consultation and discover how we can make bookkeeping easier for you.
marianne@accreditedbookkeeping.com
Marianne Kirwan
352-626-0116
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