These compliance problems can begin well in advance of the due date.
You hire a contractor. You wait until your quarterly return to make your payroll tax deposit. Your license expiration notification gets buried in your inbox.
According to the SBA’s Office of Advocacy, the IRS accounts for more than 80% of the federal paperwork burden on small businesses.
So what are some of the common deadlines?
Don’t Wait Until Tax Season To Determine Worker Status
Just because you have a contract doesn’t mean that the worker is classified correctly.
When it comes to determining worker status for employment tax, there are many factors that the IRS will look at. These include control over the work, financial arrangements and the type of relationship.
It all depends on the situation, not what the job title may be. If you classify them as a contractor, there are implications on your employee withholding, payroll taxes and year end forms you may need to issue.
If you get this wrong, you could owe payroll taxes and may need to correct forms issued.
Decide if the worker is an employee or contractor when you hire them. Write down how you determine the situation and revisit this if anything changes. You may hire someone for sporadic jobs and they become full time working under your supervision.
If you are confident they are a true independent contractor, ask them to fill out a Form W-9 when starting to pay them. This will allow you to gather necessary information in case you need to report them. You may want to consult a professional as states may classify workers differently as well.
Forms With A Year End Due Date
January can be crazy trying to complete all the forms for the previous year.
When it comes to your contractor payments, you will likely need to file a 1099-NEC if you paid the individual at least $2,000 during 2026. There are instances where you may need to report lower amounts if backup withholding applied.
Payments through credit/debit cards and certain payment card networks will not be reported on a 1099-NEC by the payer. These payments may be reported on Form 1099-K from the payment settlement entity.
Once you have your list of payments to contractors and your wages to employees, make sure you are ready to file your year end forms. If you would like to learn more about filing W-2 and 1099 forms, see more.
February 1, 2027 is the due date to file your 2026 Form W-2 with the SSA and most of your 2026 Forms 1099-NEC with the IRS. Normally this date is January 31, but since it falls on a Sunday, the deadline shifts to the next business day. Most of your recipient copies are also due on this date.
Having the incorrect taxpayer id or not having enough payment information will cause delays.
You may also need to file your 1099’s electronically if you meet the requirement. If you have 10 or more information returns combined, you generally must e-file. This can be difficult for those that only have a couple of contractors, but if you include your W-2s you may meet this requirement as well.
Payroll Tax Deposit Deadlines
Form 941 will need to be filed after the end of each quarter, however you may be required to make payroll tax deposits before this occurs.
Depending on your liability, you may need to make payroll tax deposits monthly or semiweekly. This has nothing to do with how frequently you pay your employees.
Filing your 941 on time will not help if you didn’t make your deposits on time.
Know your deposit schedule early in the year and make sure you are making your payments accordingly. Check special next-day deposit rules if a large tax liability builds up.
There are also payroll tax deposits you may need to make for Federal Unemployment taxes. Each state will have different requirements as well.
If the IRS requires you to file Form 944, you may not need to file a 941. However, you may still have to make your payroll tax deposits.
Due Dates For Business Returns & Estimated Tax
Your business may not be due in April.
If you have a calendar year partnership or s-corp, you will typically file in March. If you are a sole proprietor filing on your individual return or you operate a calendar-year C corporation, you will most likely file in April. Extensions usually do not allow you to extend your payment due date.
April, June, September and January are your typical estimated payment due dates. Your last payment for 2026 will generally be due on January 15, 2027.
See the pattern? You are not paying estimated tax every 3 months. So if you just throw that on your calendar, you may not have the correct dates listed.
Find out if you need to make estimated payments and then revisit your numbers as your income fluctuates.
State & Local Compliance
Not only will you have federal taxes to worry about, you may have other compliance items to keep up with.
Sales tax, state withholding, unemployment, annual business registrations, licenses, etc. It all depends on where you do business and what type of business you have.
Some months may not seem busy, but you could have paperwork due. Some states require you to file a sales tax return if you are registered, even if you did not make any sales.
Be sure to find out the frequency and due date with each state/agency you have to file with. Revisit this if you open a new state, hire an employee or change products you are selling.
Creating Your Own Calendar
You don’t have to memorize all of these dates, but you need to have them written down somewhere.
- List what needs to be done (i.e. Form, Payment, Registration, Permit, etc.). Also, note who you are responsible for filing with.
- Use the due date, not a reminder to file every month, week, etc.
- Who will be completing the information, approving the information and verifying it was filed.
- Have a due date to gather information and double check before the final due date.
- File your documentation. Make sure to save your proofs of filing and payments.
Go over your calendar each quarter and have someone back up the person that is responsible for filing.
If you have someone that does this for you, make sure you know what was filed and what hasn’t been completed yet.
Final Thoughts
Just remember that it starts from day one, not when tax season comes around.
Every time you do something for your business, see if there is a deadline associated with it. It’s better to know now, than fix it later.
