Tax Roadmap for 2026

The beginning of one year and the end of the previous are always the busiest times for taxes, with multiple deadlines and different filings. We created this blog so you can follow along and make sure you don’t miss any important deadlines. I do want to remind everyone that it is not too late to get caught up and be on top of all these things so that your taxes and accounting are accurate and prepared.

If you need any help, you can always reach out to Waterford Business Solutions at info@waterfordbusiness.com or 864-351-0852. We specialize in ensuring our clients’ books are as tax-ready as possible throughout the year.

Also, prepare for this year and rush, we really recommend focusing on 2 different aspects. 1 is going to be payroll, including your W-2 employees and all the filings that go along with them. The second one is 1099s, which are how you will send information to your contractors and the IRS about what you paid them. These are due January 31st because you must provide this information to people so they can file their own taxes. It has a very early deadline.

1099 Contractors

We’ve done a couple of blogs about who gets 1099s and why they are sent. Please review those here to get an idea of which contractors you need to reach out to. We will also be releasing another blog next week about who needs 1099s as a refresher during tax season. As soon as you finish this blog, I really recommend collecting W-9s from any contractors you paid more than $600 to, so you can file 1099s before the deadline.

If you do not send a 1099, you are the one who is liable in the eyes of the IRS unless you can prove that they refuse to give you the information required to file a 1099. The IRS requires that you have reached out in writing at least three times to gather that information.

You should also consider backup withholding at 24% of any future payments that you might work with this contractor on. Honestly, the best practice is to get the W-9 before you even start working with any contractors.

In the end, if the contractor refuses to give you the information required to file a form 1099 on their W-9, you can still file a paper filing and write ‘refused’ in the box for the information they did not provide.

Payroll & End of Year Tasks

There are many different quarterly payroll filings for W-2 employees. Making sure you are 941-compliant and that your 940s have been filed throughout the year is an important step in your year-end closeout. The 941 filing will cover any payroll taxes, social security, or Medicare that were withheld compared to anything that you may still owe. The 940 references federal unemployment.

There are a lot of different types of tax filings for W2 employees including: federal payroll taxes and state payroll taxes. Those taxes are broken down even further into income tax withholdings, social security and medicare taxes, federal unemployment tax.

You may also have specific forms that must be filed, along with the timely processing of W-2s for your employees and the federal government. The W3 is important for your business taxes because it summarizes all the W2s.

This is usually handled by your payroll company, or you should be reaching out to them to see what steps you need to take for them to handle it. Payroll software like QBO and Gusto will send them on your behalf, whereas I know payroll companies will sometimes charge extra to file these forms.

Both the 1099s and the W2 filings are due on January 31, which is only 25 days away from the release of this blog. If you do not reach these deadlines, there are steep penalties for the business owners.

There are quite a few other dates that need to be on your timeline about filing income taxes for you and your businesses. Even though you can file for extensions, those extensions do not apply to making the due payment. If you do not make the payment on time, even with the extension, you will get penalties and interest.

Ensuring that your business’s books are closed out by the end of February at the latest will help you meet any income tax deadlines, depending on its status.

I’ve included a little chart showing your deadlines by filing status, just to give you a quick rundown of all your deadlines for the beginning of 2026. I do want to note that there are certain instances, such as natural disasters or other unpredictable events, that may result in deadline extensions for your state or federal region. We will go into more detail on these topics and deadlines as we move into 2026, but I just wanted to get this in your head.

Upcoming Tax Deadlines
January 15 –
Q4 2025 Estimated Tax Payment Due (Sept-Dec)
February 2 –
1099 and W-2 Mailing Deadline
March 16 –
Form 1065 (Partnership) Tax Return Due
Form 1120S (S-Corp) Tax Return Due
Last day to file for six-month filing extension for Form 1065 or Form 1120S*
April 15 –
Q1 2026 Estimated Tax Payment Due (Jan-Mar)
Form 1120 (C-Corp) Tax Return Due
Form 1040 (Individual) Tax Return Due
Last day to file for six-month filing extension for Form 1120 or Form 1040*
June 15 –
Q2 2026 Estimated Tax Payment Due (Apr-May)
September 15 –
Extension Deadline for S-Corps and Partnerships
Q3 2026 Estimated Tax Payment Due (Jun-Aug)
October 15 –
Extension Deadline for C-Corps and Individuals
January 15, 2027 –
Q4 2026 Estimated Tax Payment Due (Sept-Dec)

I know it’s already crazy to think about, but once you do get your books squared away for taxes, I really recommend that you start planning for 2027.

At the end of the day, this is never a fun season, not for you and not for us, especially. We are here to help you, though. If you need an analysis of your business, are worried about these deadlines, or are completely freaked out about meeting them, please do not hesitate to reach out to us. We offer support and bookkeeping services to make this time of year less stressful for you, so you can focus on what the numbers mean, not the deadlines.

Check out our YouTube video Your Tax Roadmap – Welcome to 2026! James for a first-hand recap.

Our goal is not just to have accurate numbers, but to ensure everyone understands what their numbers mean for their business.