Essential Tax Deadlines Every Tradesman and Small Business Owner Should Know

Essential Tax Deadlines can’t be ignored when you’re running a trade or contracting business. Your calendar may be packed with job deadlines, supply runs, and crew coordination—but missing a tax date, even by a single day, can lead to costly penalties and draw attention from the IRS.

Whether you’re a sole proprietor, LLC, S Corporation, or independent contractor, understanding your filing responsibilities—and how extensions work—can protect your business and your bottom line.

At James D. Miller CPA, we specialize in helping tradesmen and small business owners stay on top of their tax obligations year-round. Here’s what you need to know.

Key IRS Deadlines for Individuals and Self-Employed Contractors

If you’re a sole proprietor or receive income via 1099s or cash jobs, your deadlines generally follow the individual tax calendar.

April 15 – Individual Tax Return Due

File Form 1040 with Schedule C if you operate as a sole proprietor.
This is also the last day to contribute to a Traditional or Roth IRA for the prior tax year.

Need More Time?

File Form 4868 by April 15 to receive an automatic 6-month extension to October 15.
Important: You still must estimate and pay any taxes due by April 15 to avoid interest and late-payment penalties.

Quarterly Estimated Tax Deadlines

If you’re self-employed, the IRS expects you to pay taxes throughout the year—not just at filing time.

Estimated Tax Due Dates (2025)

April 15 – Q1
June 16 – Q2 (June 15 falls on a Sunday)
September 15 – Q3
January 15 (2026) – Q4

Failing to pay quarterly taxes may lead to penalties—even if you pay everything at once when you file. James D. Miller CPA helps clients calculate accurate quarterly payments to stay penalty-free.

Business Tax Deadlines for Partnerships, S Corps, and C Corps

If your business is structured as a partnership, S corporation, or C corporation, these are your major tax deadlines.

March 15 – Partnership and S Corporation Returns Due

File Form 1065 (Partnership) or Form 1120-S (S Corp).
Distribute Schedule K-1s to partners/shareholders by this date.
Form 7004 can be filed to extend the deadline to September 15.

April 15 – C Corporation Returns Due

File Form 1120 for calendar-year C corporations.
Form 7004 grants an automatic extension to October 15.

Note: Fiscal-year businesses may have different deadlines depending on their year-end date.

Subcontractors and Form 1099-NEC

Did you hire independent contractors or subcontractors during the year?

January 31 – Deadline to issue Form 1099-NEC for payments over $600.
Ensure you collect Form W-9 from all contractors ahead of time.

Late or missing 1099s can result in steep penalties. James D. Miller CPA can assist with accurate and timely 1099 filings.

Payroll and Employment Tax Deadlines

If your business has employees, don’t forget your payroll tax obligations:

Form 941 – Quarterly payroll tax return (due last day of month following each quarter)
Form 940 – Annual unemployment tax return (due January 31)
W-2 Forms – Due to employees and the IRS by January 31
Payroll Tax Deposits – Depending on your deposit schedule (monthly or semi-weekly)

Missing these deadlines can lead to penalties and loss of good standing with the IRS.

Filing Extensions: What You Need to Know

If you’re not ready by your original deadline, you can request an extension—but that doesn’t stop interest from accruing.

Common IRS Extension Forms:

Form 4868 – Individual extension (adds 6 months)
Form 7004 – Business extension (varies by entity type)

Filing an extension gives you more time to file paperwork, but you must estimate and pay taxes due by the original due date.

Tip: Avoid Penalties with Proactive Planning

The IRS and many state agencies assess failure-to-file and failure-to-pay penalties that can stack up quickly. Staying on top of your deadlines isn’t just responsible—it’s smart financial management.

Final Thoughts

Whether you’re a general contractor, electrician, HVAC technician, or landscaper, being aware of tax deadlines is crucial to protecting your income and your business.

At James D. Miller CPA, we make tax planning simple. We monitor your deadlines, handle your extensions, and ensure you’re always a step ahead.

Need help managing your tax deadlines or filing an extension?
Contact James D. Miller CPA today and let’s take the stress out of tax season—for good.