Important Tax Deadlines Every Small Business Owner Needs to Know (Unless You Love Penalties)

Written by Top Dog Tax Relief          
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Overview

Running a small business is like walking a tightrope while juggling flaming torches – you’ve got a lot going on. The last thing you need is the IRS breathing down your neck because you missed a deadline. The good news? We’ve rounded up the biggies so you can stop Googling “When are my taxes due?” at 11:59 p.m. and start feeling like the boss you are.

Bookmark this bad boy now – your future self (and your bank account) will thank you.

Key Takeaways

  • Know your deadlines. From W-2s to quarterly estimated taxes and annual returns, marking these dates saves you headaches (and money).

  • Penalties are no joke. Missing deadlines can trigger failure-to-file, failure-to-pay, and underpayment penalties – some as high as 25%.

  • Extensions only extend filing, not payment. Forms 7004 and 4868 buy you time for paperwork, but taxes owed are still due by the original deadline.

Tax Deadlines For Sole Proprietors: AKA The “Me, Myself & I” Crew

Flying solo? These are your can’t-miss dates.

  • January 31: Time to play mailman. Send W-2s to employees and 1099-NECs to contractors before the end of January. (Yes, even that freelancer who still hasn’t learned to use Venmo properly.)
  • April 15: The Big One. Your Form 1040 and schedules are due, unless April 15 falls on a weekend or holiday, then you get a tiny reprieve.
  • Quarterly Estimated Tax Payments: These are due on April 15, June 15, September 15, and January 15 of the following year. (Remember: these dates love to crash on weekends, so double-check the next business day rule.)

Partnerships: Two’s Company, But the IRS Still Wants Its Cut

Got a partner? Lucky you. More support, more paperwork.

  • March 15: File your Partnership Return (Form 1065) if you’re on a calendar year. Fiscal year? It’s the 15th day of the third month after your year ends.
  • All other filing and estimated tax deadlines mirror those of sole proprietors.

Corporations & LLCs: Big Kids, Big Deadlines

If you’re running as a corporation or LLC taxed like one, listen up:

  • April 15: File your Corporate Tax Return (Form 1120) if you’re a calendar-year filer.
  • Fiscal-Year Corporations: Deadline is the 15th day of the fourth month after year-end, unless you’re one of those quirky June 30 year-enders, then you’re up September 15.
  • And yes, you’ve got quarterly estimated payments too. Get cozy with your calendar.

State Deadlines – Why Would Anything Be Simple?

Many states mirror IRS deadlines. Others… don’t. (Thanks for nothing, State of Whatever.) Double-check with your state’s tax agency so you’re not blindsided.

What If You Miss a Deadline? (Spoiler: It’s Not Great)

If you drop the ball, the IRS doesn’t send you a sad emoji – they send you penalties.

  • Failure-to-File: Up to 25% of what you owe. Ouch.
  • Failure-to-Pay: 0.5% per month until you pay up.
  • Missed Estimated Payments: They’ll ding you for those, too. Even if you double-up your next payment, you’ll still need to pay the penalty fee.

Moral of the story? Don’t ghost the IRS.

Can I Get an Extension? (A.K.A. “Help, I’m Not Ready!”)

Yes, but there’s a catch:

BUT (and this is a big but), an extension only gives you extra time to file, not to pay. If you owe taxes, you still have to pony up by the original deadline.

How to Stay Out of Hot Water

  • Automate reminders. Your phone is smarter than you—use it.
  • Get professional help. (With taxes, not therapy. Though… maybe both.)
  • Don’t procrastinate. Future You will either hug you or hate you.

Stay ahead of these deadlines and you’ll spend less time stressing over taxes and more time doing what you love – like actually running your business (or finally taking that weekend off).