Tax Season Part 2 Explained: September 15 & October 15 Deadlines

Avoid Thousands in IRS Penalties This Tax Season

Tax deadlines don’t end in April. Many business owners and resellers face what I call “Tax Season Part 2” in September and October. Missing these deadlines can cost you thousands of dollars in IRS penalties and interest.

In this video, I break down exactly what you need to know about the September 15 and October 15 deadlines, who they apply to, and how to avoid costly mistakes. Whether you’re a reseller, small business owner, or filing as an S corporation, partnership, or sole proprietor, this guide will help you stay compliant and stress-free.

🔹 The difference between March 15, April 15, September 15, and October 15 deadlines
🔹 Who needs to file by March 15 (S corporations, partnerships, multi-member LLCs)
🔹 Who needs to file by April 15 (sole proprietors, individuals, C corporations)
🔹 What happens when you extend your return — and what penalties are still in play
🔹 The difference between failure-to-file vs. failure-to-pay penalties
🔹 How much penalties really cost: 5% per month vs. $245 per month
🔹 The 90%/100% safe harbor rule for estimated taxes
🔹 How to apply for a one-time penalty abatement if you qualify
🔹 Why proper tax planning can save you money and stress year-round

Check the video for 1040 File Extention here:    • Avoid a 50% IRS Penalty: File Your 1040 Ex...  

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CHAPTERS:
00:00 Intro – Tax Season Part 2 (Sept & Oct Deadlines)
00:22 Who I Am – IRS Enrolled Agent for Small Businesses
00:29 Part 1 vs Part 2: Key Tax Deadlines Explained
00:55 Extensions & What They Actually Cover
01:30 Penalty to File vs Penalty to Pay
01:59 October 15th Final Deadline Rules
02:12 How Estimated Taxes Affect Penalties
02:38 First-Time Penalty Abatement Option
02:46 S Corporation & Partnership Deadlines (Sept 15)
03:19 Penalties for Late Business Filings
03:53 Multi-Member LLC & Partnership Filing Rules
04:15 Final Tips – Avoid Penalties & Get Help

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