How Often Should S Corp Owners Run Payroll | Payroll Timing 101
Wed Feb 04 2026
When should you pay yourself? Paying yourself on the wrong payroll schedule can create IRS red flags, cash flow crunches, and painful cleanup later.
In this episode, we break down monthly, quarterly, and annual payroll for S Corp owners. You’ll learn what the IRS actually expects, how reasonable salary works, why quarterly “true-ups” can create cash flow problems, and how to structure payroll to stay compliant without overpaying in taxes.
We also cover catch-ups, slowdowns, bonuses, zero payroll returns, and a critical but often-missed strategy involving self-employed health insurance and HSA contributions that can reduce FICA taxes.
If you’re an S Corp owner trying to pay yourself the right way and avoid IRS attention, this episode walks you through exactly how to do it.
👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:
https://www.taxsavingspodcast.com/starterkit
🚀 Book your free demo call today. Click here or visit:
https://taxelm.com/demo/
Chapters
(01:00) The Reasonable Salary Requirement for S Corps
Why S Corp owners must take W-2 payroll and why determining reasonable salary is the first step.
(03:10) Payroll Software and Filing Requirements
Why using payroll software matters and how missed filings create serious problems.
(04:00) Monthly and Biweekly Payroll Explained
How spreading your salary evenly works and why this is the most common recommendation.
(05:30) True-Up Payroll. Quarterly and Annual Options & Cash Flow Risks
How quarterly and annual true-ups work and how draws get reclassified as wages. Large quarterly tax payments can create cash crunches.
(08:45) Zero Payroll Returns and Compliance Traps
Why you still need to file payroll returns even when no payroll is run.
(09:30) Catch-Ups, Slowdowns, and Bonus Payrolls
How to adjust payroll when income, workload, or profitability changes.
(11:45) Self-Employed Health Insurance and HSA Adjustments
How S Corp owners can increase reasonable salary without paying extra FICA taxes.
(15:30) The Safest Payroll Strategy for Most Owners
Why consistent payroll timing protects cash flow and reduces IRS risk.
Podcast Host:
Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com
🚀 Visit: https://www.TaxSavingsPodcast.com
🚀 Check Out TaxElm: https://taxelm.com/
🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/
🚀 YouTube: www.TaxSavingsTV.com
👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏
🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐
🎙 ABOUT THE PODCAST
The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.
More
When should you pay yourself? Paying yourself on the wrong payroll schedule can create IRS red flags, cash flow crunches, and painful cleanup later. In this episode, we break down monthly, quarterly, and annual payroll for S Corp owners. You’ll learn what the IRS actually expects, how reasonable salary works, why quarterly “true-ups” can create cash flow problems, and how to structure payroll to stay compliant without overpaying in taxes. We also cover catch-ups, slowdowns, bonuses, zero payroll returns, and a critical but often-missed strategy involving self-employed health insurance and HSA contributions that can reduce FICA taxes. If you’re an S Corp owner trying to pay yourself the right way and avoid IRS attention, this episode walks you through exactly how to do it. 👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners: https://www.taxsavingspodcast.com/starterkit 🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ Chapters (01:00) The Reasonable Salary Requirement for S Corps Why S Corp owners must take W-2 payroll and why determining reasonable salary is the first step. (03:10) Payroll Software and Filing Requirements Why using payroll software matters and how missed filings create serious problems. (04:00) Monthly and Biweekly Payroll Explained How spreading your salary evenly works and why this is the most common recommendation. (05:30) True-Up Payroll. Quarterly and Annual Options & Cash Flow Risks How quarterly and annual true-ups work and how draws get reclassified as wages. Large quarterly tax payments can create cash crunches. (08:45) Zero Payroll Returns and Compliance Traps Why you still need to file payroll returns even when no payroll is run. (09:30) Catch-Ups, Slowdowns, and Bonus Payrolls How to adjust payroll when income, workload, or profitability changes. (11:45) Self-Employed Health Insurance and HSA Adjustments How S Corp owners can increase reasonable salary without paying extra FICA taxes. (15:30) The Safest Payroll Strategy for Most Owners Why consistent payroll timing protects cash flow and reduces IRS risk. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join TaxElm: https://taxelm.com 🚀 Visit: https://www.TaxSavingsPodcast.com 🚀 Check Out TaxElm: https://taxelm.com/ 🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/ 🚀 YouTube: www.TaxSavingsTV.com 👋🏼 GET IN TOUCH You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏 🙌LEAVE A REVIEW If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐ 🎙 ABOUT THE PODCAST The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.