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Missed the Tax Deadline? Getting Your Business Back on Track

August 29, 2025 by Nick Magone, CPA, CGMA, CFP®

Falling behind on tax filings can quickly put your business on the IRS’s radar.

Whether due to financial constraints, staffing shortages or organizational transitions, missing even a single filing deadline can make your business vulnerable to penalties, interest charges and potential compliance investigations that can impact your company’s financial health and reputation.

With a practical strategy in place, you can help mitigate any damage — before it’s too late. Keep the following tips in mind:

Time is not on your side. When addressing unfiled business returns, urgency is key. IRS failure-to-file penalties accrue at five percent of unpaid taxes per month, capped at 25%. And failure-to-pay penalties add 0.5% per month, also maxing out at 25%. The compounding result? A $10,000 tax liability that can add up to over $15,000 in just 24 months.

Plus, the statute of limitations for IRS assessment (typically three years) doesn’t begin until returns are filed, creating unlimited financial exposure that hangs over your business.

Voluntary disclosure is your best strategy. Don’t wait for the IRS to find you. Taking proactive steps to file back returns allows you to:

  • Maintain control over the narrative and presentation of information
  • Demonstrate good faith compliance efforts
  • Potentially qualify for penalty abatement programs

There are tactics to tackle documentation challenges. Reconstructing financial records for past periods can be daunting. Remember that the burden of proof falls on you as the taxpayer, so the more documentation you can provide, the better.

Start by:

  • Gathering all bank and credit card statements for the unfiled years
  • Collecting available expense receipts and income documentation
  • Securing prior year depreciation schedules if applicable
  • Retrieving copies of previously filed returns for context

Your catch-up approach matters when facing multiple unfiled years. Has your business gone multiple years without filing? The good news is that you don’t need to file everything simultaneously to catch up.

Consider these approaches:

  • Most recent return first: Filing current year returns establishes compliance going forward while you address back years.
  • Refund years first: If you’re expecting refunds, prioritize years still within the refund statute (generally three years).
  • Highest exposure first: Address years with significant tax liabilities to minimize ongoing penalty accrual.

The most important thing is to take action now. Each day that passes potentially increases your tax liability through additional penalties and interest.

 Looking ahead

After resolving your back tax issues, ensure your business remains in good standing by taking preventive measures to keep your tax compliance on track.

  • Schedule quarterly financial reviews with your team and accountant to identify potential issues early
  • Establish estimated tax payment schedules to avoid underpayment penalties
  • Develop document retention policies that support future compliance
  • Consider outsourcing tax compliance functions

At Magone & Company, we provide expert support and solutions to help you navigate complex tax laws, identify deductions and credits, minimize penalties and interest, and create systems to prevent future compliance issues. Don’t hesitate to reach out at (973) 301-2300 to schedule a no-obligation, confidential consultation.

 

This document is for informational purposes only and should not be considered tax or financial advice. Be sure to consult with a knowledgeable financial or legal advisor for guidance that is specific to your unique circumstances

 

 

Filed Under: IRS woes, Tax Tips for Individuals

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