Why IRS Penalties Feel Overwhelming

Every year, thousands of taxpayers in Connecticut receive IRS letters not only demanding back taxes but also piling on penalties and interest. These penalties can add 25% or more to your balance, sometimes doubling what you owe. For families and small business owners in Westport and the surrounding Fairfield County area, this can be devastating.

The good news is that many IRS penalties can be reduced—or even eliminated—if you know the right process.

The Common Types of IRS Penalties

The IRS doesn’t just charge one flat fee. They stack multiple penalties, including:

  • Failure to File Penalty – For missing tax deadlines.

  • Failure to Pay Penalty – For not paying taxes owed.

  • Accuracy-Related Penalty – For mistakes on your return.

  • Trust Fund Recovery Penalty – For payroll tax issues.

  • Estimated Tax Penalty – For underpayment of quarterly taxes.

Each of these can snowball quickly when combined with interest.

How Penalties Affect Your Debt

Imagine owing $20,000 in taxes. Within months, penalties and interest can push that to $25,000 or more. If ignored for years, it may double. That’s why waiting only makes things worse.

Options for Reducing IRS Penalties

Here are a few of the programs that might help:

  • First-Time Penalty Abatement – If you’ve had a clean history, you may qualify to remove one year of penalties.

  • Reasonable Cause Relief – If circumstances like illness, job loss, or natural disaster prevented you from paying on time, the IRS may grant relief.

  • Statutory Exceptions – If the IRS gave you bad instructions or made an error.

  • Administrative Waivers – Available in certain IRS notices.

Each of these requires proper documentation and a strong case.

Why Work with a Local Attorney

While some firms try a “cookie-cutter” approach, David Rappaport of Rappaport Tax Relief in Westport, CT knows that every IRS case is unique. As a tax resolution professional with years of experience, David helps clients present the strongest possible case to the IRS.

Case Examples (Hypothetical)

  • A small business owner facing $15,000 in penalties after a payroll tax issue was able to reduce the balance by nearly half.

  • A family hit with penalties due to illness secured reasonable cause relief and had their penalties waived.

These aren’t one-size-fits-all solutions—they’re tailored to the facts of each case.

Protect Your Future

IRS penalties don’t have to define your financial future. With the right help, you may be able to cut your debt significantly and prevent further damage.

Contact Rappaport Tax Relief in Westport today for a free consultation and learn whether you qualify for penalty relief.