Facing a tax problem can feel like being lost in a dense New England fog. The complexity of tax law, the relentless stream of notices from the IRS and the Connecticut Department of Revenue Services (DRS), and the fear of collection actions can be a paralyzing combination. For individuals and businesses across Connecticut, from the bustling cities to the quiet suburbs, a tax issue can disrupt financial stability and cause immense stress.

At Rappaport Tax Relief, we believe that no one should have to face a tax problem alone. Based in Westport, Connecticut, our firm is dedicated to providing strategic and compassionate tax resolution services. Our owner, David Rappaport, is a seasoned professional with over 30 years of experience. As an Enrolled Agent and Certified Tax Resolution Expert, he is authorized to represent clients before the IRS and state taxing authorities. David’s philosophy is built on “Concierge Accounting,” a personal, hands-on approach where he builds a relationship with each client to provide a support system during their time of need.

This guide will walk you through some of the most common tax problems we handle in Connecticut and explain how a professional can help you find a clear path to resolution.

The Connecticut Department of Revenue Services: A Local Authority

While the IRS is a major concern, the DRS is a powerful state agency with its own set of rules and collection powers. Ignoring a state tax issue can lead to serious consequences that can impact your financial life just as much as a federal one. The DRS can issue tax warrants, seize assets, and offset a state tax refund against an outstanding liability. Connecticut also participates in the Treasury Offset Program, which allows the DRS to seize a federal tax refund to pay a state tax debt.

A comprehensive tax relief strategy must address both federal and state tax liabilities simultaneously. We have a deep understanding of the unique procedures and timelines of the Connecticut DRS, ensuring that your case is handled correctly from day one.

Specific Problems and Strategic Solutions

Regardless of whether your tax debt is with the IRS or the DRS, the problems you face often feel the same. Here are some of the most common issues we help our clients resolve.

1. The Back Taxes Burden

Owing back taxes is a problem that only gets worse with time. Daily-accruing penalties and interest can turn a small, manageable debt into an overwhelming liability. The fear and stress of this growing debt often lead taxpayers to ignore notices, which only gives the tax agencies more power.

  • Our Solution: The key is to take action. David Rappaport’s hands-on approach starts with getting you into filing compliance by preparing and filing any delinquent returns. This is a critical first step, as many tax relief programs, including those offered by the IRS and DRS, require all of your returns to be filed. We will then work with the tax agencies to negotiate a settlement that is affordable and sustainable for you.

2. Audits and Assessments

A tax audit is a serious business. The DRS can audit your returns based on various factors, including a mismatch between your state and federal filings. Auditors are trained to find discrepancies and assess additional tax.

  • Our Solution: You have the right to be represented by a professional during an audit. As an Enrolled Agent, David Rappaport can represent you, acting as a buffer between you and the auditor. We will meticulously review your financial records, prepare all necessary documentation, and build a strong argument to challenge any unfair assessments. If an informal hearing is necessary, we will be there to represent you.

3. Overwhelming Penalties and Interest

It’s not uncommon for penalties and interest to make up a significant portion of a tax bill. For many taxpayers, this is the most demoralizing part of their tax problem, as it feels like an endless cycle of debt.

  • Our Solution: We can request a Penalty Abatement from both the IRS and the DRS. This is a formal request to have the penalties removed or reduced. The DRS is known to be strict with penalty waivers, often requiring that the tax and interest be paid in full before they will consider a request. However, with a strong case and proper documentation, it may be possible to get relief.

Proven Tax Relief Programs

Both the IRS and the DRS offer several programs to help taxpayers resolve their debts. A successful tax resolution strategy requires a deep understanding of these options and a personalized approach.

  • Offer in Compromise (OIC): An OIC allows you to settle your tax debt for less than the full amount you owe. Both the IRS and the DRS offer this program. It is an ideal solution for taxpayers who have overwhelming tax debt and a demonstrated inability to pay it in full. David Rappaport will analyze your financial situation and prepare a compelling offer that is most likely to be accepted.
  • Installment Agreement: If you can pay your tax debt but need more time to do so, an installment agreement is a structured payment plan. This allows you to make manageable monthly payments over a set period, bringing you back into compliance and stopping all aggressive collection actions.
  • Currently Not Collectible (CNC) Status: For those experiencing a temporary financial hardship and who cannot afford to pay their tax debt or even enter a payment plan, we can work to have your account placed into CNC status. While the debt is not forgiven, the government will cease all collection efforts for a period of time, giving you the breathing room you need to get back on your feet.

Your Trusted Partner in Connecticut Tax Resolution

At Rappaport Tax Relief, we believe in providing our clients with a clear path to resolution. Our owner, David Rappaport, is a seasoned professional who is dedicated to fighting for his clients. We handle the paperwork, the phone calls, and the negotiations, taking the stress and burden off your shoulders.

If you are a Connecticut resident struggling with back taxes, an audit, or any other tax issue, don’t wait for the situation to get worse.

Contact Rappaport Tax Relief today at (917) 488-8295 for a confidential consultation.