Westport, CT – September 16, 2026 – Rappaport Tax Relief, the Westport-based tax resolution firm led by Enrolled Agent David Rappaport, marks more than 30 years of representing individuals and small business owners before the IRS and state taxing authorities. The milestone arrives as IRS enforcement activity has expanded significantly: according to the IRS Data Book FY2023, the agency issued more than 2.3 million liens and levies during that fiscal year, with collection actions intensifying in subsequent filing seasons. For taxpayers in those notices’ path, the gap between a manageable resolution and a financial crisis often comes down to when they picked up the phone.
Key Facts
The milestone: David Rappaport has practiced as an Enrolled Agent for more than 30 years, with a focus on IRS debt resolution, installment agreements, offers in compromise, and release of wage garnishments and bank levies. The location: Rappaport Tax Relief is based in Westport, Connecticut, serving individuals and small business owners throughout the New York metro area. IRS enforcement context: The IRS Data Book FY2023 reported over 2.3 million liens and levies issued in that fiscal year, a figure that reflects the agency’s ongoing commitment to collecting outstanding balances. Free consultation: The firm offers a no-cost initial consultation for taxpayers who want to understand their options before committing to a resolution path. Free resource: A downloadable guide is available at rappaporttaxrelief.com for taxpayers who want to understand IRS collection procedures and resolution programs before making any decisions.
What Three Decades of IRS Negotiation Actually Teaches
Thirty years of representing taxpayers before the IRS doesn’t just build a resume. It builds pattern recognition. The same situations appear again and again, and the outcomes aren’t random. They track directly to specific decisions taxpayers made, or didn’t make, early in the collection process.
The most repeated mistake isn’t failing to pay. It’s waiting. When an IRS notice arrives, most people spend the first two to three weeks hoping it’s an error or that it will resolve on its own. It won’t. The IRS notice system follows a precise procedural calendar. A CP14 balance-due notice starts a clock. A Notice of Federal Tax Lien can follow within weeks of a missed response. Once a lien is filed, it attaches to property, damages credit, and limits options that were fully available before it was filed. The window to act is real, and it closes.
The second pattern involves program misunderstanding. The Offer in Compromise is the resolution option taxpayers have heard of, and it’s the one most often misapplied. An OIC allows the IRS to accept less than the full balance owed, but it’s based on a specific financial formula: Reasonable Collection Potential. Whether a taxpayer qualifies depends on documented income, allowable expenses, and asset equity, not on the size of the debt or how long it’s been outstanding. Applying for an OIC without a realistic assessment of those numbers wastes time and can reset collection timelines in ways that make a previously straightforward installment agreement harder to negotiate. Not every taxpayer qualifies, and saying so up front is part of what a 30-year practitioner is there to do.
The third pattern is scope. Taxpayers often contact a resolution firm about one year’s debt and discover during the intake process that multiple unfiled years are behind them. The IRS can’t finalize most resolution agreements while returns are outstanding. That means the path to an installment agreement or OIC runs through compliance first: getting every unfiled return prepared and submitted before the negotiation can begin. That’s not a complication. It’s the sequence. Handling past debt, current returns, and future compliance as a single connected case rather than three separate problems is what makes resolution stick.
What changes when you have 30 years of those cases behind you is the ability to read where a case is likely to go before the IRS has said a word. That read shapes the strategy.
About Rappaport Tax Relief
Rappaport Tax Relief is a Westport, Connecticut-based tax resolution firm led by Enrolled Agent David Rappaport, who brings more than 30 years of experience negotiating with the IRS and state taxing authorities on behalf of individuals and small business owners. The firm handles the full lifecycle of tax problems, from unfiled returns and back taxes to wage garnishment releases, bank levy releases, installment agreements, and offers in compromise. Rappaport Tax Relief offers a concierge approach to tax resolution, meaning clients work directly with David Rappaport throughout their case, not with rotating staff or call centers.
Media ContactCompany Name: Rappaport Tax ReliefContact Person: David RappaportEmail: Send EmailPhone: 917-488-8295City: WestportState: ConnecticutCountry: United StatesWebsite: http://rappaporttaxrelief.com/
