DEBT RELIEF
If you owe the IRS more than you can realistically pay, the right solution depends on your income, assets, tax history, collection status, and ability to pay overtime. Attorney Michael Goldstein helps Massachusetts individuals and small business owners evaluate Mass Dept of Revenue and IRS resolution options, including Offers in Compromise, installment agreements, Currently Not Collectible status, penalty relief, lien issues, and other tax workout strategies.
Michael Goldstein is licensed to practice law in Massachusetts. For certain matters involving Maryland or Washington, D.C., Michael works in conjunction with Phillips Law Offices and appropriately licensed local counsel.
Resolve your Tax Debt
An Offer in Compromise, or OIC, is an IRS program that allows qualifying taxpayers to resolve federal tax debt for less than the full amount owed. The IRS generally considers an OIC when it does not expect to collect the full liability through available assets, income, and other payment options, or when special circumstances justify compromise.
The IRS evaluates factors including income, allowable living expenses, asset equity, and future ability to pay. In most cases, the amount offered must equal or exceed the taxpayer’s reasonable collection potential. A taxpayer who can fully pay through an installment agreement or other means generally will not qualify for an OIC.
OIC applications require detailed financial disclosures and supporting documentation, and the offer amount must be supported by the IRS’s financial-analysis rules. Errors, missing documentation, or an unsupported offer can delay the process or lead to rejection.
An Offer in Compromise may be worth evaluating when you cannot fully pay your IRS debt through available assets or a realistic payment plan and your financial information supports a lower reasonable collection potential. It is not simply a program for negotiating a discount; eligibility depends on IRS financial standards and your specific circumstances.
Important: The IRS accepts only a fraction of all OIC applications submitted each year. Proper preparation, documentation, and negotiation strategy are critical to a successful outcome.
IRS RESOLUTION OPTIONS
Depending on your financial situation, tax history, income, assets, and collection status, possible tax relief options may include:
An OIC may allow qualifying taxpayers to resolve federal tax debt for less than the full amount owed when the IRS determines that full collection is unlikely or other qualifying circumstances exist. The analysis generally includes income, allowable expenses, asset equity, and future collection potential.
The IRS generally has a limited collection period, commonly measured from the assessment date. Certain events can suspend or extend that period, so understanding the Collection Statute Expiration Date can materially affect which resolution strategy makes sense.
An installment agreement allows eligible taxpayers to pay IRS debt over time through scheduled payments. Collection treatment depends on the type and status of the agreement, and interest and applicable penalties generally continue while the balance remains unpaid.
Currently Not Collectible status may temporarily suspend active collection when the IRS determines that paying the tax debt would prevent the taxpayer from meeting necessary living expenses. Interest and penalties may continue to accrue, and the IRS can review the taxpayer’s financial condition later.
Reduce or eliminate IRS penalties, either through first-time abatement (available if you have a clean compliance history) or reasonable cause (illness, disaster, or other circumstances beyond your control). Penalties can account for a significant chunk of what you owe, so this is often worth pursuing even alongside another resolution option. It requires specific documentation tied to the reason for the request.
Protection from tax liability created by a spouse or ex-spouse, for example, unreported income or improper deductions on a joint return you didn't know about. The IRS has specific criteria for what you knew, or should have known, at the time you signed the return. This is a fact-intensive process, and the type of relief you qualify for (innocent spouse, separation of liability, or equitable relief) depends on your specific circumstances.
The IRS generally has 10 years from the date of assessment to collect a tax debt, and in some cases that window has already partially run, or can be strategically managed. Certain actions (like filing an OIC or an appeal) can pause the clock, so understanding your specific collection statute expiration date is essential before deciding on a strategy. This is often the most overlooked option, and sometimes the most effective.
Address trust fund recovery penalties and business payroll tax liabilities, which the IRS treats far more aggressively than personal income tax debt. Business owners can be held personally liable for unpaid trust fund taxes even after the business closes. Because these cases move fast and carry personal liability, early intervention matters more here than almost any other tax issue.
Understand your tax Relief Options
You can pay the debt, but not all at once.
An installment agreement may be more appropriate than an OIC.
Paying the IRS would leave too little for necessary living expenses.
Currently Not Collectible status or another hardship-based option may need to be evaluated.
Your assets and future income are not enough to fully pay the liability.
An Offer in Compromise may be worth evaluating.
Penalties make up a meaningful part of the balance.
Penalty abatement may reduce part of the liability if the applicable requirements are met.
A federal tax lien is blocking a sale, refinance, or transaction.
The lien itself may require a separate release, discharge, withdrawal, or subordination analysis.
The debt involves payroll taxes or personal exposure from a business.
Trust Fund Recovery Penalty issues can create personal liability and should be evaluated quickly.
The best tax-resolution strategy depends on what the IRS can realistically collect, how old the liabilities are, whether returns are current, what assets you own, and whether you can make payments without creating financial hardship.
WORK DIRECTLY WITH MICHAEL
You do not need to know whether you need an Offer in Compromise, installment agreement, Currently Not Collectible status, or another IRS resolution option before speaking with an attorney. The first step is understanding the tax liability, collection status, available assets, income, and realistic ability to pay.
Michael personally handles the legal analysis, strategy, and representation on matters he accepts. Paralegal staff may assist with information gathering, document preparation, and administrative support, while Michael reviews the work, provides the legal advice, and remains responsible for the matter.
The first step is a confidential consultation where we review your tax history, outstanding balances, and the best path forward.
Read more about how the IRS calculates a taxpayer’s ability to pay and what they can accept
THE PROCESS
A clear, step-by-step approach from first contact to resolution.
Review your IRS notices, outstanding balances, and overall tax situation confidentially.
Analyze all available resolution options and recommend the best path forward for your case.
Prepare all required IRS forms, financial statements, and supporting documentation.
Negotiate directly with the IRS on your behalf and guide you through to final resolution.
JURISDICTIONS SERVED
Attorney Michael Goldstein is licensed in Massachusetts and admitted to the United States District Court for the District of Massachusetts, the United States Bankruptcy Court for the District of Massachusetts, and the Federal Court for the First Circuit.
For Maryland and Washington, D.C. clients, tax resolution matters may be handled in coordination with local counsel admitted in those jurisdictions. Attorney Goldstein also works in an of-counsel relationship with Phillips Law Offices, which includes attorneys licensed in Maryland and Washington, D.C.
This allows clients in Massachusetts, Maryland, and D.C. to receive practical guidance on IRS tax debt matters while ensuring that any jurisdiction-specific legal issues are handled appropriately.