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Why Connecticut Residents Are Seeing Larger Balances on IRS Notices

Connecticut taxpayers often receive IRS letters showing balances far higher than expected. These adjustments typically come from automated systems.

Multiple Income Streams

CT residents often have:

• Remote work income

• Commuter job income

• Side income

• Investment accounts

Any discrepancy triggers an IRS recalculation.

Incorrect Credits

Credits for children, education, and insurance are common sources of IRS corrections.

State-Level Changes

When Connecticut updates your state return, the IRS may use that data to adjust the federal return.

Rappaport Can Help

Rappaport Tax Relief reviews each notice, challenges incorrect figures, and negotiates directly with the IRS to protect clients from enforcement.

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by David Rappaport

Can You Really Settle IRS Tax Debt for Less Than You Owe? A Connecticut Taxpayer’s Guide to the Truth

IRS tax problems are more common in Connecticut than most people realize — not because people are reckless, but because the financial landscape here is unpredictable.
High housing costs, inconsistent contract work, medical expenses, layoffs, shifting industries, and unexpected 1099 income all combine to create tax debt unbelievably fast.

Then the IRS notices arrive.
Then the penalties compound.
Then the debt becomes bigger than what most families can realistically manage.

That’s when people type the same question into Google:

“Is it actually possible to settle my IRS debt for less than I owe?”

Yes — but only under circumstances that the IRS considers genuine hardship.
This guide explains how IRS settlements really work for Connecticut taxpayers, and how Rappaport Tax Relief helps people qualify.

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There Is Only One Real IRS Settlement Program

Television ads oversell it. Radio ads oversimplify it.
But there is a real program that allows taxpayers to settle their balance for less. It’s called the:

Offer in Compromise (OIC)

An OIC isn’t about negotiation.
It is not about bargaining.
There is no “name your price.”

The IRS applies a strict formula called:

Reasonable Collection Potential (RCP)
= What the IRS believes it could collect from you over time

If RCP is lower than your total debt → settlement may be possible.
If RCP is equal or higher → the IRS will expect full payment or another resolution method.

Understanding how RCP works is the key to whether an OIC is worth pursuing.

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Why Connecticut Taxpayers Often Make Strong Settlement Candidates

The IRS’s national “allowable expense standards” don’t match reality in Connecticut.

1. Housing costs exceed national norms

Fairfield County, Stamford, Norwalk, Westport, Danbury, and parts of Hartford and New Haven have housing costs far above IRS allowances.

2. Commuting costs are uniquely high

Metro-North, gas prices, parking, tolls — they all inflate monthly expenses.

3. Many taxpayers have variable income

Connecticut is full of:

• Contractors

• IT professionals

• Consultants

• Healthcare workers

• Self-employed tradespeople

Income fluctuates dramatically in these sectors.

4. Elder care and medical expenses are widespread

CT has an older-than-average population and high medical costs.

5. Dual-income families shift to single-income households after divorce

Two homes. Two sets of bills. Two childcare setups.

6. Student loan burdens

IRS charts don’t fully account for the size and impact of student loan payments in CT.

When documented correctly, these realities help show the IRS why a taxpayer cannot pay the full balance.

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How the IRS Calculates Eligibility

The IRS examines two main components:

1. Future income

They review:

• Net monthly income

• Average bank deposits

• Self-employment swings

• Seasonal earning patterns

• Spousal income

• Family size

• Childcare and dependents

• Medical needs

Then they apply “allowable expense” subtractions — but in Connecticut, those allowable numbers need to be expanded with documentation to reflect real living costs.

2. Equity in assets

The IRS reviews:

• Home equity

• Vehicle equity

• Retirement accounts

• Investments

• Cash value insurance

• Business equipment

Homeowners in CT often worry about equity — but IRS equity isn’t always full market value.
There are discounts, limitations, shared ownerships, refinancing barriers, and community-specific adjustments.

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Who in Connecticut Often Qualifies for an OIC?

Retirees or near-retirees

Fixed income and limited earning potential create strong OIC cases.

Self-employed workers

Contractors, stylists, barbers, mechanics, IT consultants, and tradespeople often have income dips the IRS must consider.

Single parents

Childcare costs in CT frequently exceed IRS expectations.

Families with medical expenses or caring for elderly parents

These expenses, when documented, shift RCP significantly.

Taxpayers whose income decreased after the tax was assessed

A strong year followed by two weak years is a textbook OIC scenario.

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When an OIC Isn’t the Best Approach

Not everyone is a settlement candidate. Fortunately, the IRS has alternatives:

• Partial-pay installment agreements

• Penalty abatement

• Currently Not Collectible (CNC)

• Full installment agreements

• Appeals and audit reconsiderations

• State-specific relief (CT DRS programs)

Rappaport Tax Relief always runs your RCP numbers first — before filing anything — to determine whether an OIC is worth the time.

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What a Strong Connecticut OIC Package Looks Like

A successful OIC includes:

• A complete, precise financial statement

• Three–six months of bank statements

• Proof of childcare, medical, commuting, and housing expenses

• Correct valuation of assets

• Documentation of income instability

• A narrative explaining why CT economics exceed IRS standards

• A clean filing history

• Consistent numbers across every form

Weak OIC packages are denied not because the taxpayer doesn’t qualify — but because the IRS wasn’t given enough clarity.

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Why Rappaport Tax Relief Succeeds Where National Firms Fail

Connecticut has unique cost patterns and regional pressures.
Rappaport understands:

• Fairfield County cost-of-living

• Metro-North commuting

• Student loan burdens

• High medical insurance premiums

• High childcare and after-school costs

• Property tax variations

• How IRS reviewers treat Connecticut cases

This local knowledge dramatically increases the strength of an OIC submission.

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Final Thought

Yes — IRS settlements are real.
But they only work when your financial story is carefully prepared and clearly documented.

Rappaport Tax Relief helps Connecticut taxpayers make informed decisions and build settlement packages that resonate with the IRS — increasing the odds of meaningful relief.

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by David Rappaport

Unfiled Tax Returns in Connecticut — How Serious Is It?

If you’ve missed one or more tax filings, you might worry that it’s too late to fix. The truth? You’re not alone — and with the right help, it’s never too late to make things right with the IRS.

What Happens When You Don’t File

If you don’t file, the IRS will eventually file a Substitute for Return (SFR) for you, based only on your reported income. Because it excludes deductions and credits, it usually shows a much higher balance than what you actually owe.

Once that happens, the IRS can issue liens, garnish wages, or seize refunds.

Why You Should File Voluntarily

Filing voluntarily gives you the advantage. It allows you to:

• Reclaim deductions and credits you’re entitled to

• Qualify for payment or settlement options

• Avoid or reduce penalties

How Rappaport Tax Relief Can Help

At Rappaport Tax Relief, we help Connecticut taxpayers file old returns, correct IRS records, and negotiate fair resolutions. You’ll work directly with a trusted professional who knows how to simplify the process and protect your best interests.

If you’re behind on taxes, take the first step toward peace of mind.

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by David Rappaport

How Long the IRS Can Collect Back Taxes — The 10-Year Limit Explained

If you’ve been dealing with tax debt for years, you may be closer to the finish line than you think. By law, the IRS generally has 10 years from the date your taxes are assessed to collect. This time frame is known as the Collection Statute Expiration Date (CSED).

When the 10-Year Clock Starts

The clock starts when the IRS officially records your tax liability — usually after you file your return, or when the IRS files one on your behalf. Once 10 years pass, the debt becomes legally uncollectible.

What Stops or Extends the Time Limit

Some actions temporarily pause the countdown, including:

• Filing for bankruptcy

• Submitting an Offer in Compromise

• Living abroad

• Requesting Innocent Spouse Relief

• Having an open appeal or hearing

When those situations end, the clock resumes.

Why This Rule Matters

Understanding your CSED helps you and your tax professional decide the best strategy — whether that means negotiating a settlement or allowing the statute to expire.

At Rappaport Tax Relief, we review IRS transcripts, determine your true CSED dates, and help Connecticut taxpayers plan their path to financial freedom.

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by David Rappaport

IRS Wage Garnishment in Connecticut — What You Can Do About It

When the IRS starts taking money directly from your paycheck, it can quickly become overwhelming. The good news? You don’t have to face it alone — and with the right help, you can often stop a garnishment before your next payday.

What Is an IRS Wage Garnishment?

A wage garnishment (or levy) allows the IRS to collect unpaid taxes by requiring your employer to send a portion of your wages directly to them. This usually happens after the IRS has sent multiple warnings, including a Final Notice of Intent to Levy.

Once it begins, it continues until your balance is paid or the IRS approves another arrangement.

How to Stop Wage Garnishment

You have several ways to stop a wage garnishment:

• Set Up a Payment Plan. A negotiated installment agreement can pause collection.

• Apply for Hardship Status. If you can’t pay without severe financial strain, the IRS can stop enforcement.

• Submit an Offer in Compromise. Settle for less than you owe if you qualify.

• File an Appeal. Challenge improper or excessive collection action.

How Rappaport Tax Relief Helps

At Rappaport Tax Relief, we work directly with the IRS to stop garnishments, protect your income, and negotiate solutions that fit your financial situation. We’ve helped countless Connecticut taxpayers regain control and peace of mind.

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by David Rappaport

10 Benefits of Letting a Professional Negotiate With the IRS in Connecticut

Connecticut Taxpayers Need an Advocate

IRS debt is more than just numbers — it’s stress, fear, and the risk of losing what you’ve worked for. Once penalties start adding up, the IRS moves quickly with garnishments, liens, and levies.

At Rappaport Tax Relief, we’ve built our practice on defending Connecticut taxpayers. Here’s why professional help makes the difference.

1. Knowledge of Federal and State Tax Laws

Connecticut residents often face state tax issues on top of IRS problems. An expert who understands both ensures nothing slips through the cracks.

2. Stopping Collections

IRS levies and garnishments can devastate your finances. Professionals know how to stop or release these actions.

3. Negotiating Fair Settlements

Experts present your case strategically to secure affordable payment terms or reduced balances.

4. Requesting Penalty Relief

Late filing and underpayment penalties can be reduced or removed if handled correctly.

5. Support During Audits

IRS audits are stressful. A debt relief expert ensures you’re prepared and represented throughout.

6. Protecting Assets

Professionals know how to safeguard your bank accounts, wages, and property.

7. Ensuring Accurate Filing

Errors increase debt. Experts keep filings clean, correct, and strategic.

8. Handling Unfiled Returns

Years of unfiled returns make debt worse. A professional brings your record current without triggering unnecessary penalties.

9. Stress Relief

Knowing someone is fighting for you allows you to sleep at night and focus on your life.

10. A Path Forward

The ultimate goal is financial freedom and a fresh start.

Why Work With Rappaport

David Rappaport combines years of experience with personal dedication. Clients trust his commitment and results.

Call Today

Don’t let IRS problems grow worse. Call Rappaport Tax Relief today and get the ally you need.

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by David Rappaport

IRS Notices Explained: What to Do When You Receive a CP501 or CP504

When the IRS Comes Knocking

For taxpayers in Connecticut, nothing creates anxiety quite like an IRS notice. The CP501 and CP504 are among the most common — and they escalate quickly if ignored.

CP501: The First Reminder

This is often the IRS’s initial contact about your unpaid balance. It outlines how much you owe, due dates, and basic payment instructions. While it may seem mild, ignoring it will trigger harsher action.

CP504: The Final Notice

The CP504 is far more serious. It’s a Notice of Intent to Levy — meaning the IRS can seize your state refund and move toward other assets if you don’t act.

Consequences of Ignoring Notices

• Liens on your home or property.

• Garnishment of your wages.

• Seizure of bank accounts.

Steps to Take Immediately

1. Don’t panic, but don’t ignore it.

2. Read the deadlines carefully.

3. Explore payment options like installment agreements, Offers in Compromise, or hardship status.

4. Get professional help to avoid costly mistakes.

Why It Matters in Connecticut

With high living costs and property values, liens or levies can devastate households. Waiting until garnishment begins leaves you with little leverage.

Rappaport Tax Relief helps Connecticut taxpayers respond to IRS notices before they escalate. Call today for a free consultation.

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by David Rappaport

The Truth About IRS Penalties and How to Remove Them

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.

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by David Rappaport