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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.

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.

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.

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.

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.

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.

by David Rappaport

The High Stakes of Ignoring IRS Letters

An IRS notice isn’t a suggestion — it’s a formal warning that demands a response. Ignoring it can cost you far more than the original issue.

It starts with a basic letter explaining a discrepancy or balance due. With no reply, the IRS moves forward with collection. That can mean wage garnishments, liens against your property, or direct withdrawals from your bank account. Once those actions begin, stopping them is far harder than preventing them in the first place.

At Rappaport Tax Relief, we take immediate action to address IRS correspondence. We work to resolve the underlying issue, challenge incorrect claims, and negotiate solutions that protect your income and assets.

If there’s an IRS notice in your mailbox, don’t wait. Contact Rappaport Tax Relief now to keep the problem from getting worse.

by David Rappaport

IRS Bank Levies: Immediate Steps to Take

An IRS bank levy is more than an inconvenience — it’s a sign that the government is done waiting for payment. With this action, the IRS can legally freeze your bank account and, after 21 days, take the funds to cover your tax debt.

By the time a levy happens, the IRS has already sent multiple notices, including a Final Notice of Intent to Levy. If you don’t respond, they move forward — and your access to your own money is cut off.

At Rappaport Tax Relief, we treat bank levies as urgent emergencies. We work to open negotiations with the IRS immediately, pursuing solutions such as payment arrangements, hardship relief, or, in some cases, an Offer in Compromise. Our goal is to stop the levy, protect your remaining funds, and prevent future seizures.

Don’t wait until your account is emptied. Call Rappaport Tax Relief now if you’ve received a levy notice or found your funds frozen.

by David Rappaport

The Truth About IRS Penalties — And How to Get Them Removed

When tax debt starts piling up, IRS penalties often make the situation worse. What begins as a manageable balance can quickly become overwhelming once late fees, interest, and additional charges are added on.

At Rappaport Tax Relief, we’ve seen countless clients come in discouraged by penalty notices — not realizing that many of these penalties can be challenged or removed. If you're feeling buried under IRS charges, here’s what you need to know.

Why the IRS Issues Penalties

The IRS uses penalties to enforce compliance. Some of the most common include:

• Failure to File – Up to 25% of the unpaid tax (5% per month)

• Failure to Pay – 0.5% per month, with interest added on top

• Failure to Deposit (for payroll taxes) – Up to 15% depending on how late the deposit is

While they’re meant to be a deterrent, penalties often hit people already facing financial or personal hardship — and in many cases, the IRS is open to reconsidering them.

Three Ways to Reduce or Eliminate IRS Penalties

1. First-Time Penalty Abatement (FTA)

If you’ve filed and paid on time for the past three years, you may qualify for this one-time waiver — even if your current situation is messy. It’s the easiest option for eligible taxpayers.

2. Reasonable Cause Relief

This requires proving that something outside your control prevented you from filing or paying on time. Examples include:

• Natural disasters

• Serious illness or injury

• Loss of records

• Death in the family

• Unavoidable financial hardship

The IRS reviews each case individually, and documentation is critical.

3. Statutory Exceptions

In some rare cases, the IRS may reduce penalties if they made a mistake or if the taxpayer received bad advice from a qualified professional. This usually applies to complex cases — and requires specific legal arguments.

Timing Matters

Penalty relief isn’t automatic — and there are deadlines. Some must be requested within a specific time window, or you risk losing the right to challenge the charge.

At Rappaport Tax Relief, we help clients:

• Identify which penalties they’ve been assessed

• Determine which relief options apply

• Prepare and submit effective requests

• Appeal any unjust denials

Why a Professional Approach Works Better

A well-crafted penalty abatement request makes a difference. Simply saying, “I couldn’t afford to pay” often isn’t enough. We know how to build a persuasive case using the IRS’s own criteria and language — and we don’t hesitate to escalate a denial to the Office of Appeals when needed.

Take Control of Your Tax Debt

Penalties are frustrating, but they’re not final. In many cases, you may be able to reduce what you owe and get back on the path to resolution — especially with the right support.

If you’re struggling with tax debt and want to explore penalty relief, contact Rappaport Tax Relief today. We’ll help you understand your options and fight for a fair outcome.

by David Rappaport