Chat with us, powered by LiveChat

The Tax Implications of Debt Restructuring

The Tax Implications of Debt Restructuring

Debt restructuring can have significant tax implications that need to be considered carefully. This process involves changing the terms of debt agreements to help reduce financial stress. It often involves reducing interest rates, extending repayment periods, or reducing the total amount owed.While debt restructuring can provide financial relief, the tax consequences can be complex. Here is an overview of some key tax issues to keep in mind with debt restructuring:

Canceled Debt and Taxable Income

If any portion of debt is forgiven or canceled as part of a restructuring agreement, this typically counts as taxable income. This canceled debt is treated as income even if no money changes hands.For example, if a lender agrees to reduce total loan balance by $50,000, that $50,000 could be viewed by the IRS as income for tax purposes. There are some exceptions to this tax treatment, which are covered later in this article.

Capital Gains Taxes

Exchanging debt obligations can also trigger capital gains taxes. For instance, if bonded debt is exchanged for a new bond issue with different terms, capital gains taxes may apply based on the difference between the original price paid for the bonds and the fair market value at the time of exchange.Similarly, the exchange of loans between a borrower and lender can be viewed as the sale of an “old” loan and purchase of a “new” loan. If the principal amount of the new loan is less than the principal of the original loan, this difference could be subject to capital gains tax.

Original Issue Discount

If debt is reissued at a discount to its original principal amount, this can create an “original issue discount” (OID) . The OID is generally treated as taxable interest income over the life of the loan.For example, if a $100,000 loan is reissued with a principal amount of $80,000, the $20,000 discount would likely be viewed as OID. Even though no interest payments are made on the discount amount, it accrues taxable interest income each year.

Tax Reporting Requirements

Any debt reductions, canceled balances, capital gains or OID triggered by a restructuring may need to be reported to tax authorities. In the U.S., lenders are required to issue Form 1099-C for canceled debt over $600.Borrowers who have over $20,000 of OID may need to calculate a portion of this OID each year and report it as interest income on their tax returns, even if actual cash interest payments are not being made. Careful tracking of new loan terms and tax reporting is essential.

Exceptions for Tax Treatment

There are certain exceptions that allow canceled or restructured debt to be excluded from taxable income:

  • Bankruptcy: Debt discharged through bankruptcy proceedings may be exempt from income tax under the U.S. insolvency exclusion.
  • Insolvency: To the extent a borrower is insolvent (liabilities exceed assets), canceled debt may not be taxable under the insolvency exclusion.
  • Mortgage Debt: Up to $2 million of forgiven mortgage debt from a primary residence may be excluded under the Mortgage Debt Relief Act (expires 2025) .
  • Farm Debt: Canceled farm business debt can be excluded in some cases.

These exceptions can eliminate or reduce tax bills on restructured debt but require meeting specific legal criteria. Consultation with a tax professional is key to determine eligibility.

State Tax Considerations

Income, gains and interest triggered at the federal level by debt restructuring often flow through to state tax returns as well. However, some states like California, Pennsylvania and New Jersey do not conform to federal tax treatment of canceled debt.The taxability of debt relief depends on the specific state. For high tax states like California and New York, the state tax impact of debt restructuring should be evaluated.

Strategies to Minimize Taxes

While legal exceptions may shelter some borrowers from taxes on restructured debt, taxes may still apply in many cases. Proactive tax planning strategies should be considered, such as:

  • Negotiating with lenders: Work with lenders to structure debt relief in a tax-exempt manner where possible.
  • Tax-deferred exchanges: Seek to exchange debt on a tax-deferred basis instead of recognizing losses/gains.
  • Tax attribute monitoring: Carefully track tax losses and credits that could offset gains on debt relief.

With proper planning and lender negotiations, some of the tax sting of debt restructurings may be minimized.

When to Seek Tax Advice

The tax implications of debt restructuring can be very situation-specific. The type of debt involved, exact nature of restructuring, timing/amounts of gains or losses, and a taxpayer’s unique tax position all impact outcome.Consulting with a tax professional is highly recommended when considering or undertaking any kind of debt restructuring transaction. An experienced CPA or tax attorney can provide guidance on forecasting tax liability, navigating reporting rules, claiming available exceptions and developing tax-efficient structures.With proper tax planning, debt restructuring can provide critical financial relief without undue tax burdens. But careful navigation of the complex tax code is key to optimize outcomes.


For more information, check out the following additional resources:

Delancey Street is here for you

Our team is available always to help you. Regardless of whether you need advice, or just want to run a scenario by us. We take pride in the fact our team loves working with our clients - and truly cares about their financial and mental wellbeing.

"Super fast, and super courteous, Delancey Street is amazing"
$500,000 MCA Restructured Over 3 Years
"Thanks for helping me in literally 24 hours"
$250,000 SBA Loan Offer in Compromise
"Great choice for business owners who need a trustworthy partner"
$350,000 MCA Restructured Over 2 Years

In The Media

Delancey Street CEO discusses ways to reward employees
Delancey Street CEO discusses the benefits of franchising on Forbes.
Delancey Street CEO discusses management on AMEX.
What Should I Do If OneMain Financial Is Taking Me to Court?

What Should I Do If OneMain Financial Is Taking Me…

How to Wind Down a Small Business With Too Much Debt

  How to Wind Down a Small Business With Too…

Coping With Debt-Related Marriage or Relationship Problems

  Coping With Debt-Related Marriage or Relationship Problems Money issues…

When Starting a Small Business to Pay Off Debt is Risky

When Starting a Small Business to Pay Off Debt is…

What is Debt Settlement and How Does it Work?

What is Debt Settlement and How Does it Work? Debt…

Delancey Street simply gets it. You're talking to experts.
Steven Norris
Get Help Today

Ready To Get Started?

If you have questions, feel free to shoot us an email, or fill out our live chat.

Schedule Consultation