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Navigating S-Corp Losses: When Can You Claim a Write-Off?

Facing Investment Losses: What Are Your Tax Options?

Investments don’t always yield the expected returns. If you’ve put your faith—and cash—into an S Corporation and things have turned sour, the silver lining might be a tax deduction. Dreaming big is essential, but financial pragmatism governs tax laws.

So, when your optimism fades and you’re left with an inkling of doubt peering over your tax returns, the big question rings: “Can I write this off and just move on?” Here’s the real deal from Thompson-Smith CPA, LLC: it’s a conditional yes—but let’s dive into those conditions.

1. Defining "Worthless" in Tax Terms

Business struggles don’t inherently spell worthlessness for tax purposes. The IRS provides a stringent framework: stock such as S-corp shares must have no current or expected future value to qualify as worthless. This means the company must:

  • Cease operations entirely,
  • Hold no assets,
  • Abandon future business activity plans,
  • Offer zero realistic recovery prospects to shareholders.

Essentially, that business should be clinically dead, not simply on life support. The IRS finds value in a business that still shows any operational sign—no deduction can be claimed until it’s all truly over.

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2. Substantial Proof Required by the IRS

A mere declaration of worthlessness doesn’t suffice. The IRS demands evidence, such as identifiable events:

  • Formal dissolution or liquidation filings,
  • Bankruptcy documentation where debts trump assets without a reorganization plan,
  • Asset foreclosure or sales,
  • Complete termination of operations,
  • Statements affirming zero future equity recovery.

These paper trails are your safety nets—feelings won’t cut it. what doesn’t satisfy the IRS:

  • Your perceived end of days for the company,
  • Lack of recent updates,
  • Non-profitability but continued formal operations.

3. Timing Your Deduction Wisely

Deductions are a one-time event, only applicable in the year your stock is genuinely worthless. Claiming too early can trigger denial from the IRS; push past the deadline, and the opportunity vanishes. This window calls for documentation about when operations ceased or when the last asset disappeared, turning accounting into a precise art.

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