In this episode, Cary Sinnett is joined by renowned CPA and tax expert Bob Keebler to unpack the complexities of theft and casualty loss deductions under IRC Section 165. From pig butchering scams to IRA fraud and Ponzi schemes, this episode dives deep into the kinds of losses the IRS will—and won’t—let you deduct, what qualifies as a profit motive, and how financial planners can guide their clients through one of the most emotionally and financially painful tax situations.

Five Key Insights for CPA Financial Planners:

Profit Motive Determines Deductibility
To qualify under Section 165(c)(2), a theft or loss must stem from a transaction entered into for profit. Losses from romantic or emotional scams—where no profit motive exists—do not qualify.
Five Scam Archetypes to Know
A recent IRS CCA outlined five fraud scenarios:
- Compromised account scams
- Pig butchering (crypto fraud)
- Phishing and impersonation
- Romance scams
- Kidnapping/extortion schemes
  Only the first three had profit motives and were deductible.
The IRA Trap: The Tax Hit Before the Scam
If a client is duped into withdrawing funds from an IRA and then loses the money to a scam, they face a double blow—taxable income and no deductible loss. CPA advisors must flag this risk early.
Documentation Is Critical for IRS Support
To substantiate a theft loss, clients need:
- Bank records (e.g., wire transfers)
- Law enforcement reports
- A clear, detailed paper trail showing the loss and the attempt to recover funds
  Directing the IRS to the assigned FBI agent can strengthen the claim.
Mitigation and Planning: Protecting Vulnerable Clients
Encourage older or high-net-worth clients to follow a “1–2% rule” on risky investments. Foster opens dialogue with family members and advisors to prevent fraud and ensure support if it occurs.

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IRC Section 165
IRS CCA 2025-101015 (the ruling discussed)
Revenue Procedure 2009-20 (Ponzi Scheme Safe Harbor)
AICPA PFP Section
Guiding your clients who are financial caregivers
Scam Tracker Risk Report

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When theft gets taxing with Bob Keebler

AICPA Personal Financial Planning (PFP)