December 9, 2026

Webcast

2 CPE Credits

Don Farmer's All Bets Are Off: Navigating Gambling Tax Rules

December 9, 2026
Webcast
2 CPE Credits

Don Farmer's All Bets Are Off: Navigating Gambling Tax Rules

  • Instructor

    Jason
    Dinesen

Gambling tax reporting is often misunderstood, creating confusion and compliance risk for tax professionals and their clients. This comprehensive course clarifies Form W-2G reporting requirements, withholding rules, and the tax treatment of gambling income and losses. Participants will examine federal reporting thresholds, how treatment differs by type of gambling activity, and complex scenarios involving multiple winners, foreign persons, and noncash prizes.

The course also examines critical compliance issues, including penalty exposure for incorrect withholding, Form 5754 reporting requirements, state tax considerations, and recent legislative changes affecting gambling loss deductions. Through practical examples and real-world scenarios, participants will be better prepared to advise clients with gambling winnings and losses and to apply best practices for form preparation and recordkeeping.

Learning Objectives

1. Determine when a gambling establishment is required to issue Form W-2G, based on reporting thresholds by activity type

2. Apply federal regular and backup withholding rules to gambling winnings, including situations involving foreign persons, multiple winners, and noncash prizes

3. Determine the proper individual income tax reporting of gambling winnings and deductible gambling losses

4. Analyze the impact of the 2026 wagering loss limitation changes on casual and professional gamblers

5. Identify recordkeeping best practices and common compliance and penalty issues associated with Form W-2G reporting and withholding

Major Topics

• Form W-2G issuance requirements and thresholds by activity type

• Federal withholding obligations and backup withholding procedures

• Reporting for foreign persons, shared winnings, and noncash prizes

• Individual income tax return reporting of gambling income and losses

• 2026 changes to wagering loss deduction limitations under H.R. 1 (the One Big Beautiful Bill Act)

• Compliance strategies and penalty avoidance

• Recordkeeping and documentation requirements

CPE Credits Available

2 CPE Credits
2
Taxes

Things to Know About This Course

Course Level

  • Intermediate

Professional Area of Focus

  • Tax

Prerequisites

Working knowledge of federal individual income tax return preparation, including reporting of other income and itemized deductions.

Advanced Preparation

None

Intended Audience

CPAs, tax professionals, and accounting practitioners who advise clients on federal tax compliance and individual income tax reporting.

Provider

Don Farmer Tax Education

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