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

Overview

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Gambling tax reporting is often misunderstood, creating confusion and compliance risks for tax professionals. This comprehensive course clarifies Form W-2G reporting requirements, withholding rules, and the tax treatment of gambling income and losses. Participants will master federal reporting thresholds, understand different treatment rules by gambling activity type, and navigate
complex scenarios involving multiple winners, foreign persons, and noncash prizes.The course 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 gain the knowledge to properly advise clients with gambling winnings and losses, while developing best practices for form preparation and recordkeeping.

Speaker Bio:

Jason Dinesen, Dinesen Media Ventures, LLC

Jason Dinesen, EA is a tax practitioner and long-time presenter of continuing education courses. Jason’s experience includes extensive tax preparation background in individual income taxes, and tax situations for small businesses in Dinesen Tax & Accounting, P.C., and now Dinesen Tax Advisory, LLC. Jason is an Iowa native and was president of the Iowa Society of Enrolled Agents from 2011–2017. He currently teaches on dozens of tax topics and also teaches Special Enrollment Exam (aka “the Enrolled Agent exam”) review, as well as review courses for AFTR and California CTEC. He has also been an adjunct instructor at Simpson College in Indianola, Iowa, where, through 2022, he taught individual income tax and intro to business analytics.

Highlights

Form W-2G issuance requirements and thresholds by activity type
Federal withholding obligations and backup withholding procedures
Reporting for foreign persons, share winnings, and noncash prizes
Individual income tax return reporting of gambling income and losses
2026 changes to wagering loss deduction limitations under the HR-1 bill
Compliance strategies and penalty avoidance
Recordkeeping and documentation requirements

Prerequisites

General knowledge of federal income tax reporting requirements; recommended for practitioners who serve clients with gambling-related income.

Designed For

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

Objectives

Upon completion of this course, participants will be able to:

Determine when a gambling establishment is required to issue Form W-2G
Apply federal withholding rules to gambling winnings, including regular and backup withholding requirements
Analyze reporting issues involving foreign winners, multiple winners, and noncash prizes
Advise clients on proper tax reporting of gambling winnings and deductible gambling losses
Evaluate the impact of 2026 wagering loss limitation changes on both casual and professional gamblers
Identify best practices for clients engaging in gambling activity
Recognize common compliance and penalty issues associated with Form 2-2G reporting and withholding