Sweepstakes, Contests, and Giveaways: Mastering the Legal and Regulatory Landscape 2026

Morgan Spina
Morgan Spina
Olshan Frome Wolosky LLP

Morgan’s work includes structuring sweepstakes, games of skill and promotions, and preparing applicable terms and conditions, clearance of advertising and marketing materials, privacy policies and practices, trademark and copyright prosecution, maintenance and enforcement, and all types of intellectual property and advertising agreements, including licenses.

Andrew B. Lustigman
Andrew B. Lustigman
Olshan Frome Wolosky LLP

Andrew Lustigman offers comprehensive counsel to domestic and international clients on advertising, marketing and promotions matters and represents them in regulatory investigations, enforcement actions, and litigation. He chairs Olshan’s Advertising, Marketing & Promotions Group and co-chairs its Brand Management & Protection Group.

Live Video-Broadcast: March 19, 2026

2 hour CLE

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Program Summary

What Will You Learn

Attendees will learn how to structure and evaluate sweepstakes, contests, and giveaways within applicable federal, state, and international legal frameworks. The program examines intersections with gambling and lottery laws, consumer protection statutes, privacy regulations, advertising standards, tax obligations, and intellectual property rights. Participants will also learn how to draft compliant rules, manage registration and bonding requirements, oversee winner selection and prize administration, and address platform-specific and industry-specific compliance risks.

What Will You Gain

Attendees will gain practical, risk-focused insight to advise clients on promotional campaigns with greater confidence and precision. Participants will be better equipped to identify exposure before launch, mitigate regulatory and litigation risk, and respond to compliance challenges. The program delivers actionable guidance that strengthens attorneys’ ability to support marketing and business teams while ensuring legally compliant and commercially sound promotional strategies.

Key topics to be discussed:

  • Structuring lawful promotional campaigns
    • Examination of how giveaways, sweepstakes, contests, and hybrid promotions are designed and structured to avoid illegal lotteries and ensure legal compliance from inception.
  • Federal, state, and international regulatory compliance
    • Analysis of the legal frameworks governing promotions, including federal oversight, state gambling and consumer protection laws, registration and bonding requirements, and international considerations.
  • Drafting, disclosure, and transparency obligation
    • Guidance on drafting compliant promotional rules, ensuring clear disclosures, managing odds and prize representations, and maintaining transparency in winner selection and administration.
  • Operational compliance and risk management
    • Practical considerations for administering promotions, including eligibility verification, prize fulfillment, recordkeeping, tax reporting, and dispute management.
  • Digital, advertising, and platform-specific legal requirements
    • Coverage of social media platform rules, FTC advertising standards, influencer compliance, and the legal risks associated with digital and multi-platform promotional campaigns.
  • Data protection, intellectual property, and industry-specific risks
    • Evaluation of privacy and data protection obligations, intellectual property rights, user-generated content issues, and heightened compliance requirements for promotions in regulated industries.

This course is co-sponsored with myLawCLE.

Date / Time: March 19, 2026 

  • 1:00 pm – 3:10 pm Eastern
  • 12:00 pm – 2:10 pm Central
  • 11:00 am – 1:10 pm Mountain
  • 10:00 am – 12:10 pm Pacific

Closed-captioning available

Speakers

Morgan Spina | Olshan Frome Wolosky LLP

As a member of Olshan’s Brand Management and Protection Group, Morgan helps guide clients on all facets of brand management, including privacy, advertising and intellectual property optimization, enforcement and defense. Efficient, pragmatic, proactive and creative, Morgan works through complex issues, devising solutions to meet client needs.

Morgan’s work includes structuring sweepstakes, games of skill and promotions, and preparing applicable terms and conditions, clearance of advertising and marketing materials, privacy policies and practices, trademark and copyright prosecution, maintenance and enforcement, and all types of intellectual property and advertising agreements, including licenses. Morgan also advises on various compliance matters including automatic renewal/subscription issues and helps represent clients in federal and state government regulatory investigations and enforcement matters brought by the Federal Trade Commission and state attorneys general. She also advises on truth-in-advertising issues and assists in representing clients in proceedings before the National Advertising Division (NDA).

Always current on the latest trends and legal developments, Morgan makes certain to keep the firm’s clients informed and has published a number of articles focused on advertising, privacy, and intellectual property law issues.

Legal Focus

  • Advertising, Marketing & Promotions
  • Intellectual Property Law
  • Brand Management & Protection
  • White Collar & Government Investigations

Professional Experience

  • Represented an online travel company in a state attorney general investigation related to advertising practices.
  • Representing the subscription radio broadcaster in connection with advertising, marketing and business practices, ensuring compliance with a myriad of federal and state laws. Specifically, providing guidance with respect to telemarketing, automatic renewal, billing disclosures, and collection issues.
  • Advising a news publication on automatic renewal issues.
  • Represented a pharmaceutical company in a series of NAD challenges related to over-the counter drug claims.
  • Representing a leading interactive promotion agency in structuring contests, drafting rules, and reviewing advertising and promotional materials, and providing ongoing legal support throughout the contest period and winner selection process.

Honors & Awards

  • Recognized as a “Recommended Lawyer”in The Legal 500 U.S. in Media, technology and telecoms – Advertising and Marketing, 2023-2025 and as a “Key Lawyer” in the same category, 2022.

Credentials & Leadership

  • New York State Bar

Education

  • LL.M., Brooklyn Law School, 2016
  • LL.B. and B.A., University of Wollongong, 2013 (Australia)

Select Media & Speaking

  • Advertising Law Blog 12.30.2025 NEWSLETTER: Advertising, Marketing & Promotions – Hot Topics 2026
  • Advertising Law Blog 12.30.2025 Automatic Renewal Laws: 2026 Regulatory and Legislative Outlook
  • Advertising Law Blog 11.25.2025 Olshan Wins 2025 Media Law International Award for Law Firm of the Year
  • CLE Webinar 12.03.2024 Sweepstakes, Contests, and Giveaways: Mastering the Legal and Regulatory Landscape
  • CLE Seminar|10.18.2023 Cybersecurity, Privacy and Data Protection and the Practice of Law

 

Andrew B. Lustigman | Olshan Frome Wolosky LLP

Andrew Lustigman offers comprehensive counsel to domestic and international clients on advertising, marketing and promotions matters and represents them in regulatory investigations, enforcement actions, and litigation. He chairs Olshan’s Advertising, Marketing & Promotions Group and co-chairs its Brand Management & Protection Group.

Marketers, advertisers, agencies and suppliers, among others, regularly seek Andy’s counsel regarding legal aspects of their advertising and promotional marketing businesses. He’s pragmatic and always looks for solutions that meet each client’s specific needs.

Andy advises them on the clearance of advertising, promotions, and marketing materials, and structures some of the most creative sweepstakes, games of skill, fundraising promotions, and other contests, development of social media programs, and direct marketing campaigns from both legal and compliance standpoints. He also conducts advertising and marketing due diligence in the context of mergers, acquisitions and investments. He is frequently called upon to help clients navigate the nation’s complex subscription marketing laws.

Andy advises clients across all media channels—social media, Internet, television, print, radio, direct mail, mobile, telemarketing, and other electronic media. He has significant experience with FTC and FDA regulatory requirements regarding health claims, advertising, labeling and distributing health-related products including OTC products, dietary supplements, medical devices, cosmetics, and medical foods. Clients also rely on Andy’s pragmatic approach in representing them in investigations, enforcement actions, and litigation brought by those agencies, the United States Department of Justice, the FCC, the U.S. Postal Service, state attorneys general, district attorneys, and other governmental authorities. Andy’s experience also extends to single-plaintiff, multiparty and class action cases and related commercial litigation alleging false and deceptive advertising, intellectual property-related claims, and corporate disputes, as well as a wide array of competitor advertising, IP and privacy challenges.

Proactive and strategic, Andy takes on emerging threats and conceives creative and aggressive defense theories to protect his client’s interests both in and out of court, including in alternative dispute venues. In prosecuting and defending his clients’ cases, he frequently appears in federal and state court and before the National Advertising Division of the Better Business Bureau.

Repeatedly recognized as a leader in his field and as an authority on advertising and promotional marketing law, Andy regularly appears on television, radio, and in publications such as The Wall Street Journal, New York Post, The National Law Journal, New York Law Journal, Inside Counsel, Bloomberg BNA, Law360, Mobile Marketer, and Luxury Daily, discussing important new cases and trends that advertisers and marketers need to know about. He has testified as an expert witness on advertising compliance in federal court.

A growing area of work Andy handles includes advising on and structuring a broad range of international business transactions. He also is retained by Am Law 100 and other leading firms as special counsel on advertising compliance matters in connection with their clients’ business investments.

In addition to maintaining his active practice, Andy is a co-managing partner of the firm and a member of its Executive Committee. He frequently speaks on advertising and promotional marketing law topics throughout the country and has been the publisher of Olshan’s Advertising Law Blog since its inception in the early 2000s.

Legal Focus

  • Advertising, Marketing & Promotions
  • Brand Management & Protection
  • Intellectual Property Law
  • International Law
  • Advertising Litigation
  • Advertising, Marketing & Promotions Advisory Services
  • Advertising, Marketing & Promotions Transactions
  • Direct Marketing Law
  • Food, Drug, Dietary Supplement, Medical Device & Cosmetics Compliance & Transactions
  • Green Advertising & Claims
  • Internet & Digital Marketing Law
  • Litigation
  • Media, Entertainment & Technology Litigation
  • Privacy, Data & Security
  • Regulatory Compliance, Investigations & Enforcement
  • Social Media Law
  • Sweepstakes & Contests Law
  • White Collar & Government Investigations

Professional Experience

  • Advised as specialty counsel global investment banking firm in connection with lending to a leading consumer finance provider. Services included review of advertising, lead generation practices, TCPA exposure, privacy, and marketing practices.
  • Representing a leading subscription marketer of wine products on continuity compliance. Successfully resolved a significant investigation brought by the California Automatic Renewal Task Force in connection with the client’s enrollment and cancellation practices.
  • Defended an ecommerce marketer in connection with a high-profile investigation brought by the New York Attorney General. Developed a strategy, assisted in responding to the investigation, and ultimately obtained a satisfactory resolution. We continue to represent the company in ongoing matters.

Honors & Awards

  • Repeatedly ranked as a “Leading Lawyer” in Advertising: Transactional & Regulatory by Chambers USA annually since 2008.
  • Recognized as a “Leading Lawyer” in The Legal 500 U.S. in Media, technology and telecoms – Advertising and Marketing from 2023-2025 and as a “Recommended Lawyer” in the same category annually since 2016.
  • Recognized in The Best Lawyers in America® for Advertising Law since 2016.
  • Consistently named to the New York Metro Super Lawyers list since 2008.
  • Named to the Top 100 by New York Metro Super Lawyers list, 2019-2020.
  • Recognized as a Distinguished Adviser in Advertising & Marketing by Financier Worldwide Magazine, 2025.
  • Martindale-Hubbell AV Preeminent® 5.0/5.0 Peer Rated for Highest Level of Professional Excellence.

Credentials & Leadership

  • New York State Bar Association
  • New Jersey Bar Association
  • Treasurer, International Bar Association, Intellectual Property and Entertainment Law Committee
  • Association of the Bar of the City of New York, Consumer Affairs Committee
  • Brand Activation Association/Promotion Marketing Association, Legal Affairs Committee (19962019)
  • Past Chair, American Bar Association, Committee on Promotion and Marketing Law
  • American Bar Association, Consumer Protection Committee
  • Federal Communications Bar Association
  • Fellows of the American Bar Foundation
  • Past Chair, LAWorld International Legal Network

Education

  • J.D., magna cum laude, American University Washington College of Law, 1991
  • Managing Editor, The American University Law Review
  • B.A., University of Michigan, 1988

Select Media & Speaking

  • Advertising Law Blog01.22.2026
    • Andrew Lustigman Speaking at ACI’s 9th Annual Legal, Regulatory, and Compliance Forum on Advertising Claims Substantiation
  • Advertising Law Blog01.13.2026
    • Andrew Lustigman to Speak on False Advertising Litigation: Affirmative Challenges, Defense Strategies, and Risk Mitigation for myLawCLE Webinar
  • Advertising Law Blog01.08.2026
    • Andrew Lustigman Quoted in NYLJ on Leading With Expertise, Not Expediency in the AI Age of Content Churn

Agenda

I. Promotional event structures | 1:00pm – 1:10pm

Promotional campaigns can take many forms, including giveaways, sweepstakes, contests, loyalty programs, and hybrid promotions that combine elements of each. Understanding how these structures differ is critical because the legal classification of a promotion depends on the presence or absence of consideration, chance, and skill. This discussion will break down how these elements operate in practice and how small structural changes such as requiring a purchase, adding voting mechanics, or incorporating judging criteria can significantly alter legal treatment. Focus will be placed on avoiding the inadvertent creation of an illegal lottery, which occurs when consideration, chance, and prize are improperly combined. Attorneys will learn how to analyze promotional mechanics at the conceptual stage to prevent regulatory violations. The session will also explore how loyalty and reward programs intersect with promotional law and when hybrid models introduce heightened compliance risks. By the end of this portion, participants will have a structured analytical approach to evaluating promotional format decisions.

II. Understanding legal frameworks for promotions | 1:10pm – 1:20pm 

Promotional campaigns operate within a layered regulatory structure that includes federal oversight, state statutory schemes, and, in some cases, international regulation. This portion examines the role of federal agencies, particularly the Federal Trade Commission, in enforcing consumer protection and advertising standards. It also reviews key state-specific laws governing gambling, lotteries, and promotional practices, emphasizing how state variations affect nationwide campaigns. Differences in eligibility restrictions, disclosure mandates, and enforcement priorities across jurisdictions will be analyzed. For promotions that extend internationally, the discussion will address cross-border advertising rules, prize delivery restrictions, and compliance challenges in global campaigns. Attendees will gain insight into how regulatory authority overlaps and how to assess risk when campaigns operate across multiple legal regimes. The goal is to provide a working understanding of the legal infrastructure that shapes every promotional strategy.

III. Crafting effective and compliant promotional rules | 1:20pm – 1:30pm 

Well-drafted official rules serve as both a compliance tool and a risk management instrument. This section explores the essential components of promotional rules, including eligibility requirements, permitted entry methods, entry deadlines, prize descriptions, odds disclosures, and dispute resolution provisions. Clear articulation of timing, selection methods, and prize limitations is essential to avoid ambiguity and enforcement exposure. The discussion will emphasize plain  language drafting guidelines that enhance transparency and enforceability while reducing consumer confusion. Common pitfalls such as inconsistent eligibility criteria, unclear prize valuation, or inadequate odds disclosures will be analyzed with practical examples. Attention will also be given to structuring alternative methods of entry to eliminate unlawful consideration. By strengthening drafting practices, attorneys can significantly reduce litigation and regulatory risk for clients.

IV. Registration and bonding requirements | 1:30pm – 1:40pm 

Certain states impose registration and bonding obligations when promotions exceed specified prize value thresholds. This portion reviews requirements in jurisdictions such as New York, Florida, and Rhode Island, including pre-promotion filing procedures, bond calculations, and required documentation. Participants will examine timelines for submission and the administrative processes necessary to maintain compliance. Consideration will also be given to managing promotional changes, including extensions, modifications to prize pools, or cancellations after filing. Failure to meet registration or bonding obligations can result in penalties or invalidation of promotion, making administrative precision critical. Practical compliance strategies and tracking mechanisms will be discussed to help organizations maintain regulatory alignment. Attorneys will leave with a clearer understanding of how these state-specific requirements affect campaign planning and execution.

V. Ensuring compliance with privacy & data protection regulations | 1:40pm – 1:50pm 

Promotional campaigns frequently require collecting personal information, creating obligations under evolving privacy and data protection laws. This discussion addresses the lawful collection, storage, and use of consumer data under federal and state frameworks, including CCPA/CPRA and other emerging state statutes. International regulations such as GDPR will also be considered where campaigns involve global participants. Key issues include consent mechanisms, limitations on secondary data use, retention policies, and safeguarding sensitive personal information. Special attention will be paid to promotions involving minors, where additional legal restrictions apply. The integration of privacy disclosures into promotional rules and marketing materials will be examined as a compliance best practice. By aligning promotional mechanics with privacy law requirements, organizations can reduce exposure to regulatory enforcement and consumer claims.

VI. Verifying winner eligibility & prize administration | 1:50pm – 2:00pm 

Effective promotional administration depends on reliable eligibility verification and defensible selection procedures. This portion examines identity verification protocols, residency confirmation, and age restrictions to ensure compliance with stated rules and legal mandates. The use of affidavits of eligibility, liability releases, and, where appropriate, background checks will be addressed. Proper documentation practices are essential to demonstrate fairness and transparency. The mechanics of prize fulfillment, including delivery logistics, substitution policies, and handling unclaimed prizes, will also be analyzed. Operational errors in this phase often lead to disputes or reputational harm. Establishing consistent administrative safeguards minimizes risk and reinforces the integrity of the promotional campaign.

Break | 2:00pm – 2:10pm

VII. Prize considerations & valuation | 2:10pm – 2:15pm

Accurate prize representation is central to consumer trust and regulatory compliance. This section reviews proper prize descriptions, valuation methodologies, and disclosure requirements, including calculation of approximate retail value. Restrictions affecting certain categories such as alcohol, firearms, travel packages, and cash equivalents will be examined considering applicable regulatory limitations. The importance of clear disclaimers and contingency language will be emphasized to address availability, substitutions, and eligibility conditions. Inadequate valuation or misleading descriptions may trigger consumer protection enforcement. Attorneys will learn how to structure prize disclosures to ensure clarity and defensibility. Thoughtful prize design reduces legal exposure while maintaining marketing effectiveness.

VIII. Navigating tax obligations for prizes | 2:15pm – 2:20pm

Prize awards carry federal and state tax implications that sponsors must manage carefully. This portion explains IRS reporting requirements, including collection of W-9 forms and issuance of 1099 documentation. The tax consequences for winners, including income recognition and potential withholding obligations, will be discussed. Sponsors must also consider state-level tax requirements that may vary depending on residency or prize type. Failure to comply with reporting obligations can result in penalties and administrative burdens. Clear communication with winners regarding tax responsibilities helps mitigate misunderstandings and disputes. Integrating tax compliance into promotional planning ensures smoother administration and regulatory alignment.

IX. Adhering to social media & platform-specific guidelines | 2:20pm – 2:25pm 

Digital promotions must satisfy not only legal requirements but also the contractual obligations imposed by platform operators. This discussion reviews promotional policies applicable to platforms such as Meta, X, TikTok, and YouTube, including disclosure mandates and prohibited promotional tactics. Influencer marketing introduces additional compliance considerations related to endorsement disclosures and transparency. Platform terms of service may impose eligibility, disclaimer, or content restrictions beyond statutory requirements. Coordinating marketing objectives with platform policies reduces the risk of account suspension or reputational harm. Attorneys advising on digital campaigns must integrate platform governance into their compliance analysis. This portion clarifies how digital distribution channels affect promotional legality.

X. Compliance with FTC advertising & marketing guidelines | 2:25pm – 2:30pm 

Truth-in-advertising principles apply fully to promotional campaigns and are enforced actively by the FTC. This section examines the prohibition against deceptive or misleading representations and the requirement that material terms be disclosed clearly and conspicuously. Substantiation standards for promotional claims will be analyzed, particularly where prize descriptions or odds statements are involved. Endorsements, testimonials, and influencer partnerships present additional disclosure obligations that must align with federal guidance. Enforcement trends illustrate the reputational and financial consequences of noncompliance. Integrating advertising law principles into promotional strategy helps avoid enforcement exposure. Attorneys will gain practical insight into evaluating marketing materials through regulatory lens.

XI. Intellectual property considerations | 2:30pm – 2:35pm 

Promotional campaigns frequently involve the use of trademarks, copyrighted materials, and participant-submitted content. This portion addresses clearance processes, licensing agreements, and risk mitigation strategies to prevent infringement claims. Special consideration will be given to user-generated content in contests, including ownership rights and permissible sponsor usage. Drafting rule provisions that define content ownership and grant necessary usage rights is critical to avoid disputes. Trademark usage in advertising materials must comply with brand protection standards. Intellectual property compliance supports both legal defensibility and brand integrity. Attorneys will learn how to integrate IP protections into promotional planning.

XII. Promoting transparency in winner selection & disclosure | 2:35pm – 2:40pm 

Transparent winner selection processes strengthen defensibility and public trust. This discussion addresses random drawing procedures, documentation standards, and audit protocols designed to ensure fairness. Publication requirements and public disclosure laws applicable in certain jurisdictions will be reviewed. Clear communication of selection methodology reduces allegations of favoritism or manipulation. Maintaining records of drawings and notifications provides evidentiary support in the event of disputes. Transparency measures also enhance consumer confidence in the campaign. Establishing structured protocols helps organizations withstand scrutiny.

XIII. Jurisdictional & multi-Region considerations | 2:40pm – 2:45pm 

Promotions conducted nationwide or internationally must account for differing eligibility standards, disclosure requirements, and priorities for enforcement. This portion explores compliance coordination across states and regions, including conflict-of-law considerations. International expansion introduces additional regulatory hurdles, including advertising restrictions and prize delivery limitations. Attorneys must evaluate whether a single rule set can satisfy multiple jurisdictions or whether localized modifications are required. Proactive jurisdictional analysis reduces regulatory friction. Multi-region campaigns demand careful planning and cross-border awareness.

XIV. Avoiding misleading advertising & consumer harm | 2:45pm – 3:00pm

Promotional claims must be evaluated carefully to avoid deceptive practices or bait-and-switch tactics. This discussion examines how material omissions, exaggerated representations, or unclear disclosures create consumer harm and enforcement exposure. Handling disputes and responding to consumer complaints in a structured manner reduces reputational damage. Preventative review of marketing materials supports compliance with consumer protection standards. Aligning promotional messaging with operational reality is essential. Attorneys play a critical role in mitigating these risks before launch.

XV. Special rules for highly regulated industries | 3:00pm – 3:10pm

Promotions in industries such as alcohol, cannabis, tobacco, pharmaceuticals, and financial services are subject to heightened regulatory scrutiny. This portion reviews age restrictions, advertising limitations, required approvals, and licensing considerations specific to these sectors. Vendor and partner compliance obligations may also apply, increasing operational complexity. Regulatory agencies in these industries often impose stricter promotional boundaries. Attorneys must ensure that campaigns align with both general promotional law and industry-specific rules. Careful compliance planning is essential to avoid severe penalties or enforcement actions.

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