“Not-Quite-Gambling”: The Fast-Growing Gray Zone Regulators Can’t Ignore

Across North America, gambling regulators are facing a new class of products that look, feel, and behave like gambling, but are engineered to avoid being regulated as gambling. The result is a widening enforcement and policy gap: consumers experience wagering-like risk and reward, yet regulators may lack clear jurisdiction, licensing hooks, data visibility, and responsible-gambling levers.

This “not-quite-gambling” trend is not a single product category. It’s a playbook, 1) Structure the offering so it resembles “promotional contests,” “social play,” or “financial event contracts,” then, 2) Scale quickly through digital distribution before statutes and policy catch up.

In the following analysis, we take a look at what “not-quite-gambling” means in practice, where it’s showing up in U.S. and Canadian markets right now, and how regulators are likely to respond—plus how modern gambling control platforms like POSSE GCS can help agencies move from reactive whack-a-mole to durable oversight.

What counts as “not-quite-gambling”?

1) Sweepstakes-style “casinos” (dual-currency models)

These platforms commonly use two virtual currencies—one for “fun play,” another that can be redeemed for cash or prizes—while claiming they are lawful promotions rather than gambling. In many jurisdictions, operators lean on “no purchase necessary” mechanisms and contest/sweepstakes law framing to argue they are outside gambling statutes.

Regulators’ concern is straightforward: the consumer experience can mirror online casino play (slots/table games), but without the guardrails required of licensed operators (KYC/age verification, RG tools, integrity controls, complaints pathways, AML expectations, etc.).

U.S. example: In June 2025, the New York Attorney General, working with the New York State Gaming Commission, announced action to stop online sweepstakes casinos operating in New York, describing platforms using virtual coins exchangeable for cash and prizes.

Canada example: Major sweepstakes operators have also adjusted their Canadian posture amid growing scrutiny. For example, industry reporting in 2025 described Virtual Gaming Worlds scaling back/ending certain offerings in Canada in the context of heightened regulatory pressure in multiple jurisdictions.

2) Prediction Markets: "Event contracts” that resemble sports betting

Another rapidly emerging front is sports-related event contracts offered by entities positioning themselves as federally regulated financial markets rather than gambling. State gaming regulators argue these products function as sports wagering and should be licensed and restricted accordingly; operators often counter that states lack jurisdiction because the product is regulated under federal commodities law.

U.S. example: Reporting through 2025 highlights multiple states issuing cease-and-desist actions and litigation involving Kalshi and similar “prediction market” offerings in the context of sports outcomes. This matters to gambling regulators because it challenges the foundational post-PASPA model: states and provinces set the rules for gambling within their borders. Prediction markets introduce a credible “preemption” argument that, if expanded, could undermine state/provincial licensing regimes.

3) Gamblification mechanics in adjacent products

While this analysis focuses on “not-quite-gambling” impacting gambling regulators, it’s worth noting the adjacent pressure from randomized monetization mechanics (e.g. loot boxes/gacha), where consumer harms can resemble gambling harms. Research and evidence centers continue to track gamblification harms and the regulatory difficulty of enforcement in practice.

Why regulators are concerned

“Not-Quite-Gambling” tactics scale faster than regulation

Digital distribution, influencers/affiliates, and app-store style growth mechanics allow gray-market offerings to hit scale before regulators can align definitions, enforcement authority, and inter-agency coordination.

“Not-Quite-Gambling” tactics create “shadow gambling” without the accountability stack

Licensed gambling typically comes with required controls (licensing suitability, audits, game integrity, geolocation, player protection, AML, self-exclusion coordination, dispute resolution). “Not-quite-gambling” offerings can deliver similar risk/reward dynamics while evading the accountability stack—raising consumer protection and public confidence risks.

“Not-Quite-Gambling” tactics blur jurisdiction and fragments enforcement

Even when regulators believe an offering is gambling, enforcement can involve multiple actors: gaming commissions, attorneys general, consumer protection agencies, financial regulators, and sometimes federal agencies or courts. That fragmentation slows outcomes and creates inconsistent precedent.

Current “not-quite-gambling” examples in the U.S. and Canada

United States: crackdown momentum, but uneven outcomes

  1. Sweepstakes casinos: Enforcement actions, subpoenas, and state legislative activity have accelerated. New York’s 2025 action is a prominent illustration of state authorities using consumer protection and gaming law tools against sweepstakes-style offerings.

  2. Prediction markets: Multiple states have taken steps to restrict sports-related event contracts, while operators test the boundaries in court. A Reuters report in late 2025 underscores how contested the jurisdiction question has become.

Canada: dual reality—regulated markets plus broad unregulated access

Canada’s framework is distinct: provinces “conduct and manage” gambling, with Ontario operating a unique private-market iGaming model. At the same time, Canadians can still access a wide range of unregulated online offerings (including sweepstakes-style sites), creating a persistent “oversight gap” and pressure on regulators to act through advertising, payments, and platform accountability measures.

A concrete Canadian signal is Ontario’s public stance urging media platforms to stop promoting unregulated online gambling sites—an approach that targets the distribution and acquisition layer, not just the operator.

What regulators are likely to do next: tactics and approaches

No single lever solves “not-quite-gambling.” Expect a layered response that combines law, enforcement, market messaging, and platform pressure:

1) Tighten statutory definitions and “functional tests”

Regulators and legislatures will increasingly define gambling by function, not labels—focusing on whether the player is risking value for the chance at a prize, how redemption works, and whether consideration is present in practice (even if “no purchase necessary” exists on paper). This reduces the ability of operators to arbitrage loopholes through product design.

2) Coordinate with Attorneys General and consumer protection agencies

The New York sweepstakes action is a template: use AG powers (unfair/deceptive practices, consumer fraud statutes) in tandem with gaming expertise to move quickly.

3) Focus on “chokepoints”: payments, platforms, and advertising

Rather than chasing every operator domain, regulators will pressure:

  • Ad networks / media platforms (Ontario’s approach),
  • payment processors, and
  • platform distribution (app ecosystems, affiliate networks, influencers).


This is often faster than operator-by-operator litigation and can materially reduce reach.

4) Expand investigative capacity for digital products

Expect more investment in:

  • undercover play and evidence capture,
  • data requests and preservation,
  • cross-border information sharing,
  • technical capability for identifying “substantially similar” clones and rebrands.

5) Build clearer pathways for compliant innovation

Some regulators may offer regulatory guidance or safe-harbor pathways so that borderline offerings can be brought into compliance (e.g., by requiring licensing or restricting redemption mechanics), rather than leaving the market in limbo.

Where POSSE GCS fits: making oversight enforceable at scale

The hardest part of mitigating “not-quite-gambling” isn’t spotting the problem—it’s operationalizing a repeatable response. Modern gambling control software can help regulators treat these issues as a managed workflow rather than a series of one-off fire drills.

As a unified platform for gaming regulators, POSSE GCS supports a streamlined, risk-based model for licensing and enforcement.

In conjunction with robust data-sharing, the practical ways in which systems like POSSE GCS can be configured to support “not-quite-gambling” regulation can include:

Centralized case intake and triage

  • Create a standardized “Not-Quite-Gambling Intake” workflow for complaints, referrals (AG, police, consumer protection), and proactive monitoring of leads.
  • Attach evidence snapshots, URLs, payment rails, marketing creatives, affiliate identifiers, and related entity records.


Entity resolution and “single source of truth”

  • Tie together operators, brands, domains, payment identifiers, key individuals, vendors, and affiliates into a single regulatory graph—so the 12th rebrand still resolves to the same underlying organization.


Risk scoring and prioritization

  • Use configurable risk factors (youth targeting signals, redemption mechanics, volume indicators, prior actions, cross-jurisdiction presence) to prioritize scarce investigative and legal resources.


Inspection, enforcement, and action tracking

  • Track cease-and-desist actions, subpoenas, administrative hearings, outcomes, penalties, and compliance deadlines in one auditable workflow—reducing institutional memory loss and supporting consistent enforcement posture. 


Reporting and transparency

  • Produce consistent management reporting: active investigations, repeat offenders, time-to-action, compliance rates, and recidivism—helpful for executive oversight and legislative briefings.

The forecast: Not-Quite-Gambling becomes a permanent regulatory category

In 2026 and beyond, “not-quite-gambling” won’t disappear; it will evolve. As some states/provinces crack down on sweepstakes casinos, you can expect migration into adjacent models: event contracts, skill wrappers, crypto rails, influencer-led micro-communities, and “prize-based” mechanics that are harder to pin down.

The regulators who will fare best are those who:

  • modernize definitions and policy,

  • coordinate enforcement across agencies,

  • target distribution chokepoints,

  • and build strong operational systems that turn ambiguous products into repeatable regulatory workflows.

That’s the key shift: not just “is it gambling?”—but “can we supervise, evidence, and enforce at the speed the market moves?”