Massive Undercover Police Sting Targets Tobacco Sales in Orange County, NY

In a recent effort to curb the sale of tobacco products to minors, the City of Middletown Police Department (MPD) in Orange County, New York, conducted a large-scale undercover sting operation targeting 24 retail businesses. The operation, held on Thursday, June 19, 2025, aimed to enforce compliance with state laws that prohibit the sale of tobacco products to individuals under the age of 21.

Background: Tobacco Laws in New York

Since 2019, New York State law has required all individuals purchasing tobacco or vaping products to be at least 21 years old and to show valid photo identification. Despite these regulations, underage access to tobacco remains a persistent issue, particularly in communities where store policies are not strictly enforced.

Recognizing this ongoing problem, local police departments across New York have ramped up their efforts to identify and penalize businesses that fail to comply with the law.

The Operation: Undercover Agents and Surprise Visits

The June 19th operation in Middletown involved undercover agents under the age of 21 who visited 24 retail locations across the city. Their mission: to attempt to purchase tobacco-related products and determine whether businesses were checking IDs and enforcing the age restriction.

According to the Middletown Police Department, 20 out of the 24 businesses complied with the law, refusing the sale when no valid identification was provided. However, four stores did not follow proper procedures and allowed the underage agent to purchase tobacco products.

Stores That Violated the Law

The following four businesses were found in violation:

Middletown Smoke Shop, 14 Railroad Ave.
Smoke n Vape, 207 Dolson Ave.
Right Stop, 94 Wickham Ave.
Gulf, 220 Dolson Ave.

Employees at each of these locations were arrested and charged with Unlawfully Dealing with a Child in the Second Degree, a Class B misdemeanor under New York State Penal Law. Their identities have not been released at this time.

Previous Compliance Checks

This is not the first time the MPD has carried out such an operation. The department recently collaborated with the New York State Liquor Authority to conduct a similar undercover operation targeting the sale of alcohol to minors. That effort resulted in just two arrests, indicating a high level of compliance among local alcohol retailers.

In a statement following the tobacco operation, MPD emphasized the importance of regular enforcement:

“If you recall, our agency recently conducted a joint operation with the New York State Liquor Authority to test identification compliance with many of the same establishments regarding the purchase of alcohol. In that operation, only two individuals were charged for failing to require proper identification.”

Community and Police Response

The MPD praised the businesses that complied with the law, stating that the “overwhelming majority” of the 24 retailers properly verified the undercover agent’s age and refused the sale of tobacco products without valid ID.

“We want to thank those businesses for helping protect the young members in our community,” the department said.

By highlighting both the successful enforcement and the stores that followed regulations, MPD aims to send a clear message: compliance with state laws is not optional, and failure to do so will result in legal consequences.

What’s Next?

The investigation into tobacco and alcohol sales compliance is likely to continue, with more surprise checks expected in the near future. Police urge local business owners to train their employees properly and ensure that all staff understand the importance of verifying ID before selling age-restricted products.

Retailers caught violating these laws could face not only criminal charges but also penalties from state licensing authorities, including fines or suspension of business licenses.

For now, the MPD’s operation stands as a strong example of proactive community policing, focused on protecting youth from early exposure to harmful substances.