Massive Undercover Police Sting Targets Businesses in Orange County, NY

Police have released the results of an undercover operation that targeted 24 retail establishments in Middletown, New York.

Since 2019, anyone purchasing tobacco products in New York has been required to show identification stating they are 21 or older. For as long as New York law has stated that anyone under the age of 21 is prohibited from buying alcohol or tobacco products, there have been places where the law isn't enforced.

Underage Problems in New York

The ongoing problem of minors under the age of 21 attempting to purchase items including tobacco and alcohol isn't new, nor is it something local police aren't aware of and attempting to enforce.

Police Target Businesses in Middletown, NY

A recent example of enforcement happened in Orange County, NY, last week when the City of Middletown Police Department (MPD) conducted an "enforcement detail" to ensure that some of its local retail establishments that sell tobacco products were requiring proper identification for anyone attempting to make a purchase.

The detail was conducted on Thursday, June 19, 2025, and consisted of undercover agents under the age of 21, who visited 24 businesses within the City of Middletown to attempt to purchase a tobacco-related product.

4 Businesses Sold to Minors

According to the MPD, 4 of the 24 establishments allowed the undercover agent to buy the tobacco product, leading to four arrests. The employees, who weren't identified by name, were arrested and charged with Unlawfully Dealing with a Child in the Second Degree, a Class B misdemeanor.

SEE ALSO: Health Care Company Announces Layoffs in Middletown, NY

The following stores in Middletown sold to the undercover agent:

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

MPD did point out that this isn't the first time they've conducted an operation similar to this, saying,

"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 2 individuals were charged for failing to require proper identification."

 

Most Businesses Follow the Law

Police also highlighted that the "overwhelming majority" of the stores they visited in both operations properly followed the law and required individuals to provide identification to purchase alcohol and tobacco.

MPD thanked those businesses for "helping protect the young members in our community!" Here is the full list of the businesses checked in the tobacco operation...