A dozen businesses, including five in New York City, are being charged with violating state laws regulating the sale of vaping products in what Gov. Kathy Hochul is calling the biggest-ever crackdown of its kind in New York.

“These companies built their business models around breaking New York’s laws and targeting our kids — now, we’re holding them accountable,” Hochul said in a statement Wednesday. “With the largest criminal vape enforcement operation in state history, New York is sending a message: If you sell vapor products in violation of our laws, you will face serious consequences.”

The companies are accused of illegally shipping vaping products via online stores and distribution networks across the state. The overall enforcement action includes more than a dozen arrests and 38 criminal charges following a monthslong investigation by the state health department and state police, Hochul’s office said.

Investigators staged undercover online purchases to charge the businesses with unlawful shipment and transport of vapor products, a misdemeanor that can lead to felony charges in the event of future violations, according to the governor’s office. Many of the shipments contained bright-colored disposable e-cigarettes and e-liquids in flavors designed to appeal to adolescents, according to state officials. Some contained disposal vapes with digital display screens that mimic smartphones, handheld video games and other electronic devices popular with young people, officials said.

“The widespread availability of e-cigarettes and vapor products poses significant public health challenges, with particularly alarming consequences for adolescents such as addiction and damage to their developing brains and lungs,” state Health Commissioner James McDonald said in the release from Hochul’s office. “These arrests are a direct result of the state’s dedication to decreasing vaping, especially among young people.”

State officials said 28 criminal charges in the bust have been filed to date, and 10 more are pending. Additional arrests and arrest warrants are planned this week.

The five companies targeted in New York City include Vaporush, ePuffer, Vape4Style, Beyond Vape and NYC Glass 718. They all either declined to comment on the state action or could not immediately be reached. A representative for ePuffer said its U.S. operations shut down last month.

The other distributors are located on Long Island, in the Capital Region, and in Western and Central New York, according to the governor’s office.

State law prohibits retail sales of flavored vape products, as well as sales of vapor products to anyone under 21 years old. But officials say some businesses have gotten around the rules through online platforms that provide direct delivery and often fail to verify customers’ ages.

State authorities also say they’re also leading school-based and public awareness campaigns encouraging young people to avoid or quit vaping.