In 2011, Kenneth Hochstein, a federal corrections officer and father of four, responded to Craigslist ads soliciting sex. But the Lake County man says he didn’t know the offer included meeting up with a minor. So when the 46-year-old traveled to a house to see the woman he had been talking with, he was stunned to find a team of undercover cops waiting to arrest him.

A state judge agreed with Hochstein’s side of the story and dismissed his criminal charges, citing errors made by Orange County Sheriff’s Office detectives during the massive child-sex sting which netted 50 arrests from around the state. Hochstein’s experience underpins a federal lawsuit he filed last week alleging unlawful arrest and civil-rights violations. “The problem with these kinds of shows of force, where police go out and go fishing, for lack of a better term, for people who might be child molesters is the way they are going about it,” said attorney Patrick Megaro, who filed the suit in U.S. District Court. “The collateral damage is so great.”

The case raises questions about entrapment, an issue long-fought over by groups seeking to reform sex-offender laws in Florida and across the country. But law-enforcement agencies view the strategy of posting ads in online forums as a way to proactively stop people from sexually targeting minors.

Loriana Fiorino, a detective in the special victims unit with the Orlando Police Department, said entrapment is always used as a defense when her cases go to court. But in the 10 where she’s been called to testify, judges have never upheld the entrapment argument. According to the U.S. Department of Justice, entrapment happens when the government induces someone to commit a crime and the suspect wasn’t predisposed to that behavior.

Fiorino, who frequently posts ads in online groups and before that monitored Internet chartrooms, said law enforcement officials can avoid that problem by waiting for the suspect to make the first move.

“We don’t bring up sex if we posted the ad as children, and we were the ones soliciting,” said Fiorino, who was not involved with Hochstein’s case. “If we are dangling sex in front of people’s face then that could possibly be viewed as entrapment.” She would not elaborate further, saying she did not want to give away investigative techniques.

And it doesn’t matter that officers are posing as children. Florida state law makes clear that a person will be arrested if the minor is an imaginary figure as long as a person travels to meet someone they believe is under 18 and will engage in sex.

The law also includes a provision that makes it illegal for someone to solicit the parent or guardian of a child to have sex with a minor. Both of these issues played a role in Hochstein’s case. The Orange County Sheriff’s Office would not comment due to the pending litigation.

The Clermont man responded to a craigslist post on Aug. 8, 2011 advertising “Your baby is back – w4m – Orlando,” according to arrest records. Hochstein and an undercover agent with the Orange County Sheriff’s Office began chatting and the conversation turned sexually explicit. But the interaction ended after it became clear the ad was also soliciting sex for a 14-year-old girl. During the conversation, Hochstein sent a message saying he was open to anything “as long as they are 18 and up I’m GOOD,” records show.

Two months later, Hochstein responded to a different ad for “Woman in need of help – w4m – 34 (Orlando).” It was posted by the same undercover agent posing as the same woman. Again, the conversation turned sexual. And after a few days of chatting, Hochstein drove to an address that was provided to him by the undercover agent.

In their correspondence, the undercover agent made fleeting references to a 14-year-old daughter and mentioned the pair had chatted before. But it was unclear if Hochstein put the two ads together because he was asking whether the girl was her roommate and seemed generally confused.

That’s why Orange County Circuit Judge Marc Lubet threw out the case. Hochstein had been charged with traveling to meet a minor for unlawful sexual act, solicitation of a minor by computer and lewd or lascivious battery.

Across the country, groups and individuals alike have challenged carefully crafted laws they say can be unjustly applied.

An Indiana teenager labeled as a sex offender and his parents contested his punishment for having consensual sex with a 14-year-old who lied about her age on a dating app. The story made national news and the teenager was issued a new sentence that took him off the list.

But many people living with the stigmatized classification here found themselves in situations similar to Hochstein, said Gail Colletta, president of the Florida Action Committee, a group that seeks to reform the state’s sex-offender laws.

Colletta said she has no problem with law-enforcement officers monitoring ads and conversations on online forums. But she takes issue with investigators who create their own ads and wait for responses to flow in.

“From my opinion, there would be no crime without the efforts of law enforcement,” Colleta said.

After a state judge threw out the case against Hochstein, prosecutors appealed. They later withdrew that action.

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