Substantial jury confusion in an entrapment case led a federal appeals court Monday to order a new trial for a man convicted of shipping child pornography.

A divided panel of the U.S. Court of Appeals for the Second Circuit said the trial of 20-year-old Scott Kopstein in Brooklyn federal court was marred by a poor jury instruction and made worse by supplemental instructions that “could be understood to say that the jury could convict even if the entrapment defense was successful.”

A majority of Judge Dennis Jacobs (See Profile) and Gerard Lynch (See Profile) vacated Kopstein’s conviction and his 66-month prison sentence and remanded to Eastern District Judge Joanna Seybert (See Profile).

Judge Debra Ann Livingston (See Profile) dissented in United States v. Kopstein, 13-417-cr.

Kopstein was a college student in 2009 when he initiated an instant message chat with what he thought was a 12-year-old girl in California but was actually an undercover federal agent.

He sent naked pictures of himself to the agent, who in return send back a photo of a girl in a dress. Kopstein detailed sexual acts he wanted to perform on the girl in the picture, and the agent encouraged him to send images of child pornography.

But Kopstein only sent more pictures of himself, and it was only after the agent chided him for sending only pictures of himself that Kopstein on two occasions sent images of child pornography.

Kopstein was arrested and put on trial in 2011 for three counts of transporting and shipping child pornography.

His attorney, Norman Trabulus, argued that he was entrapped—that Kopstein only sent the pictures because the agent, requesting “good” pictures of “girls,” had implied he would terminate the chat if Kopstein did not comply. The agent, Trabulus said, had induced the transport and the government failed to show Kopstein was predisposed to send the images.

Seybert in 2012 sentenced Kopstein to the five-year mandatory minimum prison term and then added an additional six months because he believed he was shipping the child pornography to a 12-year-old girl.

Writing for the circuit majority Monday, Jacobs explained that a valid entrapment defense required the defendant to present credible evidence that the government induced him. Once that burden was met, Jacobs said, the government must then prove beyond a reasonable doubt the defendant was predisposed to commit the crime anyway.

Here, he said, the government relied on Kopstein’s “ready compliance” or prompt response to agree to commit the offense.

However, Jacobs said that “confusion set in” with the lower court’s instruction on the lesser included offense of possession of child pornography. Seybert told the jury that, if it found the government had not met its burden of proof on any of the elements of the shipping and transporting offense, then before the jury entered a verdict of not guilty to that offense, it had to must determine whether Kopstein was guilty of possession.

The jury, Jacobs said, could have been misled into “thinking it could return a verdict of guilty on the greater offense even if the prosecution had failed to prove a necessary part of its case, simply because Kopstein was guilty of the lesser offense.”

Jacobs said, “This source of potential confusion would recur throughout the instructions.”

The trial court received a “cryptic” note from the jury reflecting “basic confusion about some critical points,” Jacobs said.

“The jury was wondering why it should not ‘render’ verdict for defendant if the government did not ‘disprove the defense of entrapment.’ One might wonder,” Jacobs said. “The jury does not know what it means to ‘disprove the defense of entrapment.’ If it did not understand that, it understood nothing.”

After a long colloquy with the attorneys, Seybert issued a supplemental instruction that Jacobs said added to the confusion through language on who took the “first step” toward the idea of sending the images, language Jacobs said “offered insufficient guidance for the jury to untie the knotty issues of inducement.”

The trial court also made “inconsistent statements on whether the government was required to ‘prove’ or ‘disprove’ entrapment,” he said.

“In sum, the jury instructions compounded the jury’s bewilderment regarding Kopstein’s only viable defense,” he said.

In her 41-page dissent, Livingston had a number of problems with the majority opinion, including its take on the standard of review and its failure to appreciate Kopstein’s failure to object below to the court’s instructions.

The evidence, she said, “overwhelmingly established his predisposition to transport child pornography,” for it was Kopstein, not the agent, who “first raised the prospect,” and that he did so almost immediately after the chat began, acting quickly to send additional images.

“Kopstein also admitted to possessing child pornography and to having numerous sexual chats with girls as young as nine over a three-year period,” Livingston said, and had some 200 images depicting child pornography seized from his computer.

“Simply put, this is a vacatur in search of a justification,” she said.

Trabulus argued the appeal for his client. He declined comment Monday.

Assistant U.S. Attorney William Campos argued for the government.