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When a teenage boy identified in court filings as R.K.C. didn’t understand his father, he turned to ChatGPT for help.

“My dad Said that I’m will get a settlement worth of 1million dollar,” R.K.C. said to the chatbot in October 2024, according to court filings. “He said that If that doesn’t make me happy what does. What does he mean.”

The millions of queries Americans pose to artificial intelligence chatbots each day generally stay between them and their AI interlocutors. But R.K.C.’s question and his other intimate conversations with ChatGPT were swept into the public record by defense attorneys responding to a lawsuit he filed in 2023 against Meta, Snapchat, TikTok and YouTube. He argued in the case that the companies’ apps caused him to suffer years of social media addiction and mental health problems.

By late July, R.K.C.’s attorneys had settled with Snap, TikTok and YouTube, and dropped his case against Meta, citing in part concerns about the boy’s ability to go through a “grueling weeks-long trial.” The companies have denied the teen’s allegations. Snapchat owner Snap declined to comment. Meta, TikTok and YouTube did not respond to a request for comment.

R.K.C. is one of a growing number of Americans who have had their private conversations with AI chatbots made public in court. As more people turn to AI for help with work, health issues and for companionship, chatbot operators have become custodians of a fast-growing trove of intimate data that can be sought by law enforcement, or companies or other opponents in civil litigation.

A Washington Post review of public records and local news stories found that chatbot logs were cited in 12 court cases over the past two years. It’s hard to know how often chatbot material is drawn into investigations and legal proceedings more broadly, because police, and parties in civil cases, don’t have to present in court all the evidence they obtain.

“A fifteen-year-old may type things into a chatbot that he may not say to a therapist, a parent, or a friend, and he does it without realizing that it could end up in a defense expert’s report,” Mike Morgan, a partner at Morgan & Morgan, one of the law firms that represented R.K.C., said in a statement. The teen’s ChatGPT logs had “no bearing” on how the case was resolved, Morgan said. R.K.C. will turn 16 at the end of August.

In some cases, AI companies have reported people on their platforms to the FBI, leading to prosecutions and at least one conviction.

In May, the FBI notified police in Palm Beach County, Florida, that it had been contacted by ChatGPT-maker OpenAI after a user had since March repeatedly told the chatbot of his plans to rape and murder his ex-girlfriend, according to a police affidavit. The user, identified in court documents as Darren Zhou, had allegedly spent months describing how he would violently harm his ex-girlfriend, including how he planned to wait outside her car for her to return from volleyball practice to shoot her. Zhou also allegedly told the chatbot that he planned to harm himself, the documents said.

Local police identified the woman based on information forwarded from the FBI and learned that Zhou had been sending her anonymous texts since they broke up, with messages such as “Cant wait to smell you,” according to court documents.

Zhou was arrested in May and charged with stalking and making electronic threats on the basis of his messages to his ex-girlfriend and to ChatGPT, which police said in court documents reinforced the credibility of the threats. He pleaded guilty this month and was sentenced to eight years of probation. An attorney for Zhou declined to comment.

OpenAI has said the company uses software to scan conversations for signs of dangerous behavior and flag them to human reviewers. If a reviewer determines a chat indicates “an imminent and credible risk of harm to others,” they report the user to law enforcement, the company said in an April blog post. A spokesperson for OpenAI declined to disclose how many times the company had reported users to police. (The Post has a content partnership with OpenAI.)

Number of user accounts from which OpenAI disclosed content such as ChatGPT conversations to law enforcement or government agencies.

The personalized nature of conversations with chatbots, creating an atmosphere of privacy that encourages frank disclosure, can make logs held by AI companies richer than more conventional digital evidence such as search logs, according to legal experts.

“It’s not just the question, it’s the whole prompt and the background you provided and the back and forth. There’s no guessing at what your thought process is and what you intended, it’s very plain,” said Michael Price, the litigation director for the Fourth Amendment Center at the National Association of Criminal Defense Lawyers.

“If ever there was a window into the soul to reveal the privacies of life, this seems like a good one,” he said.

‘Is there any way they could know’

Data released by OpenAI shows requests by government agencies and law enforcement for user data growing rapidly. In the second half of 2025, the company disclosed data from more than 80 accounts, an increase of more than four times as many over the same period the year before.

But when chatbot conversations show up in criminal cases, it’s often because the person involved in the chats allowed law enforcement to access them, Price said. When police ask someone to open their phone during questioning or after an arrest, they often do so, allowing officers to scroll through the apps they use, he said.

In general, the Fourth Amendment, which protects people against unreasonable searches and seizures of their property, provides the right to refuse a search of the contents of their phone unless police have a warrant.

“The short answer is that most people consent,” Price said. “They shouldn’t, but they do.”

In September 2025, police in Springfield, Missouri, woke Ryan Schaefer, then a student at Missouri State University, according to an arrest warrant and police report. He was suspected of damaging 17 cars in a campus parking lot late one night the previous month, the police report said. After police arrived, Schaefer agreed to allow them to search his phone, according to the report.

“How f—-d am i bro,” he wrote into ChatGPT around 3:47 a.m. the night of the incident, according to the police report. “What if i smahsed the s— oitta mutlipls cars.”

“Is there any way they could know it was me,” he later added, according to the report.

Schaefer was arrested several days later based on those statements, according to the police report and his arrest warrant. He later pleaded guilty to felony property damage, and in July a county judge sentenced him to five years of probation.

“In Ryan’s case, it wasn’t the exception,” said Adam Woody, one of Schaefer’s attorneys. “What these conversations show is, it’s an intimate look into the individual. It’s their thoughts and feelings that they don’t believe anybody else is going to see.”

In civil litigation, conversations with a chatbot can be collected during the discovery process, which can allow broad searches of the devices of people involved in a case. In one Michigan case, an attorney for a tire salesman sued by his former employer last year volunteered a complete search of his client’s devices as a show of transparency after several months of discovery, according to court filings.

The employer, which alleged the salesman had solicited its customers after leaving to work for a rival, seized on a conversation in which he had asked ChatGPT whether his email provider could recover deleted emails, according to court records.

“I deleted a email a year ago from my yahoo account. Can yahoo still retrieve the email?” the salesman asked the chatbot, according to the court filings. “So even with a court ordered subpoena yahoo cannot retrieve the deleted email?”

The employer argued in court that the conversation undermined the salesman’s claim that he had not electronically signed a noncompete agreement while working for the company. His chatbot conversations, which took place after the case began, indicated he had tampered with evidence, the company said.

In August, a judge awarded the employer an undetermined amount of attorneys’ fees for extra work performed as a result of the salesman’s conduct, which she ruled was “compelling evidence” of intentionally holding back information.

The judge allowed the lawsuit to proceed with further discovery. Attorneys for both sides declined to comment.

No legal protections

OpenAI CEO Sam Altman has argued that conversations with chatbots should receive special legal protections, similar to conversations between clients and their attorneys.

“If you talk to a doctor about your medical history or a lawyer about a legal situation, we have decided that it’s in society’s best interest for that information to be privileged and provided higher levels of protection,” he wrote last year. “We believe that the same level of protection needs to apply to conversations with AI which people increasingly turn to for sensitive questions and private concerns.”

Chatbot conversations don’t currently have such protections, said Laura Abelson, a law professor at Southern Methodist University who is an expert in evidence rules. “In an unregulated space it’s very unlikely that any court is going to find that these communications are privileged,” she said.

That’s what a federal judge in New York ruled in February in the case of a financial executive who, after learning that he was the subject of a federal criminal investigation for fraud, consulted the AI model Claude about potential defense strategies.

The executive, Bradley Heppner, argued that prosecutors could not examine the conversations, which were obtained from his devices as part of a broader search warrant, because they were privileged, according to the judge’s ruling. But the judge said that protections for conversations between clients and their attorneys did not apply: Claude is not a lawyer, and the executive’s attorneys did not ask him to talk to the chatbot.

In May, Heppner was convicted of securities fraud and wire fraud, among other charges. Attorneys for Heppner did not respond to a request for comment.

In a handful of publicly known criminal cases, AI companies have taken it upon themselves to tell authorities about information users have shared with their chatbots.

In addition to the Florida stalking case, OpenAI told the FBI earlier this year about a man in Brazil who told the chatbot he wanted to hire a hit man to kill him and his 8-year-old son. The FBI passed on the information to Brazilian authorities, who arrested the man, according to a report from the BBC. OpenAI declined to comment on the incident.

After the deaths by suicide of some heavy users of ChatGPT and shootings by other users in Canada and Florida, OpenAI has said it will be more proactive about flagging potentially concerning conversations to authorities. In September 2025, the company introduced parental controls following the death by suicide of Adam Raine, 16, who had discussed his plans for self-harm with ChatGPT.

In Florida, state officials have sued OpenAI and opened a criminal investigation into the company. The company has also been sued by families of victims of the shootings in both Florida and Canada, who alleged that OpenAI failed to implement adequate safeguards.

OpenAI had banned the account of the alleged perpetrator of the February mass killing in Tumbler Ridge, British Columbia, for violating its policies, but declined to report the conversations to Canadian authorities. Altman later apologized for not alerting law enforcement. The alleged shooter at Florida State University, where two people were killed, had discussed a mass shooting with ChatGPT.

OpenAI has said that it was not responsible for the Florida State case and that it has a “zero-tolerance policy” for use of its tools for violence.

As AI becomes a bigger part of everyday life, its use as evidence and in trials is likely to become more prevalent. Surveys and company data suggest that more people are turning to chatbots with personal questions and that AI “agents” that take action on behalf of users and require greater data access are becoming more popular.

Chatbots are “just the tip of the iceberg,” said Andrew Ferguson, a law professor at George Washington University and the author of a book about digital surveillance. He expects AI to open much more of people’s lives to digital scrutiny. “Your entire world is going to now be available for police.”