Undercover FBI Agents Helped Autistic Teen Plan Trip to Join ISIS

Humzah Mashkoor had just cleared security at Denver International Airport when the FBI showed up. The agents had come to arrest the 18-year-old, who is diagnosed with a developmental disability, and charge him with terror-related crimes. At the time of the arrest, a relative later said in court, Mashkoor was reading “Diary of a Wimpy Kid,” a book written for elementary school children.

Mashkoor had gone to the airport on December 18 to fly to Dubai, and from there to either Syria or Afghanistan, as part of his alleged plot to join the Islamic State. The trip had been spurred by over a year of online exchanges starting when Mashkoor was 16 years old with four people he believed were members of ISIS. According to the Justice Department’s criminal complaint, the four were actually undercover FBI agents. As a result of his conversations with the FBI, Mashkoor could face a lengthy sentence for attempting to provide material support to a terrorist organization.

At an initial court hearing, family members said that Mashkoor, who had turned 18 just a few weeks prior to the arrest, had intellectual difficulties and been diagnosed with autism. Despite acknowledging Mashkoor’s family support and his young age, the judge ordered that he be detained while awaiting trial.

“It’s not lost on this court that Mr. Mashkoor is a young man with possible mental illness and the diagnosis of high-functioning autism. It is clear he has a sea of familial support,” the judge said. “But based on this evidence, there’s no reasonable assurance here that the court can simply chalk all this up to the defendant simply being a young man.”

Law enforcement agents first became aware of Mashkoor’s online activities in support of ISIS in November 2021. But instead of alerting his family, Mashkoor’s lawyers told The Intercept, FBI agents posing as ISIS members befriended him a year later and strung him along until he became a legal adult.

“It is appalling that the government never once reached out to his parents, even while they were sending undercover agents to befriend him online starting when he was 16 years old,” said Joshua Herman, a defense attorney representing Mashkoor. “Almost all of the conduct he is alleged to have committed took place when he was a juvenile.”

“It is appalling that the government never once reached out to his parents, even while they were sending undercover agents to befriend him online starting when he was 16 years old.”

More details may emerge on the circumstances of Mashkoor’s ill-fated attempt to join ISIS, but the facts as laid out in the complaint are hallmarks of terrorism prosecutions based on FBI stings: a young man with developmental disabilities, already on the police’s radar due to mental health episodes and conflicts with family, groomed as a minor over a long period by a group of undercover FBI agents. Mashkoor’s case also follows a pattern of FBI sting operations in which a teenager is arrested shortly after their 18th birthday. As in similar cases, the court documents suggest that Mashkoor was limited in his ability to execute a terrorist plot on his own.

“This case appears consistent with a common fact pattern seen in tens, if not hundreds, of terrorism-related cases in which the FBI has effectively manufactured terrorist prosecutions,” said Sahar Aziz, a national security expert and law professor at Rutgers University. “In this case, it was a 16-year-old kid who otherwise would have just sat in his relatives’ basement posting offensive content in a manner similar to a white supremacist or Proud Boy — people whom the FBI does not spend enormous resources to entrap just so they can get a high-profile press release.”

Known to Police

Mashkoor first came onto the authorities’ radar for social media posts around the time of his 16th birthday. According to the complaint, Mashkoor began posting in support of terrorism in November 2021, and a platform he used alerted the FBI of suspicious activity.

In July 2022, local police were called to Mashkoor’s home after he allegedly assaulted a family member during a dispute. At the time, according to court filings, a relative told police about Mashkoor’s mental illness and autism diagnosis. Two months later, Mashkoor began communicating with an undercover FBI agent posing as a member of ISIS.

That agent eventually introduced Mashkoor to three other FBI agents impersonating ISIS members. With their encouragement, Mashkoor developed a plan to support the terror group. Along with extensive discussions of what types of services he might provide ISIS, Mashkoor regularly confided in the agents about his boredom, family problems, hopes of getting married, and struggles with his mental health. He constantly referred to being a minor, complaining that being under 18 and subject to the monitoring of family members made it hard for him to travel or send funds, including cryptocurrency transactions that he could not figure out how to conduct.

Mashkoor’s anxieties come through in the chats included in the indictment — most of which are limited to his sides of the conversations. At one point, he told an agent that he was considering finding a wife who might be willing to join him in Afghanistan, but he worried about the possibility of abandoning her if he was killed.

Mashkoor went back and forth about whether he even wanted to join ISIS.

Mashkoor also went back and forth about whether he even wanted to join ISIS. Throughout the chats with the undercover agents, Mashkoor expressed support for ISIS and fantasized about fighting with militants abroad. But he also shared doubts about joining the group as well as concerns that he lacked connections of his own in Afghanistan and Syria. In one message, he worried that “the brothers there might not support me in getting married and may just strap something on me and throw me out into the field.” He may, he suggested at one point, instead get a job and finish high school.

In early December, Mashkoor failed to show up to a flight he had booked to Dubai. It’s unclear whether his apprehensions played a role; he told the FBI agents that he had come down with Covid.

“The whole case demonstrates the low level of maturity and social skills often found in people who suffer from autism,” said Thomas Durkin, one of Mashkoor’s lawyers. “He is fantasizing and making up plans to go to Afghanistan that he could not possibly realize on his own.”

In their conversations, agents warned Mashkoor that “life won’t be easy” after joining ISIS, while continuing to offer to help plan his journey. Despite second thoughts, Mashkoor eventually appeared to take the FBI up on their offer and went to the airport weeks after he turned 18.

“Staying here even another second is torture and I’ve only been putting up an act to please those around me,” he had told one of the agents. “But what will any of it matter once I’m 18 and gone.”

Security fencing outside FBI headquarters in Washington, D.C., on Aug. 22, 2022.

The FBI’s Terror Plan

Throughout the period that he was under investigation, it’s unclear how much meaningful contact Mashkoor had with actual members of ISIS. When he originally came onto law enforcement’s radar, he was alleged to have been in communication with other supporters of the group, some of whom were later arrested in foreign countries.

At one point during the investigation, he gave an undercover FBI agent contact information for someone he said he had found in an online ISIS publication. That individual, unnamed in court documents, solicited cryptocurrency from the undercover agents and appeared to offer them assurances that it was possible to travel to ISIS territories. In conversations with an agent, Mashkoor also alluded to an ISIS contact who had suggested he conduct an attack in the U.S., but Mashkoor said he preferred to travel abroad.

But Mashkoor’s most substantive planning — the actions that landed him under a federal terrorism indictment — took place entirely with the group of undercover FBI agents who were in close contact with him over several months, testing the willingness of a vulnerable young man to commit a crime.

“It’s clearly a waste of government resources,” said Aziz, the law professor. “If there was a serious terrorist threat in America, the FBI would not be spending its time entrapping a mentally ill minor.”

The family member who went with Mashkoor to the Denver airport the day he was arrested had been unaware of his plans, according to court documents, and did not know why he was leaving the country. In one of his final conversations with an FBI agent, Mashkoor had worried about his upcoming trip and the toll it would have on his family. He asked the agent whether it would be permissible to leave behind a message for them. As he told another agent, he had tried “to think of something to say” to his father, but whenever he tried to convey that he was leaving for good, his “throat clenches and nothing comes out.”

“My family know I am leaving but don’t know why and they are very sad and it’s been having a toll on my mental health,” Mashkoor told the agent. “I don’t know how to properly say my final goodbyes to them or how to convey the reasons why I left without compromising myself.”