ABC News

Among the most combative Twitter accounts supporting the Islamic State as its fighters stormed through Iraq last summer was one called @AmreekiWitness. With a profile photo of an ISIS flag flying over the White House, the account's bio told followers it was “dedicated to raising awareness about the upcoming conquest of the Americas, and the benefits it has upon the American people." (Amreeki means American in Arabic.)

With more than 4,000 followers and 7,000 tweets, it tweeted a stream of pro-ISIS rhetoric, calling for the death of infidels and suggesting that jihadists use bitcoin to raise money anonymously. @AmreekiWitness, which has since been suspended, even got into a tweet war with a U.S. State Department account:

https://twitter.com/ThinkAgain_DOS/status/497068852824784897

https://twitter.com/ThinkAgain_DOS/status/497416497229492225

As it turns out, the person writing the tweets was not some grizzled militant but a 16-year-old kid in northern Virginia.

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On Friday, that kid—Ali Shukri Amin, now 17—was sentenced to more than 11 years in prison for providing "material support" to ISIS by helping a high school friend travel to Syria to join the terrorist group, and by his prolific tweeting. He also will face lifetime monitoring of his internet use.

Amin, the youngest person ever to be successfully prosecuted as an adult for giving material support to a terrorist group, according to his attorneys, pled guilty to the charges in a June following a plea deal. He's one of more than 60 people who have been charged with Islamic State-related crimes in the U.S.

Court files, including letters to the judge from family members and teachers of Amin, paint a picture of how a disaffected young man feeling alienated from his family and questioning his faith fell into an online network of jihadist supporters.

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Amin immigrated with his mother from Sudan to the U.S. when he was 18 months old. He only met his father once, for a week-long visit at age four. He was a sickly boy, according to family members, suffering from Crohn's Disease and other ailments. He didn't have many friends, and slept in his mother's bed until age 13, she writes.

He was bright, and was accepted into a rigorous college-prep program. After a flareup of his Crohn's forced him to quit the program after a few months, however, he fell into a downward spiral, and eventually moved out of his home to stay with relatives for two months.

At the same time he was clashing with his mother and his new stepfather, he began to get more and more interested in his faith. But when he had questions about Islam, “the adults in my life could not provide adequate answers or seemed too busy to try,” Amin wrote in his letter to judge Claude Hilton. People he met on the internet “filled in the gaps and provided increasingly radical answers to my questions.”

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Reaching out to people on Twitter, he eventually started talking online with a group of older men around the world who supported ISIS. One of the men, who lives in Finland and is named Abdullah, told the Daily Caller that he communicated with Amin over Kik, WhatsApp, and Skype, at times talking daily. “We were like hipsters,” Abdullah, who has since renounced the terrorist group, said. “We supported ISIS before it was popular. We weren’t floating with the trend.” Another contact was “a South African jihadist who treated Ali like a son,” according to the defense filing.

Ali began the @Amreekiwitness account on June 26, 2014—just days before the group announced its plans to create an Islamic State. He was soon tweeting and blogging about infidels and traveling overseas. He urged ISIS to create its own official website "ASAP," arguing that the group needed a single place to post its media. He operated an ask.fm account answering questions about jihad.

He also wrote blog posts in Arabic about bitcoin and encryption software, encouraging supporters to use the technologies to raise funds. It's not clear how in-depth these postings went—one of Amin's former teachers who read them wrote to the judge that they appeared to be simply summarizing what could be found online.

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“There’s not a single dime that has been raised by his bitcoin ideas,” Amin's attorney, Joseph Flood, told Fusion. "He’s a very, very naive, simple, emotionally immature kid."

In January, Amin also helped an 18-year-old high school classmate, Reza Niknejad, fly to Turkey in order to join the group. He rode in the same car Niknejad took to the airport, and told him what to do when he got there, according to the statement of facts. With a third friend, he later delivered a letter from Niknejad, who is believed to be in Syria, to his parents.

That, Flood said, was the big mistake—if it was just tweets, he could argue that what he said was protected speech, as other defendants accused of supporting ISIS have done. But helping someone join a terrorist group is a way of providing material support to the group.

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“Where the First Amendment ends and crimes begin is fuzzy enough that it’s not really clear if any of his communications really crossed the line,” Flood said. “But he did other things that constitute criminal behavior… such as riding in the car with someone who left the U.S.”

When Amin's parents first searched his computer and found that he was chatting online about ISIS, they were terrified. They eventually brought him to the police to admit what he was done. But the FBI was already monitoring him, and he was arrested a month later, in February.

The length of his sentence—for someone so young and with no criminal history, who never made any move to personally leave the U.S. or plan any kind of attack—might make future parents think twice before turning their kids in to the authorities.

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Niknejad is now being charged in absentia. But it's Amin who will be going to prison for more than a decade.

“Any unpopular cause—and I think right now ISIS is the current cause du jour—anyone who expresses sympathy for them is on a bulls-eye,” Flood said.

There's a chance that Amin could get out of prison early if he cooperates with the government. Twice in the 10 days before the sentencing, he provided “evidence and information in connection with terrorist investigations abroad led by agents from foreign countries,” according to the defense filing.

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"I am deeply ashamed for becoming so lost and adrift from what I know in my heart is right," Amin wrote in his letter to the judge. "I became absorbed in a 'virtual' struggle while disconnecting from what was real: my family, my life, and my future."

Related: Do this man’s tweets, eBay purchases, and WhatsApp messages make him a terrorist?

Casey Tolan is a National News Reporter for Fusion based in New York City.