Samir Khan needed a computer "as soon as possible."
In October 2009, the Charlotte, North Carolina–based blogger traveled to a store with two other men — one who was wearing camouflage, one who was wearing a prayer cap — and purchased a white ACER laptop and a travel adapter. He declined a salesman's offer for an extended warranty plan.
The salesman suspected the men "were up to something" after Khan bought the travel adapter and then spoke to the two other men in a language the salesman assumed to be Arabic.
By the time an FBI special agent interviewed the salesman later that month, Khan had left the United States for Yemen, where he planned to meet up with Anwar al-Awlaki, a radical preacher who the US government later identified as the "leader of external operations" for al Qaeda in the Arabian Peninsula, commonly referred to as AQAP.
These tidbits of new details about Khan's last days in the US — he was killed with al-Awlaki in a notorious CIA drone strike in September 2011 — emerged in hundreds of pages of FBI documents [pdf at the end of this story] turned over to VICE News in response to a Freedom of Information Act (FOIA) request. This is the seventh installment in our long-running series about the FBI's investigation of Khan, a US blogger turned "global extremist." The FBI has identified tens of thousands of pages of records and has been releasing the Khan files to VICE News on a rolling basis. The bureau withheld more than 700 pages from the latest release citing a threat to national security and other exemptions.
Khan, who an FBI agent characterized in the documents as a "frustrated misfit," was the founding editor of al Qaeda's English-language Internet magazine, Inspire. He penned numerous articles for the publication, including one about how to build improvised explosive devices "in the kitchen of your mom" that apparently inspired the Boston bombers and may have also been the instructional manual the San Bernardino shooters used to build pipe bombs. The way Khan recruited followers via his blog, Inshallahshaheed — an Arabic phrase that means "Martyr, God willing" — chat rooms, and the articles he wrote for Inspire was adapted by the Islamic State and has proven difficult for federal law enforcement and intelligence agencies to counter.
'Khan is a man of words and a fanatic who, based on his ideology, history and recent events, may possibly present a violent danger in the future.'
Khan had been under FBI surveillance for three years. He landed on the FBI's radar after he authored incendiary blog posts supporting violent jihad, terrorist groups like al Qaeda, and the death of Americans. Over the years, the FBI collected evidence that showed Khan graduated from spouting anti-American rhetoric to recruiting people to make jihad abroad and that he may have been planning to martyr himself.
But when he left the US, the FBI's surveillance of Khan apparently ended, much to the dismay of the Charlotte field office agents who had been trying to build a terrorism case against him for years.
"Khan is gone," a government employee wrote in a heavily redacted email to another government employee. The employee apparently had been responding to a request for approval to extend surveillance or wiretapping of Khan. (Presumably both employees work for the FBI, but their names and the identities of the government agency for which they work was redacted.)
"It could be for electronic surveillance, it could be for a number of different techniques where you have to get headquarters approval," said Martin Reardon, a former FBI counterterrorism agent who currently serves as the vice president of the New York City–based security intelligence firm the Soufan Group. Reardon reviewed the FBI files for VICE News.
Still, the FBI seemed intent on working with a major new source it cultivated that was going to require "significant funding" in order to deal with Khan once he left the US, according to a set of files the FBI previously disclosed to VICE News.
"Can we get your blessing on this," an FBI agent wrote in an email outlining what appears to be a plan for dealing with Khan. Another FBI agent responded, saying it seemed "like a good plan." It's unclear whether it was approved.
What has long remained a mystery is how Khan was able to leave the US while being under FBI scrutiny. Did the FBI allow him to leave and travel to Yemen, or did he slip out of the country undetected?
The new FBI files for the first time show that the bureau knew in advance that Khan was planning to travel to Yemen. In a December 2, 2009 FBI report, an FBI agent wrote, "Plans by North Carolina based extremist USPER [US person] Samir Khan to travel to Yemen in September 2009 was released."
One FBI report dated November 3, 2009 contained an FBI agent's analysis of Khan's "radicalization." The report said Khan was a "man of words and a fanatic who, based on his ideology, history and recent events, may possibly present a violent danger in the future."
The same report said Khan's friends were also worried about what he may do after he left the US.
"Individuals close to Khan have expressed concern that Khan may become a martyr and he himself has indicated an interest in becoming a martyr," the FBI agent wrote. "Finally, in October 2009 Khan traveled to Yemen with the possible intention of making hijra."
Reardon told VICE News the FBI agent who tried to connect hijra with martyrdom misunderstood what it was.
"He said that a few times in the files, 'making hijra' in the context of being a martyr," Reardon said. "Hijra is a totally legitimate religious obligation. It takes place in Saudi Arabia, in Mecca. There's nothing terrorist about it. I was just surprised that he did that, that's sort of like how-to-intelligence 101."
An FBI "liaison contact" interviewed by an FBI special agent from the Charlotte field office on November 10, 2009 described Khan as "calm and quiet" and in need of "help" due to his "lack of knowledge about Islam."
Yet a November 12, 2009 FBI report said Khan had developed a "strategy" of instilling "fear in non-believers, a common goal of Khan's efforts."
Reardon, who used to run the FBI's 24/7 Terrorist Screening Operations Center, said that even though Khan was under FBI surveillance and was the subject of an FBI terrorism investigation, it would not have been difficult for him to leave the country. And, despite the fact that the FBI had prior knowledge of his travels, the bureau would not have been able to stop him.
"In 2009, there were two options for a terrorism subject: You are either put on a watchlist or you're put on a no-fly list," Reardon said. "If you're put on a no-fly list, you're not going to be flying in the United States and you're not going to be flying international. At the time, in order to be on the no-fly list, you had to be considered a danger to aviation security. That was changed in 2010 to danger to aviation security, operationally capable, or anyone who has been trained at a terrorist camp overseas. Most terrorism subjects are not considered dangerous to aviation security and… are not even operationally capable. They have support capabilities. So most terrorist subjects are not put on a no-fly list. They're put on a watch list. And all a watchlist [means] is you're subject to secondary screening."
Once he arrived in Yemen, the FBI's Charlotte field office struggled to determine with who Khan was associating. Agents sought "any available intelligence on Samir Khan, to include his current whereabouts, current activities, and the identification of his associates" from FBI headquarters' counterterrorism division.
An FBI report, dated November 19, 2009, said if it turned out Khan had contacted "known extremists overseas, this information will be used to request immediate assistance from OGAs [other government agencies]," such as the CIA.
Several FBI reports in the new batch of files link Khan and al-Awlaki and suggest the two had extensive communications before Khan traveled to Yemen. What they discussed, however, remains a mystery due to the vast swaths of redactions in the documents.
On September 30, 2011, armed drones operated by the CIA fired hellfire missiles at a car in which Khan and al-Awlaki were traveling, and both men were killed.
According to a letter Attorney General Eric Holder sent to members of Congress, Khan was not "specifically targeted."
Follow Jason Leopold on Twitter: @JasonLeopold