In some he was a believer intent on supporting terrorists and intrigued with the idea of U.S. soldiers killing comrades in the name of Islam. In others he was a man looking for help finding an appropriate wife.
In the end, they weren't enough for the FBI to identify Army Maj. Nidal Malik Hasan as a terrorist threat or, as it would turn out, as a man who now stands accused of the shooting spree at Fort Hood that killed 13 and wounded 23 others in November 2009.
The emails attracted the attention of FBI and anti-terrorism task force agents in December 2008, and eventually prompted them to dig up Hasan's personnel records and evaluation reports.
But gaps in the bureau's systems, poor training, antiquated technologies and an underlying fear that approaching Hasan would reveal the ongoing investigation into Awlaki prevented the FBI from pursuing the matter much further.
An independent review released Thursday by the FBI lays out a series of gaffes the bureau made as agents evaluated Hasan's correspondence with Awlaki, and ultimately decided the Army major was not a terror threat. The report, by former FBI Director William Webster, concludes that FBI personnel made mistakes in their handling of intelligence information, but that no one person was responsible.
"We do not find, and do not believe, that anyone is solely responsible for mistakes in handling the information," Webster wrote to FBI Director Robert Mueller in a letter with the report. "We do not believe it would be fair to hold these dedicated personnel, who work in a context of constant threats and limited resources, responsible for the tragedy that occurred months later at Fort Hood."
Much was already known about the series of oversights and missteps the government made leading to the terror attack at the Fort Hood Army post, but the report revealed new details.
The report describes the back-and-forth that went on between agents in Washington and task force members reviewing the emails in San Diego.
The FBI in San Diego had been investigating al-Awlaki, a former San Diego resident, for his possible connections to the 9/11 hijackers. When agents saw emails between Hasan and al-Awlaki, they asked the FBI's Washington office to talk to Hasan's bosses.
The Washington office said no.
The agents in Washington told Webster's investigators that an interview might have jeopardized the FBI's probe of Hasan by revealing that the bureau had access to his emails with al-Awalaki.
And, the report said, the FBI agents believed that an interview and contact with Hasan's chain-of-command might jeopardize Hasan's military career
The FBI ultimately concluded that Hasan's communications were in keeping with his research at the time, and as a result, no formal investigation of Hasan was opened. Hasan was writing a research paper about the effects of combat in Iraq and Afghanistan.
Webster's report says that al-Awlaki deserved scrutiny by the FBI in Washington beyond a simple records check and said it was a mistake not to have interviewed Hasan.
The emails began in December 2008 and the last one was sent in June 2009. His first one laid out a question. What would Awlaki think of Muslims who have joined the military and "have even killed or tried to kill" other U.S. soldiers.
Other emails laid out a defense of Hamas, while a series of others pressed Awlaki to make it easier for people to donate money to his website.
In one he mentions a survey about the U.S. trying to undermine Islam, and in another he talks about a speaker he heard that defended suicide bombers.
Another note added a "PS": "I'm looking for a wife that is willing to strive with me to please Allah," Hasan wrote. "I will strongly consider a recommendation coming from you."
Awlaki responded only twice. Once to thank him for fundraising efforts, and a second time thanking him again for the offers to help, and adding: "Tell more about yourself. I will keep an eye for a sister."
Webster's report makes 18 recommendations for policy changes, improvements in training, information technology and other systems. Many of the recommendations have already been implemented by the FBI, or are in progress
The report also makes some broader observations about the difficulties in identifying lone wolf terrorists.
"Nidal Malik Hasan's transformation into a killer underscores the dilemma confronting the FBI," the report said. "He was a religious person. He had no known foreign travel. Other than his eighteen communications with Anwar al-Awlaki, he had no known contact and no known relationships with criminal elements, agents of foreign power, or potential terrorists."
Webster noted that the case also underscores the challenges presented by the new information age. Advancing technologies, he said, demand changes in the way the FBI acquires, stores and acts on intelligence.
Mueller called the Webster review thorough, and said the FBI constantly strives to improve its procedures.
The FBI and Defense Department have said that they've made several policy changes since the 2009 attack to help stave off similar attacks in the future. One major change was that if al-Awlaki comes up as part of a terror investigation, FBI headquarters would be alerted, Mark Giuliano, assistant director for the FBI's National Security Branch, said last year.
Al-Awlaki, implicated in other terror plots, was killed in a drone strike in Yemen last fall.
Hasan is currently being tried in a military court.
Associated Press writer Pete Yost contributed to this report.