Testifying before a Chicago court during the recently-concluded trial of co-accused Tahawwur Rana, Headley conceded that he was still working with DEA when he first attended an LeT meeting in 1999.
"Yes," Headley told the court, when the defence attorney for Rana asked: "1999 (the year when Headley visited Pakistan for Lashkar meeting). But you were still working with the DEA when you went into the first Lashkar meeting, where you made a donation, correct?"
"Did you report to the DEA that you had gone to Lashkar meetings?" Headley was asked, to which he replied in negative.
"When you say working for the DEA, I was signed because I would sign up for periods of time. So I was working for them but not on any case at that time. I was signed up with them at that time," Headley clarified soon thereafter.
Responding to the questions from the defence attorney, Headley said even though he was not assigned any particular task by DEA, he was in contact with them and was under obligation to tell them if he came to know something of interest to them.
Headley told the court that he started attending LeT meetings on a regular basis from 2000 onwards and that Kashmir was the prime motivation for him to join this Pakistan-based terrorist outfit.
Headley said he started going for LeT training soon after the 9/11 attacks in the US. He also conceded that he was called by FBI for questioning after there was a complaint against him.
During the FBI questioning, Headley was confronted about his anti-American statements and his wish to fight 'jihad' in Kashmir.
And instead, he told the FBI that he was working for the US government trying to infiltrate mosques, etc.
"I had visited, on the instruction of a DEA agent, one mosque, and I told him that I had," Headley told the court in response to a question from the defence attorney.
"So you covered those statements by saying, I am working for the United States; I am going into mosques working for you. Correct?" the defence attorney asked.
"Yes", Headley said, adding that he stopped working for the DEA in September next year.
Headley told the court that LeT taught them "small unit tactics," for "conventional and guerrilla warfare" in both "urban and country settings," so that LeT terrorists could fight against the Indian army.
"And that was your aim, that you were going to fight in that battle?" he was asked.
"That is correct", Headley responded.
"They really didn't teach you ...in the intelligence course, the intelligence was designed to help you with that type of a battle, correct, fighting in the guerrilla war, so to speak?" he was asked.
"No. The intelligence was a little different from that. That was geared toward living... small groups of Lashkar operatives that would go in and live inside of India. That was geared for that mainly," Headley said.
"Small groups. Where were they going to live, in Kashmir or India itself?" the defence attorney asked.
"In India or Kashmir, both," Headley said.
"And do what type of work?" he was asked.
"Surveillance or checking out some locations as well as VIPs or personnel," he said.
After he was working for LeT for four-five years, Major Iqbal of the ISI got in touch with him in 2006.
"How do you know he was in ISI?" the defence attorney asked.
"Because I had been introduced to him by a person who had met -- who I had met inside a military cantonment in Landi Kotal," Headley said.