Testifying before a Chicago court on the fourth-day of the trial of co-accused Pakistani-Canadian Tahawwur Rana today, Headley, 50, said the first planned attack was in September, then in October and it finally happened in November.
Sajid Mir, one of Headley's Pakistani handlers, told him that the attack would occur on the 27th night of Ramadan (considered as the night of glory in Islamic calender), which in 2008 would fall on September 29, according to documents presented to the court earlier.
However, the plan had to be abandoned as the boat carrying the attackers got stuck on a rock and was destroyed, the court documents said.
"Sajid told Headley that everyone on board survived, in part because they had life vests. Headley subsequently met with (Major Abdur Rehman) Pasha and told him about the failed attempt. Pasha said that the failed attempt was a sign that God was not happy with Lashkar," it said.
Sajid told Headley that there would be a second attempt at the Mumbai attack in October 2008. Soon thereafter, Sajid told Headley that the second attempt also failed.
The attackers on board the boat had spotted an Indian fishing vessel and attempted to open fire on it, but the vessel escaped.
"Sajid said that the 'boys' were demoralised and sent back to a safe house in Karachi," the court papers said.
During today's deposition, Headley told the court that "on the 9th of November his Pakistani handlers were working on it (attack) more closer than ever."
Headley also told the court that there was a plan to hit Mumbai in May 2008 but it was postponed due to inclement weather. "During the briefings that I had in Pakistan they did not consider that period safe to travel to the sea," he said.
It was on November 26, 2008, Headley received a text message from Sajid with words to the effect of "turn on your TV." Headley then learned that the attacks had begun, according to the court papers.
When asked by Defence Attorney Patrick W Belgan if he was still proud of the Mumbai attacks that killed 166 people including six American nationals, Headley said, "No".
Headley, who carried our extensive surveillance of the strike site for months before the attacks by LeT, said he was "proud" of what he did at the time of the attacks.
People, who knew that he was involved in the planning stage of the strike sent him congratulatory messages after the Mumbai mayhem, including Pasha, his wife Shazia and Sajid Mir, Headley said.
Questioning of Headley would resume on Tuesday.
Earlier, responding to questions from Belgan, Headley said he feels that the Mumbai attacks were in retaliation of the alleged killing of people by the Indian Army in Kashmir.
