September 2006: Visits India for several weeks, then travels to Pakistan.
February 2007: Visits India for several weeks, then Pakistan.
September 2007: Visits India for several weeks, then Pakistan.
April 2008: Visits India for several weeks, and at Lashkar's behest, makes a surveillance video of his boat ride through the Mumbai harbor. Authorities later say this video was used by the 10 Lashkar gunmen to identify the best landing sites after traveling by boat from Pakistan.
July 2008: Visits India for several weeks, then Pakistan.
October 2008: Apparently comes to the attention of the FBI after posting inflammatory messages on a Yahoo discussion group, including that he felt "disposed toward violence" against Danish cartoonists and others he thought were "making fun of Islam."
February (approximately): Travels to Pakistan's Federally Administered Tribal Areas, where former Pakistan army Maj. Abdur Rehman Hashim Syed takes him to meet a senior Lashkar official. Before returning to Chicago in June, Headley sends his will to Rana.
Aug. 5: Arrives in Atlanta after a trip to Copenhagen.
Oct. 3: Arrested as he prepares to board a flight in Chicago with Pakistan as his ultimate destination. Intercepted conversations indicate he planned to meet with the senior Lashkar leader and Ilyas Kashmiri, a leader in another terrorist group.