This field observation examines 58 police interrogators’ rapport-based behaviors with terrorist suspects; specifically, whether rapport helps elicit meaningful intelligence and information. The Observing Rapport-Based Interpersonal Techniques (ORBIT; Alison, Alison, Elntib & Noone, 2012) is a coding framework with 3 elements. The first 2 measures are as follows: (i) 5 strategies adopted from the motivational interviewing (Miller & Rollnick, 2009) literature in the counseling domain: autonomy, acceptance, adaptation, empathy, and evocation and (ii) an “Interpersonal Behavior Circle” (adopted from Interpersonal theories, Leary, 1957) for coding interpersonal interactions between interrogator and suspect along 2 orthogonal dimensions (authoritative-passive and challenging-cooperative); where each quadrant has an interpersonally adaptive and maladaptive variant. The third (outcome) measure of ORBIT includes a measure of evidentially useful information (the “interview yield”) and considers the extent to which suspects reveal information pertaining to capability, opportunity and motive as well as evidence relevant to people, actions, locations and times. Data included 418 video interviews (representing 288 hours of footage), with all suspects subsequently convicted for a variety of terrorist offenses. Structural equation modeling revealed that motivational interviewing was positively associated with adaptive interpersonal behavior from the suspect, which, in turn, increased interview yield. Conversely, even minimal expression of maladaptive interpersonal interrogator behavior increased maladaptive interviewee behavior as well as directly reducing yield. The study provides the first well-defined and empirically validated analysis of the benefits of a rapport-based, interpersonally skilled approach to interviewing terrorists in an operational field setting.