The majority of research on investigative interviewing has been on police attempting to solve a crime by obtaining a confession or gathering information, and comparatively fewer studies have examined interviewing at points “downstream” in the process, such as in the courts or correctional system. Furthermore, the focus of the research has been to measure the variable techniques or questioning strategies that produce confessions or information at the expense of analyzing factors related to the interview itself. Thus, we analyzed a sample of 50 corrections-based interviews for “dynamic” interviewing methods and interviewee responses that were measured at three points throughout the interview, and we measured 10 “static” interview factors. In the final multilevel model, we found that productive questioning methods increased a component score that combined interviewee cooperation, engagement, and forthcomingness, the several measures of accusatorial interrogation methods decreased the outcome measure, and the case-level variable of interviewee-initiated interviews increased it.