Researchers agree that one in two doctoral students will not complete their degree, but there is little agreement on how to support and encourage these students in their scholarship. A qualitative inquiry was used to examine the reasons for delayed or expedited dissertation completion by doctoral students in an educational leadership program at a Midwestern university. Identified challenges of the dissertation process included imposter syndrome, writing anxiety, and overall productivity. Also identified were supports for the dissertation process, including the cohort model and strong mentorship. Findings indicated that doctoral candidates were highly influenced by personal or environmental factors and the perceived value of institutional support. Additionally, once delayed completers overcame their barriers and engaged in the dissertation process, their behaviors and strategies mirrored expedited completers.