Transportation and vehicle fleet management in humanitarian logistics have characteristics virtually unexplored by OR researchers. We provide evidencebased insights into the logistics challenges imposed by the dual objective of relief and development, decentralization, earmarked funding, and field operating conditions. We comment on why these characteristics help explaining the persistence of aging fleets, excessive fleet sizes, low fleet standardization, and service delays: problems humanitarian fleet managers fight on a daily basis to improve their service levels. We propose avenues for future research to address strategic, tactical, and operational challenges derived from the defining characteristics of humanitarian logistics discussed in the paper.