The introduction of dry ports to transport networks facilitates trade allows containers to be distributed between transport modes and ensures optimal use of networks. However, dry ports face several challenges, which have a significant impact on their operations, often reducing the benefits from developing dry ports in national or regional freight transport systems. In this regard, this paper investigates the influential factors of dry port operations. We firstly identify five categories of influencing factors and their respective sub-factors. Subsequently, we conduct an empirical study through a web-based survey of Malaysian dry port stakeholders. Multiple regression is employed for data analysis. Findings suggest 12 factors of significant importance to Malaysian dry port operations, including the need for sufficient information sharing; accurate freight forecasting, customs clearance, value-added services, adequate highway infrastructure; existence of appropriate operational equipment and sufficient space for current and future container storage; implementation of public–private partnerships; impact of seaport and short sea shipping policy; road connectivity and the location itself of dry ports. The paper is expected to be of managerial value to dry port operators, when developing strategies to enhance operational efficiency.