Background: Urban freight transport is essential for the functioning of cities. The COVID-19 pandemic accelerated the growth of e-commerce, creating new challenges for courier services. While consumer satisfaction has been extensively studied, little attention has been paid to courier drivers’ own perceptions and preferences. This study aims to fill that gap. Methods: A questionnaire survey was conducted among 139 drivers employed in eight courier companies in Serbia. Data were analyzed using parametric statistical methods (Independent Samples T-Test, Paired-Samples T-Test, and One-way ANOVA), with additional post hoc tests to explore group differences. Results: Statistically significant differences were observed across demographic, operational, and safety-related factors (gender, age, residence, occupation, license ownership, delivery area, and type of goods). A strong preference emerged for passenger vehicles as the safest mode of delivery, highlighting a misalignment between current operational practices and drivers’ safety perceptions. Conclusions: The findings emphasize the importance of tailoring delivery strategies to demographic and operational contexts. Practical recommendations include improving transport safety, optimizing delivery zones, and addressing driver satisfaction as a determinant of service quality. The study contributes new insights into last-mile delivery by focusing on the perspectives of courier drivers rather than consumers.