The rapid digitalization of the transport industry necessitated the adoption of online booking systems to remain competitive and meet evolving customer expectations. This study examined the benefits and challenges associated with implementing an online bus booking system, focusing on how such technological interventions affected business operations, customer service delivery, and organizational sustainability. The research addressed the critical need for empirical evidence to guide transport companies in making informed technology investment decisions. The study employed a case study research design with mixed-methods approach. Data were collected from 180 participants including 120 customers, 45 company employees, and 15 management staff across three bus companies that had implemented online booking systems within the previous two years. Research instruments included structured questionnaires, in-depth interviews, focus group discussions, and analysis of company performance records. Quantitative data were analyzed using descriptive statistics and comparative analysis, while qualitative data were thematically coded to identify patterns in benefits and challenges experienced during implementation. The findings revealed substantial benefits including improved revenue collection efficiency (increase of 34%), enhanced customer convenience (satisfaction score of 4.1/5.0), reduced operational costs (decrease of 28%), and expanded market reach (new customer acquisition increased by 45%). However, significant challenges emerged including high initial implementation costs (average UGX 85 million), technical infrastructure limitations (affecting 42% of operations), staff resistance to change (35% of employees), cybersecurity concerns (reported by 58% of management), and customer adaptation difficulties (31% of traditional customers). The benefit-challenge ratio suggested overall positive outcomes despite substantial implementation hurdles. Online bus booking systems offered significant strategic advantages for transport companies but required careful planning, adequate resource allocation, and comprehensive change management to overcome implementation challenges. Success depended on balancing technological capabilities with organizational readiness and customer needs. The study recommended phased implementation approaches, substantial investment in technical infrastructure and staff training, development of hybrid booking systems accommodating diverse customer preferences, robust cybersecurity measures, and continuous system evaluation and improvement based on stakeholder feedback.