AnBer Trucking Services was established as a sole proprietorship located in Padre Garcia, Batangas City. The trucking service specializes in freight transportation, specialized hauling, and rental services, catering to the logistical needs of clients who depend on the movement of heavy materials, equipment, and bulk goods. The purpose of this paper was to examine the operational and market challenges faced by AnBer Trucking Services concerning the unavailability of vehicles due to road regulations, such as plate number coding schemes and limitation of allowed vehicles on the road. The study utilized a case study approach and applied strategic tools such as PESTLE analysis, SWOT, Internal and External Factor Evaluation matrices, and the Grand Strategy Matrix. The analysis revealed that AnBer Trucking Services held a strong competitive position in a growing market, enabling it to pursue aggressive strategies for expansion and operational improvement. Key recommendations included invest in provinces and vehicles, implementing a structured scheduling system, expanding service coverage to nearby provinces, and enhancing digital engagement through social media. The findings concluded that with strategic reinvestment and modernization, AnBer Trucking Services could strengthen its resilience, improve service reliability, and secure long-term growth in the logistics industry.