This research paper in its entirety tries to articulate the various types of challenges faced by the Indian Transportation Sector in implementing new age technologies for better control and visibility throughout the entire Supply Chain. It mostly focuses on the road and rail mode of transportation, though briefly it also touch-bases upon the water and air modes. Indian railways and roads position themselves as the third and second largest network respectively worldwide. In addition to a set of questionnaires circulated among individuals working in the logistics domain to capture their point of view, a thorough literature review of the previous works in this field was done to identify the causes – both external and internal to an organization, which affects implementation of digital solutions to present transportation problems. In this paper, we discuss along with others, two of the greatest challenges posed to the digital transformation – firstly, adamant attitude of traditional players operating in this space, who have for long, functioned through traditional processes and legacy systems and secondly, the complexity of the road and rail network running through the length and breadth of the country. Though the average time taken by enterprises to digitize their transportation business has reduced tremendously due to need of remote operations in these unprecedented times during COVID-19, but still there exist some of the challenges which need to be addressed. Some of the major drivers of identifying these challenges are the need to - reduce lead times by setting up a platform/control tower which can automate the management of transportation with minimized touch points between organizations and their customers, need to reduce risk of manipulated data by minimizing human intervention and need to increase customer satisfaction by incorporating functionalities like real-time tracking, automated exception handling and other. The challenges which were identified in this study can be further analysed to improve on it and conceptualize a framework for transforming Indian logistics (majorly the transportation space). This paper is written from the point of view of current scenario of Indian transportation industry.