The global and local business environment is varying at a different pace. Due to this variation, complexity in the transportation system is becoming a vital issue to be addressed. Literature in the domain of intermodal freight transportation suggests several drivers including globalization, variability in demand patterns and recent advancement in facilitation technologies i.e. Information and Communication Technologies (ICT). To address these issues with an aim to improve freight transportation system performance, it is critical to incorporate synergized IT system and decision system with a pragmatic approach. In developing country like India, where expansion of inland waterways along with inland and global regulations requires research intervention. This paper will attempt to propose and analyze DIS-IFT framework in the Indian context.  This novel framework will incorporate decision and information flexibility scenarios. The DIS-IFT framework will facilitate transport operators, planners, designers, policymakers etc to strategize synergy in the intermodal freight transportation system.