The search for more sustainable freight transport has been the focus in the last decades. In this way, the concept of synchromodality was built considering the collaboration of shippers and logistic service providers to enable real-time switching between transport modes and mode-free transport bookings, encouraging more flexible and sustainable freight transportation. However, there are several challenges to its implementation in real life, which is the focus of this paper. To achieve this, in addition to a literature study, a case study was conducted in Flanders, using a combination of qualitative methods, i.e., focus groups (FG) and expert interviews, aiming to bridge the gap between theory and practice. Challenges such as real-time decision making, limited infrastructure capacity, and the need for stakeholder collaboration were emphasized. Expert insights highlight the need for a forecast-based approach to facilitate mode shift decisions, particularly from roadway to inland waterway transport (IWT). The analysis underscores the potential benefits of the proposed synchromodal technology while acknowledging the requirements needed to make it real.