Background  Global warming caused by greenhouse gas emissions necessitates a decrease in carbon emission caused by the truck transport industry. To combat the threat of global warming, goals are being set up on a global, national and corporate level. These goals are putting pressure on logistics service providers to decrease the emissions within the truck transport industry. Implementation of green practices is found to be especially challenging within heavy truck transport due to weight and distance of the transport characteristics. In order to achieve emission reductions, logistics service providers are dependent on the alignment with their transport buyers, known as shippers to implement green logistics practices. Purpose The purpose of this study is to identify challenges and enablers for sustainable green transitions within heavy truck transports among shippers and logistics service providers. The study formulates two research question to help achieve the purpose, these questions are focused on challenges and enablers among both shippers and logistics service providers.  Method The study employs an explorative research approach in a multiple case study setting. Three configurations of shipper-LSP relationships are studied and analyzed through thematic analysis, the researchers also conducted a cross-case analysis to compare and identify similarities and differences between the cases in order to draw conclusions.  Conclusion A green transition within the heavy truck transport sector face numerous challenges. The challenges include a high dependency on vehicle development, lacking infrastructure, alignment issues between shippers and logistics service providers and trade off dilemmas. In order to overcome the issues findings, suggest that shippers and LSPs should focus on creating shared goals in order to facilitate implementation of green logistics practices and mitigate the challenges.