This paper gives an overview of management considerations required for better control of deicing chemicals in the unsaturated zone at sites with winter maintenance operations in cold regions. Degradable organic deicing chemicals are the main focus. The importance of the heterogeneity of both the infiltration process, due to frozen ground and snow melt including the contact between the melting snow cover and the soil, and unsaturated flow is emphasised. In this paper, the applicability of geophysical methods for characterising soil heterogeneity is considered, aimed at modelling and monitoring changes in contamination. To deal with heterogeneity, a stochastic modelling framework may be appropriate, emphasizing the more robust spatial and temporal moments. Examples of a combination of different field techniques for measuring subsoil properties and monitoring contaminants and integration through transport modelling are provided by the SoilCAM project and previous work. Commonly, the results of flow and contaminant fate modelling are quite detailed and complex and require post-processing before communication and advising stakeholders. The managers’ perspectives with respect to monitoring strategies and challenges still unresolved have been analysed with basis in experience with research collaboration with one of the case study sites, Oslo airport, Gardermoen, Norway. Both scientific challenges of monitoring subsoil contaminants in cold regions and the effective interaction between investigators and management are illustrated.