Land degradation and soil erosion, intensified by frequent intense hydro-meteorological events, pose significant threats to ecological processes. In response to the environmental challenges, there is a growing emphasis on employing Nature-Based Solutions (NBS), such as Soil and Water Bioengineering (SWBE) techniques, which promote a sustainable approach and materials for the restoration of natural areas damaged by climate events, unlike traditional “grey” engineering works. However, the effective implementation of SWBE interventions requires a multidisciplinary monitoring approach, considering engineering, geological, ecological, biological, and landscape aspects. The success of these interventions depends on evaluating both short-term stabilities provided by the non-living supporting structure and the long-term development of vegetation introduced during the work. Monitoring should regard structural integrity assessments, vegetation evolution studies, and analyses of root system efficiency (distribution, mechanical characteristics, etc.). This study wants to fill the research gap in SWBE management by proposing a comparison of two study techniques for a root system development evaluation, within a multi-approach methodology for the assessment of these interventions in terms of soil stability and natural evolution. The paper provides insights into geotechnical analysis within a shallow landslide, comparing two different methods for the evaluation of root system evolution. Direct methods (RAR) and indirect methods (ERT) were used for root development monitoring and then compared. Vegetation development was assessed by NDVI parameter by analysing Landsat satellite images. An overall analysis of the data obtained from monitoring the study area shows good plant development, thanks to the SWBE intervention, which in addition to the slope stability effect contributes to better water regulation and initiates a natural ecological succession. The findings contribute to advancing the understanding of the effectiveness of SWBE techniques, offering valuable information for future bioengineering projects and environmental conservation efforts, and promoting them as sustainable techniques for natural recovery.