<p>The Green Legacy Initiative (GLI) was launched aiming to re-green Ethiopia, improve livelihoods and maintain climate resilience. However, its effectiveness has not been comprehensively evaluated. This study assessed the challenges and opportunities in the implementations of the GLI. A mixed-method approach was used, combining qualitative and quantitative data collected from primary and secondary sources. Socio-economic data were collected through household surveys, focus group discussions, and key informant interviews conducted in selected kebeles representing different watershed contexts and analysed using SPSS version 20. Landsat 8 and 9 satellite images were processed and classified using a Maximum Likelihood Classifier in ERDAS Imagine. The socio-economic data revealed that in adequate planning, less caution in planting and protecting tree seedlings were significant challenges accounting for 19.7%, 23.1% and 35.8%, respectively. Opportunities included government support for seedlings, communal land availability and technical support. Landsat analysis revealed that Ganji Challa has shown a promising increase in shrub lands and forest cover, while Wogecha showed low improvements in GLIs effectiveness. Overall, the GLI produced environmental and socioeconomic benefits, including employment creation for rural residents and the conversion of degraded land into productive forest regions. However, the lack of a clear land use policy, advanced planning, and adequate post-planting management remain significant problems. The study recommends improving land use planning and post-planting management through ongoing community engagement, institutional coordination, and scientific support to ensure the GLI's long-term viability.</p>