Street Level Bureaucrats (SLBs) play a crucial role as frontline public officials tasked with implementing policies on the ground. Despite their significance, the specific challenges that they face in the context of agroforestry policy implementation remain understudied. This research aims to fill this gap by investigating the challenges and coping strategies of the SLBs who implement agroforestry policies in Namibia. In addition, we aim to understand how these coping strategies hinder or facilitate the implementation of agroforestry. Drawing upon Lipsky’s theory of Street Level Bureaucracy, a qualitative research approach was employed which included document analysis, on-field observation, and interviews. We interviewed eighteen (18) SLBs from the Forestry and Agriculture departments across five regions in Namibia. The findings show that organisational settings, personal norms, and coping strategies of rationing, husbanding and ambidexterity influence policy implementation and consequently the outcomes of agroforestry initiatives. The study emphasizes the critical role of government support, clear policy formulation, resource alignment, and creating an enabling environment to empower SLBs in their implementation activities. Furthermore, this study contributes to exploring Lipsky’s Street-Level Bureaucracy theory within the context of agroforestry policy implementation, and in settings that are similar to Namibia. We conclude that while the theory offers valuable insights, it may not fully capture the complexity of policy implementation in these contexts, especially considering the influence of informal factors. Acknowledging this, future research should consider integrating the informal and cultural context to better address these complexities.