Left Wing Extremism (LWE) or Maoism in India has been an ongoing internal security challenge since the late 1960s. The current phase of this insurgency has its ground zero in the forests of Dandakaranya (DK) in general and in the Bastar division of Chhattisgarh in particular. The region forms a part of the resource-rich tribal belt in central-eastern India. Tribals constitute the majority of rank and file of Maoists. The driving force for local tribals to fall prey to Maoism is the sense of deep-rooted alienation that these people suffer from. The article delves into the historical roots of tribal alienation that originated a couple of centuries ago during the colonial era and continues in present times under different manifestations. It is pertinent to possess a thorough background knowledge of tribal alienation so as to be able to evolve policies and programmes towards a long-term resolution of Maoist challenge, which is certainly beyond a security-centric approach. In addition, the article also analyses statutes and government initiatives to include their implementation, challenges and impact towards alleviating tribal alienation. The region of study is pan-India in general and the Bastar division of Chhattisgarh in particular.