Authors - Jay Joshi, Avneesh Jadhav, Ishita Deshpande, Ameya Dharap, D. D. Sapkal Abstract - As medical insurance adoption continues to grow and its complexities continue to increase, insured members require trustworthy and clear guidance, transparency and timely progress updates throughout the insurance lifecycle. However, users often run into fragmented information, confusion in policy selection, incomprehensible policy documents due to tremendous technical jargon and limited procedural guidance. This makes it difficult to understand coverage details and navigate claims smoothly; particularly during medical emergencies. The absence of unified communication channels frequently leaves policyholders uncertain about eligibility, documentation requirements and claim progress, leading to stress and reduced trust in insurance services. This paper proposes a user-centric, AI-enabled digital platform designed to improve transparency and communication between insured members and insurance service providers. The system focuses on simplifying policy discovery through personalized policy recommendations and interpretation through NLPbased clause summarization. These features enable users to gain a clear understanding of inclusions and exclusions, which help them to make informed decisions. Additionally, to support users during claims, the RAG-based assistance module provides step-by-step guidance on eligibility, document submission and claim procedures. By emphasizing clarity, continuous guidance and transparency, the proposed solution enhances user experience, reduces claim-related anxiety and encourages trust and adoption of digital healthcare insurance services.