The document proposes Contextually Proactive Media Managers (CPMM) to simplify media sharing between devices. CPMM uses context information like user proximity and device presence to infer user intentions and proactively transfer content between devices. This allows media sharing scenarios to occur with minimal user input by setting up connections and transferring content automatically when context conditions are met. Examples show how CPMM could detect paused media and proactively share it between nearby screens. The goal is to reduce complexity and latency in networked media sharing through contextual awareness and proactive actions.