A Controlled Environment Secure Media Streaming System with Digital Video Recording (DVR) manages the delivery of content to Secured Devices. Cloud Services provide content to Integration Hub. The Integration Hub interfaces with various cloud services providers and prepares content for consumption by a resident of a secured facility. Integration Hub utilizes Content Filter to inspect content received from cloud service providers for suitability for use in a secured environment. Once content is retrieved, filtered, formatted, and packaged by Integration Hub, the content is stored in Data Warehouse. When requested content is not available, the system schedule a future retrieval or DVR of the content when it becomes available. When the system detects that the content is stopped, the system creates a bookmark, so the user can resume the content at the bookmarked portion at a later time.