A method is performed by one or more devices within a closed distribution network to provide context-sensitive transactional advertisements. The method includes sending, to a video client, a trigger for initiating a context-specific transactional advertisement associated with a linear program segment and sending the linear program segment for presentation by the video client. The method also includes receiving, based on the trigger, a request from the video client for instructions for the context-specific transactional advertisement; determining, based on the request, contextual information for the linear program segment; and sending, to the video client and based on the contextual information, the instructions for the context-specific transactional advertisement.