A video on-demand (“VOD”) system receives a request for a VOD program, thereby generating a VOD session for the viewer. The VOD system generates a dynamic playlist incorporating at least one advertisement, where the playlist is provided to the VOD server, causing said VOD server to stream the playlist to the viewer. Upon suspension of viewing the VOD program by the viewer, the VOD system terminates the VOD session. Upon receiving a subsequent request from the viewer for the same VOD program, a second VOD session is established by the VOD system with a second dynamic playlist incorporating at least one other advertisement. The VOD system streams the program beginning at the same point in the program where the original interruption occurred.