The insertion of an advertisement or other new content into a time slot between content segments advantageously occurs by selecting the new segment to fill its associated slot as closely as possible. Play out of a successive content segment occurs for distribution over at least one of a first set of channels and at least one second channel until the occurrence of the time slot whereupon the new content segment undergoes play out for distribution over the at least one second channel. If the new content segment has a duration longer than the time slot, the length of at least one content segment gets reduced to provide substantially seamless play out.