Example methods and systems for inserting information into content playing via a playback device are described. In some example embodiments, the methods and systems may identify a break type in content playing. The break type is either a bounded type (e.g., a break in a live broadcast) or an unbounded type (e.g., a podcast, audio book, song or the like stored on the playback device). Thereafter, select an information segment to present during the identified break is selected that is representative of information associated with the playback device, wherein the selected information segment is dependent upon the break type. Thereafter, the information segment is inserted into the content playing via the playback device upon an occurrence of the identified break type.