A method performed in a portable computing device for intelligently performing audio playback, upon connecting with an audio output system. The portable computing device detects that a connection is made with an audio output system. The portable computing device determines a first audio playback application that last played audio and when the first audio playback application last played audio. If the first audio playback application played audio within a specified amount of time in the past, then the portable computing device signals that audio playback be performed from the first audio playback application (through the connection made with the audio output system.) If the first audio playback application did not play audio within the specified amount of time in the past, then the portable computing device determines a second audio playback application that last played audio when the portable computing device was previously connected to the audio output system and signals audio playback from the second audio playback application (through the connection made with the audio output system.) Other embodiments are also described and claimed.