Method of calibrating audio output device with playback of adjusted audio

The disclosed technologies calibrate audio output based on a computer-based hearing evaluation. In an embodiment, the disclosed technologies perform operations that include playing an electronic file that contains segments of digital music that have different playback attributes, wherein playback attribute include at least one of volume data, frequency data, left/right data; during the playing of the electronic file, recording timestamp data and user account data that are associated with a user input; mapping the timestamp data to a set of playback attributes of a segment of the digital music; determining calibration data based on the timestamp data and the set of playback attributes; storing the calibration data in a user profile that is associated with the user account data; when different digital music is played, automatically calibrating the playing of the different digital music based on the user profile that is associated with the user account data.