Communication is a social act, therefore learning to communicate cannot develop in a social vacuum. This thesis investigates vocal development in a songbird species, the Zebra finch, from an ecological perspective to understand the principles by which the naturalistic environment facilitates song learning. I focus my thesis on two such principles: the ways in which song learning is dependent on social affordances of the naturalistic social environment, and the ways in which structural regularities within the communication signal can be exploited to facilitate vocal learning. In Chapter 2 of the dissertation, I investigate what and how juvenile songbirds learn when provided with opportunities to interact with family members. Chapter 3 reveals that based on the structural variability in their father's song, juvenile males learn to sing statistically coherent grammatical structures. This is the first description of a new parallel between birdsong and language. In Chapter 4, I explore the contribution of social feedback in a strictly controlled vocal environment, by using contingent song playback on juvenile vocalizations to mimic naturalistic interactions. Overall, this thesis provides evidence that there is great potential for social interactions to guide the song learning process in the zebra finch, and song acquisition can only fully understood when it is studied in the context of a communication system.