A source device can transmit initial streaming content to a playback device (e.g., wireless ear buds) using first settings and measure playback performance of the content at a plurality of times. The measured performance values can relate to a quality of communication of the initial streaming content between the source device and the playback device, e.g., relating to packet loss, retransmission rates and patterns, fluctuations in a playback (jitter) buffer, and/or other values. The measured performance values can be used to determine one or more second settings to be used for a playback of subsequent streaming content between the source device and the playback device. In this manner, each source device can account for variations in communication behavior specific to a user (e.g., due to differences in body type as electromagnetic waves travel through the body when a source device is in a pocket).