It can be difficult for user researchers to explore how people might interact with interactive systems in everyday contexts; time and space limitations make it hard to be present everywhere that technology is used. Digital music services are one domain where designing for context is important given the myriad places people listen to music. One novel method to help design researchers embed themselves in everyday contexts is through remote-controlled speech agents. This paper describes a practitioner-centered case study of music service interaction researchers using a remote-controlled speech agent, called DJ Bot, to explore people’s music interaction in the car and the home. DJ Bot allowed the team to conduct remote user research and contextual inquiry and to quickly explore new interactions. However, challenges using a remote speech-agent arose when adapting DJ Bot from the constrained environment of the car to the unconstrained home environment.