This exploration of online applied music lessons focused on nine trumpet lessons between Jeremy, a college trumpet professor on the East Coast, and Kate, an eighth-grade trumpet player in the Midwest. These lessons followed an entry-level videoconferencing approach using personal computers, Web cams, and Skype videoconferencing software. These lessons demonstrated that the format was functional on a basic level. Jeremy was able to provide helpful feedback and Kate showed progress. However, the limitations of video delay and limited visual controls presented sufficient challenges so that this format appears to be only a supplement for face-to-face lessons at the current time. In this study some unique features of online lessons are addressed and recommendations are made for future practice.