Even though there are demonstrated benefits of using online tools to support student musicians, there is a persistent challenge of providing sufficient and effective professional development for independent music teachers to use such tools successfully. This paper describes several methods for helping teachers use an online tool called iSCORE, including embedded online support, targeted email messages, webinars, and face-to-face workshops. Using contemporary frameworks for characterizing continuing professional development, the success of each of these teaching approaches, separately and in combination, is considered through an examination of teacher feedback, uptake of the tool by students, and the interview data from an advisory board made up of teachers, educators, software designers and developers, publishers, and business leaders. Inherent tensions and difficulties in designing appropriate professional development are discussed.