This case study explores ten undergraduate music education students' experiences with reflective self-assessment using web-hosted materials in a choral conducting course. To provide participants with opportunities to engage in reflective self-assessment in a web-based environment, these participants were given web-hosted materials in order for them to: (a) view and edit videos of their conducting to describe their performance; (b) complete self-assessments after reviewing the videos to evaluate their conducting performance; and (c) write and share peer feedback to experience different perspectives. Each of the three steps was documented in a web environment. Data were collected through semi-structured interviews with each participant and the instructor, open-ended questionnaires, and notes from the author's research journal. Through several processes, the study found potential benefits in using web-hosted materials to promote students' self-reflection and assessment in a choral conducting course. These processes included having participants describe their experiences (criteria comprehension, determining conducting strengths and weaknesses), evaluate their experiences (determining the benefits of a single-location platform/website, reviewing conducting in the future), and learn from multiple perspectives (sharing ideas in a safe environment, improving vocabulary and critical skills).