The International Dyslexia Association estimates that on average, as many as 15% to 20% of the population may display symptoms of dyslexia, which include inaccurate or laborious reading, and weak spelling and writing. Unfortunately, many individuals with dyslexia have found themselves surrounded by school and community members who do not understand this pervasive and well-documented language-learning disability. Data on experiences of diverse practitioners attempting to gain expertise in dyslexia are one critical path for identifying potential mechanisms for mitigating these challenges. In this article, the authors report on a multiple-case study designed to better understand the experiences and contexts of graduate students enrolled in an online dyslexia assessment and intervention professional development program. Analysis revealed common contextual barriers to practice across unique settings and also common supports acquired as participants built their internal capacity through their online learning experiences.