During a period spanning more than 2 decades, the author assessed approximately 2,000 school-age students, about 50 of whom were educated entirely at home. In many respects, the data gathering activities were similar regardless of the settings involved, but the uniqueness of homeschooling sometimes made assessment adaptations necessary in order for a comprehensive understanding of home-taught students to emerge. In this article, the author discusses some similarities and differences regarding traditional and homeschool student assessments, as well as ways that practitioners might adapt their assessment practices when attempting to determine whether the needs of homeschool students are being met.