This chapter concerns a year-long, United States federally-funded evaluation of Educate Online, an online, at home, 1:1 tutoring program aimed at improving reading performance for middle school students who are below grade level. Participating students receive after-school instruction from teachers in real-time over Voice over Internet Protocol (VoIP) connections. The researcher discusses study findings, the methodological challenges of conducting research on online tutoring, the multiple perspectives for understanding the effectiveness of a tutoring program, and areas for additional research. The chapter examines a key aspect of the evaluation, a delayed treatment control group design study to determine the effect that involvement in the tutoring program has upon student academic achievement in reading. [This chapter was published in: F. J. García-Peñalvo, A. M. Seoane Pardo (Eds.), "Online Tutor 2.0: Methodologies and Case Studies for Successful Learning," (pp. 264-279). Hershey, PA: IGI Global, 2014. (978-1-4666-5832-5 / 2326-8905).]