Information and Communications Technologies have become tightly woven into the fabric of most middle school and high school students' lives throughout the United States. However this is true, for the most part, only when students step outside the physical and mental confines of school. Today many students find that the technology they have access to outside of school is newer, faster, and far less restrictive than the technology they have access to in school. This dichotomy is creating a situation where, for the first time, students have more access to information and resources out of school than they do in school. This exploratory case study examines the viewpoints of Middle School (MS) and High School (HS) students in a technology-affluent, rural, United States school district relative to Information and Communications Technologies (ICT) use in and out of school. Students in our study 1) perceived technology in school as limited and restrictive, 2) recognized teachers' ICT skills determined classroom instruction, 3) provided suggestions to help teachers with ICT, 4) articulated the learning environments they prefer, 5) experienced a disconnect between ICT use in school and out of school, and 6) perceived educators as not caring.