This case study documents the struggles and successes encountered by a pre-calculus teacher while using Classroom Connectivity Technology (CCT) daily in her community college mathematics course. CCT refers to a wireless communication system that connects a teacher's computer with an individual student's handheld calculator and has been associated with positive academic outcomes (Author, 2011b). CCT allows the instructor to send documents, collect student responses, and project student work for classroom discussion. Due to the increased complexity of teaching using CCT, however, teachers often struggle with initial implementation. For example, the teacher struggled with a lack of time to plan and execute activities using CCT. She also had to develop an understanding of how to use CCT effectively and how to resolve technical issues that arose during the lesson. The teacher also experienced numerous successes. CCT was used for formative assessment, to promote involvement among students, and to exhibit and connect multiple representations of a mathematical concept. This case study provides mathematics educators seeking to understand the costs and benefits of implementing CCT with valuable insight into issues of early implementation. (Contains 3 figures and 1 note.)