Background: Though instructional technologies can engage, expand, and enhance learning experiences, technology integration at the K-12 level has many external (such as access to technology, time, and support) and internal (such as teacher beliefs, motivation, and knowledge) challenges. The Technological Pedagogical Content Knowledge framework (TPACK) can inform solutions to these challenges through the lens of equipping educators in their TPACK capacities (Ching-Chung & Ching Sing, 2012). Within TPACK research, exploration focused on teachers’ perceptions of internal forces involving their expectancies, values, and costs of the integration efforts is just emerging. Understanding these perceptions can provide a greater depth of insight into full, partial, and non-implementation of specific technology integration initiatives. Purpose: This study aimed to 1) reveal and explicate the underlying issues of partial and non-implementation of select district technology initiatives among teachers who have strong TPACK; 2) understand issues between efforts of school districts and results by teachers; 3) recognize the importance of contextualizing TPACK implementation; and 4) illustrate the struggles that teachers with strong TPACK may have when weighing the benefits of implementing technology-enhanced activities with the merits of relative value, expectancies, and costs of the integration efforts. The study was motivated by two research questions: What factors do core content area TPACK-enabled teachers perceive as affecting the integration of select district technology initiatives? How do the experiences of core content area TPACK-enabled teachers affect their implementation of select district technology initiatives? Methods: This study utilized a qualitative case study design to explore how teachers perceive the comparative benefits, expectancies, values, and costs of technology integration. Participants represented a homogenous sample of 18 core content area teachers (based on self-ratings indicating their technological knowledge necessary for the ability to act within the intersection of technological pedagogical knowledge, pedagogical content knowledge, and technological content knowledge) and two educational technology administrators. Data were collected via semi-structured interviews. Teacher interviews consisted of completing the Graphic Assessment of TPACK Instrument (GATI) and the interview protocol. Interviews with administrators consisted only of the interview protocol. Interview responses were recorded, transcribed, and coded for recurrent themes. Member checks were conducted with each participant to review their interview transcription as well as the researcher’s interpretation of the data. Results: The findings of this research suggested that teachers’ perceptions of expectancies, values, and costs play a critical role in their implementation of district technology initiatives. Teachers often weigh their expectancies, values, and costs of a select district technology initiative against the overall benefits of implementing the technology. Discussion: The findings prompt a rethinking of how context is examined in the TPACK framework. While motivations and beliefs are present in some variants of the TPACK framework, the expectancy-value-cost model offers an enhanced microscopic view of how benefits of implementing technology-enhanced activities are balanced with the merits of relative values, expectancies, and costs of the integration efforts. The resulting conceptual model can be useful in order for school district leaders in understanding barriers and issues between district technology initiatives and classroom implementation.