Teaching with technology is a required skill for today's teachers and the technological pedagogical content knowledge (TPACK) is a commonly used framework that is used to assess the effective usage of this skill. In this framework, teachers' knowledge is assessed under various individual and blended knowledge domains. The effect of contextual factors on TPACK is a relatively recent focal point of this framework. Therefore, this study investigates pre-service teachers' enactment of different TPACK domains and interprets the results according to contextual factors that underlie their decisions and their knowledge levels. For this purpose, a case study involving four pre-service teachers was conducted. The contextual factors are extracted from the pre-service teachers' reflection and teaching philosophy statements. Then their demonstration of TPACK levels are found both during planning and teaching stages. The results indicate that pre-service teachers with low TPACK enactment are mostly preoccupied with contextual elements related to practical concerns, whereas those with higher levels exhibited a greater degree of contextual elements related to beliefs and external priorities. It was also found that this latter group's planning and teaching artifacts are more balanced with respect to TPACK levels, whereas a more significant drop in TPACK levels from planning to teaching was observed for the former group.