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The integration of technology by teachers to support student learning and prepare students for contemporary times is best accomplished by matching integration with teaching practices grounded in contemporary theories of learning and teaching. This matching is difficult to cultivate, and this research seeks to provide insight into this “wicked problem.” This research uses illustrations by undergraduate teacher candidates of what teaching with technology looks like as a primary data source. The analysis utilized activity theory to understand the contextualized relationships between practices and mediating artifacts. This research provides grounding for supporting the development of teaching practices with technology at an early stage as well as raising awareness of persistent practices that may make meaningful educational change difficult.