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This study examines the challenges and successes of preservice teachers participating in a university partnership whose purpose is to learn how to use educational technology to support learning and instruction. To attempt to improve technology training in higher education, this research was guided by the collaborative apprenticeship model, using a constructivist grounded theory design with thematic analysis. Emergent coding and constant comparative analysis of the electronic worksheets and digital portfolios revealed challenges such as disconnected collaboration and instructional misalignment. Partnership successes included authentic connections that were made between learning standards and instructional planning, a depth in preservice teacher thinking, and positive attitudes toward instructional design. The university partnership offers promising technology training by noting our challenges and successes from this experience.