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It is becoming increasingly important for students to be able to use technology to be considered literate. Therefore, it is critical for teachers to be able to integrate technology into their instruction. Yet, little is known about teachers’ longer-term efforts to integrate technology, nor how teachers may engage in that work independently. This study utilized holistic case study design to explore two teachers’ experiences implementing a long-term technology integration plan with different levels of professional development support. Results describe successes, barriers, and modifications made to the long-term plan. The teachers’ abilities to use new digital tools indicates that there is merit in further research on how teachers can be supported to independently plan to support students’ digital literacy skills.