Technology is an integral component of a 21st century education. In order to streamline digital learning, many schools are turning to digital learning management sites like Schoology. Sites like Schoology allow educators to organize and deliver content to improve student learning for both in-person and at-home education models. Coupled with platforms like Google Workspace for Education, they are effective tools in a teacher's digital toolbox for integrating and managing online components of learning. However, their effectiveness is dependent on a teacher's digital fluency including teachers' self-efficacy. This school improvement plan seeks to build teachers' digital fluency, especially in these two platforms—Google Workspace for Education and Schoology. This will be accomplished through the use of group training sessions in a situated context, individualized peer coaching, and on-demand tutorial videos which cover topics the educators indicated as areas of need. The literature review contained in this plan establishes these three approaches as effective components of technology professional development.