As learners engage, test, and apply new subject knowledge, they often expend their cognitive capacity on the technological tools designed to capture their learning progress and outcomes. The energy and attention spent on these tools reduces their capacity to engage deeply with new learning concepts. Digital literacy skills require both cognitive and technical skills to develop a learner's ability to locate, use, and communicate information. Increasingly complex information environments create various barriers for student learning, and as our learning and working industries continue to evolve and integrate technologies, students must overcome these barriers by bridging learning needs and technology expectations. This research explores the value of developing digital literacy to improve learners' cognitive flexibility by decreasing technological cognitive load and increasing learning fluency. The findings highlight the need for establishing scaffolded digital literacy skills and digital tool selection, and expand college readiness requirements to include digital literacy as a prerequisite skill for learners.