The rapid expansion of computers and digital technology requires citizens to be digitally literate. Teachers must prepare students for a digital world despite the lack of consensus on a definition or its components. This multiple case study explored the digital literacy instruction and interactive decision making of teachers with varied levels of expertise. Each participant completed a survey and the General Decision Making Style Questionnaire prior to a series of interviews and classroom observations. Findings from a qualitative analysis of the data suggest variations in the use of digital literacy components during instruction and that skills are related to one another. Findings also indicate similarities and differences in interactive decision making and teaching expertise behaviors related to instruction. Based on these findings, recommendations to better promote digital literacy are directed toward teachers, administrators, teacher preparation institutions, and future researchers. Current events emphasize the need for increased efforts in turning the key of digital literacy for students.