This paper examines the nature of academic classroom tasks middle school teachers are designing and using that integrate one-to-one technological devices/computers: technology integration (substitution/augmentation/modification/redefinition-SAMR); 21st century skill (4Cs) integration; task complexity (DOK); and student work aspects (work product, cognitive processes). Changes made to the instructional environment and pedagogical shifts resulting in greatest impact were also explored. Since the tasks used in our classrooms today will predict the future performance of our students, we as education leaders must ask: If our students continue to experience learning/engage in daily tasks the way they are currently designed and delivered, will these learning experiences/tasks produce student performance to be competitive in the global economy or are they creating inequities and variability in our systems?