Online and blended forms of learning has been increasingly common in K-12 settings, along with the technological advancement with always-on and connected devices. The study purports to understand teachers' attitudes towards the middle school's one-laptop-per-student (1:1) policy and students' frequent use of always-on and connected technology, as well as their concerns about middle school students' capabilities of using mobile devices and technologies in 1:1 environments. Using a transcendental phenomenological approach, data was obtained through semi-structured interviews, pre- and post- teacher open-ended surveys, along with classroom and lab observations. The study concluded that teachers typically embraced student use of school issued connected technology, as well as personal, connected mobile devices in a 1:1 environment. Meanwhile, teachers are cognizant of the potential drawbacks, implementing differing strategies to balance the use of such device for productive classroom learning and student engagement of personal non-course related activities. The pivotal role of teacher guidance is reiterated by teachers' perceptions of students' inability to engage in self-directed and self-motivated learning. The challenges reveal what middle school teachers' may face when planning a curriculum and instruction for connected digital age learners.