Using a navigational metaphor, this chapter introduces readers to the sometimes stormy seas of implementing new learning technologies into a course, especially those that have pre-existing design flaws (lack of rigor, accountability, content and time constraints, etc.). In addition to presenting what we feel are some best practices in using iOS devices, we analyze nearly 600 students' reactions to these devices related to how they were used in a 100 level survey style course. For every student who told us that they were "awesome" or helped them "learn and discover new things through [the] course," there were multiple students who felt that "they are damaging [the] learning experience because they are distracting." The central argument of this chapter is that without engaging in a dialectic course (re)design process that puts the affordances of the learning technology in conversation with classic principles of instructional design, the utility of adding iOS devices will be limited at best and distracting at worst. The instructors in the course described here did use the devices in a variety of ways and many students were satisfied with the learning experience. However, for others, the combination of the course being too easy and too forgiving along with putting the Internet into students' hands was a recipe for incivility and off-task uses of technology.