Teaching students in the inner city has been likened to hugging a porcupine--teachers nudge them toward success while getting pricked along the way. Many urban students perform below proficiency level and are difficult to manage. Their apathy toward completing class assignments, let alone homework, compounds the problem. As a whole, educators do their best to reverse the tide, despite the student's resistance. In this article, the author suggests that educators must take the time to assess how technological innovations might assist them in delivering relevant instruction in the 21st century classrooms. The use of technology forms the bridge into real-world relevance and creates a more authentic learning experience for students. Innovative teachers can enhance student learning processes and even thwart the would-be dropout by employing effective delivery of instruction. Teachers who are willing to go the extra mile to personalize the education of students and provide a rigorous and engaging curriculum are rewarded by greater student connection and gains.