This article, "The Web-Savvy Urban Teacher," addresses the question of what educational technology educators and scholars can do to close the pedagogical mismatch, which exists today between "digital native" secondary students and their predigital educators. The infrequent use of the Internet as a resource in urban schools is detrimental for today's generation of students, the majority of whom consider the World Wide Web as the source of all knowledge. The purpose of his article is to: (a) introduce and establish the rationale that the Internet is an appropriate medium by means of which differentiated instruction and multiple intelligences can help foster content literacy among struggling and reluctant adolescent learners, (b) provide secondary educators with teacher-specific website criteria that will facilitate the website selection process, and (c) supply a sampling of timeless websites for students and teachers interested in working in a self-regulated environment. (Contains 9 tables.)