This study examined the instructor experience of teaching college courses (discussion-based and mathematics) over the Web, versus in the classroom, in terms of teaching, social issues, and emergent issues such as media effects. We interviewed, by e-mail and telephone, 22 college instructors who taught in both formats. We categorized interview fragments to highlight trends. Results indicated Web courses have profoundly different communication than classroom courses, resulting in greater student-instructor equality, explicitness of written instructions required, greater workloads for instructors and deeper thinking in discussions. Initial feelings of anonymity give way later to online identities. Disciplines involving reading, writing, and discussion seem well suited to online education. Mathematics instructors feel the shortcomings of Web-based distance learning environments more than do instructors from more writing-based disciplines. A follow-up needs-assessment of distance mathematics instructors indicated current Web distance education environments do not provide the basic communication tools for mathematics courses.