The chapter explores how teachers use information technology for their online courses, and the possible variations in the meaning they derive from their online teaching experiences. The interviewed teachers share their online experiences and offer several interesting suggestions. Technology is ubiquitous in everybody’s life nowadays, and teachers are no exception to this rule. Whether teaching in the traditional classroom only, or online, the greatest majority of instructors include technology in their teaching process. For example, they prepare course materials on the computer, typing up lectures, student assignments, and presentations. They are definitely not afraid to use technology in support of their teaching, and are not avoiding it. However, the online educational environment is fundamentally different in that it poses specific challenges to teachers. Among the issues that concern them are those related to the instructional processes, media richness, technology reliability, uneven access to technology, and the social isolation of the online teacher. The contents of this chapter should help increase teachers’ awareness of what challenges awaits for them in the online classroom.