In this article, we examine the possibilities of technologies as lifelines as we have witnessed them, as artists, teachers, and students traversing the Internet for information, teaching, making art, dialog/chat, sanity and survival. Theoretically, we call these lifelines transgressive (acts of liberation) in that they are acts of knowing often not permitted in many public, social, or educational venues. First, we describe the creation of an online distance art appreciation course. Next, we present one week of online conversations with students and an artist. Then, we describe a few interviews from artists and students that further examine the concept of technologies as lifelines. In conclusion, our observations are presented to reveal alternative influences of technological lifelines through distance learning. (Contains 1 footnote.)