When teaching mathematics with technology, the author does so in the belief that technology enables students to experience mathematical ideas in a way that might not otherwise be possible. However, teachers must be careful: Sometimes technology does not produce results in the way that they or their students expect. Rather than allowing unexpected results to be a barrier to teaching mathematics with technology, the author tries to capitalize on the mathematical ideas elicited in such a situation. Of these unexpected responses, the author labels one category "pathological examples." In this discussion of pathological examples, the author builds on work similar to that presented in Lee (2005) and Lesser (2005/2006, 2006/2007). These authors focused on what they called "technology pitfalls." Each example they provided illustrated how a student's misinterpretation or lack of awareness of a calculator procedure led to an error in understanding calculator output. (Contains 6 figures.)