In an effort to expand existing research on the barriers of instructors experience in online learning environments (OLEs), a qualitative study was conducted at a large mid-Atlantic university. Six instructors teaching in different OLE formats (e.g., asynchronous, hybrid, and synchronous via videoconferencing) participated in two focus groups in order to explore their emotional experiences and ways to regulate the emotions when teaching in OLEs. The overarching themes included emotions of feeling (a) restricted, (b) stressed, (c) devalued, (d) validated, and (e) rejuvenated. The article also provides practical strategies on how participating instructors attempted to manage the challenging emotions. A consensus among all participants is that continuous dialog in a community of practice about strategies to enhance OLEs is imperative. (Contains 1 table.)