Eighteen transgender-identified individuals participated in semi-structured interviews regarding emotional and coping processes throughout their gender transition. The authors used grounded theory to conceptualize and analyze the data. There were three distinct phases through which the participants described emotional and coping experiences: (a) pretransition, (b) during the transition, and (c) posttransition. Five separate themes emerged, including descriptions of coping mechanisms, emotional hardship, lack of support, positive social support, and affirmative emotional experiences. The authors developed a model to describe the role of coping mechanisms and support experienced throughout the transition process. As participants continued through their transitions, emotional hardships lessened and they used facilitative coping mechanisms that in turn led to affirmative emotional experiences. The results of this study are indicative of the importance of guiding transgender individuals through facilitative coping experiences and providing social support throughout the transition process. Implications for counselors and for future research are discussed.