Given the extensiveness of rejection and discrimination that transgender individuals experience (Lombardi, Wilchins, Priesing, & Malouf, 2001), the purpose of the current study was to examine the process of coping and how this relates to well-being at different stages of the gender transition. A total of 357 transsexual individuals (n = 226 male-to-female [MTF] transsexual and n = 131 female-to-male [FTM] transsexual) participated in this study. Path modeling was used to analyze the data--four separate paths were hypothesized, based on transgender identity (either MTF or FTM) and reports of anxiety or depression. The path models yielded results that suggest that the processes for MTF and FTM transsexual individuals differ. Although the MTF and FTM models for depression and anxiety differed, two themes emerge from these models. First, the perception of loss is extremely important for transsexual populations. In each of the models, the more perceived loss an individual experienced, the more depression, anxiety, and avoidant coping mechanisms were reported. Interestingly enough, the only variable that did not predict any paths was the perception of a transgender community. It could be that experiencing loss is more imperative to well-being than the importance of a transgender community. The second major finding was that there appears to be a more complex model for MTF individuals when compared to FTM individuals. Comparatively, there were only three significant paths for FTMs and 10 significant paths for MTFs across all four models. Several authors have noted the impact of male privilege for FTMs (see, for example Schilt, 1997). It may be that the added discrimination and difficulty that MTFs experience during their transitions indicate a more complex process for their coping and well-being. It is more likely that the process is just as complex for FTM individuals, however, the complexity has not been captured within the variables for the current study. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]