Transgender (trans) experiences have greatly changed in the past few decades as Internet use has become more widespread. This has resulted in unprecedented access to resources for the trans community. HCI researchers have only recently examined trans technologies, and there is a need for greater understanding of the role that technology plays in gender transition. In addition, use of these technologies may enforce rigid, standardized narratives of what it means to be trans, which can cause harm and decrease the accessibility of gender transition. Recently, a new class of apps I term transition-tracking technologies have emerged that promises trans people increased control over their transition. However, given the diversity of the trans community, it is unknown how exactly these apps might be used and what narratives they may enforce.In this dissertation, I first examined the technology needs of the trans community using interviews with a focus on health and wellness needs. I then conducted asynchronous focus groups through Discord to further understand how technology can help trans people make decisions about gender-affirming surgery. I found that there were common narratives surrounding transition, of which some may be exclusionary to many trans experiences. I took one component of these narratives, temporality, and analyzed two types of technology with a focus on how time is manifested. The focus groups also showed that trans care is an important part of trans existence, especially when navigating gender transition. Then, I studied the impact of transition tracking (with and without apps) and how they support the needs of the trans community, and found that transition tracking is a valuable tool and can even facilitate trans care. Finally, I facilitated multiple focus groups with community members to produce a transition storytelling tool that challenges these normative transition narratives and that can be integrated into a transition-tracking app. In conducting these studies, this dissertation weaves together concepts of trans technology, storytelling, transition tracking, trans care, and community-based design to produce artifacts and learnings that can benefit those (both in and outside of the trans community) who wish to use technology to support gender transition.