The current study explores the videos of eight popular transgender YouTubers. A content analysis was conducted to examine the themes present in videos, the specific issues discussed, and the educational value for viewers. In particular, the present research was interested in the amount of videos that contain transgender-specific content, and in the types of issues—both general and in terms of gender transition—about which transgender YouTubers converse. Videos were also analyzed in relation to self-identified type of transgender individual (e.g. male-to-female [MTF] or female-to-male [FTM]), and significant differences were found in both the amount of transgender-specific content as well as the educational value of videos. This article positions transgender YouTube content as an educational tool that can both help serve as guidance for transgender viewers, as well as increase mainstream audiences’ understanding of transgender persons, subjects, and struggles.