  How to handle gender with machine learning is a controversial topic. A
growing critical body of research brought attention to the numerous issues
transgender communities face with the adoption of current automatic gender
recognition (AGR) systems. In contrast, we explore how such technologies could
potentially be appropriated to support transgender practices and needs,
especially in non-Western contexts like Japan. We designed a virtual makeup
probe to assist transgender individuals with passing, that is to be perceived
as the gender they identify as. To understand how such an application might
support expressing transgender individuals gender identity or not, we
interviewed 15 individuals in Tokyo and found that in the right context and
under strict conditions, AGR based systems could assist transgender passing.
