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In this paper we discuss middle-to-late life issues of the transgender and intersex communities. We demonstrate that these mid-to-late life issues are richly complex, full of courage, coping, risk, and resilience, and are grounded in a socio-ecological landscape of systemic actual and perceived violence and abuse. We examine how this socio-ecological environment affects the “normative” mid-life cycle processes. Practical examples are drawn from the author's field interviews and survey research over the past decade. We close by examining the effects of such a landscape on the middle-age life stage and examine its potential ramifications for old age as well.