Even before entering Ukraine, Ashton-Cirillo faced expected obstacles getting into the country as a transgender woman. She intentionally flew into Berlin on her origin flight with an awareness that the city might be more progressive about her gender identity not matching the photo and details on her passport. At the Ukrainian border, she brought press clippings to prove her identity, fearful of not being let into the country.
Initially without a combat helmet, a chest protector or press plates, she made a spur-of-the-moment decision to go into the city of Kharkiv, further into a dangerous area of the war zone. Ashton-Cirillo said at the time, the danger and risks of her decision weren’t something she could process, but now knows the choice was pivotal for her future.