For Bradley Manning, a military prison may be a next-to-impossible place to begin his transition to a woman. The Army says it doesn't provide hormone therapy or sexual reassignment surgery to inmates.
But even outside of prison walls, getting this kind of medical help is often a struggle.
In the corporate world, only 42% of employers have insurance plans that cover short-term leave, mental health counseling, hormone therapy and surgical procedures for transgender employees, according to a survey by the Human Rights Campaign.
That's up from 19% in 2008, but it still means the majority of employers don't offer this coverage.
And paying out of pocket can be a heavy burden.
The cost to transition from one gender to another varies greatly.
Hormone replacement therapy can cost around $30 per month and therapist visits can cost more than $100 each. Undergoing surgery is less common but typically rings up at anywhere between $5,000 and $30,000 depending on the kind of operation, estimates Masen Davis, executive director of the Transgender Law Center.
"It can be difficult for transgender individuals -- especially the lower income and unemployed -- to pay for the medical care they need to be themselves," said Davis.
Tim Chevalier, a 32-year-old transsexual man from California, said he ended up with $50,000 in medical bills because his health insurance plan didn't cover his transition-related costs -- including an emergency visit to the hospital after the procedure.
Some people are even unable to complete their transitions because of financial constraints.
Another man said he hasn't been hired for a full-time job since he started his transition from female to male. He went through hormone therapy, but hasn't been able to afford chest reconstruction surgery -- which would cost $6,000.
Convicted WikiLeaks source Manning, who said he wants to be called Chelsea, may need to press his case by arguing that he isn't getting the medical treatment he needs, said Jillian Weiss, a professor of law and society at Ramapo College.
"It is likely to be a very long road for Chelsea Manning," she said.