When the testosterone started to flow through her system, Jessica Sunderland felt the changes immediately.

“I had to do stuff to deal with the anger,” she said. “Working out and meditating, and trying to breathe. I did anything to try to not focus on the anger.”

She was an army veteran who had served in Iraq, but at that moment, in the fall of 2012, she was in the Suffolk County Correctional Facility on charges of burglary, kept in a cell 21 hours per day, in a body at war with her conception of who she was.

She wanted medication to make it stop, and she wasn’t getting it.

On a recent afternoon in her lawyer’s office, Ms. Sunderland presented a new phase of her life, including life as a blonde, with long braided hair extensions that she flicked away from her face. She had two prescription medications to lower her testosterone and another to provide estrogen.

And she had a court ruling against two doctors at the Suffolk County jail for denying her hormone therapy, causing her to start what her lawyer described as an involuntary sex change. The jury found that the doctors had violated her constitutional right to necessary medical care and awarded her $355,000 in damages, plus a slightly larger sum that went to her lawyers.

Advocates for transgender rights say it is the first time a jury has awarded punitive damages in such a case.

For Ms. Sunderland, 32, who filed the original complaint under her given name, Jeremy, it was vindication for a long, often solitary battle.

“I started the lawsuit back in 2013, and in the beginning it was just me by myself,” she said. “Just hearing the verdict, it means that I got what I had to say across. It shows that they can’t do what they’ve been doing without some kind of punishment.

“It makes me think there are people who understand what happened and that it was wrong.”

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If you want to explore the fault lines of gender in the 21st century, you might devise an experiment like the criminal justice system. What does it mean when a person is two years into a transition and assigned to a facility that knows only male and female anatomy?

Tensions that exist on the outside become viscerally exaggerated behind bars, where privacy is limited, sexes are segregated and force is unequal. How does an institution built on order accommodate the gray areas of gender diversity?

Transgender people are several times more likely than the general population to spend time in jail or prison and, once there, to face harassment, assault and denial of prescribed medical care. Discrimination at home, school, the job market and the court system all funnel people toward jail or prison.

“Transgender folks are criminalized in our society,” said Mateo De La Torre, a racial and economic justice policy advocate at the National Center for Transgender Equality. “They get kicked out of their home, they engage in the underground economy for survival. And law enforcement profiles transgender women of color as sex workers.”

Like Ms. Sunderland, transgender women are routinely held in male facilities, subjected to strip searches or pat-downs by male guards, and are often held in near solitary confinement, ostensibly for their protection, but it can feel like punishment. Last year, the federal Bureau of Prisons reversed an Obama-era guideline that considered inmates’ gender identity when assigning them to male or female housing. The new guideline calls for housing inmates by “biological sex” except “in rare cases.”

Ms. Sunderland’s award of damages may be a break in that pattern, advocates say.

“We see this as a significant win,” said Mr. De La Torre of the National Center for Transgender Equality. “The fact of a unanimous jury decision sends a clear signal to correctional facilities that the general public understands that this is necessary treatment, and stands by transgender people.”

The decision came one month after a transgender woman in Massachusetts was transferred to a women’s prison after suing under the Americans with Disabilities Act — a potentially landmark case because it applies disability protections to people whose sex at birth clashes with their sense of self.

Representatives for the doctors did not respond to requests for interviews. Chief Michael Sharkey of the county sheriff’s office, which runs the jail, said that policies had not changed since Ms. Sunderland’s time there, but that guards had “more awareness of transgender people in general.”

The jury cleared the jail on charges that its policies denied prisoners necessary care.

Ms. Sunderland likened her experience to the plight of the characters in Jon Krakauer’s book “Into Thin Air,” which she read in jail, about a doomed climbing expedition on Mount Everest. The book spoke to her.

“Sometimes people have an inborn, personal vision where they must do something, and they’ll risk everything to accomplish what they want,” she said. “People would say, Why would someone do all this just to climb a mountain? But to the climbers, it meant the world to them. Who I am in life — people say that’s not something someone should want to be. The way I see it is, that’s who I am. I’ll do whatever I can to achieve that, as strange as it seems to some people.”

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Ms. Sunderland felt as early as age 4 that she was born into the wrong gender (she prefers feminine pronouns even in references to her childhood). She wore her sister’s dresses in private and worried about what other children thought of her. She liked her female self — “It was a good feeling,” she said — but felt a lot of anxiety and depression at home.

Her father, she said, was intimidating and critical, with a short temper she feared setting off.

By adolescence she thought she might be gay but did not have any gay friends; with her straight friends, she felt she didn’t belong.

“I wished I could just go someplace away and be who I want to be,” she recalled, “but not here.”

Like the climbers in “Into Thin Air,” she felt compelled toward something, but did not yet know how to get there. She dropped out of high school and used drugs to deal with the tensions in her body and at home. When that did not work, she took enough pills to black out and woke up in a hospital.

“I just couldn’t take it anymore,” she said in court, “and I didn’t see any other way of getting out of myself.”

Her life at home was stifling. She was in the wrong home, the wrong body, feeling increasing desire to transition, “like a weight” she was carrying around.

Several times she tried returning to high school, but did not stick. “The people I knew weren’t the best of influences,” she said.

The army looked like a way out, maybe a path to a career. In 2007, with the war going in Iraq, she enlisted, following her grandfather and father. The army represented everything her life on Long Island was not. It offered clarity and opportunity.

“I wanted the experience,” she said. “Even though I still had my issues going on, I wanted to try it to see how it felt. My parents were happy that I was getting out of the house.”

Our experience of gender is sometimes described as an interaction among anatomy, identity and expression. When our biological sex lines up with how we see ourselves and how we express ourselves to others, then gender feels like a seamless whole.

When the three panes do not line up, the condition is called gender dysphoria or incongruence. Advocates liken it to pregnancy: requiring medical care, but not a disease or a disorder.

For Ms. Sunderland, the parts clashed, and she was living in the spaces where they did not line up.

“It actually got worse as time went on,” she said. “It was becoming more of a burden keeping it inside.”

At training camp in Texas, she quit smoking and got in the best shape of her life. She became engaged to a woman and adjusted to the discipline of basic training.

When she shipped out to a base in southern Iraq, near Basra, she worked with a close group of soldiers in food services. “I was out of where I was living,” she said. “There were people I could talk to.”

She felt more than ever the need to transition, and she saw a way to get there.

The internet was full of vendors selling hormones, and how-to stories from people in transition. It did not seem that complicated, she said.

“I think I’m a pretty fairly decent researcher,” she said. “I can discern stuff. I go online and I would compare 20 people’s regimens and say, all right, these three sound like they know what they’re doing. I kind of made my own regimen.”

Still, she knew she was on shaky ground. “I’m ordering prescription drugs over the internet on a military base in Iraq,” she said. “I was wondering how that was going to play out.”

She told her fiancée that she planned to transition to living as a woman. When the engagement collapsed, she said, she was “a little heartbroken.”

But the hormones were changing her both physically and emotionally. Despite the breakup, her mood lifted, and some of the daily stress she carried around seemed to fall away. Even as the physical changes became noticeable, no one in her unit said anything.

“I felt I could accomplish more,” she said. “I could think more clearly. I didn’t have something constantly bothering me. It was like a burden got lifted off of me. It was something that was draining energy out of me for years. I was actually happy. It felt good.”

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How common was Ms. Sunderland’s experience in the Suffolk County jail? At trial, her lawyer, David Shanies, introduced records of 11 transgender inmates who he said had been denied hormone therapy for all or part of their time there. The jail disputes this.

One was Alyssa Giordano, who had legally changed her name and gender on her birth certificate and other records by the time she arrived there in 2015, three years after Ms. Sunderland.

She, too, said she was not given the hormone medication she had been taking before her arrest, and she was housed with men, even after a judge at her arraignment ordered that she be housed with women.

“I had to shower in front of men,” Ms. Giordano said. In a lawsuit filed by Mr. Shanies, she alleges that she was groped by a guard and strip-searched in front of male inmates.

Chief Sharkey, the deputy sheriff, confirmed that the jail segregates inmates according to “current anatomical status,” and that male officers search those assigned to male housing.

“I was crying almost every day,” Ms. Giordano said. “They did things for no reason. I didn’t give them a hard time. I never want to go through that again. No one should go through that.”

She added: “It haunts me. It haunts me in my sleep. It just haunts me. It’s like I’m screaming but no one hears me.

“Transgenders have always been the bottom of the pit. It’s not an easy life. I’m happy with who I am, but to go through what I had to go through, I would never want to have to go through that again.”

For Ms. Sunderland, the complications began after she returned home from Iraq in 2009. She found doctors to prescribe the hormones she had bought off the internet, including those at the Veterans Affairs hospital in Manhattan.

But she developed a growth on her liver that moved her doctors to discontinue the estrogen, maintaining only the testosterone blockers.

“I started going into menopause, having hot flashes,” she said. “It wasn’t as bad as I thought it was going to be, stopping estrogen. It wasn’t like I was transitioning back into a male. I probably looked better, because I was sweating out a lot. It was a little weird.”

Finally she had the liver growth surgically removed, through an incision running all the way across her abdomen, and her doctors cleared her to resume the estrogen. But the surgery put her out of work, and she started to buy street drugs to manage the pain from the operation, then for recreation. Soon she and an acquaintance were robbing houses to get money for drugs, including heroin and crack cocaine. In September 2012, when she took stolen goods to a pawnshop, she and her accomplice were arrested.

For 16 months, until she was finally transferred to a prison upstate, she received neither the estrogen nor the testosterone blockers.

At trial, the doctors testified that they cut off treatment out of concern that the liver growth might return. They also testified that they were unfamiliar with treating transgender people, and that they did not attempt to learn more about it.

Q. When you were assessing Ms. Sunderland’s medical care, you did not take any steps to inform yourself about the proper treatment of gender dysphoria, correct?

A. I didn’t know where to start.

The jury found that the doctors had violated her rights under the 14th Amendment to equal protection of the law. Advocates for transgender rights hope the verdict makes facilities think twice before denying care.

But for Ms. Sunderland, it has not changed her life. Though the verdict came in October, she has not received any money yet, and she has been unable to find work, even after earning a certificate in medical billing and coding at a nearby technical school.

For now she remains on Long Island with her sister and parents, stuck in the town she tried to escape a decade ago, waiting to get on with her life.

Under the conditions of her parole she cannot stay out past 9 p.m., so she is largely isolated except through her computer, with few transgender acquaintances. She gave up her car because she could not afford it.

Her classmates in the medical billing program found jobs, she said, but she has not. She was not sure what role bias played.

She said she has gotten used to using women’s bathrooms, and that no one had bothered her for it.

“A couple weeks ago, I was parked in a fire zone for two seconds, and here comes a cop behind me telling me I have to move. He’s calling me ma’am, and when he sees the registration with the name Jeremy Sunderland, he’s like, Who’s Jeremy Sunderland, is that your husband? I’m like, No, that’s me. And he’s like, Oh, O.K. That was a little weird. Most of my picture ID’s have me as a woman. But unfortunately my legal name is still Jeremy. He’s like, Have a good day, ma’am.”

Thanks to the court verdict, she was almost amused.

For Ms. Giordano, though, the wounds of her experience were still raw.

After one month in the Suffolk County jail, she was transferred to a unit for transgender women at Rikers Island, where pat searches were conducted by two guards: a woman for the top half, a man for the bottom. Now out on probation, she is seeking damages of $1 million.

“I would tell them that God is going to punish them,” she said of the Suffolk County jail staff. “Because I believe in God, and what you’re doing is wrong, and they knew what they did was wrong. It’s like a restaurant. Nobody ever leaves without paying. Life always has a way of getting a person back.”

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