She had lost 26 of her last 27 cases, a string of defeats and disappointments unlike anything she had experienced in her legal career.

“It’s my first time getting kicked in the face over and over,” Priya Rashid was telling another lawyer over the phone.

She looked over at client number 28, who was sitting in a hearing room where a separation board would soon decide whether to force him to leave the military. He was a 33-year-old transgender Army captain named Kai Proce.

He grimaced at the thought of what was to come.

“Sorry,” Ms. Rashid said.

Last year, Defense Secretary Pete Hegseth issued an order that effectively forced all trans troops out of the military. Many of the more than 4,000 who were serving accepted that the Pentagon was going to force them out and took a cash payout to leave quickly.

But others decided to stay and fight, taking their cases to special separation boards set up by the military.

The boards operate like court proceedings, with lawyers and a panel of three officers who decide whether to retain or remove the service member. It is the same process the military uses to determine whether it should kick out troops who abuse drugs, beat their spouses or steal.

The Pentagon has treated the trans separation hearings with levels of security and silence usually reserved for state secrets. They take place behind closed doors on military bases. There are no cameras and no transcripts; the public is not allowed to attend.

In some cases, service members’ spouses and even the service members themselves are kept out.

One of the few people who have seen the process over multiple hearings, at multiple bases, is Ms. Rashid.

What she has seen are troops who deployed around the world and earned the respect of their peers. They waited patiently, in some cases for years, until the Pentagon finally told them that they could serve openly.

Now, separation boards — afforded almost no leeway by the Trump administration — were punishing them for it.

“It’s in a lot of ways a public humiliation ritual,” Ms. Rashid said in an interview. “Going in, I had hoped I was paranoid, and boards’ outcomes were not predetermined. It turned out to be much worse than I thought.”

The Pentagon declined to comment on the boards.

At least six of Ms. Rashid’s clients were barred from attending their own separation board hearings because they refused to cut their hair and appear in the uniform of their sex assigned at birth. One was a master sergeant in South Korea with 17 years of service who was allowed to testify by video, but only if she turned off her camera.

“I have gone to pretrial confinement hearings where somebody is so addicted to meth that they are throwing up on my shoes,” Ms. Rashid said. “They were allowed into their own hearing.”

For Captain Proce’s hearing in June, she had assembled a nearly 500-page binder that included his personnel records, his military awards, two dozen letters testifying to his character and hundreds of pages of policy papers and legal arguments.

The night before his hearing, Ms. Rashid and Captain Proce rehearsed his testimony one last time. Ms. Rashid asked him about his 11 years in the Army.

He talked about arriving at the U.S. Military Academy at West Point when he was 18 and training to shoot down incoming enemy missiles as an air defense officer.

He deployed to Korea and the Middle East. His last assignment was at West Point, where he mentored 125 cadets and worked for the commandant, who described him in his final performance review as an exceptional leader.

“CPT Proce is easily in the top 1 percent of officers I have served with in 29 years of service,” he wrote.

Before they broke for the night, Ms. Rashid reminded Captain Proce to make eye contact with the Army officers on the panel who would decide his fate.

“It’s harder to sucker punch somebody if they’re looking you in the eye,” she told him.

She packed up her whiteboard and exhibits around 10 p.m.

“How are you feeling?” Ms. Rashid asked.

“I’m not going to be able to sleep,” Captain Proce replied.

‘A Hard No’

Mr. Trump was only a few days into his second term when he issued an executive order proclaiming that being transgender “conflicts with a soldier’s commitment to an honorable, truthful and disciplined lifestyle” and ordering the Pentagon to ban all trans troops.

Mr. Hegseth was blunter: “No more dudes in dresses,” he announced.

Their words described a problem Ms. Rashid said she had never encountered. She had grown up on military bases as the child of an Army doctor who had immigrated from India. The Army had helped her mother get her citizenship and pay her medical school loans.

Ms. Rashid, 33, had joined the Army Reserves in 2020 as a lawyer. Trans troops had been allowed to serve openly since 2016. In Mr. Trump’s first term he blocked transgender people from joining, but allowed those already in the military to continue serving. The Biden administration lifted any restrictions on transgender service members in 2021.

In every assignment — officer training, legal work, a deployment to the Middle East — Ms. Rashid had served with transgender soldiers who had largely been accepted and had thrived, she said.

When the Trump ban was announced, she knew trans troops would need experienced lawyers, so she called the colonel in charge of the Army’s defense attorneys and asked to be assigned to represent them.

The colonel told her to stand down. Trans troops were not being charged with crimes, he explained, and did not require experienced lawyers, like her.

As a new Army lieutenant, Ms. Rashid had been told it was her job to be “the Constitution in the room” for the troops facing discipline. That ethos had led her to take cases that other Army lawyers refused: Soldiers arrested at the Jan. 6 riot; soldiers who refused to get the Covid vaccine; soldiers accused of sexually abusing children.

She told the colonel that she wanted to be that same advocate for the trans troops who were fighting to hold on to their careers.

“I got a hard no,” she recalled.

If the Army was not going to assign her, she decided, she would assign herself. Army reserve lawyers can take on private clients as long as there is no conflict with their military duties.

Working as a civilian attorney, she and a handful of other lawyers reached out to trans soldiers through an online support group that was fighting the ban. She thought they would end up with at most a few dozen clients. They now have advised about 600. They represent all of them for free.

“We just can’t turn people away,” she said. “I think right now we have a budget of, like, $8.”

The separation boards began hearing cases in February. At that point, the Pentagon was required to assign the trans troops military lawyers. Ms. Rashid continued representing them as a civilian.

Her first client was a military police sergeant named Clara Davis. She was tall, with long, auburn hair and a stack of glowing performance reviews. The evidence Ms. Rashid submitted on her behalf included a memo from her battalion commander, who, at risk of retaliation from the Pentagon, recommended that the Army let her serve.

“It was a very brave thing,” Ms. Rashid recalled.

The hearing at Schofield Barracks in Hawaii was unlike any of the hundreds of criminal cases and separation boards Ms. Rashid had handled in her military career.

The Army ordered Sergeant Davis to appear with a male haircut and uniform. Sergeant Davis was willing, but Ms. Rashid said no. “The Army is not allowed to take away your dignity,” she said. “And I’m not going to ask you to do it, either.”

The Army barred Sergeant Davis from entering the hearing room, so she listened from a room down the hall via a bad cellphone connection. Ms. Rashid presented testimony from 25 soldiers who described Sergeant Davis as an asset to the Army.

The core of the hearing, though, focused on her gender dysphoria diagnosis.

The Trump administration’s ban targeted troops with gender dysphoria, a medical condition defined by at least six months of significant distress or impairment because of gender incongruence. Such troops would break under the stress of combat, the Trump administration contended.

Not all transgender people experience gender dysphoria.

Like many medical insurers, the Pentagon had required transgender troops to get a gender dysphoria diagnosis before they could receive hormone therapy or transition.

Ms. Rashid argued that Sergeant Davis had sought out the diagnosis so that she could get access to treatment, even though she did not experience gender dysphoria. The sergeant’s strong service record proved she was never impaired or in distress and was not suffering from gender dysphoria, Ms. Rashid said.

Her diagnosis was essentially used as a trap, she argued.

The board deliberated for two hours and then voted to kick her out. After the verdict, Ms. Rashid found Sergeant Davis in her room down the hall. She hugged her client.

“We were right,” said Ms. Rashid through tears. “And it didn’t matter.”

In the months that followed Ms. Rashid represented trans troops at bases all over the country, sometimes sleeping in her clients’ spare bedrooms to save money. As a lawyer and an officer, she had felt the need to maintain a professional distance from her clients. The trans troops were different.

“I don’t feel like that boundary has to be there,” she said.

As the losses mounted, she was stunned to see soldiers so quickly dismiss other soldiers who, just like them, had spent years in uniform.

One was Maj. Kara Corcoran, 40, who led an infantry platoon in combat in Afghanistan. On the day of her hearing, she was five days short of the 18 years of service she needed to secure her pension and health care benefits for herself and her two daughters.

The government struck half of her character witnesses, arguing that her competence had been established. The question for the board was not whether she was a good soldier, but whether she had gender dysphoria.

The three board members concluded that she did and kicked her out, but they recommended that the Pentagon make an exception and allow her to receive her retirement benefits. She is still waiting on a final ruling from the Army.

“People need to know that this whole thing is cruelty,” Major Corcoran said in an interview. “It was intentionally designed to hurt us.”

Ms. Rashid had hoped the hearings would be therapeutic for her clients — a chance to show they were honorable, truthful and disciplined soldiers. But as the losses piled up, her view shifted.

“Did I just put this person through hell?” she often asked herself after a loss.

The defeats were also taking a toll on her. She believed that all her transgender cases were winnable. Each new defeat brought a new wave of frustration, anger and guilt.

“Did I not explain things in a way that resonated?” she would ask herself. “Am I missing something? Am I supposed to be saying something different?”

Then something completely unexpected happened. The case involved a sergeant first class who worked with classified electronics and had deployed around the world.

The soldier showed up to her hearing in a civilian skirt suit, her hair up in a bun, fully expecting that she would be barred from her own hearing.

At the last minute, Ms. Rashid suggested that she change into camouflage and boots. The officer overseeing the board allowed her into the hearing room.

That gave Ms. Rashid a bit of ammunition: The accused could speak directly to the board members about her decade-long service and show them that she was not a dude in a dress, as Mr. Hegseth had often asserted. She was a soldier who had followed the rules and transitioned after the ban on trans people serving in the military was lifted in 2016.

The hearing ended. “We did the best we could,” Ms. Rashid told the sergeant as they waited for a decision.

A few hours later, the three-person board returned and announced that it had voted to retain her. Ms. Rashid was so stunned that the verdict did not register. She assumed they had lost again.

Then she saw the board members shaking the sergeant’s hand. The victory was a glimmer of hope. Other losses followed. Still, she thought that she had finally found an approach that could win.

Case Number 28

Now it was time for case number 28.

The heavy wooden door at the West Point hearing room swung shut. Ms. Rashid sat down at the defense table next to Captain Proce, who wore his Army camouflage uniform. His hair was cropped short in a style that met Army regulations for either a man or a woman.

The New York Times pieced together what happened next through interviews with the participants and notes from the hearing.

Ms. Rashid argued that Captain Proce’s stellar military record proved that he had never experienced a period of distress or impairment that prevented him from excelling at his job. He was transgender, she acknowledged. But he had never suffered from gender dysphoria.

She called Col. Chad Foster, West Point’s deputy commandant, who was Captain Proce’s last boss. He described Captain Proce as a mentor to the cadets, someone they regularly sought out for advice about personal problems or Army life.

He would happily serve with Captain Proce again, he testified.

Ms. Rashid called Capt. Jessica Jackson, who worked alongside Captain Proce as an air defender. She remembered Captain Proce as the best officer in their battalion.

And Ms. Rashid called Captain Proce, who took a seat in the witness box at the front of the hearing room. He reminded himself to make eye contact with the three colonels on the board.

Captain Proce talked about his grandfather, a former enlisted soldier who had been wounded fighting in Vietnam. “He sat me down and told me that his officers never seemed to care about their soldiers and made decisions with seemingly no regard for their lives,” Captain Proce said. “He made me promise that I would be fast, fair, sure and, above all else, honorable.”

He then recounted his 11 years in the Army, which had taken him to Korea, the Middle East, Texas and Oklahoma. And the 20-minute exam by an Army psychiatric nurse in 2021 that now threatened to end his career.

He had welcomed her diagnosis, which had allowed him to transition. “If I can have this happiness, why would I forgo it?” he asked.

The Army’s case boiled down to a few simple facts. Captain Proce had been diagnosed with gender dysphoria and sought out gender-affirming care, including hormone therapy. The language of the Trump ban was clear, the Army’s lawyer said. The captain needed to go.

The board members spent three hours deliberating in a small room with a coffee maker and a view of a West Point parking lot. When they returned, Captain Proce noticed that they were avoiding eye contact with him. He knew he had lost.

Ms. Rashid gathered her binders, containing the story of Captain Proce’s life and career, in a cardboard box. “I think we can head out,” she said, her voice cracking.

Captain Proce was quiet.

“Are you going to be OK?” she asked. She had started to cry.

“Don’t worry about me,” he replied. “I’ll be fine. I’m worried about you.”

The losses were breaking her faith in the Army, which had been a part of her life since childhood.

“I don’t recognize the military anymore,” she said.

She stood in the hall, tears still in her eyes, and checked her phone. She saw a new email from the Army. Her next client’s separation board hearing was a couple of weeks away.