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Ms. Manning, in a 2010 photograph. Credit U.S. Army, via Associated Press

Most mornings at 4:30, half an hour before the “first call” awakens inmates at the Fort Leavenworth military prison in Kansas, an alarm rings within an 80-square-foot cell. Inmate 89289, slightly built with short hair, rises to apply makeup and don female undergarments and a brown uniform before the still-slumbering men in the adjacent cells stir.

That is the routine for Chelsea Manning, America’s most famous convicted leaker and the prison’s most unusual inmate. She is serving the longest sentence ever imposed for disclosing government secrets — 35 years — and her status as a celebrity of sorts and an incarcerated transgender woman presents continuing difficulties for the military.

During the day, Ms. Manning, who was an Army intelligence analyst known as Bradley Manning when she disclosed archives of secret military and diplomatic files to WikiLeaks in 2010, builds picture frames and furniture in the prison wood shop. In the evenings, before the 10:05 p.m. lockdown, she reads through streams of letters, including from antisecrecy enthusiasts who view her as a whistle-blower.

“I am always busy. I have a backlog of things to do: legal, administrative, press inquiries, and writing — lots of writing,” Ms. Manning wrote in response to questions submitted by The Times because the Army does not permit her to speak directly to journalists. “Being me is a full-time job.”

But Ms. Manning, who is struggling to transition to life as a woman while enduring a bleak existence at a male military prison, has asked President Obama to commute the remainder of her sentence before he leaves office next week. She poses particular challenges as a prisoner, with a volunteer support network that helps bring global attention to her treatment, fragile mental state — she twice tried to commit suicide in 2016 — and need for treatment that the military has no experience providing.

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Her request comes as the world is again focused on WikiLeaks and its founder, Julian Assange, whom her leaks made famous. The organization last year published Clinton campaign emails, obtained in a hacking, as part of what American intelligence officials claim was a covert Russian operation aimed at tilting the election to President-elect Donald J. Trump. (Ms. Manning declined to discuss WikiLeaks, saying only that her decision to send documents to it “was neither an endorsement nor an affiliation.”)

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Ms. Manning’s mug shot from the Fort Leavenworth prison in Kansas.

It also comes at a time of flux in the military’s policies on gender identity. Last June, the Obama administration rescinded a ban on transgender people serving in the military and began overhauling its practices, which eventually would include providing gender reassignment surgery. But Mr. Trump has derided the lifting of the ban as “politically correct,” raising the possibility that his administration may roll back the changes.

The White House declined to comment on Ms. Manning’s commutation request. The Army declined to comment about her situation at Fort Leavenworth, citing privacy laws.

A military prosecutor had called Ms. Manning a “traitor” at her 2013 court-martial, and officials have said the disclosures disrupted government operations and put people at risk, although prosecutors did not claim anyone was killed because of them.

In a statement accompanying her petition asking Mr. Obama to reduce her sentence to the nearly seven years she already has served, Ms. Manning, now 29, said she never intended to hurt anyone and pleaded for a chance to start her life over.

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“I need help,” she wrote. “I am living through a cycle of anxiety, anger, hopelessness, loss, and depression. I cannot focus. I cannot sleep. I attempted to take my own life.”

Transformation in a Crucible

On Aug. 22, 2013, the day after her sentencing for sending documents to WikiLeaks, Ms. Manning’s lawyer read a statement on the “Today” show announcing that she was female, wanted to be called “Chelsea” rather than “Bradley” and would seek cross-sex hormone therapy.

To observers of her court-martial, this was no surprise. Her motivation for leaking hundreds of thousands of files she had copied from a classified computer network while serving in Iraq, as she wrote at the time, was hope that they would spark “worldwide discussion, debates, and reforms.” But at her trial, she apologized and noted that she was “dealing with a lot of issues” when she had made that decision.

Testimony showed that she had been in a mental and emotional crisis as she came to grips, in the stress of a war zone, with the fact that she was not merely gay, as she had believed while growing up in Oklahoma, but had gender dysphoria — a disconnect between one’s gender identity and sex assigned at birth. In the months before her leaks and May 2010 arrest, she had been behaving erratically and emailed a picture of herself wearing a woman’s wig to her supervisor.

The military sent Ms. Manning to serve out her sentence as a medium-security inmate at the Fort Leavenworth Disciplinary Barracks, its main prison for male inmates.

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Fort Leavenworth Disciplinary Barracks, where Ms. Manning is a medium-security inmate in a prison for men. Credit United States Army

Court documents show that Ms. Manning has had counseling sessions with a prison psychologist, Dr. Ellen Galloway, at least once a week, and military authorities have over time allowed her access to some treatments doctors prescribed for her gender dysphoria, in part because of pressure from a lawsuit filed by Chase Strangio, a lawyer for the American Civil Liberties Union, in September 2014.

She can now wear female prison undergarments, including a sports bra, and “subdued cosmetics.” In early 2015, she was permitted to get speech therapy to feminize the tone and pitch of her voice and began cross-sex hormone therapy prescribed, Mr. Strangio said, by an endocrinologist brought in from the military’s Walter Reed hospital.

Since then, Ms. Manning wrote, she has developed breasts and curvier hips. “There have been significant changes since I’ve been taking the hormones, and I am happy with them,” she said.

But, citing security risks, the military rejected the recommendation of an outside psychologist who said she should be permitted to further feminize her appearance by growing her hair longer than male military standards. Mr. Strangio is helping her challenge that restriction.

“Plaintiff feels like a freak and a weirdo — not because having short hair makes a person less of a woman — but because for her, it undermines specifically recommended treatment and sends the message to everyone that she is not a ‘real’ woman,” he wrote in a court filing.

“She is getting hormones, but it sounds like the inability to socially transition, or to have surgery, could be contributing to suicidality — especially when she is looking at decades in prison and thus a certain hopelessness about whether that might ever be available for her,” said Dan Karasic, a University of California, San Francisco psychiatrist and the chairman of the American Psychiatric Association’s work group on gender dysphoria; he cautioned that he had not examined her.

The military turned down a request by The New York Times to visit the facility. But an Army spokesman, Wayne Hall, provided written answers from the Army Corrections Command to questions posed by The Times, from which a sketch of her environment emerged.

Ms. Manning’s cell, like others at Fort Leavenworth, contains a bed, toilet, sink, locker, storage bin, chair and desk, according to the Army. She showers in a nearby communal bathroom with individual stalls. She has no access to the internet, but says she receives “at least a couple hundred pieces of mail every week.”

The Army does not permit her to see people who did not know her before her incarceration, so she is not allowed to meet with a handful of volunteers who have formed an informal network of supporters, but she calls one of them daily. A volunteer who relayed questions from The Times to her asked not to be named, citing security concerns.

Ms. Manning said she recently finished reading “Superintelligence: Paths, Dangers, Strategies,” a book about artificial intelligence by the Swedish philosopher Nick Bostrom, and “1Q84,” a dystopian novel by Haruki Murakami. She is interested in efforts to develop stronger encryption and has been “going through” the “Princeton Companion to Mathematics.” She also said she reads women’s athletic, fashion and lifestyle magazines like Shape, Vogue, Vanity Fair and Cosmopolitan.

Her cell door has a window looking onto a central “day room” with tables, chairs, pay phones and televisions. For a time, Ms. Manning played Dungeons & Dragons with a few fellow inmates, but she said she had had no time in recent months. She eats meals with other inmates in a dining facility and works on a team at the wood shop.

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Staff Sgt. Dawn Shields, who works at a housing unit at the Disciplinary Barracks, searched a cell there. Credit Sgt. Vincent Daly/United States Army

The roughly 424 inmates held at Fort Leavenworth with Ms. Manning include men accused of routine crimes as well as some who drew public attention, including Nidal Hasan, convicted in a 2009 mass shooting at Fort Hood and held on the prison’s death row wing, and Robert Bales, who murdered 16 Afghans in Kandahar and was sentenced to life without parole in August 2013.

Ms. Manning declined to say much about the guards or fellow inmates, other than to say that they have never bullied or attacked her.

“It’s best to keep to yourself and try not to get involved in any drama,” she wrote. “It’s a little harder for me to keep to myself, since the staff is constantly watching me and those that interact with me. But I’m used to it by now. I don’t feel threatened by the other prisoners. I have friends.”

Doing Hard Time

Her special status at Fort Leavenworth is evident. Nancy Hollander, one of the lawyers working on the appeal of her conviction and sentence, said the Army built a special secure information facility in a windowless basement room so she could meet with them and discuss still-classified documents she leaked.

While Ms. Manning said she could not say on her monitored phone calls “anything critical of the prison or the current administration or I can get charged for violation of a lawful general order,” her supporters pay close attention to her treatment.

Scrutiny of the military’s struggles to deal with Ms. Manning go back to her confinement at the Quantico, Va., brig after her arrest, when she was held for months in isolation, shackled during exercise and sometimes stripped of clothing and glasses to prevent her from harming herself — even after a prison psychologist said such steps were unnecessary. A military judge ruled that the treatment had been illegal.

At Leavenworth, after a minor disagreement with a guard in 2015, officials punished her, among other things, for “medical misuse” because they found a tube of toothpaste in her cell that was past its expiration date. Her supporters publicized the incident.

In September, her supporters issued a news release saying she was on a hunger strike because of an “overzealous administrative scrutiny” and lack of progress in getting more treatment.

She resumed eating after five days. Mr. Strangio said an official told her she would be eligible for the same medical treatment as non-incarcerated transgender soldiers, suggesting she would eventually be permitted to proceed with surgery. But months have passed, and Ms. Manning wrote that she has not seen a surgeon.

Later in September, a prison board disciplined Ms. Manning for the disruption a July suicide attempt had caused. The punishment: solitary confinement. While in isolation in October, she tried again to kill herself — by choking herself on a piece of clothing, according to a support network member — before guards intervened.

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At a gay pride parade in San Francisco in 2015, supporters of Ms. Manning held signs calling for her release. Credit Elijah Nouvelage/Reuters

About a week further into that stint in solitary, she experienced a bizarre episode in which four people impersonating guards simulated breaking into the prison one night and pretended to kill her regular guards, filling her with fear, according to an account she filed with the army inspector general.

A military official denied her account. Dr. Stuart Grassian, a specialist in the psychological effects of solitary confinement, said her description is consistent with hallucinations often experienced by unstable people placed in isolation.

Now, with 28 years of her sentence to go and uncertainty over whether the Trump administration will deny her sex-reassignment surgery, Ms. Manning is hoping Mr. Obama will take mercy on her and free her from military prison, which goes by the acronym U.S.D.B.

“I am not asking for a pardon of my conviction. I understand that the various collateral consequences of the court-martial conviction will stay on my record forever,” she wrote in her commutation application. “I am merely asking for a first chance to live my life outside the U.S.D.B. as the person I was born to be.”

Correction: January 13, 2017
A picture showing a cellblock for military inmates was posted in error with an earlier version of this article. The cellblock shown was for military inmates serving less than five years; it was not the cellblock Manning lives on. (She is serving more than five years.)
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