Ted Conover receives an appointment letter from the Department of Corrections and quits his journalism job to begin officer training.

Conover arrives at the Albany Training Academy to begin a seven-week corrections officer recruit training course.

Recruits visit Coxsackie prison and are brought to the yard where inmates shout obscenities and insults directly at them.

Conover finishes recruit training and is assigned to Sing Sing, described by trainers as the prison at the bottom of the barrel.

Conover is assigned to B-block galleries for his first OJT shift and is overwhelmed by the chaos and Officer Fay's total incompetence.

A red-dot emergency erupts when a guard accidentally unlocks a keeplock's cell and the freed inmate slashes another prisoner.

Conover observes Officer Smith's firm but respectful approach to gallery management and resolves to aim for a similar standard.

The new recruits are officially converted into regular correction officers on Conversion Day.

An inmate in A-block punches Conover in the face after Conover confiscates the inmate's mirror from his cell.

Conover participates in a forced cell-extraction in the Special Housing Unit and afterward questions what is won by breaking men's spirits.

Conover is assigned to suicide watch for self-harming inmate Morales, who says prison pressure drives him to injure himself.

Mama Cradle's transfer to a less demanding prison is approved, and B-block officers hold a celebration on her final day.

Conover bids B-block as his dedicated daily assignment, drawn by the challenge of working the most demanding galleries.

Conover works the New Year's Eve night shift as inmates set debris fires throughout the prison in celebration.

Newjack is published and classified as contraband in New York state prisons, with offending pages torn out by officers.

Ted Conover abandons his journalism career to secretly infiltrate Sing Sing as a corrections officer recruit, surviving seven weeks of grueling academy training before being assigned to the most chaotic prison in the state. During on-the-job training he struggles through his first violent and disorganized shifts, witnessing a brutal red-dot emergency and nearly losing control of the gallery before finally being converted to a full officer. As a regular officer, Conover is punched by an inmate, participates in a forced cell extraction in the Special Housing Unit, and is assigned to monitor a suicidal prisoner in the psychiatric ward. He watches colleagues break down and leave the job while learning to harden himself to the relentless aggression and institutional dysfunction of daily prison life. By the time Mama Cradle departs and Conover secures his own dedicated post on B-block, prison has fundamentally reshaped who he is. The book closes with Conover surviving a fiery New Year's Eve shift before his tell-all account is banned in the very prisons he spent a year documenting.

The core journey from recruit to correction officer.

Conover is awestruck by an enclosed display of inmate weapons and the hidden compartments used to conceal them at the Academy.

Recruit roommate Russell Dieter makes increasingly violent and threatening remarks until Conover is relieved to be reassigned to different housing.

During the final weeks of training, recruits are exposed to chemical agents and shown footage of officers seriously injured by inmates.

Conover arrives at Sing Sing for on-the-job training and finds the prison is a decaying, hard-to-navigate maze of corridors and gates.

A senior officer instructs Conover's group to omit key information from an official Fire and Safety report during OJT.

Conover loses the gallery keys during a red-dot emergency and is only saved when Officer Don Allen returns them to him.

Conover tries to enforce an antenna rule in A-block and realizes that power and authority are at stake in nearly every inmate interaction.

Senior officers pressure Conover to rewrite a disciplinary report and remove Officer X's name after inmate Hawkins files a grievance.

Conover discovers news footage revealing Sergeant Wickersham was both a Vietnam POW and a hostage during a Sing Sing prisoner takeover.

Warden Elam Lynds forces Auburn inmates transported by boat to a new site to build Sing Sing prison stone by stone.

Prison reformer Thomas Mott Osborne spends a week inside Auburn prison under the alias Tom Brown to experience incarceration firsthand.

Conover and other officers search B-block inmates for fresh knife wounds after a retaliatory clash between the Latin Kings and the Bloods.

Conover finds a bar of soap with a two-inch heart carved into it inside the desk drawer left by night-shift Officer Sims.

Conover meets keeplock inmate Larson in cell R-29, a calm self-educated man who serves as a spiritual father figure to fellow inmates.

On his last day on R-and-W gallery, Conover abandons a completely inexperienced relief officer to face the oncoming chaos alone.

From his first days at the training academy, Conover is immersed in the culture of intimidation and institutional rule-bending that defines corrections work, encountering threatening classmate Russell Dieter and watching senior officers casually falsify official reports. Once inside Sing Sing for on-the-job training, he nearly loses control of an entire gallery when he misplaces his keys during a crisis and discovers that the academy's strict rules bear little resemblance to how the prison actually operates. He learns to navigate unofficial pressures, including being asked to cover for colleagues in disciplinary paperwork and understanding that authority must be constantly negotiated with inmates over even minor incidents. The book pauses to trace the origins of Sing Sing itself, following Elam Lynds's brutal founding of the prison and Thomas Mott Osborne's remarkable decision to experience incarceration from the inside. Back in the present, small human moments cut through the institutional grind — a soap heart left in a desk drawer, a conversation with the eloquent keeplock Larson. Conover's time at Sing Sing ends not with ceremony but with him quietly abandoning a new officer to face the chaos of the galleries alone.

The hidden details and secondary stories behind prison life.

Conover decides to become a correction officer recruit after repeated attempts to report on prison life as a journalist are refused.

During a self-defense drill at the academy, recruits who were just subjected to abuse eagerly enact violence when the roles are reversed.

A training instructor mockingly demonstrates CPR on an imaginary inmate by pumping the chest with his boot and blowing toward the floor.

A prison union director reveals that corrections officers have the highest divorce rates, shortest lifespans, and worst substance addiction of any state employees.

At the end of his first chaotic OJT shift, an inmate surprises Conover by throwing a fake punch at his head.

During a strip-frisk procedure known as Nuts and Butts, Conover is deeply unsettled by witnessing an inmate's forced compliance.

After hearing that Officer Arno was beaten by colleagues following an inmate assault, Conover finds comfort in the story rather than revulsion.

A keeplock in Officer Michaels's block defiantly takes an unauthorized shower as a direct challenge to Conover's authority.

Alexis de Tocqueville and Gustave de Beaumont visit the Sing Sing construction site and declare it offers the spectacle of complete despotism.

Electric chair executioner John Hulbert's mental health deteriorates steadily during his years at Sing Sing until he commits suicide.

Prison reformer Thomas Mott Osborne is ousted as Sing Sing's warden within a year after attacks on his character dismantle his reforms.

Inmate Larson challenges Conover to consider that prisons being planned for the future are already being built for children who are alive today.

Conover's patience snaps after a long shift and he spanks his young son, acknowledging he has never felt meaner or more vulnerable.

A Department of Parole employee dismisses Conover's concern about releasing an unstable inmate by saying simply, 'Don't worry. They all come back.'

After Newjack's publication, former co-worker officers attend a book reading and tell Conover they appreciate his honest depiction of their work.

Conover enters the corrections system with a journalist's detachment, but the training process itself immediately begins cycling abuse from superiors to recruits, foreshadowing how that same dynamic will operate inside Sing Sing. At the academy, he is confronted with black humor about inmate lives and learns from a union director that corrections work statistically destroys officers' health, marriages, and longevity. On the job, small incidents — a fake punch, a forced strip search, a colleague's beating met with relief rather than revulsion — reveal how quickly prison reshapes moral instincts. A historical detour into Sing Sing's past shows that the despotism Conover witnesses is centuries old, having claimed the sanity and even the life of employees assigned to run the institution's most brutal machinery. Prison reformer Thomas Mott Osborne represents a road not taken, his humane vision dismantled almost as quickly as it was built. By the book's end, Conover is spanking his own child at home, hearing a parole official dismiss an inmate's future with a shrug, and sitting at his own book reading — fully reckoning with how thoroughly the prison system reshapes every person it touches.