PALM BEACH, Fla. — In 2008, a supervisor at the county jail here alerted staff members to the needs of an inmate serving an 18-month sentence for sex crimes involving a minor. Jeffrey Epstein, he wrote in a memo, was a first-time offender “poorly versed in jail routine,” and “his adjustment to incarceration will most likely be atypical.”

“For the time being, I am authorizing that his cell door be left unlocked and he be given liberal access to the attorney room where a TV will be installed,” Capt. Mark Chamberlain wrote in August of that year.

The memo does not indicate how long the cell door was to be left unlocked, but it and other documents obtained through public-records requests shed new light on the apparent deference granted to the wealthy financier while in the custody of Palm Beach County, as well as on the conditions of his confinement.

During much of his sentence, Epstein was allowed to leave the county’s minimum-security stockade 12 hours a day, six days a week, for a work-release program, a job at a nonprofit foundation he had created. Sheriff’s deputies assigned to monitor the multimillionaire on these outings allowed him to enter his Palm Beach estate on at least nine occasions toward the end of his sentence, at least once unattended and for four hours, according to the deputies’ reports.

Ric Bradshaw, the Palm Beach County sheriff then and now, on Friday announced an internal-affairs investigation into the actions of deputies assigned to monitor Epstein on work release. “All aspects of the matter will be fully investigated to ensure total transparency and accountability,” Bradshaw, whose office operates county detention centers, said in a statement.

Epstein’s time in jail has come under scrutiny in recent months amid criticism that his sentence did not match his alleged crimes: He was suspected of molesting dozens of girls, some as young as 14. A fresh wave of scrutiny followed his arrest this month by federal authorities in New York on charges similar to those he faced in Florida more than a decade ago.

In Florida, Epstein and his attorneys struck a deal with federal prosecutors that allowed him to plead guilty in state court to two felony offenses, including procuring a person under 18 for prostitution. Under an arrangement with state prosecutors, Epstein served his sentence in the custody of county authorities rather than in a state prison.

Epstein was soon transferred to the lower-security Palm Beach County Stockade, records show. At the request of his attorneys, he was housed in the “T-dorm,” an area reserved for inmates who must be separated from other inmates. In February of the following year, he was moved again. “It has been agreed upon by his legal staff that Inmate Epstein will pay for the security staff to supervise him in this previously unstaffed housing unit, the infirmary at the Stockade,” an official from the sheriff’s office wrote in an email.

Participation in the work-release program was a privilege granted to him at the discretion of the sheriff’s office. Though inmates on work release are not generally accompanied by deputies, Epstein was “monitored by a deputy the entire time he was out,” said Teri Barbera, a spokeswoman for the sheriff’s office.

Epstein paid $128,136 for the deputies to watch him, according to the records. One deputy wrote that he sought clarification of his duties and was told his job was to “provide security” for Epstein.

The deputies who monitored him were required to wear suits and to “greet inmate Epstein upon his arrival,” documents show. In internal reports about the work-release program, the deputies often describe Epstein as “the client” or “Mr. Epstein.” Two deputies refer to him as “Jeffrey.”

In 464 such reports, only rarely is he “Inmate Epstein.”

Bradshaw’s second-in-command, Chief Deputy Mike Gauger, told a film crew in April that Epstein’s wealth and notoriety warranted “special precautions.” At the same time, Gauger described Epstein as a model inmate and denied that he was granted unusual privileges because of his fortune or his association with powerful figures such as Donald Trump, former president Bill Clinton and Britain’s Prince Andrew.

“I’m just saddened that some people thought it was corruption, that he was given all these privileges because of his wealth,” Gauger said in video footage released last week by the department, which said it had been shot for a documentary. “He was made to jump through additional hoops and meet additional requirements because of his wealth.”

Palm Beach County Sheriff’s Office Chief Deputy Mike Gauger was interviewed regarding Jeffrey Epstein, who served an 18-month sentence at the jail in 2008. (Palm Beach County Sheriff's Office)

The case was brought back to public attention by a Miami Herald investigation last year. Epstein, 66, was arrested July 6 in New York. Federal prosecutors called him a “serial sexual predator” and alleged that he sexually abused dozens of children there and in Florida from 2002 to 2005.

Epstein has pleaded not guilty. His attorneys have argued in court that the new charges are an unwarranted “redo” of a case he settled years ago.

The top federal prosecutor in South Florida at the time of Epstein’s prosecution, Alexander Acosta, later became President Trump’s labor secretary, only to resign last week amid criticism of his handling of the case. Before his resignation, Acosta distanced himself from the accommodations Epstein had in jail, saying at a news conference that “the work release was complete BS.”

For the work-release program, Epstein traveled not with the sheriff’s deputies assigned to him but with a personal driver, a former mixed-martial-arts fighter from Russia named Igor Zinoviev. Epstein reported to a high-rise in West Palm Beach, where he worked at the Florida Science Foundation, a nonprofit group that state records show he founded shortly before his sentence began and dissolved shortly after his sentence was completed.

Epstein’s attorney incorporated the foundation as a nonprofit to “support through grants” organizations “involved in the fields of science and research,” according to state incorporation records. The foundation does not appear to have filed any public records with the Internal Revenue Service as a nonprofit.

Soon after Epstein was granted work release, the assistant U.S. attorney who handled his case sent a letter to the sheriff’s office. “I discovered some inaccuracies and omissions in Mr. Epstein’s file that I wanted to bring to your attention,” Assistant State’s Attorney A. Marie Villafana wrote on Dec. 11, 2008.

Villafana pointed out that the foundation Epstein said he was working at, and his 12-hour-a-day job schedule, “were all created on the eve of Mr. Epstein’s incarceration in order to provide him with a basis of seeking work release.”

In reports that logged his time in the program, deputies wrote that they “worked the front desk” while Epstein met with “guests.” A log of the visitors, a record that is county property, was kept by Epstein’s secretary in a safe in his office, according to the deputies’ reports. The log has since been destroyed as part of the sheriff’s department’s “records retention” protocol, Barbera said.

At times in the reports, the deputies appear to take direction from Epstein. In a report on Dec. 26, 2008, one deputy wrote that he “met w/Epstein I informed him I was here for the detail at which time he explained the parameters.”

Another wrote on June 12, 2009: “I provided low profile security for Mr. Epstein ensuring that no unauthorized persons entered the office or approached him. I was in charge of properly checking in welcomed guests.”

Epstein’s driver took him to outside appointments dozens of times during his work release, the records show. A deputy would follow, or meet Epstein at his destination, they show.

On July 11, 2009, another deputy drove Epstein to his house, where Epstein stayed for four hours. “I backed into the driveway and provided security to prevent unwelcome guest[s] from entering his property,” the deputy wrote in his report. “I did not go into the residence.”

Efforts to reach the deputies for comment were not successful. Chamberlain, the captain, who has since retired from the department, did not respond to messages seeking comment.

An attorney for Epstein’s accusers alleged last week that Epstein had committed “improper sexual conduct” while he was out on work release.

“He just wasn’t in jail. He only slept there,” attorney Brad Edwards said at a news conference. “He was in his office most of the day, and what I can tell you, he had visitors — female visitors.”

“They believed they were going there for something other than a sexual purpose,” Edwards said. “Once there, he used his perfect master manipulation to turn the situation into something sexual.”

Barbera said she had no knowledge of any assault while Epstein was in custody, adding that “our eyes were on him all the time.” In the video interview, Gauger said: “The only ones that were allowed to visit him were his attorneys or his business partner. And there was a sign-in sheet, and it was very closely monitored by our team.”

Roy Black, an attorney for Epstein, did not respond to requests seeking comment on Edwards’s claim.

At least 92 deputies applied to be with him while he was out of the stockade. They earned overtime pay for the jobs, ranging from $42 to $64 an hour, as Epstein’s “permit deputies.”

Some of the deputies were confused about their job duties. Lt. Steven Thibodeau wrote in an email to a colleague that he had received “several calls from confused permits deputies regarding” Epstein. “Several permit deputies weren’t sure who the client is and how far to push the work release do’s and don’t,” he wrote.

Barbera said Thibodeau could not comment, citing the internal investigation.

Gauger told the documentary crew that Epstein’s sentence was ultimately shortened by five months. He “was given gain time because of his good behavior, just like any other inmate,” he said.

Epstein was placed on house arrest, at his Palm Beach waterfront estate. He reported to a parole officer for the next year, records show.

After his sentence was completed in July 2010 — 18 months, with the time in the stockade, on work release and on parole — Epstein left Florida. He did not return until January.

He checked in regularly as a sex offender with the Palm Beach sheriff’s office, as he was required to do, and his attorneys notified the office when Epstein was shopping for a helicopter.

Epstein had friendly email exchanges with sheriff’s officers. At one point, he emailed to let them know he was coming to town. He asked a captain, Lawrence Wood, how he was doing.

“I’m good,” Wood replied in January 2011. “I hope you had a good holiday, if you need something when you fly in you can always call. Have a good day.”

Wood was not available for comment, Barbera said, citing the internal investigation.

Alice Crites in Washington contributed to this report.