By the time Rudy Fleming, the 19-year-old charged yesterday in the murder Thursday of an aspiring actress, found himself cruising the Lower East Side early that morning, he already had allegedly committed offenses that could have sent him back to prison.

Those alleged violations of his conditional release from state prison – possession of a gun, violating his curfew, and living at a residence unknown to his parole officer – went undetected at Fleming’s regularly scheduled meeting at an office of the state Division of Parole only hours before he allegedly shot and killed Nicole duFresne, 28, of Brooklyn, at 3 a.m.

Yesterday, Fleming was charged with murder, robbery, attempted robbery, and weapons possession. Charges were also brought yesterday against two other teenagers who allegedly were with Fleming that night: A 14-year-old girl was charged with second-degree murder and another 14-year-old was charged with robbery.

Friends of duFresne have been quoted as saying that after her fiance, Jeffrey Sparks, had been pistol-whipped by the assailant, she stepped into the fray and asked the gunman, “What are you going to do, shoot us?”

This week, the authorities made it known that Fleming had served nearly three years in state prison for previously wielding a gun when confronted.

On November 27, 2001, when he was 16,Fleming was picked up by truancy officers for skipping school. After refusing to be searched, Fleming reached for his “.380 Hi Point Semi-Automatic Pistol … racked the slide and got into a shooting position,” in the words of a letter sent May 12, 2003, by the Staten Island district attorney’s office to the Division of Parole. Upon conviction of a Class D felony, which the office said yesterday could have brought a sentence of up to seven years in prison, Fleming was ordered incarcerated for three years, to be followed by three years of what is known as post release supervision.

The 2003 letter, written by a Richmond County assistant district attorney, Raymond Rodriguez, strongly advised against giving Fleming parole. And the parole board did deny Fleming’s repeated requests for parole, the last one in April 2004.Three months later, because he had served six-sevenths of his three-year sentence without being penalized for bad conduct during his incarceration, under state law Fleming was automatically released. Fleming then began the second phase of his sentence: the court-imposed post release supervision, during which he was required to report to a parole officer until June 2007.

On June 18, 2004, Fleming became one of what the department’s Web site says are 45,000 people supervised by the Division of Parole. The parole officers union, the New York State Public Employees Federation, represents the approximately 1,200 parole officers statewide – which works out to a caseload of nearly 40 per parole officer. A spokeswoman for the union, Sherry Halbrook, said the number of people under an individual parole officer’s watch can be as high as 100, in part because people who have been under supervision for more than a year are counted as a fraction.

“A parole officer’s job is half law enforcement, half social work,” Ms. Halbrook said. “The parole officer has to verify the validity of the information from the parolee. The best way to do that is to get out into the street and check up on him. That’s the investigative side. The other side is the is the social worker side, to help a parolee get housing and a job.”

Fleming’s parole officer had helped secure a job for the teenager, at a restaurant that the authorities declined to identify, and helped him participate in certain rehabilitative programs that were a condition of his release, a spokesman for the Division of Parole, Scott Steinhardt, said yesterday.

On Dec. 23, Fleming passed a crucial test, when his parole officer made an unscheduled visit to his residence in the Bronx to make sure the youth was home and not breaking his curfew, which mandated he stay home every night between 9 p.m. and 7 a.m. The frequency of unscheduled visits is left to the discretion of a parole officer, but that was the last time someone checked on Fleming other than a routine office visit the day before last week’s murder.

A call to his employer January 6 by the parole officer confirmed that Fleming had showed up for work, Mr. Steinhardt said. Everything, it seemed, was in order.

And that January 26 visit by Fleming to his parole officer was “unremarkable,” Mr. Steinhardt said. No red flags were raised – and it became known only after the shooting that Fleming, who came from a broken home, had apparently been living, of late, with his godfather at an apartment at the Baruch public-housing development at Lower Manhattan. That is a change Fleming would have had to report to comply with the terms of his parole.

It is unclear at what point Fleming might have acquired the alleged murder weapon, a .357 Taurus revolver.

“Carrying a gun is clearly a violation,” Ms. Halbrook said.

Normally, such violations, including breaking his curfew and moving, would send a paroled convict to an administrative law judge to rule on his case, Mr. Steinhardt said.

Instead, the alleged violations by Fleming went undetected – at a time when the parole officers union has been complaining that unnecessary paperwork keeps officers from doing their job properly.

“You can’t take what a parolee says at face value. You have to free parole officers up so they can do their job,” Ms. Halbrook said. “This is a system-wide problem.”

The Division of Parole has maintained that such paperwork is critical to the officers’ job and does not have the effect of compromising public safety.

Fleming and four other teenagers were picked up for questioning Sunday night after police received tips from the public about the case, which was widely publicized. Two of the four were charged with attempted robbery in a related case the same night, but were not charged in the duFresne slaying. The remaining two are considered witnesses, police said. The 14-year-old girl who was charged with murder was taken to police in Brooklyn on Monday by her mother, according to the Associated Press.

Friends and family held a memorial service in Seattle for Nicole duFresne, who was originally from Minnesota and lived in the Pacific Northwest before moving to New York to pursue a career as an actress and playwright. Her resume, which includes performing in 25 theater and film productions, mentions her skills in stage combat and clowning.

If convicted of murder, Rudy Fleming could face a sentence of up to life in prison.