More insight into Matthew Perry's final moments are being uncovered. 

The Friends alum's last conversation with his assistant Kenneth Iwamasa—one of five people charged in connection to Perry's death—before being injected with his fatal dose of ketamine was revealed in a plea agreement Iwamasa made with the Department of Justice that was obtained by E! News Aug. 16. 

On the day of Perry's Oct. 28 death, Iwamasa injected Perry with a dose of ketamine—a controlled substance known for its dissociative effects—around 8:30 a.m., the plea agreement alleged. The assistant gave him a second dose at 12:45 p.m. while Perry watched a movie. Forty minutes later, Perry asked him for another injection and to prepare the hot tub, allegedly saying, “Shoot me up with a big one.”  

Shortly after the interaction, the Fools Rush In actor's third dose was administered, and Iwamasa left to run errands, per the filing. When he returned, he allegedly found Perry dead, face down in the jacuzzi.  

E! News reached out to Iwamasa's attorney for comment but has not heard back. 

Perry and Iwamasa's final exchange isn't the only detail that’s come to light about the assistant's alleged involvement in the 54-year-old's death, which was ruled a drowning and drug-related accident—the result of "the acute affects of ketamine," according to the Los Angeles Medical Examiner. The DOJ also alleged in an Aug. 15 press conference that Iwamasa had no prior medical training before injecting Perry with the drug doses. 

Additionally, prosecutors said that approximately 20 vials of ketamine were distributed to Perry between September and October 2023 in exchange for $55,000 cash from him.

Iwamasa—who allegedly worked with Perry's doctors to administer the drug to his boss—pleaded guilty to one count of conspiracy to distribute ketamine causing death in connection to Perry's passing. 

Following his guilty plea, U.S. attorney Martin Estrada spoke out on how the five defendants in the case took advantage of Perry's longtime struggle with drug addiction for their own benefit. 

"They knew what they were doing was wrong," the lawyer said in the DOJ's Aug. 15 press conference. "They knew what they were doing was risking great danger to Mr. Perry, but they did it anyways."

Estrada added, "In the end, these defendants were more interested in profiting off Mr. Perry than caring for his well-being."