PORTLAND, Ore. (KOIN 6) — Court documents are now providing new details about an elaborate operation to smuggle a wanted man – linked to the shooting of a Portland Police officer, and his K-9 dog – and his girlfriend out of the United States and into Canada.

Carli Anja Marshall turned herself into the Multnomah County Sheriff’s Office Wednesday afternoon. A warrant, accusing her of three counts of hindering prosecution, was signed March 19, 2015. Court documents also accuse Marshall’s friend, Dylan Richard McBee, of the same crimes.

At the center of the case is 26-year-old Jemaell Diamond Riley. Police said he was one of three people arrested after the April 16, 2014 shooting of K-9 Officer Jeff Dorn and his canine partner “Mick,” who was killed in the shooting. Portland Police said Riley was not the shooter, but was armed at the time of the arrest.

Riley's girlfriend, 20-year-old Carli Marshall, may be with him. (PPB)

Portland Police Homicide Detective Anthony Merrill wrote in an affidavit that Marshall, Riley’s live-in girlfriend, posted over $50,000 on Oct. 6, 2014 so he could be released from jail. Merrill wrote that on Oct. 23, Multnomah County Sheriff’s Deputy Kari Kolberg, who assigned to the Close Street Supervision Program, placed a hold on Riley after he was arrested on allegations of violating is release agreement.

Senior Deputy District Attorney Chris Ramras told Merrill that on Oct. 31, Riley was released from jail after Marshall once again posted an additional $25,000 to bail him out, the warrant states. Riley was placed under house arrest and Kolberg issued him a GPS device. Riley was ordered to stay at Marshall’s apartment in the 300-block of Southwest Lincoln Street, court documents state.

Kolberg was alerted on March 18 that Riley had cut off his GPS ankle bracelet, court documents state. Records show it was removed around 5:50 a.m. near Interstate 205 between Tualatin and West Linn. Kolberg tried to call both Riley and Marshall on their cell phones, but neither answered, court documents state. The GPS device was found by two people who turned it into the West Linn Police Department, Merrill wrote in his affidavit.

Kolberg, Merrill and other investigators went to Marshall’s apartment unit where a landlord gave them a key. When there was no answer, court documents show that Kolberg entered and started searching. She was unable to find either Riley or Marshall. Video from the apartment shows a female, wearing a sweatshirt with the hood flipped up, carrying a backpack, suitcase, get into an elevator and leave the building, court documents state. The timestamp was about 5:11 a.m., court documents state.

Around 5:12 a.m. on March 18, a man believed to be Riley is also seen exiting the building, court documents state.

The next day, on March 19, an officer with the Canada Border Services Agency alerted Merrill that Riley, Marshall and McBee were arrested around 12 p.m. trying to cross the border at the Peace Arch Port of Entry, which is on the Washington State border to Canada, court documents state.

Police said when McBee was stopped driving a 2002 Subaru Legacy, he had a Wisconsin driver’s license and told officers that “he was crossing the border alone,” Merrill wrote. The border officer searched the vehicle and found “a lot of documents and a very large sum of money in a back pack,” Merrill wrote. The cash was estimated to be about $7,000, court documents state.

Jemaell Diamond Riley, 26, allegedly cut off his ankle monitoring bracelet and is on the run in Portland. March 18, 2015 (PPB)

As border officers were searching the vehicle two people “suddenly popped their heads up from under a blanket in the back seat,” Merrill wrote. They were both identified as Riley and Marshall, police said. McBee told border officers that he had known Marshall for about one year, and that he was an acquaintance of Riley, court documents state. McBee told border officers that he knew both Marshall and Riley were in trouble and that he “picked them up in his vehicle from their apartment,” Merrill wrote.

The three reportedly had a discussion and agreed that they would drive to Canada, court documents state. When border officers search McBee, they found about $4,000 on him and he reportedly told them that he was not forced to drive Riley and Marshall, court documents state.

Deputy District Attorney Joel C. Petersen filed a motion to increase Marshall’s bail to $500,000. She and Riley, once released from the United State Border Patrol, were taken into custody by the Whatcom County Sheriff’s Office. Marshall posted bail and was released. Riley remains in custody in Whatcom County as he fights extradition back to Oregon. Court records show his bail has now been set at $2 million.

McBee is believed to be in custody with Canadian officials as they file charges of human smuggling, officials said. Calls to the CBSA have not been returned.