According to the criminal complaint, dating back to January 2018, investigators believe Osterman used an alias and attempted to meet a young girl for sex using the social networking service, MeetMe. Per the criminal complaint public wi-fi had been used, the identity of the user could not be determined.
According to the complaint, at the time, the user had suggested meeting an underage girl, but later stated it was a joke, when the recipient said they'd call the police.
Osterman's criminal complaints shows similar request at various times over the two year period until June 2020. Osterman owns internet service provider Northwoods Connect, which serves Wisconsin's Northwoods. According to the complaint, Osterman told investigators anyone of his 400 customers could be the suspect, but there was no way to track one specific customer to the IP address when the detective attempted to track the source of the messages.
According to the complaint, in February 2020, Osterman's vehicle was seen near one of the several W-Fi locations that he often used. Per the complaint a Rhinelander police officer asked Osterman what he was doing there for several hours, Osterman replied he was the owner of Northwoods Connect and was testing the internet speed of his competitors.
Per the complaint, investigators later installed a GPS device on his vehicle in April and say they matched his location to the source of the messages.
According to the complaint, in May Osterman is accused of attempting to meet a 9-year-old at a motel in Tomahawk, per the complaint Osterman never showed up and the meet up turned out to be fake.
On June 8th, multiple agencies, including the state Department of Criminal Investigations, set up an operation to meet up with Osterman. The GPS locator put his car at the park in Marathon County where he was supposed to meet up with the under-cover agent who told Osterman she could get him a 9-year-old girl.
The complaint says Osterman walked around the park but never met up with the agent, even while they continued to exchange messages.
Osterman's arrest was a collaborate effort between the Oneida County Sheriff's Office and the Internet Crimes against Children Task Force. The Tomahawk Police Department, the Rhinelander Police Department, the Wausau Police Department and the Marathon County Sheriff's Office also assisted with the investigation.