Sam and Colby went to jail because they were arrested for trespassing on a construction site at an abandoned school building near Hillsborough County, Florida, on January 16, 2019. They entered the property without a permit while filming a video. The police were alerted by a neighbor who saw them on the property. Colby faced additional charges related to unauthorized use or possession of a driver's license, which were felonies. Sam and Colby were taken to jail, and their bail amounts were set—Sam's at $2,000 and Colby's at $6,000. They were released the next day after paying bail. They later explained that they did not intend to break the law and were unaware the location was considered a construction site with restricted access.