Starting on Top – In the traditional first challenge, contestants must drive to the Maximum Security Driver Rehabilitation Centre at an abandoned prison in Guelph from a parking garage in Kitchener. Amy, Donna, and Emily are the first to leave, followed by Curt, Lindsay, Teagan (who, because he is too young to have a rental car insured, is driving in Andrew's personal truck), Ken and Ashley. En route, Ashley catches up to Ken, who engage in a brief street race. By the time Ken arrives, Andrew is so offended he refuses to allow him to park in his space. After everyone arrives (with the exception of Amy & Emily, everyone arrives in the order of their departure), Andrew confiscates everyone's drivers' licences.
Basic Assessment – In the traditional skills evaluation, the contestants must reverse the Porsche 928 out of a tight corner and then in a straight line, before going through a slalom portion at 40 km/h with both hands on the wheel at all times. After exiting that portion, they must accelerate the 928 to 60 km/h, before stopping in front of a wall of boxes. Ken, going second, is the first contestant to scratch the car (Ashley, who went first, had managed to not hit anything, save for the boxes at the end), while Emily cannot even reverse out of the corner, getting her car stuck. Ashley is the only contestant to get the slalom on the first try, and is the only contestant to not hit any obstacles in the reversing portion. However, none of the contestants could avoid hitting the wall of boxes.
Before the episode draws to a close, Cam takes Donna, Teagan, Ken, and Ashley aside for a tour of the prison, and explain to them that their actions that had led them to their nomination and arrival at the Driver Rehabilitation Centre could have caused them to be sentenced to prison time. Donna for Drinking and Driving, Teagan for Hit and Runs, Ken and Ashley for their Street Racing on their way to the Rehabilitation Centre. Each of these four, in turn, are locked in a cell for a few minutes—long enough for all four to break down. Because this is the first episode and the contestants have just arrived, no one leaves the Driver Rehabilitation Centre.