The approaches that parents take in the supervision of youth who perform hazardous tasks on family farms can affect youth safety outcomes. This research examines the most significant factors affecting youths’ decisions to enter agricultural grain storage facilities. Over 200 students attending a Midwestern land-grant university who had grain bin experience as youth completed a decision-making survey. Students chose from a list of actions in three realistic but hypothetical scenarios involving grain bin entry. Afterward, they ranked factors according to the level of importance in their decision. Although most participants chose options that emphasized safety when answering the scenario questions and held the “personal safety” factor in highest regard, some chose higher-risk options and valued “productivity.” The findings revealed that youth held little value in their parents’ authority and pressure when making decisions related to grain bin entry. The study’s limitations are addressed, as are the implications of these findings for youth safety outcomes on family farms.