Outdoor workers are at increased risk for skin cancer and melanoma. This qualitative study aimed to explore outdoor workers' perspectives and experiences of primary (i.e. sun protection) and secondary prevention, i.e. skin self-examination (SSE) of skin cancer. Purposive, snowball, and theoretical sampling was used to recruit outdoor workers in Kentucky and Indiana. Semi-structured interviews via telephone or videoconference of approximately 45 min were conducted with interviewer probes and questions about perceptions of cancer risk, prevention, and screening techniques conducted, perceived barriers and facilitators, and preferences for health dissemination venues. The recordings were transcribed verbatim and de-identified. Analysis involved constructivist grounded theory coding strategies. Using peer debriefing and consensus building around themes, the researcher established a codebook for all interviews to utilize within Dedoose software for systematizing and organizing data. Eighteen interviews were conducted. Interviewees (N = 18) ranged in age from 35 to 78 yr, with 3 females. Outdoor industries included agriculture, maintenance, and grounds maintenance. Themes derived from the data showed the underlying factors and perceptions that influence outdoor workers to conduct primary and secondary cancer prevention activities. The level of alarm attributed to disease and the level of trust in information contribute to intentions to conduct activities. The intentions and trust toward healthcare institutions and providers drive the primary or secondary prevention behaviors. Cultural and contextual factors included masculinity and self-sufficiency, familial and occupational priorities, and community ties. These data provide a basis for developing future communications and interventions to decrease skin cancer incidence in outdoor workers. They indicate that secondary prevention and building self-efficacy in conducting SSE should be emphasized in tandem or over primary skin cancer prevention methods in this population. Trusted local healthcare providers should primarily provide prevention information, and materials should utilize testimonials from the local community to best influence this population. Communications and training interventions are needed in this population to induce a proactive level of alarm about cancer and result in the performance of SSE.