This study examined Australian farmers’ engagement with skin cancer prevention behaviours and explored what made it hard for them to be ‘SunSmart’ (barriers), and what could be done to make prevention easier (facilitators). In total, 498 farmers (83.1% male, 22–89 years, 50.8% grain, sheep, or cattle farmers) participated. The least frequently performed SunSmart behaviours (reported as never practiced during summer) were using SPF 30+ sunscreen (16.6%), wearing protective sunglasses (10.5%), and wearing protective clothing (8.6%). Greater engagement (i.e., higher scores on scale from Never to Always) with SunSmart behaviours was explained by gender (female), educational attainment (trade or technical college certificate vs. high school), personal skin cancer history, and skin sun sensitivity. Barriers reported by farmers related to personal preferences (e.g., short-sleeved rather than long-sleeved clothing), comfort, and perceived impracticality of sun protection. Farmers’ solutions included making protective clothing and sunscreen more appropriate for farm work (e.g., by making clothing more breathable). A personal health scare was the most reported motivation for skin cancer prevention. Findings highlight the need for increased access to sun-protective clothing and sunscreen that is suitable for wearing when working on farms, complemented by culturally appropriate health education messaging, to encourage more farmers to perform SunSmart behaviours.