Motivated students have been shown to persist longer in post-secondary education. As a multidimensional psychological construct, motivation is shaped by within- and between-person perceptions of context. Empirical measures of distinct workplace and trade school subjective task values (STVs) were examined, and their predictions of apprentices' planned apprenticeship persistence and intentions to leave the occupation. Further, these STVs (i.e., workplace/trade school intrinsic, importance, utility and emotional cost) were explored for predictive differences across licenced and unlicensed trade apprentices. Among a representative Australian sample of 2,069 trade apprentices, STVs discriminated across learning contexts (trade school vs workplace) and between occupations (licenced vs unlicensed apprenticeships). Workplace STVs had a greater impact on both planned study persistence and occupational departure intentions, while also diminishing the effect of trade school STVs on the same outcomes due to apprentices' internal comparison of STVs across learning contexts. Findings highlight the need for employer training and regulating who should employ an apprentice to ensure apprentices are afforded workplace training in a manner that maintains interest and reduces anxiety. Other findings present the roles and practical implications of within- and between-person contextualised motivation in explaining study and occupational planned persistence.