ABSTRACTLittle research has examined how prior learning experiences influence adult learning attitudes and lifelong learning engagement. We adopted a person‐centric approach to examine past work‐related learning experiences and assessed the effects of recalled challenges on current learning attitudes, intentions, and behavior in the same domain. Surveying alumni from an online master's degree program, we found that recollected challenges from past learning entail multifaceted challenge foci (e.g., curriculum‐related vs. social obstacles). Learners reporting more challenges in curriculum and social dimensions reported less positive attitudes toward lifelong learning, supporting the notion that negative learning experiences may hinder the development of self‐identity as a lifelong learner. Limited support was obtained for predictions about relationships between past challenges and post‐graduation learning intentions and behavior. The person‐centric approach also permits the analysis of past learning experiences that are not well captured by standard assessments of “successful” adult learning.