BACKGROUND:Adolescents living with incurable cancer require ongoing support to process grief, emotions, and information as disease progresses including treatment options (phase 1 clinical trials and/or hospice/palliative care). Little is known about how adolescents become ready for such discussions. OBJECTIVE:The purpose of this study was to explore the process of adolescent readiness for end-of-life preparedness discussions, generating a theoretical understanding for guiding clinical conversations when curative options are limited. METHODS:We explored 2 in-depth cases across time using case-study methodology. An à priori conceptual model based on current end-of-life research guided data collection and analysis. Multiple sources including in-depth adolescent interviews generated data collection on model constructs. Analysis followed a logical sequence establishing a chain of evidence linking raw data to study conclusions. Synthesis and data triangulation across cases and time led to theoretical generalizations. Initially, we proposed a linear process of readiness with 3 domains: a cognitive domain (awareness), an emotional domain (acceptance), and a behavioral domain (willingness), which preceded preparedness. RESULTS:Findings led to conceptual model refinement showing readiness is a dynamic internal process that interacts with preparedness. Current awareness context facilitates the type of preparedness discussions (cognitive or emotional). Furthermore, social constraint inhibits discussions. CONCLUSIONS:Data support theoretical understanding of the dynamism of readiness. Future research that validates adolescent conceptualization will ensure age-appropriate readiness representation. IMPLICATIONS FOR PRACTICE:Understanding the dynamic process of readiness for engaging in end-of-life preparedness provides clinician insight for guiding discussions that facilitate shared decision making and promote quality of life for adolescents and their families.