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Repeated assessments in everyday life enables collecting ecologically valid data on dynamic, within-person processes. These methods have widespread utility and application and have been extensively utilized for the study of stressors and stress responses. Enhanced conceptual sophistication of characterizing intra-individual stress responses in everyday life would help advance the field. This paper provides a pragmatic overview of approaches, opportunities, and challenges when applying intensive ambulatory methods to study everyday stress responses in “real-time”. We distinguish between three stress response components (i.e., reactivity, recovery, and pile-up), and focus on several fundamental questions: 1) What is the appropriate stress-free resting state (or “baseline”) for an individual in everyday life? 2) How to index the magnitude of the initial response to a stressor (reactivity)? 3) Following a stressor, how can recovery be identified (e.g., when the stress response has completed)? 4) Stressors may not occur in isolation; how can we capture the temporal clustering of stressors and/or stress responses (pile-up)? We also present initial ideas on applying this approach to intervention research. Although we focus on stress responses, these issues may inform many other dynamic intra-individual constructs and behaviors (e.g., physical activity, physiological processes, other subjective states) captured in ambulatory assessment.