The experience sampling method (ESM) and comparable assessment approaches are increasingly becoming popular tools for well-being research. In part, they are so popular because they represent more direct approaches for assessing individuals’ experienced well-being during a specified period, whereas one-time, retrospective evaluations of that episode are believed to introduce systematic biases. Along these lines, the peak-end rule states that the most extreme and recent sensations of an episode disproportionally influence retrospective well-being judgments. However, it has yet to be determined whether such systematic effects found in experimental laboratory studies generalize to retrospective judgments of well-being in everyday life as captured in ESM studies. Across four ESM samples (overall N = 1,889, total measurements = 131,575), we found that retrospective well-being judgments were disproportionately influenced by the peak and end experiences from the assessment period. However, these effects depended on the item framing of the retrospective judgment (global vs. more specific framings) and broad versus narrow conceptualizations of peaks and ends (states, days, and weeks), pointing toward potential ways to mitigate peak/end effects. Our findings emphasize the importance of differentiating between momentary and retrospective well-being assessments and selecting an appropriate measurement approach on the basis of these conceptual considerations.