Video games are increasingly designed to provoke reflection and challenge players’ perspectives. Yet we know little about how such perspective-challenging experiences come about in gameplay. In response, we used systematic self-observation diaries and micro-phenomenological interviews to capture players’ (n=15) lived experience of perspective challenges in purposely sampled games including Hatoful Boyfriend, The Stanley Parable, or Papers, Please. We found a sequence of trigger, reflection, and transformation constituting perspective-challenging experiences, matching Mezirow’s model of transformative learning. Most of these were game-related or ‘endo-game’, suggesting that medium self-reflection could be an overlooked part of everyday game reflection and appreciation. Reflections were accompanied by a wide range of emotions, including frequent epistemic emotions, and emotions could change drastically even during short gameplay experiences. Actual perspective change or transformation was rare. We construct a model of granular types of triggers, reflections, and transformations that can aid reflective game design.