Appropriate challenges and challenge-skill balance are usually key to positive player experiences. However, some games such as the successful series Dark Souls are notorious for their excessive difficulty. Yet, there has been little empirical investigation of why players enjoy games they constantly struggle and fail with. We surveyed 95 participants right after the release of Dark Souls III about their experiences with the game, employing both open questions and different player experience measures. Players generally enjoyed challenging play sessions and mostly reported positive experiences, with achievement and learning moments strongly contributing to positive experiences. However, these factors themselves were enabled by negative events such as difficulties and avatar death. Our findings showcase that negative events bear a potential for forming positive and meaningful experiences, thus expanding previous knowledge about the role of challenge and failing in games. Moreover, the significance of hard-earned achievements extends present design conventions.