In this article we explore how activity design and learning contexts can influence youth failure mindsets through a case study of five youth who described failure as sometimes a good thing and sometimes a bad thing (a perspective we characterize as Failure as Mosaic, described in the article). These youth and their descriptions of failure-positive and failure-negative experiences offer a unique opportunity to identify how experiences can be designed to support learning and persistence. In order to understand differing views of failure among youth, we researched the following questions: