Flow, the concept developed by Mihaly Csikszentmihalyi over the last forty years or so (see Csikszentmihalyi 1975) has been invoked quite often with respect to the way players engage with digital games (e.g. Baron 2012; Cowley et al. 2008; Sweetser and Wyeth 2005; Brathwaite & Schreiber, 2009; Fullerton, Swain, & Hoffman, 2008; Schell, 2008). However, Kubey & Csikszentmihalyi (2002) have argued that ‘video games’ are in fact likely to promote undesirable experiences of a kind Csikszentmihalyi refers to as ‘entropy’ or unstructured and unsatisfying life experiences. This paper explores Csikszentmihalyi’s greater thesis and examines how a broader reading of Flow theory can potentially help us understand Flow like engagements beyond the simple mechanistic view of challenge explicitly introduce personally expressed cultural values into the conditions of Flow. By doing so we can then provide a value centric analysis and design approach, similar to that of Cockton’s (2004; 2012) proposal, to include values in general software design. That is, the very nature of challenges and rewards needs to be considered in order to investigate how overcoming or receiving such challenges would be positively or negatively perceived by individuals, from particular cultures, holding particular values. Thus we hope that we have dealt with the apparent contradiction in using Csikszentmihalyi’s concept in the study of games despite his criticism of such a move, and have provided some indication of how we can deal with unspecified rewards and the differential perception and engagement with potentially equivalent challenges while still supporting the accepted thesis of Flow.