This article explores feelings of disappointment and failure among migrants in Italy. It argues that the ubiquitous circulation of discourses of disappointment can be traced to restricted possibilities for upward mobility produced by the legal, economic, and social forms of marginalization that migrants in Italy encounter. Disappointment, it contends, is the product of an imaginary migration trajectory that views moving on from Italy as the only way to be successful. Arguing that some low-status migrants can be considered “flexible citizens,” I examine how my respondents’ desires for mobility are shaped by opportunities and restrictions that are integral to late capitalism, as well as by the differentiated inclusion into the global market that these produce. By their very nature, however, I show how these desires neglect other kinds of future imaginaries and arguably impede the chance to build greater equality for migrants and their children in the future.