Palatalization represents one of the phonological processes that restructured the Romance consonantal inventory the most. In this chapter, we examine the phonological and articulatory complexities underlying this process. We mainly deal with palatalization within Calabrese’s (2005) feature-based phonological model. We compare this analysis with a number of competing models: those based on articulatory phonetics, perception, phonological grounding, and Optimality Theory. Our take is that Calabrese’s constraint-and-repair model is the only framework able to account for the wide spectrum of variation across Romance varieties with a minimal number of theoretical, though phonologically motivated, stipulations.