In this article we take a neo-Peircean semiotic approach to analyzing an interaction in which a routine bail hearing between a defendant and a judge goes awry. Neo-Peircean semiotics is steadily gaining recognition within linguistics for providing a new perspective on meaning. One neo-Peircean approach, referred to as Relationship Thinking (Enfield 2009, 2013), has the potential to be influential for politeness research and linguistic pragmatics generally. In this article, we explore how the concept of relationship can be used to explore meaning on two dimensions: residential and representational (Kockelman 2006a, 2006b). It is our contention that both of these dimensions are crucial to developing an understanding of what happens in the courtroom data on which this special issue focusses. We begin by providing a detailed overview of neo-Peircean semiotics in order to demonstrate its utility for researchers from different disciplines. We then show how a neo-Peircean analytical approach can illuminate elements of data that may not be accounted for in other analyses. This is as a consequence of the neo-Peircean framework’s scope and its capacity for coping with a range of interactionally significant phenomena, from individual linguistic tokens to institutional norms. In our analysis of the data at the heart of this special issue, the Penelope Soto case, we show that problems can arise when interactants have different understandings of what is a sign and what is an interpretant (Peirce 1955). We make the case that it is a misunderstanding at this level (specifically the interpretations of the word “value”) that is ultimately what causes the interaction to conclude in the way that it does. Ultimately, we suggest that a neo-Peircean approach to the study of in/appropriate behaviour can facilitate links between the traditional (and sometimes disparate) methods of analysis used in politeness research.