The notion of “context” is currently being deployed in Discourse Analysis within approaches that subscribe to its constitutive nature. Rather than being extraneous to talk and text, context is conceptualized as an integral part of discourse, in a mutually constitutive text-context relationship. This chapter will cover key insights from three influential and affiliated ways of analyzing context: context as dynamically and interactionally achieved; context as rooted in metapragmatic awareness; and context as historicized and multidimensional. The chapter will then illustrate how these three key insights manifest themselves in the framework of small stories research. After presenting these three features of context, the chapter will focus on two core issues at the forefront of current concerns, namely ambiguity in delineating “context,” and occurrences where what can be postulated as “relevant context” is not readily retrievable from textual data. Picking up on these issues, we argue that future research will need to address discourses and contexts becoming ever more fragmented, dispersed, and even disintegrated through new communication technologies. In this respect, an analytical focus on metapragmatic awareness may aid the identification of interactionally relevant features of context as well as of the (re)affirmation of participants’ shared meanings.