When languages have more than one dedicated imperative, the distinct forms often correspond to different person/number combinations. But what happens when there is variation between two forms for the same person/number combination, e.g. 2nd person singular? This chapter analyzes the competing 2sg imperatives in Brazilian Portuguese (BP), which illustrate this situation. BP permits this option in both affirmative and negative contexts, where the historical imperative tu form for 2sg alternates with the 3sg present subjunctive form used with the 2sg pronoun você (cf. Lamberti & Schwenter 2018). Through the multivariate analysis of an experimental survey, we argue that the variation between the two forms can be accounted for in terms of the semantic-pragmatic notion of presumed settledness (Hoff 2019), i.e. speaker confidence about how the future will unfold, and can be operationalized in terms of contextual characteristics such as markers of temporal immediacy and addressee specificity. More broadly, we suggest that these characteristics are relevant to accounting for contrasts between imperative forms across languages such as those with “delayed/deferred imperatives” (Aikhenvald 2014).