Rational accounts of language use such as the uniform information density hypothesis, which asserts that speakers distribute information uniformly across their utterances, and the rational speech act (RSA) model, which suggests that speakers optimize the formulation of their message by reasoning about what the comprehender would understand, have been hypothesized to account for a wide range of language use phenomena. We here specifically focus on the production of discourse connectives. While there is some prior work indicating that discourse connective production (...) may be governed by RSA, that work uses a strongly gamified experimental setting. In this study, we aim to explore whether speakers reason about the interpretation of their conversational partner also in more realistic settings. We thereby systematically vary the task setup to tease apart effects of task instructions and effects of the speaker explicitly seeing the interpretation alternatives for the listener. Our results show that the RSA-predicted effect of connective choice based on reasoning about the listener is only found in the original setting where explicit interpretation alternatives of the listener are available for the speaker. The effect disappears when the speaker has to reason about listener interpretations. We furthermore find that rational effects are amplified by the gamified task setting, indicating that meta-reasoning about the specific task may play an important role and potentially limit the generalizability of the found effects to more naturalistic every-day language use. (shrink)