Contrary to economic theory, psychological research has demonstrated increased choice can undermine satisfaction. When and why this 'excess choice effect' (ECE) occurs remains unclear. Building on theories of counterfactual thinking we argue the ECE is more likely to occur when people experience counterfactual thought or emotion and that a key trigger is a negative versus positive task outcome. Participants either selected a drink (Experiment 1) or chocolate (Experiment 2) from a limited (6) versus extensive (24) selection (Experiment 1) or were given no choice versus extensive (24) choice (Experiment 2). In both experiments, however, the choice was illusory: Half the participants tasted a 'good' flavour, half a 'bad' flavour. As predicted, extensive choice was only detrimental to satisfaction when participants tasted the 'bad' drink or chocolate, and this was mediated by the experience of counterfactual thought (Experiment 1) or emotion (Experiment 2). When outcomes were positive, participants were similarly satisfied with limited versus extensive and no choice versus extensive choice. Implications for our theoretical understanding of the ECE and for the construction of choice architectures aimed at promoting individual satisfaction and well-being are discussed.