Interpreting phenomena under uncertainty stands as a substantial cognitive activity in our daily life. Furthermore, in probability education research, there is a need for developing a unified model that involves several probabilistic conceptions. From this aspect, a central inquiry has been raised through this study: how do preservice mathematics teachers (PSMTs) reason under uncertainty? A multiple case study design was operated in which a purposive sample of PSMTs was selected to justify their reasoning in two probabilistic contexts while their responses were coded by NVivo, and corresponding categories were developed. As a result, PSMTs’ probabilistic reasoning was classified into mathematical (M), subjective (S), and outcome-oriented (O). Besides, several biases emerged along with these modes of reasoning. While M thinkers shared equiprobability and insensitivity to prior probability, the prediction bias and the belief of Allah’s willingness were yielded among S thinkers. Also, the causal conception spread among O thinkers.