In this paper, we give means to analyze obligation with deadline policies in order to predict all undesired situations. The previous studies were focused on obligation with deadline when deadlines are defined using temporal constraints, and the most of them were interested in how obligations impact and depend on authorization state. We particularly investigate obligations with deadlines when the deadlines are triggered by the execution of actions. A novel notion of overlapping obligations is introduced. Two obligations are overlapping when each one of them depends on an action which triggers the deadline of the other one. Thus, the paper starts by giving a formal definition of dependency between actions and then defines formally the overlapping obligations. The undesired situations are those that leads inevitably to violations. They are defined using the overlapping obligations and characterized using executable situations. The paper presents an algorithm to predict these situations based on a planning tool. We also provide an implementation of this algorithm and show how the dependency between actions and the number of actions impact the execution time needed to fully analyze obligation with deadline policies.