Goal-models (GM) have been used in adaptive systems engineering for their ability to capture the different ways to fulfill the requirements. Contextual GM (CGM) extend these models with the notion of context and context-dependent applicability of goals. In this paper, we observe that the interpretation of a goal achievement is itself context-dependent. Thus, we introduce the notion of Pragmatic Goals which have a dynamic satisfaction criteria. We also developed and evaluated an algorithm to decide the Pragmatic CGM's achievability. Finally, we performed several experiments to evaluate and to compare our algorithm against human judgment and concluded that the specification of context-dependent goals' applicability and interpretations make it hard for domain stakeholders to decide whether the model covers all possibilities, both in terms of time and accuracy, thus showing the importance and contribution of our algorithm.