The assertion of a state which is unconditioned and beyond temporal change creates unavoidable tensions for any Buddhist account that concerns the shift from worldly experience to a liberated one. The presence of such tensions can be found in the controversy between simultaneous (cig char; yugapad) and gradual (rim gyis; krameṇa) conceptions of the contemplative path and the state of liberation itself. This controversy found its early Tibetan expression in the so-called bSam yas debate, in which representative figures of both approaches argued about basic contemplative and soteriological issues. Later on, Klong chen pa, the renowned 14th century Tibetan teacher, explicated several contemplative typologies that included elements from both approaches. This research belongs to qualitative research using two interpretative perspectives, namely the Pragmatic attitude that focuses on the actual results of the scheme and the Transcendental point of view. The results showed that by examining the typologies and their presuppositions it becomes clear how the efficacy of each approach is closely related to individual capacities of practitioners. As such, the tension between simultaneous and gradual models is revealed as deeply contextual and not binary.