In the introduction to the Critique of Pure Reason (2nd edition), Kant claims that a transcendental cognition is a one ‘that is occupied not so much with objects but rather with our mode of cognition of objects insofar as is this ought to be possible a priori (a priori möglich sein soll)’. In this paper, I argue that Kant scholarship should take into account the specific signification of the term ‘sollen’, which might require us to reconsider the usual distinction between the system of freedom and the system of nature. Following a Fichtean perspective, I will try to show that, even if ‘sollen’ in this context does not refer to a duty in the strict sense, it does refer to the demand that transcendental philosophy itself be possible. I will argue that this demand is contingent at its very origin and, accordingly, expresses a particular kind of ‘freedom’. On this basis I will consider the tribunal of reason enacted in the Critique of Pure Reason as a tribunal that emerges from a free decision, in which the transcendental philosopher imagines its own possibility. Because it is a ‘free’ and ‘contingent’ tribunal, it cannot exceed the status of a problematic philosophical strategy.