The article is about the meaning of the word ‘transcendental’ in Kant and Fichte. Its aim is not merely exegetical. It is a common hermeneutical insight (now revitalised by research on conceptual engineering and conceptual genealogy for analytic philosophy) that analysing the use and definitions of concepts in history, and their shifts in the development of the history of philosophy, is a crucial tool we have to understand those concepts and to assess their viability for philosophy today. In this paper, I focus on Kant’s use and definitions of the word ‘transcendental’ and suggest that they are symptomatic of a fundamental question that is not completely answered in Kant’s philosophy. If transcendental philosophy deals not with objects but rather the conditions of possibility of objective knowledge, then important questions emerge: What are these possibility conditions? Do they exist? Are they special objects? What is their nature? I show that the shift in Fichte’s use and understanding of the concept of ‘transcendental’ leads to a possible solution of the problem Kant was struggling with.