The present article aims to examine the roots of pictorial poetic thinking in Paul Klee’s image-making, with an emphasis on Martin Heidegger’s view on reflective thinking as thinking-in-liberation and the emergence of beings’ existential truth. Therefore, to reach the gist of Heidegger’s perception of poetic character as art’s true nature and its relation to Paul Klee’s artistic creations this paper tries to answer the main question of whether the existential truth in Paul Klee’s pictorial expression is in line with his specific viewpoint towards existence. While examining Heidegger’s ideas on the manifestation of truth in an art work and comparing it to Paul Klee’s reflections on the emergence of the elements of an image in the process of formation, it is argued that according to Heidegger, reflective thinking is a way of life for humans in the universe and in relation with other beings which gives them freedom from any invasive inculcation; and unlike most other modern artists, Paul Klee has managed to express this perspective in his artistic creations. This is why, Heidegger appreciates his images for revealing the existential truth about beings. The paper follows a descriptive analytical methodology and data collection has been done through library work and exploration of the cyberspace.