The transformations and reassessments in the understanding of art and creativity that took place in the 20th century, together with the impact of computers on architects’ work, have caused the concepts of ‘architectural drawing’ and ‘handdrawn architectural drawing’ to no longer be the dominant category in the day-to-day professional practice of architectural designers and urban planning teams. The creation of floor plans and visualisations has become computer-based to such a degree that materials are now being shared between architects, the construction site and clients in the form of 3D BIM models, with no need for printed copies. The definitions of drawing, painting, sculpture and architecture in the 20th century have become blurred, and contemporary art seems to have no need for such distinctions, as they are merely labels and may limit the way a work is perceived. In the work of an architect and during studies, the term ‘architectural drawing’ is frequently used, and during education the ‘hand-drawn’ qualifier is often added. Architects have been drawing since time immemorial, and the very concept of architectural drawing is extremely broad. The aim of these analyses is to highlight some of the issues surrounding the boundaries of the concept of ‘drawing’ and the term ‘architectural,’ and to critique the examples selected by the author regarding the evaluation of artistic work based on the concept of ‘technique,’ the role of time in the creative process, and the degree of fi nish of a work of art. The juxtaposition of works by prominent architects and artists with common statements about drawing aims to highlight the frequent paradoxes in the understanding of the issues discussed here and to facilitate an understanding of the shift ing boundaries of ‘hand-drawn architectural drawing.’