This is an auto ethnographic account of the author’s personal experience of teaching in Art and Design in a public university in Cyprus. The challenges are broadly divided into: a) societal, which refers to the prevalent perceptions and values of Cypriot society in general vis-à-vis Art and Design education, b) structural, which relates to the (in)ability of educational institutions to structure and deliver educationally sound Art and Design Higher Education (HE) programmes of study, and c) the nature of the prospective learners i.e. their attitude towards learning in general. The experiences of the author and his critique - as articulated in this paper - provide for a reflexive investigation based on three years of teaching and learning experience as an academic and researcher working exclusively with Cypriot students and within the Cypriot culture. From this contextual backdrop that is largely disorienting for it cannot be compared to the author’s previous experiences, the inference – and epiphany - is that the challenges are enormous and without the sustained and parallel effort of different agents, Art and Design education in Cyprus will remain under-developed.