This paper presents a psychological perspective of the educational dilemma of assessing highly (high-level) creative ability (with some connections to contemporary philosophical debate). Assessment of highly-creative ability is a topic of longstanding debate involving questions of what constitutes creativity; whether the creative mental process is essentially intuitive or essentially rational; whether creative ability could or should be reduced to quantifiable parameters; and whether the most important aspects of creative achievement reside in the initial thinking (invention of ideas) or in the subsequent process of development of the idea (making a work of art, design, etc) or in the end product (the work of art or design itself). The debate is fueled by various philosophical, psychological and educational perspectives, all of which are continuously evolving. As a consequence, learning objectives and assessment criteria are ambiguous and confound the enhancement of creative ability that is the primary purpose of higher education. This paper traces the research and development path that led to an innovative "authenticative assessment" approach to assessing highly-creative ability that offers a promising solution.