This chapter investigates correlations between learning theory and outcomes. Based on the hypotheses that in university pedagogy the assessment strategy should be interrelated with desired learning outcomes of the student, it is clear that assessment directly impacts student minds and behavior. Therefore, within the global context of assessment, measurement, and testing strategies, this chapter critically explores novel educational assessment methodology as a response to the following research questions: What are the main issues, controversies, and problems in the educational assessment? What are the most effective solutions for the development of life-long competence through an affordable assessment strategy? This study presents insights into the assessment theory concerning deviations in the acquisition settings between training and testing. It also provides an outlook for the potential of transfer assessment methodologies to metacognitive training of a particular target group.