Academic integrity to uphold intellectual honesty and transparency has become the focus in higher education. Currently, the HE sectors worldwide have taken additional measures to minimise the likelihood of academic misconduct cases. Most of these interventions are student focussed, aiming to develop an integrity culture amongst students. A few studies have explored ways to deter plagiarism (or reduce the chances to plagiarise) by effective assessment strategies. It is an accepted argument that authentic assessment methods coupled with clear assessment briefs will reduce academic misconduct. Despite the continuous monitoring and careful mentoring, there were some reported incidences of ambiguous assessment briefs contributing to student misconduct. It is still not clear whether the assessment and their briefs are effectively produced with clear instructions about what is expected from the students (a) regarding literature surveys, (b) using data from collaborative group work, (c) using internet resources. This chapter aims to revisit examples of ambiguous assessment briefs from different institutions worldwide and their role in contributing to plagiarism and academic misconduct cases. It will highlight reported cases of how the following assessment modalities: (a) restricted time constraint exams, (b) open book online tests, (c) take home assessment and (d) assessment briefs with contradictory instructions have provided chances for cheating and affected the performance of students with Specific Learning Difficulties (SpLDs). The chapter will elaborate examples of academic misconduct, especially plagiarism, resulting merely from ambiguous assessment briefs and inappropriately transformed online assessments. It will also discuss ways to reduce ambiguity in assessment briefs.