This paper concerns the ethical judgment that lies at the heart of assessing requests for Medical Assistance in Dying (MAID) in Canada and Quebec, namely is it ethically right to help the person requesting assistance to end his or her life? We address situations in which making this judgment may be challenging despite the person fulfilling legal eligibility requirements. Using three clinical cases that are challenging by virtue of the legal requirement that a person experience intolerable suffering we explore this issue. We review practice guidance provided to providers and assessors in six jurisdictions and discuss potential resources to inform the ethical judgments involved in MAID assessments.