The sedation-assessment conundrum is the struggle to balance the need for sedation against the need to awaken the patient and perform a neurologic examination. This article discusses the nuances of the sedation-assessment conundrum as well as approaches to resolve this and reduce the negative impact of abruptly stopping sedative infusions. Both oversedation and undersedation affect critically ill patients. This article discusses methods of assessing sedation and interpreting individualized patient responses to sedation. The use of neurofunction monitors and periods of sedation interruption are discussed within the context of addressing the sedation-assessment conundrum.