Clinicians are fairly comfortable with the management of acute mania because of the abundance of research studies available. However, there are several important aspects of bipolar disorder that the field has been far less successful with, including management of acute and preventive treatment of bipolar depression, comorbid illnesses, and break-through depression in the context of long-term treatment. There is tremendous complexity in the various symptoms and behavioral dimensions associated with bipolar depression. To facilitate understanding of bipolar depression, this article focuses on treating and managing the bipolar outpatient at risk for a depressive relapse. The discussion poses several challenges associated with bipolar depression and addresses the morbidity of depressive states as well as acute and long-term management of this disorder. The best practices for the varying clinical states of bipolar depressive disorder will be demonstrated through two case examples of patients struggling with disturbances common in bipolar patients.