Clinicians often encounter patients whose presentations are characterized by long lists of complaints about their biological, psychological, interpersonal, and social conditions. The problems on which the complaints are based are variably reality-based and variably modifiable. Some of these patients display chronic complaining as a core, distinguishing feature. Accordingly, the aims of this article are to consider excesses of chronic complaining as psychiatric phenomena, explore possible pathogenetic contributions, describe approaches for treating conditions marked by clinically pertinent chronic complaining, and suggest areas for future research. Based on clinical observations enhanced by selective narrative literature review, we delineate and differentiate four groups of patients: 1) situational complainers; 2) chronic complainers due to unidentified medical problems; 3) mood-induced chronic complainers; and 4) personality-driven pan-dimensional chronic complainers. The last-mentioned group consists of help-seeking versus help-rejecting subtypes, the latter including a subset we designate as malignant chronic complainers. Strategies for managing these patients begin with detailed assessment of all complaints, ascertaining reality-based contributions to the complaints, including those initiated by patients themselves. Management approaches use specific biopsychosocial techniques based on patient-centered particulars. Psychotherapeutic strategies center on compassionate, empathic witnessing. Specific tactics include attending to unresolved grief and trauma, behavioral activation, cognitive and narrative restructuring and reframing methods, mentalizing and imaginal approaches, and psychodynamic methods including attention to attachment issues and transference. Sources of countertransference reactions to these patients should be identified and can be addressed. The many questions raised by these patients’ presentations merit further research.