Research on the personalities of hostagetakers has classified some as inadequate personalities. The Diagnostic and Statistical Manual II characterizes the inadequate personality as being ineffectual in responses to emotional, social, intellectual, and physical demands. While such a person appears neither physically nor mentally deficient, he does manifest inadaptability, ineptness, poor judgment, social instability, and lack of physical and emotional stamina. As a hostagetaker, the inadequate personality is likely to begin negotiating by making excessive demands, or he may refuse to negotiate with the police, preferring that a hostage negotiate for him. This is because he fears further failure. Further, because of his dependent needs, the inadequate person is the most likely of any type of hostagetaker to become involved in the Stockholm Syndrome, where the positive feelings of the captives toward the captor are accompanied by negative feelings toward the police. Suicide rather than surrender is also likely for the inadequate personality. The negotiator should be a law enforcement officer who has investigative experience. The inadequate personality may prefer a female negotiator, since he is seeking acceptance and may have a history of inability to relate to females. If the female negotiator can provide acceptance while maintaining control and provide the hostagetaker the feeling that they are working together to bring the incident to a successful outcome, then the subject may surrender with a sense of achievement rather than failure. Eight references are provided.