Security managers use cameras, undercover agents, listening devices, polygraphs, and blood and urine tests in attempting to resolve security problems. However, they often disregard such legal considerations as entrapment, invasion of privacy, eavesdropping, and self-incrimination. Entrapment occurs when a law enforcement agent is involved in using persuasion or other means likely to cause law abiding persons to commit an offense. The right to privacy is an issue allowing evidence getting on the record in criminal cases as well as action for damages against employers in civil suits. Eavesdropping is an sense of the privacy question that has resulted in legislation. Self-incrimination allows individuals the right to remain silent and not testify against themselves in a criminal matter. A clear line differentiates between causing a person to commit a crime and setting a trap to to catch a person committing a crime. The author cautions security investigators to remember that courts require trickery not be used to induce a person to commit a crime. It is suggested that many legal obstacles bar the way to concluding a successful investigation. Familiarity with the law is essential, as is the use of common sense, and concern about the fair treatment of people. A case study is used for demonstration purposes.