Law enforcement officials are permitted to intercept, record, and use conversations of the subjects of their investigations as evidence, as long as the interception is obtained legally. This article examines the importance of criminal investigators to understand when, where, and why conversations may be lawfully intercepted and recorded. It discusses the two categories in which a warrantless recording of a subject’s conversation falls into: (1) interception of those undertaken with the consent of one party and (2) interception of those undertaken without the consent of any party. Within both categories, the Fourth Amendment and statutory ramifications must be understood and considered. In addition, law enforcement officers must consider several issues when considering the interception of subjects’ conversations: (1) whether entrapment could be successfully argued; (2) whether the conversations involve privileged communications; and (3) whether Fifth or Sixth Amendment rights are impacted. It is explained why the Fourth Amendment and Title III (governing the interception of wire, electronic, and oral communications by the government and private parties) does not prevent the interception and recording of conversations. However, some State laws will prohibit this technique even when Federal law clearly would not. Twelve States have statutes more restrictive than the Federal Title III statute requiring all parties to a conversation to consent to its recording before it could be lawfully recorded. It is imperative for law enforcement officials to understand and recognize when, where, and why the warrentless interception of communications is a viable investigative technique to employ.