In the case Connecticut v. Mooney, the court faced the issue of whether the defendant had a reasonable expectation of privacy in his makeshift home. The author describes the background of the Fourth Amendment and describes the current scope of the homelessness crisis as it relates to the Fourth Amendment and to societal understanding of homelessness. The author also examines the unusual facts of Mooney. The reasoning of the majority and dissenting opinions and their degree of reliance on the defend ant's homelessness in assessing the defendant's expectation of privacy within his possessions are analyzed. The author proposes that societal understanding of the privacy associated with a home afford an expectation of privacy to a homeless individual in the area the individual reasonably considers home. The author concludes that an expectation of privacy by the homeless in their homes may be considered reasonable if the area is clearly recognizable by a reasonable person as a home that convey s an expectation of privacy, and should therefore be protected by the Fourth Amendment.