In 2007 it came to light that town officials in Crestwood, Illinois had intentionally caused residents to use contaminated well water for more than twenty years. A group of residents sued the town and its officials and alleged that the contaminated water had caused illness (and in some cases death) to themselves and their relatives. In response, the town sought indemnification from its insurer, Scottsdale Indemnity Co. The insurance company refused to provide coverage on the grounds that the contamination had triggered the “pollution exclusion” included in Crestwood’s insurance contract. This Comment argues that when analyzing the applicability of a pollution exclusion, courts should adopt a “reasonable expectations” test. This test requires a court to look beyond the plain meaning of an insurance policy. Instead, courts should consider the reasonable expectations of the policyholder at the time the insurance policy was purchased. This test vindicates the rights of policyholders and ensures that victims of pollution harms are compensated for damage to their health and environment.