It is known that wastewater treatment plants are one of the major routes through which pharmaceuticals enter the environment. The following work investigated the effect of previously unrecognized sources of pharmaceuticals that enter water resources via wastewater treatment plants. Specifically, this work focuses on determining the role of healthcare facilities in the load of pharmaceuticals to solid waste and wastewater, examining whether landfill leachate may contribute to the pharmaceutical concentration in wastewater treatment plants more significantly than previously known, and investigating pharmaceutically active transformation products as pharmaceuticals go through wastewater disinfection (with antibiotics as a subset of pharmaceuticals investigated). The research revealed that most healthcare facilities dispose of unregulated pharmaceuticals in a responsible manner. However, a single facility can make a significant impact due to the large amounts of pharmaceuticals discarded. The study found improved recovery and reproducibility when size exclusion is used in solid phase extraction for emerging contaminants from leachate. Lastly, active transformation products were discovered in four of the six antibiotics studied in wastewater disinfection. This work found three previously unrecognized sources of pharmaceuticals in water resources that will be of great importance to the scientific community and to public health awareness and education.