This article provides a greater understanding of the contract monitoring process by identifying barriers that prevent contracted providers from using service monitoring tools properly. To evaluate barriers to proper tool use, seven case studies were conducted on early childhood programs in three communities in upstate New York. The case studies specifically focused on the reporting forms that the early childhood programs completed. Data sources included (a) interviews with government agency and contracted provider employees, (b) content analysis of key documents relating to the service monitoring tools, and (c) attendance at meetings between government agencies and contracted providers on the service monitoring tools. This article identifies lack of contracted provider ability and misunderstandings between government and contracted providers as key barriers to proper tool use. This study also finds evidence suggesting a link between the overall strength of technical assistance systems and understanding problems.