This study explores employees' desire to embrace both a legacy operating system and a new workflow engine utilized in the workplace. The goal is to better understand the partnership and relationship the users build with the technologies and how that impacts usage behavior. The research is centered on a mixed-method case study using survey and episodic interview techniques of data collection. Models and methodologies providing the foundation for this study include Venkatesh and Davis's technology acceptance model 2 (TAM 2) and Venkatesh, Morris, Davis, and Davis' unified theory of acceptance and use of technology (UTAUT) model, coupled loosely with concepts from Brooks and Atkinson's StructurANTion Theory. A new, adapted model is created to capture and understand the anthropomorphic characteristics users apply to the technology. This study yields important information for the future theoretical frameworks as elements such as trust and control, and descriptive variables like age and tenure have not factored into existing theoretical frameworks and models. Users can often anthropomorphize technology, viewing it as part of the social team to help improve their work. Through this lens, users expect information systems to be controllable and trustworthy to respond to their needs both alone and within the function of the team.