Transportation infrastructure is an integral part of the world’s overall functionality; however, current transportation infrastructure has aged since it was first developed and implemented. Consequently, given its condition, preservation has become a main priority for transportation agencies. Billions of dollars annually are required to maintain the United States’ transportation system; however, with limited budgets the prioritization of maintenance and repairs is key. Structural Health Monitoring (SHM) methods can efficiently inform the prioritization of preservation efforts. This paper presents an acoustic monitoring SHM method, deemed tap testing, which is used to detect signs of deterioration in structural/mechanical surfaces through nondestructive means. This method is proposed as a tool to assist bridge inspectors, who already utilize a costly form of SHM methodology when conducting inspections in the field. Challenges arise when it comes to this method of testing, especially when SHM device deployment is done by hand, and when the results are based solely upon a given inspector’s abilities. This type of monitoring solution is also, in general, only available to experts, and is associated with special cases that justify their cost. With the creation of a low-cost, cyber–physical system that interrogates and classifies the mechanical health of given surfaces, we lower the cost of SHM, decrease the challenges faced when conducting such tests, and enable communities with a revolutionary solution that is adaptable to their needs. The authors of this paper created and tested a low-cost, interrogating robot that informs users of structural/mechanical defects. This research describes the further development, validation of, and experimentation with, a tap testing device that utilizes remote technology.