This research investigates how ultrasonic damage monitoring in civil structures can be implemented on a small, battery-powered, self-contained device. The device is intended for the continuous monitoring of surface breaking cracks in steel using Rayleigh waves. This study in detail presents the challenges that are to be considered for the intended ultrasonic monitoring, with the objective to provide a foundation for the future development of a fully autonomously operating device. The study proposes a suitable hardware and software layout, and a prototype device is built using a digital signal processor, a commercial wireless transceiver, and custom amplification circuits. With the help of two narrowband ultrasonic contact transducers in a pitch-catch setup and appropriate contact wedges, the wave field that arises from scattering of an incident tone burst wave at a crack is measured. A data analysis algorithm extracts wave burst signals from the acquired output in order to minimize the data that is to be transmitted. Additional compression of the data and the implementation of a communication protocol allow for a reliable and efficient wireless transmission. In order to demonstrate the feasibility of the proposed approach, measurements of notches in a steel plate with different depths are taken. Measurement results from experiments with commercial ultrasonic equipment are compared to measurements taken with the prototype device. The influence of the sampling distortions on the signals are analyzed. The scope of this study is limited to a qualitative analysis of the experimental results; quantitative methods to determine the dimensions of a crack or notch from the measured data are not included. The research conducted demonstrates that taking ultrasonic measurements with a small, self-contained device is feasible. Comparison of frequency-based to time-based signal analysis methods yields that frequency-based methods are preferable, as they are affected less by sampling effects. The experimental results show that the intended ultrasonic examination technique can be used for qualitative damage assessment. The knowledge gained in this study contributes to improving the safety of civil infrastructure. Continuous local damage monitoring as proposed helps to detect critical conditions in-time, and to take countermeasures to avoid catastrophic failures.