Measuring soil moisture is essential in various scientific and engineering disciplines. Over recent decades, numerous technologies have been employed for in situ monitoring of soil moisture. Currently, dielectric-based sensors are the most popular measurement technology and provide acceptable accuracy for various measurement purposes. However, these sensors are relatively expensive, and alternative technologies, which are cheaper, are not accurate enough for scientific purposes. Recently, the idea of using a Wi-Fi signal to measure soil moisture has been presented. Theoretically, the use of Wi-Fi technology in soil sensing follows the same concepts as the previous dielectric sensors. The main advantage of Wi-Fi technology is the possibility of providing a relatively accurate and cost-effective solution for soil moisture measurement. In this work, we try to investigate the possibility of using Wi-Fi signal characteristics for soil sensing. Therefore, a series of small-scale laboratory and field experiments were conducted to test the concept. The results of these experiments were promising, showing strong linear relationships between Wi-Fi signal properties (received signal strength indicator, RSSI) and soil water content, with R2 values ranging between 0.92 and 0.99, indicating a strong correlation. They also illustrate the possibility of using this technology to develop an inexpensive and accurate device for measuring soil moisture. However, observations from the experiments also point to problematic factors involving the hardware and software used in the measurements. It is important to control these factors in the next steps to develop a reliable measurement device.