The number of deep groundwater wells in the arid lands of Egypt has increased greatly since the mid-twentieth century. Modern well drilling technology using rotary drilling rigs and pumping tests came to Egypt with the beginning of the New Valley Project in 1958, bringing significantly increased water discharge. Taking Rashda Village in Dakhla Oasis as a case study, this paper documents the expansion of agricultural lands as a result of the development and application of well drilling technologies. The materials used include satellite images from 1968 until 2018, and groundwater well data obtained from field visits and governmental reports. The analysis makes clear that there has been a huge change in land use/cover over the past 50 years (1968–2018) with the largest expansion of agricultural lands occurring between 1988 and 2003 driven by acceleration in well drilling. One of the complex phenomena that appeared is the increase in drainage ponds from 15.6 ha in 1968 to 194.4 ha in 2018 where growth of drainage ponds was correlated with the rapid increase in agricultural lands (1998–2003). In the past two decades, Rashda village has been under continuous pressure from population growth and increasing water demand for agricultural, domestic, industrial, and institutional uses. However, the development has continued without attention to its sustainability.