Pesticides are frequently applied in large quantities in agriculture, resulting in their widespread presence in agricultural areas. Additionally, processes such as drift and volatilization contribute to their dispersion far beyond treated sites. However, systematic soil monitoring remains limited. To assess pesticide exposure to soil organisms, highly sensitive, accurate, and robust multi-residue analytical methods are essential. Given the wide variety of pesticides applied, monitoring those most likely to adversely affect soil health and terrestrial ecosystems is a prerequisite. Soil is one of the most complex environmental matrices, posing significant challenges throughout the entire analytical workflow. Here, we summarize the historical evolution of pesticide analysis in soil, outline key methodological advances, and discuss major challenges that must be addressed along the whole analytical workflow to enable effective soil monitoring. Ultimately, protecting soil requires both analytical and regulatory progress, as part of a broader set of measures.