Cover crops have emerged as a crucial tool in promoting sustainable agricultural practices, particularly in improving soil quality and soil–plant health. This study investigates the impact of single cover crop plants each with varying fungal and/or bacterial symbiosis capacities in a pot experiment. The growth of non-symbiont Ethiopian mustard (Brassica carinata), the associative bacterium symbiont black oat (Avena strigosa) and the double (fungus–bacterium) endosymbiont broad bean (Vicia faba) was studied on three distinct soil types, namely a less-fertile sandy soil (Arenosol), an average value of loam soil (Luvisol) and a more productive chernozem soil (Chernozem). Beside the biomass production, nitrogen content and frequency of AM fungi symbiosis (MYCO%) of cover crops, the main soil health characteristics of electrical conductivity (EC), labile carbon (POXC) and fluorescein diacetate enzyme activity (FDA) were assessed and evaluated by detailed statistical analysis. Among the used soil types, the greatest biomass production was found on Chernozem soil with the relatively highest soil organic matter (2.81%) content and productivity. Double symbiotic activity, assessed by soil nitrogen content and mycorrhiza frequency (MYCO%), were significantly improved on the lowest-quality Arenosols (SOM 1.16%). In that slightly humous sandy soil, MYCO% was enhanced by 45%, indicating that symbiosis was crucial for plant growth in the less-fertile soil investigated. After the initial cover crop phase, the accumulated biomass was incorporated into the Luvisol (SOM 1.64%) soil, followed by the cultivation of corn (Zea mays, DK 3972) as the main crop. The results indicate that incorporating cover crop residues enhanced labile carbon (POXC) by 20% and significantly increased the FDA microbial activity in the soil, which positively correlated with the nutrient availability and growth of the maize crop. This study emphasizes the importance of selecting suitable cover crops based on their symbiotic characteristics to improve soil quality and enhance soil–plant health in sustainable agricultural systems.