Pyrolytic treatment offers the potential for the rapid remediation of contaminated soils. However, soil fertility restoration can be highly variable, underscoring the need to understand how treatment conditions affect soil detoxification and the ability to support plant growth. We report here the first pilot-scale study of pyrolytic remediation of crude-oil-contaminated soil using a continuously fed rotary kiln reactor. Treatment at 420 °C with only 15 min of residence time resulted in high removal efficiencies for both total petroleum hydrocarbons (TPH) (99.9%) and polycyclic aromatic hydrocarbons (PAHs) (94.5%) and restored fertility to clean soil levels (i.e., Lactuca sativa biomass dry weight yield after 21 days increased from 3.0 ± 0.3 mg for contaminated soil to 8.8 ± 1.1 mg for treated soil, which is similar to 9.0 ± 0.7 mg for uncontaminated soil). Viability assays with a human bronchial epithelial cell line showed that pyrolytic treatment effectively achieved detoxification of contaminated soil extracts. As expected, TPH and PAH removal efficiencies increased with increasing treatment intensity (i.e., higher temperatures and longer residence times). However, higher treatment intensities decreased soil fertility, suggesting that there is an optimal system-specific intensity for fertility restoration. Overall, this study highlights trade-offs between pyrolytic treatment intensity, hydrocarbon removal efficiency, and fertility restoration while informing the design, optimization, and operation of large-scale pyrolytic systems to efficiently remediate crude-oil-contaminated soils.