A comparison of the nitrogen distributions in two hydrotreated whole shale oils, one from a bench scale hydroprocess and the other from a commercial scale hydroprocess, is presented. The characterization data are interpreted in terms of hydrodenitrogenation processes. The distribution of nitrogen base types in hydrotreated shale oil was seemingly independent of the conditions and scale of hydroprocessing. However, the distribution of nitrogen compound types in each base type that survive hydrodenitrogenation does depend upon the hydroprocessing conditions. The distribution of nitrogen compound types in a hydrotreated whole shale oil produced by a single pass, bench scale hydroprocess is distinctively different from that in a whole oil produced by a commercial scale hydroprocess which recycled the bottoms with the raw feed. Nitrogen compounds resistant to hydrodenitrogenation apparently build up in the recycled bottoms. Better knowledge of the nitrogen type redistribution occurring during upgrading could enable the process engineer to optimize hydroprocessing conditions to remove nitrogen compounds more effectively.