Deep learning techniques have recently been experimented for map generalization. Although promising, these experiments raise new problems regarding the evaluation of the output images. Traditional map generalization evaluation cannot directly be applied to the results in a raster format. Additionally, the internal evaluation used by deep learning models is mostly based on the realism of images and the accuracy of pixels, and none of these criteria is sufficient to evaluate a generalization process. Finally, deep learning processes tend to hide the causal mechanisms and do not always guarantee a result that follows cartographic principles. In this article, we propose a method to adapt constraint-based evaluation to the images generated by deep learning models. We focus on the use case of mountain road generalization, and detail seven raster-based constraints, namely, clutter, coalescence reduction, smoothness, position preservation, road connectivity preservation, noise absence, and color realism constraints. These constraints can contribute to current studies on deep learning-based map generalization, as they can help guide the learning process, compare different models, validate these models, and identify remaining problems in the output images. They can also be used to assess the quality of training examples.