Developmental dysgraphia, being observed among 10–30% of school-aged children, is a disturbance or difficulty in the production of written language that has to do with the mechanics of writing. The objective of this study is to propose a method that can be used for automated diagnosis of this disorder, as well as for estimation of difficulty level as determined by the handwriting proficiency screening questionnaire. We used a digitizing tablet to acquire handwriting and consequently employed a complex parameterization in order to quantify its kinematic aspects and hidden complexities. We also introduced a simple intrawriter normalization that increased dysgraphia discrimination and HPSQ estimation accuracies. Using a random forest classifier, we reached 96% sensitivity and specificity, while in the case of automated rating by the HPSQ total score, we reached 10% estimation error. This study proves that digital parameterization of pressure and altitude/tilt patterns in children with dysgraphia can be used for preliminary diagnosis of this writing disorder.