The selection of texts for second language learning purposes typically relies on teachers’ and test developers’ individual judgment of the observable qualitative properties of a text. Little or no consideration is generally given to the quantitative dimension within an evidence-based framework of reproducibility. This study aims to fill the gap by evaluating the effectiveness of an automatic tool trained to assess text complexity in the context of Italian as a second language learning. A dataset of texts labeled by expert test developers was used to evaluate the performance of three classifier models (decision tree, random forest, and support vector machine), which were trained using linguistic features measured quantitatively and extracted from the texts. The experimental analysis provided satisfactory results, also in relation to which kind of linguistic trait contributed the most to the final outcome.