Abstract. The introduction of computers as an assisting tool in the ﬁeld of education has aﬀected the way teachers plan their classes and in- teract with their students.The Intelligent Computer Assisted Language Learning (ICALL) ﬁeld addresses this evolution in the teaching process and has fomented great interest for the last few decades in the academic community. REAP.PT is a Portuguese system from this research area and aims to teach the Portuguese language to both foreign and native speakers. This is done by employing a series of automatically generated exercises focusing on several semantic and syntactic aspects of the lan- guage, speciﬁcally tailored to the users needs. The goal of this work is to expand the REAP.PT system, namely, its syntactic exercises. A state of the art review was elaborated and it focuses on similar CALL sys- tems already available. The proposed approach is also formalized and the challenges are described. Finally, the evaluation method for assert- ing the quality of these new exercises is speciﬁed.