Many students exhibit a special type of learning disability in writing. Yet, teachers spend relatively little time helping children and youth with severe writing difficulties overcome their struggles or prevent emerging problems from becoming more severe. A major reason for this lack of attention is that many educators feel overburdened by the complex task of teaching students how to compose meaningful texts. The purpose of this explorative study was to determine the extent to which certain theory-based text- and person-related variables influence the way a written story is rated by experts and subsequently enable practitioners to make more informed decisions about where to start in supporting struggling writers. Sixty German secondary students (ages 10-13 years old) wrote stories that were evaluated by eight independent raters. Structural equation models were then used to examine the relationships between seven dependent variables and the quality of the texts. The analysis showed that rather short and illegible stories were generally rated unfavorable. Other factors (e.g., performance on alphabetic and copying tasks or spelling skills) also played a role, but to a lesser extent. These findings provide teachers with useful information about where to start when trying to prevent learning disabilities in writing. In particular, educators should focus on instructing students (a) how to brainstorm story ideas in order to enable them to produce texts of an acceptable length and (b) on how to improve the legibility of their handwriting.