We examined representations of attachment security using story stem narratives (Manchester Attachment Story Task, MCAST) and a family drawing task in 50 Greek children between 4 and 6 years old. Additionally, we examined the association between attachment classification based on the family drawing task and maternal reports of social and emotional symptoms assessed using the Strengths and Difficulties Questionnaire. Attachment security classification based on the MCAST was not significantly associated with attachment security classification based on the family drawings. There was a small to medium strength significant association between drawing-based insecure attachment classification and higher scores on conduct problems and inattention/hyperactivity ratings. However, the associations were not statistically significant after controlling for the effects of child gender, and maternal education and age. The findings are discussed in relation to the properties of the family drawing task to measure attachment security in the preschool and early middle childhood years.