Children with developmental disabilities are slower to develop skills at intentional and symbolic communication than typically developing children, and may rely on atypical patterns of preintentional behaviors to support more complex communication development. The present study compared complex gaze engagement behaviors elicited by 25 preintentional children with developmental disabilities during two interactive contexts: structured object-based play with an examiner and free play with parents that included social play. Children with developmental disabilities demonstrated more onlooking and complex engagement behaviors (i.e., coordinated joint and combined joint), and less unengagement in structured play than in free play. The degree of change in engagement behaviors between play settings was not significantly associated with children's receptive language, motor, or overall developmental scores. Clinical implications for adapting play and partner behaviors to support more complex engagement behaviors in this population are discussed. (Contains 5 tables.)