Background: Despite widespread use of digital toys, research evidence of how a digital toy's features affect children's development and the nature of parent-child interactions during play is limited. Objective: The present study aimed to examine how mother-child dyads experience a traditional stuffed toy and an animated digital toy by comparing children's conceptions of the toys, their play behaviors, and maternal interactive behaviors. The relationship pattern of how and degree to which children's conceptions and maternal interactive behaviors are associated with children's play were explored to examine how the toys' animated and interactive function affected children's play level and mother-child interaction. Method: Forty-eight children (mean age 49.77 months; 32 boys and 16 girls) and their mothers participated in the present study. Mother-child play with the toys was observed, and the children's conceptions of the toys were obtained through interviews. Results: Children seemed to perceive that a digital puppy doll had psychological attributes. The mothers showed more interactive behaviors overall when playing with their children using digital toys. However, the associations between maternal interactive behaviors and children's play in the two different play settings showed that a digital toy changed mother-child interaction owing to its technological features. Both children's conception and maternal interactive behaviors of pretend play in the two different play contexts independently contributed to children's pretense level. Conclusions: The current findings confirmed the facilitating as well as mediating effects of a digital toy on children's play and the role of parents during play with digital toys.