Prosocial behavior is a highly heterogeneous construct, and young children use distinct prosocial actions in response to differing emotional needs of another person. This study examined whether toddlers' prosocial responses differed in response to two understudied emotional contexts--whether or not children caused a victim's distress and the specific emotion expressed by the victim. Toddlers (N = 86; M[subscript age] = 35 months) and their parent participated in two separate mishap paradigms in which parents feigned pain and sadness, respectively. Half of the sample was led to believe they had transgressed to cause their parent's distress, whereas the other half simply witnessed parent distress as bystanders. Results indicated that toddlers were overall equally prosocial when they were transgressors compared to when they were bystanders and significantly more prosocial in response to sadness than pain. Toddlers were significantly more likely to use affection as transgressors than bystanders, information seeking as bystanders than transgressors, and affection in response to pain than sadness. All children used greater helping in response to sadness than pain, and this was especially true when they were bystanders. Findings add to mounting evidence of the complexity of prosocial action in early childhood by identifying that two, distinct emotional contexts influence the amount and type of prosocial behaviors that toddlers use to help others.