Purpose: The aim of this study was to examine the role of familiarity of a communication partner on Dutch parents’ perception of their child’s intelligibility, for children with typically-developing speech (TD) or speech sound disorder (SSD). Method: Participants were 67 Dutch-speaking children (48–84 months), 48 with TD and 19 with SSD. Item scores on the parent-rated Intelligibility in Context Scale: Dutch (ICS-NL) were compared between groups and related to naive listeners’ ratings of children’s intelligibility (IR), and a measure of speech accuracy (i.e. percentage of consonants correct-adjusted, PCC-A). Result: Statistical analysis yielded a significant Group by Familiarity interaction on the ICS-NL. Parents rated the intelligibility of their child with SSD as higher with more familiar communication partners than less familiar, more so than parents of children with TD. In the SSD group, IR was more strongly correlated with ICS-NL item scores for less familiar partners. PCC-A was only correlated with ICS-NL item 7 (strangers). Conclusion: Parents perceive their children as more intelligible with people in close relationships, likely due to their higher familiarity with the child’s speech. Children’s relationships should be considered with respect to communicative participation. PCC-A may be a less reliable predictor of participation in family and community life.