This study investigated how individuals’ perceptions of features of online social interaction may foster communicative disinhibition that predicts problematic Internet use (PIU). The value that study participants placed on the unique features of computer-mediated communication (CMC; i.e., reduced nonverbal cues and enhanced message control) was associated with greater feelings of disinhibition, which in turn predicted higher levels of preference for online social interactions (POSI). POSI was found to be associated with negative outcomes due to Internet use. Variables accounted for 28% of the variance in participants’ online disinhibition, 27% of the variance in POSI, and 30% of the variance in the negative outcomes. The study represents a step toward a better understanding of the psychological mechanisms underlying the link between CMC characteristics and PIU.