Children’s use of the Internet comes with both risks and opportunities. To minimize risks and maximize opportunities, parents may choose to observe, enable, and/or restrict their children’s Internet use. However, parents’ high confidence in their children’s online safety can itself be a risk factor inhibiting parental awareness of online risks. This research aims to test whether confident parents are accurately aware of how frequently their child has experienced risks online. To this end, construct validity and reliability of scales measuring parental self-efficacy, restrictive-enabling-observant mediation, awareness, and Internet use were established first. Next, a conceptual model of parental awareness was proposed. These results were based on a two-parameter-logistic-model of item response theory, minimum-rank factor analysis, and parallel-mediation analysis of self-reports by a convenience sample of 388 parents in Ireland (Autumn 2019). Confident parents mostly reported their child experienced no online risk in the past couple of months, whereas unconfident parents reported their child experienced an online risk once, twice, or more times. Results of the mediation analysis indicated that confident parents likely underestimated, whereas unconfident parents overestimated, how frequently their child experienced an online risk. The accuracy of parental awareness depended on their mediation strategies, particularly restrictive mediation. Further research is needed to test whether training parents on self-efficacy and mediation of children’s Internet use raises their awareness of the children’s online risks.