Web-based learning has transformed education. Its ability to overcome physical barriers and deliver knowledge at the click of a button has made web-based learning popular and ensured that it will continue to be used in the future. The involvement of parents in web-based learning is fundamental to the success of the educational process, but limited attention has been paid to the impact of web-based learning on parents. This study examined parental experiences with school-aged children receiving web-based learning in Jeddah, Saudi Arabia. We sent cross-sectional, anonymous web-based questionnaires to school-aged children's parents. A total of 184 parents completed the survey. Parents' negative experiences of web-based learning (mean 4.13, SD 0.62) exceeded their positive experiences (mean 3.52, SD 0.65). The most negative experience reported by parents was their child's boredom due to prolonged sitting in front of a device (mean 4.56, SD 0.69). The most positive experience was their child's technological skill enhancement (mean 3.98, SD 88). Their child's lack of social interaction and friendship building promoted stress among parents (r=-0.190; P=.01). At the same time, their child's technological skill enhancement reduced stress among parents (r=0.261; P=.001). The most reported (63/184, 34.2%) obstacle to web-based learning was having multiple learners in the same household. Web-based learning is a fundamental learning method and will continue to be used in the future because of its ability to overcome many barriers to education. Parental involvement in the continuity and success of the web-based learning process is crucial. However, the findings of this study illustrated that parents' experiences of web-based learning were more negative than positive. Parents who reported negative experiences reported an increase in stress and faced more obstacles due to web-based learning. Thus, more attention and intervention are needed to promote positive web-based learning experiences among parents.