This study investigated the factors that parents considered when sending their children back to school after the COVID-19 outbreak and analyzed the dilemma that parents were facing. A total of 1067 questionnaires were collected through snowball sampling. After three levels of coding based on Grounded Theory and Field Theory, parents' key concerns were categorized as four personal factors (i.e., intuitive expectation, health issue, learning effectiveness, perceived epidemic safety) and three environmental factors (i.e., school environment, family environment, social environment). By factor weight analysis using the Kruskal-Wallis H test, a field model of factors that affect parents' willingness was set up. Results indicated that learning effectiveness is the most critical factor affecting parents' willingness. By considering both personal and environmental factors, most parents were not satisfied with the effect of home-based online education and expressed their willingness to send their children back to school and resume classes; however, they also worried about students' epidemic awareness and self-protection abilities. Students' development highly depends on the social atmosphere, a regular schedule, and environmental support from schools, which can hardly be achieved by home-based online learning. The findings suggest that the joint efforts of society, schools, and families are needed on the issue of students returning to school after the COVID-19 outbreak.