The transition to elementary school (i.e., 1st grade) is not the first major life-course transition that children have experienced. However, due to its nature and expanded intervention in children’s lives, transition to 1st grade is a significant, exciting, and magical event. In the academic domain, new elementary school students are expected to gain mastery over literacy. This is not an easy task, especially in cases of diglossia, and it is considered as a first step in school adjustment. However, elementary school adjustment is more than literacy; it includes a vast list of demands, such as: wake up earlier, wear uniform, carry/pull a (heavy) bag, sit on a chair for hours, exposure to punishments, concerns with toilet needs, managing well socially during class breaks, encountering parents’ questions, worries, and higher expectations, etc. Several figures are important along this process, especially the homeroom teacher. Yet, parental and familial reactions to various events are also crucial, calling for an efficient school–family collaboration. Altogether, successful adjustment to elementary school will significantly shape students’ feelings toward learning until graduation from high school.