Aim: The aim of this current case series is to propose various design modifications of the conventional distal shoe space maintainers in relation to complex clinical scenarios. Background: Primary dentition plays a significant role in preserving space for underlying unerupted permanent teeth; early childhood caries (ECC) is a serious public health problem in both developing and developed countries, and it is often left untreated. Its consequences can have an immediate and long-term impact on the child's quality of life and overall health. Premature loss of primary dentition can result in loss of arch length, thereby hampering the eruption of the succeedaneous tooth, which can further lead to malalignment, crowding, rotation, and impaction of the permanent teeth. Space maintainers are advocated in cases where extraction of primary molars is inevitable. In the early loss of the second primary molar, a distal-shoe space maintainer is advocated to guide the eruption, as well as prevent mesial migration of the first permanent molar (FPM) during the eruption. In clinical scenarios where multiple losses of deciduous molars occur bilaterally, obtaining adequate anchorage is questionable and futile. The following clinical modifications, however, are useful in overcoming the problems related to the same. The following case series intends to project various modifications of distal shoes in complex scenarios. Case description: Various modifications of the distal shoe have been proposed in our current case series. The appliances were adjusted individually on a case-to-case basis depending on the clinical scenario. A 1-year clinical follow-up was carried out on all the patients. Conclusion: All the clinical modifications were successful in guiding the eruption of a FPM; there were no complications during any follow-up visit. Clinical significance: In cases where the traditional design is not indicated, certain modifications in distal shoes by adding new components to the appliance will allow the appliance to be placed and the space to be maintained effectively. Along with this, reinforcement of parents and the child for oral hygiene maintenance will maintain the remaining healthy tooth structure and increase the success of treatment.