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This article examines how kisses and knocks in Marcel Proust’s The Way By Swann’s and Samuel Beckett’s Molloy serve as coping mechanisms to combat fear-driven insomnia. Since childhood, the Proustian narrator endures insomnia, finding solace either in his mother’s tender kiss or its cherished memories. In contrast, the adult eponymous protagonist in Samuel Beckett’s Molloy develops child-like anxiety about embodying his old mother’s neurodegenerative afflictions by sleeping in her bed. Molloy’s fear not only shapes the dynamics of his relationship with his mother but also the general maternal figure-son bond. This becomes evident when he absconds from Lousse’s home and rejects her care when she replaces her dead dog with Molloy. Although the Proustian narrator and Molloy have profoundly different relationships with their mothers, it is evident that fear underlies the emotional complexities of their mother-son bond. While the former is afraid of being abandoned by his mother, the latter is scared of mirroring his old mother’s neurodegenerative illness by sleeping in her bed. The fear-oriented mother-son relationship impacts their quality of sleep. Hence, the Proustian narrator uses his mother’s kiss as an antidote to insomnia. On the other hand, Molloy knocks on his sleeping mother’s head, emphasising the transactional nature of their relationship, thereby rejecting their genetic relationship as he is scared of inheriting her illness. Here, Mary Ainsworth’s pioneering research on developmental psychology helps us delve deeper into the emotional intricacies of the mother-son relationship that cause sleep disorders experienced by the Proustian narrator and Molloy. This paper aims to bridge gaps in the existing scholarship on Proust and Beckett by examining the impact of mother-son relationship on the protagonists’ quality of sleep and their coping mechanisms to combat insomnia.