People with chickenpox often gain lifelong immunity after one infection. In most cases, chickenpox's natural immunity provides significant protection against reinfection. However, patients with a second reinfection have been encountered periodically. Neither population-based nor individual data are available on the frequency of reported second Varicella infections among Indians. The possibility of third-time reinfection is very rare, even in reputed literature. Here, we discuss a 68-year-old patient with four reinfections of chickenpox. Two reputed dermatologists confirmed his infection, and he recovered fully with Acyclovir and bed rest. The primary objective of this case report is to highlight the risk of chickenpox reinfections and reinfections occurring more than two times.