The advent of vaccines has drastically reduced the incidence, morbidity, and mortality related to COVID-19, and with the increase in the number of vaccinated subjects, there have been reports of some adverse events, including skin reactions. In this paper, we report a clinical case of Purpura Annularis Telangiectodes of Majocchi following a third-dose administration of the Pfizer-BioNTech COVID-19 vaccine. Almost 30 days after the third dose, the patient presented erythematous annular patches on the lower limbs with purpuric peripheral areas and a central clearing with no other symptoms. A dermoscopic examination showed capillaritis, reddish-brown dot-clods on a coppery-red background caused by leaky capillaries. To date, the causes of Majocchi’s disease are not well-defined; in the literature, three vaccination-related cases have been reported: one after a flu vaccination and two after an anti-SARS-CoV-2 one. Dermatologists should be trained to promptly recognize these clinical manifestations after vaccination, which will likely become a common finding in daily clinical practice, especially given the large diffusion of SARS-CoV-2 vaccinations.