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While the majority of COVID-19 cases are mild and can be managed in the outpatient setting, more severe cases have proven to be a clinical challenge. While some cases demonstrate a more slow and indolent decline, others seem to deteriorate rapidly with little forewarning. The current literature has connected Retiform Purpura as a cutaneous manifestation associated with severe COVID-19 infections, however timing of cutaneous presentation and severe clinical COVID-19 symptoms has not been well described. Here we report a case of a 58-year-old female who developed Retiform Purpura nearly a week prior to the development of any significant COVID-19 symptoms. This case demonstrates that Retiform Purpura is not only associated with severe COVID-19 disease, but can present prior to symptom onset and should be seen as a harbinger for impending clinical deterioration.