Cutaneous metastasis (CM) of head-and-neck squamous cell carcinoma is rarely reported. Here, we report a case of a 78-year-old male who had already had a surgically treated case of carcinoma of the right buccal mucosa one and a half months back but presented with a near local site recurrence and subsequently developed distant skin metastases to the lower neck and upper trunk during treatment. Local site recurrence was confirmed with a biopsy, but benign-looking lesions in the lower neck and upper trunk were developed during the last week of treatment, which later on kept growing in size and after the biopsy came positive for malignancy. Although there was a complete response at the recurred site of malignancy, there was a progression of disease at the initially benign-looking lesion in the lower neck and upper trunk, which later on was proven to be cutaneous malignancy on histopathology. This case has cemented the fact that the chance of the presence of occult skin metastasis at the time of diagnosis in primary or recurrent malignancies. Thus, tissue biopsy should be done with a high index of suspicion for cutaneous malignancy associated with head and neck cancers.