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This phase II trial studies the effect of pembrolizumab alone compared to the usual approach (chemotherapy [cisplatin and carboplatin] plus radiation therapy) after surgery in treating patients with head and neck squamous cell carcinoma that has come back (recurrent) or patients with a second head and neck cancer that is not from metastasis (primary). Radiation therapy uses high energy radiation or protons to kill tumor cells and shrink tumors. Cisplatin is in a class of medications known as platinum-containing compounds. It works by killing, stopping or slowing the growth of cancer cells. Carboplatin is also in a class of medications known as platinum-containing compounds. It works in a way similar to the anticancer drug cisplatin, but may be better tolerated than cisplatin. Carboplatin works by killing, stopping or slowing the growth of cancer cells. Immunotherapy with monoclonal antibodies, such as pembrolizumab, may help the body's immune system attack the cancer and may interfere with the ability of tumor cells to grow and spread. Giving pembrolizumab alone after surgery may work better than the usual approach in shrinking recurrent or primary head and neck squamous cell carcinoma.

This phase II trial tests whether reduced dose radiation therapy after transoral robotic surgery works in treating patients with human papillomavirus (HPV)-positive oropharyngeal cancer. HPV positive oropharyngeal cancer has a better prognosis than oropharyngeal cancer not caused by HPV. A standard of care treatment for HPV positive oropharyngeal cancer is transoral robotic surgery followed by radiation therapy. However, this treatment is associated with many long-term side effects including difficulty swallowing. Radiation therapy uses high energy rays to kill tumor cells and shrink tumors. Giving reduced dose radiation therapy after transoral robotic surgery may improve swallowing outcomes and quality of life compared to standard of care dose radiation therapy after transoral robotic surgery.