Objectives: There is a paucity of literature on what contributes to 30-day readmission rates from the patient’s perspective in head and neck cancer patients. Post-operatively, these patients are often discharged with multiple surgical sites and home equipment requiring education and a large responsibility upon arriving home. Patients have a unique understanding of the discharge process and rationale behind presenting for care following initial discharge. Understanding the experience of the readmitted patient may be critical in finding effective methods to prevent unnecessary readmissions. Methods: Through key-informant interviews, we assessed factors that impact readmission rates from the patient perspective. Patients were eligible if they were discharged within the last 30 days and subsequently readmitted following an admission for a head and neck cancer surgery. Inductive coding was used to analyze interview transcripts and develop themes. Results: Thirteen respondents were interviewed. 46% (n = 6) did not feel ready for discharge after the index admission. Out of these 6 patients, 83% (n = 5) felt their readmission could have been avoided. Patients often encountered unexpected events after returning home from the index admission and felt their readmissions were potentially avoidable with more information regarding what to expect at home, prior to discharge. Although medically stable upon discharge, these findings indicate some patients might be discharged sooner than they should be due to factors outside of medical indications. Conclusions: To address the various biopsychosocial components of patient care in addition to medical aspects, an otolaryngology-specific, prior-to-discharge checklist could aid in lowering 30-day readmissions. Since the amount of education each patient requires to feel competent managing their health at home varies, more work is needed to craft post-education assessments of patient/caregiver competencies for home equipment, prior to discharge to reduce avoidable readmissions.