Background: Advance Directives (ADs) play a critical role in ensuring patient autonomy, particularly among patients with Head and Neck Cancer (HNC). However, the factors influencing AD utilization among HNC patients, especially with respect to varying cancer stages and patient care settings, remain understudied. Our study aims to compare the use of AD between patients Free of Recurrence and/or Metastasis (FRM) from HNC with patients with Recurrent and/or Metastatic (RM) HNC. Methods: In this comparative observational study at a tertiary cancer care center, we analyzed the utilization of ADs in two distinct patient cohorts diagnosed with HNC: Recurrent and/or Metastatic (RM, n = 96) and Free of Recurrence and/or Metastasis (FRM, n = 389). Data collection involved examining the frequency, motivations, and modes of AD creation of both cohorts Results: Our comparative analysis revealed a higher presence of ADs in the RM cohort compared to the FRM cohort (58.3% vs. 46.5%, p = 0.038). The type of AD or the reasons against its creation were similar in both groups. Motivations differed notably: 52.4% of the RM cohort was influenced by advice from acquaintances or professionals versus 27.6% in the FRM cohort (p = 0.054, Cramer’s V = 0.223). Concerns about abandonment or over-therapy motivated 23.4% of the FRM cohort, but only 16.7% of the RM group (p = 0.054, Cramer’s V = 0.223). Decisions to defer AD creation were pronounced in the RM group at 67.4% compared to 55.1% in the FRM group. In terms of AD forms, the RM cohort prepared multiple forms significantly more frequently (9.3% vs. 0.7%, p = 0.002*, Cramer’s V = 0.294). Both groups predominantly sought legal (26.5% vs. 22.9%, p = 0.624, phi = 0.034) or other consultation (20.0% vs. 39.6%, p = 0.006*, phi = 0.193) during AD formation, with no significant differences in medical consultation (12.9% vs. 12.5%, p > 0.999, phi < 0.001) preferences. Conclusion: While approximately every other patient with localized disease had an AD, the rate in patients with recurrent and/or metastatic disease was only slightly higher. Related to the drastically worse prognosis of recurrent and/or metastatic disease, effort should be made to encourage these patients to create an AD. This analysis provides evidence that advice from acquaintances or professionals effectively motivated patients with recurrent and/or metastatic disease to consider their end-of-life wishes and document them in the form of an AD or other advance care directives.